Document:

Form of Amended and Restated Warrant to Purchase Series E-1 Preferred Stock

 Exhibit 4.6 
 THIS WARRANT AND THE UNDERLYING SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR UNDER THE SECURITIES LAWS OF ANY STATE. THESE SECURITIES
MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED EXCEPT AS PERMITTED UNDER THE ACT AND APPLICABLE STATE SECURITIES LAWS IN ACCORDANCE WITH APPLICABLE REGISTRATION REQUIREMENTS OR AN EXEMPTION THEREFROM. THE ISSUER OF THESE
SECURITIES MAY REQUIRE AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE ISSUER THAT SUCH OFFER, SALE, TRANSFER, PLEDGE OR HYPOTHECATION OTHERWISE COMPLIES WITH THE ACT AND ANY APPLICABLE STATE SECURITIES LAWS. THIS WARRANT MUST BE SURRENDERED TO
THE COMPANY OR ITS TRANSFER AGENT AS A CONDITION PRECEDENT TO THE SALE, TRANSFER, PLEDGE OR HYPOTHECATION OF ANY INTEREST IN ANY OF THE SECURITIES REPRESENTED HEREBY. 
 AMENDED AND RESTATED 
 WARRANT TO PURCHASE SHARES OF SERIES E-1
PREFERRED STOCK 
 of 
 WAGEWORKS, INC. 
 Dated as of December 28, 2009, amended and
restated as of July 30, 2010 
 Void after the date specified in Section 8 

Warrant to Purchase 
 [—] Shares of 
 Series E-1 Preferred Stock 

as Set Forth in Section 1 
 (subject to adjustment) 
 THIS CERTIFIES THAT, for value received,
[—], or its registered assigns (the “Holder”), is entitled, subject to the provisions and upon the terms and conditions set forth herein, to purchase from WageWorks, Inc., a Delaware corporation (the
“Company”), [—] shares of the Company’s Series E-1 Preferred Stock, par value $0.001 per share (the “Shares”), at the price per share set forth in Section 1. The term
“Warrant” as used herein shall include this Warrant and any warrants delivered in substitution or exchange therefor as provided herein. This Warrant is issued in connection with the transactions described in the Note and
Warrant Purchase Agreement, dated as of December 28, 2009, as amended, by and among the Company and the purchasers described therein (the “Purchase Agreement”). This Warrant is one of a series of warrants referred to as
the “Warrants” in the Purchase Agreement. Capitalized terms used but not defined herein shall have the meanings ascribed to such terms in the Convertible Promissory Notes (the “Notes”) to be issued
pursuant to, and the form of which is attached as Exhibit A to, the Purchase Agreement. 
 The following is a statement of the
rights of the Holder and the conditions to which this Warrant is subject, and to which Holder, by acceptance of this Warrant, agrees: 
 1. Exercise Price; Exercise Period. 
 (a) Exercise
Price. The Exercise Price per Share of this Warrant (the “Exercise Price”) shall be $2.29; provided, however, that such Exercise Price shall be subject to adjustment as provided in this Warrant. 

  

 (b) Exercise Period. This Warrant shall be exercisable, in
whole or in part, after the Automatic Conversion Date (as defined in the Notes) and prior to (or in connection with) the expiration of this Warrant as set forth in Section 8 hereof. 

2. Exercise of the Warrant. 
 (a) Exercise. The purchase rights represented by this Warrant may be exercised at the election of the Holder, in whole or in part, in accordance with Section 1 hereof, by: 

(i) the tender to the Company at its principal office (or such other office or agency as the Company may designate) of a
notice of exercise in the form of Exhibit A (the “Notice of Exercise”), duly completed and executed by or on behalf of the Holder, together with the surrender of this Warrant; and 

(ii) the payment to the Company of an amount equal to (x) the Exercise Price multiplied by (y) the number of
Shares being purchased, by (a) wire transfer or certified, cashier’s or other check acceptable to the Company and payable to the order of the Company; (b) surrender and cancellation of promissory notes or other instruments
representing indebtedness of the Company to the Holder; or (c) a combination of (a) and (b). 
 (b)
Net Issue Exercise. In lieu of exercising this Warrant pursuant to Section 2(a)(ii) hereof, if the fair market value of one Share is greater than the Exercise Price (at the date of calculation as set forth below), the Holder may
elect to receive a number of Shares equal to the value of this Warrant (or of any portion of this Warrant being canceled) by surrender of this Warrant at the principal office of the Company (or such other office or agency as the Company may
designate) together with a properly completed and executed Notice of Exercise reflecting such election, in which event the Company shall issue to the Holder that number of Shares computed using the following formula: 

 

							
	 X
	  	 	=	  	  	    Y (A – B)    
	  	  	            A

 Where: 
  

							
	 X
	  	 	=	  	  	The number of Shares to be issued to the Holder
			
	 Y
	  	 	=	  	  	The number of Shares purchasable under this Warrant or, if only a portion of the Warrant is being exercised, the portion of the Warrant being cancelled (at the date of such
calculation)
			
	 A
	  	 	=	  	  	The fair market value of one Share (at the date of such calculation)
			
	 B
	  	 	=	  	  	The Exercise Price (as adjusted to the date of such calculation)

 For purposes of the calculation above, the fair market value of one Share shall be determined by the Board of Directors of the Company, acting in good faith; provided, however, that: 

(i) where a public market exists for the Company’s common stock at the time of such exercise, the fair market value
per Share shall be the product of (x) the average of the closing bid prices of the common stock or the closing price quoted on the national securities exchange on which the common stock is listed as published in the Wall Street Journal,
as applicable, for the ten (10) trading day period ending 

  
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five (5) trading days prior to the date of determination of fair market value and (y) the number of shares of common stock into which each Share is convertible at the time of such
exercise, as applicable; and 
 (ii) if the Warrant is exercised in connection with the Company’s initial
public offering of common stock, the fair market value per Share shall be the product of (x) the per share offering price to the public of the Company’s initial public offering and (y) the number of shares of common stock into which
each Share is convertible at the time of such exercise, as applicable. 
 (c) Stock Certificates.
The rights under this Warrant shall be deemed to have been exercised and the Shares issuable upon such exercise shall be deemed to have been issued immediately prior to the close of business on the date this Warrant is exercised in accordance with
its terms, and the person entitled to receive the Shares issuable upon such exercise shall be treated for all purposes as the holder of record of such Shares as of the close of business on such date. As promptly as reasonably practicable on or after
such date, and in any event within thirty (30) days thereafter, the Company shall issue and deliver to the person or persons entitled to receive the same a certificate or certificates for that number of shares issuable upon such exercise. In
the event that the rights under this Warrant are exercised in part and have not expired, the Company shall execute and deliver a new Warrant reflecting the number of Shares that remain subject to this Warrant. 

(d) No Fractional Shares or Scrip. No fractional shares or scrip representing fractional shares shall be
issued upon the exercise of the rights under this Warrant. In lieu of such fractional share to which the Holder would otherwise be entitled, the Company shall make a cash payment equal to the Exercise Price multiplied by such fraction. 

(e) Conditional Exercise. The Holder may exercise this Warrant conditioned upon (and effective immediately
prior to) consummation of any transaction that would cause the expiration of this Warrant pursuant to Section 8 hereof by so indicating in the notice of exercise. 

(f) Automatic Exercise. If the Holder of this Warrant has not elected to exercise this Warrant prior to
expiration of this Warrant pursuant to Section 8 hereof, then this Warrant shall automatically (without any act on the part of the Holder) be exercised pursuant to Section 2(b) hereof effective immediately prior to the expiration of the
Warrant to the extent such net issue exercise would result in the issuance of Shares, unless Holder shall earlier provide written notice to the Company that the Holder desires that this Warrant expire unexercised. If this Warrant is automatically
exercised, the Company shall notify the Holder of the automatic exercise as soon as reasonably practicable, and the Holder shall surrender the Warrant to the Company in accordance with the terms hereof. 

(g) Reservation of Stock. The Company agrees during the term the rights under this Warrant are exercisable
to take all reasonable action to reserve and keep available from its authorized and unissued shares of Series E-1 Preferred Stock solely for the purpose of effecting the exercise of this Warrant such number of shares of Series E-1
Preferred Stock (and shares of common stock for issuance on conversion of such shares) as shall from time to time be sufficient to effect the exercise of the rights under this Warrant; and if at any time the number of authorized but unissued shares
of Series E-1 Preferred Stock (and shares of common stock for issuance on conversion of such shares) shall not be sufficient for purposes of the exercise of this Warrant in accordance with its terms and the conversion of the Shares, without
limitation of such other remedies as may be available to the Holder, the Company will use all reasonable efforts to take such corporate action as may, in the opinion of counsel, be necessary to increase its authorized and unissued shares of its
Series E-1 Preferred Stock (and shares of common stock for issuance on conversion of such shares) to a number of shares as shall be sufficient for such purposes. The Company represents and warrants that all Shares that may be issued upon the
exercise of this Warrant will, when issued in accordance with the terms hereof, be validly issued, fully paid and nonassessable. 

  
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 3. Replacement of the Warrant. Subject to the receipt of evidence reasonably
satisfactory to the Company of the loss, theft, destruction or mutilation of this Warrant and, in the case of loss, theft or destruction, on delivery of an indemnity agreement reasonably satisfactory in form and substance to the Company or, in the
case of mutilation, on surrender and cancellation of this Warrant, the Company at the expense of the Holder shall execute and deliver, in lieu of this Warrant, a new warrant of like tenor and amount. 

4. Transfer of the Warrant. 
 (a) Warrant Register. The Company shall maintain a register (the “Warrant Register”) containing the name and address of the Holder or Holders. Until this Warrant is
transferred on the Warrant Register in accordance herewith, the Company may treat the Holder as shown on the Warrant Register as the absolute owner of this Warrant for all purposes, notwithstanding any notice to the contrary. Any Holder of this
Warrant (or of any portion of this Warrant) may change its address as shown on the Warrant Register by written notice to the Company requesting a change. 
 (b) Warrant Agent. The Company may appoint an agent for the purpose of maintaining the Warrant Register referred to in Section 4(a) hereof, issuing the Shares or other securities then
issuable upon the exercise of the rights under this Warrant, exchanging this Warrant, replacing this Warrant or conducting related activities. 
 (c) Transferability of the Warrant. Subject to the provisions of this Warrant with respect to compliance with the Securities Act of 1933, as amended (the “Securities
Act”) and limitations on assignments and transfers, including without limitation compliance with the restrictions on transfer set forth in Section 5 hereof, title to this Warrant may be transferred by endorsement (by the transferor
and the transferee executing the assignment form attached as Exhibit B (the “Assignment Form”)) and delivery in the same manner as a negotiable instrument transferable by endorsement and delivery.

 (d) Exchange of the Warrant upon a Transfer. On surrender of this Warrant (and a properly
endorsed Assignment Form) for exchange, subject to the provisions of this Warrant with respect to compliance with the Securities Act and limitations on assignments and transfers, the Company shall issue to, or on the order of, the Holder a new
warrant or warrants of like tenor, in the name of the Holder or such name as the Holder (on payment by the Holder of any applicable transfer taxes) may direct, for the number of shares issuable upon exercise hereof, and the Company shall register
any such transfer upon the Warrant Register. This Warrant (and the securities issuable upon exercise of the rights under this Warrant) must be surrendered to the Company or its warrant or transfer agent, as applicable, as a condition precedent to
the sale, pledge, hypothecation or other transfer of any interest in any of the securities represented hereby. 

(e) Taxes. In no event shall the Company be required to pay any tax which may be payable in respect of any
transfer involved in the issue and delivery of any certificate in a name other than that of the Holder, and the Company shall not be required to issue or deliver any such certificate unless and until the person or persons requesting the issue
thereof shall have paid to the Company the amount of such tax or shall have established to the satisfaction of the Company that such tax has been paid or is not payable. 
 5. Restrictions on Transfer of the Warrant and Shares; Compliance with Securities Laws. By acceptance of this Warrant, the Holder agrees to comply with the following: 

(a) Restrictions on Transfers. In addition to the restrictions applicable to this Warrant set forth in
Section 1.15 of the Amended and Restated Investors’ Rights Agreement dated as of December 22, 

  
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2005, as amended, and subject to Section 5(b) hereof, this Warrant may not be transferred or assigned in whole or in part without the Company’s prior written consent (which shall not be
unreasonably withheld), and any attempt by Holder to transfer or assign any rights, duties or obligations that arise under this Warrant without such permission shall be void. Any transfer of this Warrant or the Shares or the shares of common stock
issuable upon conversion of the Shares (together, the “Securities”) must be in compliance with all applicable federal and state securities laws. The Holder agrees not to make any sale, assignment, transfer, pledge or other
disposition of all or any portion of the Securities, or any beneficial interest therein, unless and until the transferee thereof has agreed in writing for the benefit of the Company to take and hold such Securities subject to, and to be bound by,
the terms and conditions set forth in this Warrant to the same extent as if the transferee were the original Holder hereunder, and 
 (i) there is then in effect a registration statement under the Securities Act covering such proposed disposition and such disposition is made in accordance with such registration statement, or 

(ii) (A) such Holder shall have given prior written notice to the Company of such Holder’s intention to make
such disposition and shall have furnished the Company with a detailed description of the manner and circumstances of the proposed disposition, (B) the transferee shall have confirmed to the satisfaction of the Company in writing, substantially
in the form of Exhibit A-1, that the Securities are being acquired (i) solely for the transferee’s own account and not as a nominee for any other party, (ii) for investment and (iii) not with a view toward
distribution or resale, and shall have confirmed such other matters related thereto as may be reasonably requested by the Company, and (C) if requested by the Company, such Holder shall have furnished the Company, at the Holder’s expense,
with (i) an opinion of counsel, reasonably satisfactory to the Company, to the effect that such disposition will not require registration of such Securities under the Securities Act or (ii) a “no action” letter from the
Securities and Exchange Commission to the effect that the transfer of such Securities without registration will not result in a recommendation by the staff of the Securities and Exchange Commission that action be taken with respect thereto,
whereupon such Holder shall be entitled to transfer such Securities in accordance with the terms of the notice delivered by the Holder to the Company. 
 (b) Permitted Transfers. Permitted transfers include (i) a transfer not involving a change in beneficial ownership, or (ii) transactions involving the distribution without
consideration of Securities by any Holder to (x) a parent, subsidiary or other affiliate of a Holder that is a corporation, (y) any of the Holder’s partners, members or other equity owners, or retired partners or members, or to the
estate of any of its partners, members or other equity owners or retired partners or members, or (z) a venture capital fund that is controlled by or under common control with one or more general partners or managing members of, or shares the
same management company with, the Holder; provided, in each case, that the Holder shall give written notice to the Company of the Holder’s intention to effect such disposition and shall have furnished the Company with a detailed
description of the manner and circumstances of the proposed disposition. 
 (c) Investment Representation
Statement. Unless the rights under this Warrant are exercised pursuant to an effective registration statement under the Securities Act that includes the Shares with respect to which the Warrant was exercised, it shall be a condition to any
exercise of the rights under this Warrant that the Holder shall have confirmed to the satisfaction of the Company in writing, substantially in the form of Exhibit A-1, that the Shares so purchased are being acquired solely for the
Holder’s own account and not as a nominee for any other party, for investment and not with a view toward distribution or resale and that the Holder shall have confirmed such other matters related thereto as may be reasonably requested by the
Company. 

  
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 (d) Securities Law Legend. The Securities shall (unless
otherwise permitted by the provisions of this Warrant) be stamped or imprinted with a legend substantially similar to the following (in addition to any legend required by state securities laws): 

THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR UNDER
THE SECURITIES LAWS OF CERTAIN STATES. THESE SECURITIES MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, PLEDGED OR HYPOTHECATED EXCEPT AS PERMITTED UNDER THE ACT AND APPLICABLE STATE SECURITIES LAWS IN ACCORDANCE WITH APPLICABLE REGISTRATION
REQUIREMENTS OR AN EXEMPTION THEREFROM. THE ISSUER OF THESE SECURITIES MAY REQUIRE AN OPINION OF COUNSEL REASONABLY SATISFACTORY TO THE ISSUER THAT SUCH OFFER, SALE OR TRANSFER, PLEDGE OR HYPOTHECATION OTHERWISE COMPLIES WITH THE ACT AND ANY
APPLICABLE STATE SECURITIES LAWS. THIS CERTIFICATE MUST BE SURRENDERED TO THE COMPANY OR ITS TRANSFER AGENT AS A CONDITION PRECEDENT TO THE SALE, TRANSFER, PLEDGE OR HYPOTHECATION OF ANY INTEREST IN ANY OF THE SECURITIES REPRESENTED HEREBY.

 (e) Market Stand-off Legend. The Shares and common stock issued upon exercise hereof or
conversion thereof shall also be stamped or imprinted with a legend in substantially the following form: 
 THE SHARES
REPRESENTED BY THIS CERTIFICATE ARE SUBJECT TO RESTRICTIONS ON TRANSFERABILITY AND RESALE, INCLUDING A LOCK-UP PERIOD IN THE EVENT OF A PUBLIC OFFERING, AS SET FORTH IN THE WARRANT PURSUANT TO WHICH THESE SHARES WERE ISSUED, A COPY OF WHICH MAY BE
OBTAINED AT THE PRINCIPAL OFFICE OF THE COMPANY. 
 (f) Instructions Regarding Transfer
Restrictions. The Holder consents to the Company making a notation on its records and giving instructions to any transfer agent in order to implement the restrictions on transfer established in this Section 5. 

(g) Removal of Legend. The legend referring to federal and state securities laws identified in
Section 5(d) hereof stamped on a certificate evidencing the Shares (and the common stock issuable upon conversion thereof) and the stock transfer instructions and record notations with respect to such securities shall be removed and the Company
shall issue a certificate without such legend to the holder of such securities if (i) such securities are registered under the Securities Act or (ii) such holder provides the Company with an opinion of counsel reasonably acceptable to the
Company to the effect that a sale or transfer of such securities may be made without registration or qualification. 
 6.
Adjustments. Subject to the expiration of this Warrant pursuant to Section 8 hereof, the number and kind of Shares purchasable hereunder and the Exercise Price therefor are subject to adjustment from time to time, as follows: 

(a) Merger or Reorganization. If at any time there shall be any reorganization, recapitalization, merger or
consolidation (a “Reorganization”) involving the Company (other than as otherwise provided for herein or as would cause the expiration of this Warrant under Section 8 hereof) in which shares of the Company’s capital
stock are converted into or exchanged for securities, cash or other property, then, as a part of such Reorganization, lawful provision shall be made so that the Holder shall thereafter be entitled to receive upon exercise of this Warrant, the kind
and amount of securities, cash or other property of the successor corporation resulting from such Reorganization, equivalent in value to that which a holder of the Shares deliverable upon exercise of this Warrant would have been entitled in such

  
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Reorganization if the right to purchase the Shares hereunder had been exercised immediately prior to such Reorganization. In any such case, appropriate adjustment (as determined in good faith by
the Board of Directors of the successor corporation) shall be made in the application of the provisions of this Warrant with respect to the rights and interests of the Holder after such Reorganization to the end that the provisions of this Warrant
shall be applicable after the event, as near as reasonably may be, in relation to any shares or other securities deliverable after that event upon the exercise of this Warrant. 

(b) Reclassification of Shares. If the securities issuable upon exercise of this Warrant are changed into
the same or a different number of securities of any other class or classes by reclassification, capital reorganization, conversion of all outstanding shares of the relevant class or series (other than as would cause the expiration of this Warrant
pursuant to Section 8 hereof) or otherwise (other than as otherwise provided for herein) (a “Reclassification”), then, in any such event, in lieu of the number of Shares which the Holder would otherwise have been
entitled to receive, the Holder shall have the right thereafter to exercise this Warrant for a number of shares of such other class or classes of stock that a holder of the number of securities deliverable upon exercise of this Warrant immediately
before that change would have been entitled to receive in such Reclassification, all subject to further adjustment as provided herein with respect to such other shares. 

(c) Subdivisions and Combinations. In the event that the outstanding shares of the securities issuable upon
exercise of this Warrant are subdivided (by stock split, by payment of a stock dividend or otherwise) into a greater number of shares of such securities, the number of Shares issuable upon exercise of the rights under this Warrant immediately prior
to such subdivision shall, concurrently with the effectiveness of such subdivision, be proportionately increased, and the Exercise Price shall be proportionately decreased, and in the event that the outstanding shares of the securities issuable upon
exercise of this Warrant are combined (by reclassification or otherwise) into a lesser number of shares of such securities, the number of Shares issuable upon exercise of the rights under this Warrant immediately prior to such combination shall,
concurrently with the effectiveness of such combination, be proportionately decreased, and the Exercise Price shall be proportionately increased. 
 (d) Notice of Adjustments. Upon any adjustment in accordance with this Section 6 hereof, the Company shall give notice thereof to the Holder, which notice shall state the event giving
rise to the adjustment, the Exercise Price as adjusted and the number of securities or other property purchasable upon the exercise of the rights under this Warrant, setting forth in reasonable detail the method of calculation of each. The Company
shall, upon the written request of any Holder, furnish or cause to be furnished to such Holder a certificate setting forth (i) such adjustments, (ii) the Exercise Price at the time in effect and (iii) the number of securities and the
amount, if any, of other property that at the time would be received upon exercise of this Warrant. 
 7. Notification of
Certain Events. Prior to the expiration of this Warrant pursuant to Section 8 hereof, in the event that the Company shall authorize: 
 (a) the issuance of any dividend or other distribution on the capital stock of the Company (other than (i) dividends or distributions otherwise provided for in Section 6 hereof,
(ii) repurchases of common stock issued to or held by employees, officers, directors or consultants of the Company or its subsidiaries upon termination of their employment or services pursuant to agreements providing for the right of said
repurchase; (iii) repurchases of common stock issued to or held by employees, officers, directors or consultants of the Company or its subsidiaries pursuant to rights of first refusal or first offer contained in agreements providing for such
rights; or (iv) repurchases of capital stock of the Company in connection with the settlement of disputes with any stockholder), whether in cash, property, stock or other securities; 

  
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 (b) the voluntary liquidation, dissolution or winding up of the Company; or

 (c) any transaction resulting in the expiration of this Warrant pursuant to Section 8(b) hereof;

 the Company shall send to the Holder of this Warrant at least ten (10) days prior written notice of the date on which a record shall be
taken for any such dividend or distribution specified in clause (a) or the expected effective date of any such other event specified in clause (b) or (c), as applicable. The notice provisions set forth in this section may be shortened or
waived prospectively or retrospectively by the consent of the Holder of this Warrant. 
 8. Expiration of the Warrant.
This Warrant shall expire and shall no longer be exercisable as of the earlier of: 
 (a) 5:00 p.m., Pacific
time, on June 30, 2014; or 
 (b) (i) the acquisition of the Company by another entity by means of any
transaction or series of related transactions to which the Company is a party (including, without limitation, any stock acquisition, reorganization, merger or consolidation, but excluding any sale of stock for capital raising purposes and any
transaction effected primarily for purposes of changing the Company’s jurisdiction of incorporation) other than a transaction or series of related transactions in which the holders of the voting securities of the Company outstanding immediately
prior to such transaction or series of related transactions retain, immediately after such transaction or series of transactions, as a result of shares in the Company held by such holders prior to such transaction or series of transactions, at least
a majority of the total voting power represented by the outstanding voting securities of the Company or such other surviving or resulting entity (or if the Company or such other surviving or resulting entity is a wholly-owned subsidiary immediately
following such acquisition, its parent), or (ii) a sale, lease or other disposition of all or substantially all of the assets of the Company and its subsidiaries taken as a whole by means of any transaction or series of related transactions,
except where such sale, lease or other disposition is to a wholly-owned subsidiary of the Company. 
 9. No Rights as a
Stockholder. Nothing contained herein shall entitle the Holder to any rights as a stockholder of the Company or to be deemed the holder of any securities that may at any time be issuable on the exercise of the rights hereunder for any purpose
nor shall anything contained herein be construed to confer upon the Holder, as such, any right to vote for the election of directors or upon any matter submitted to stockholders at any meeting thereof, or to give or withhold consent to any corporate
action (whether upon any recapitalization, issuance of stock, reclassification of stock, change of par value or change of stock to no par value, consolidation, merger, conveyance or otherwise) or to receive notice of meetings, or to receive
dividends or subscription rights or any other rights of a stockholder of the Company until the rights under the Warrant shall have been exercised and the Shares purchasable upon exercise of the rights hereunder shall have become deliverable as
provided herein. 
 10. Market Stand-off. The Holder of this Warrant hereby agrees that such Holder shall not sell or
otherwise transfer, make any short sale of, grant any option for the purchase of, or enter into any hedging or similar transaction with the same economic effect as a sale, of any common stock (or other securities) of the Company held by the Holder
(other than those included in the registration) during the one hundred eighty (180) day period following the effective date of the registration statement for the Company’s initial public offering filed under the Securities Act (or such
other period as may be requested by the Company or an underwriter to accommodate regulatory restrictions on (i) the publication or other distribution of research reports and (ii) analyst recommendations and opinions, including, but not
limited to, the restrictions contained in NASD Rule 2711(f)(4) or NYSE Rule 472(f)(4), or any successor provisions or amendments thereto). The 

  
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obligations described in this section shall not apply to a registration relating solely to employee benefit plans on Form S-l or Form S-8 or similar forms that may be promulgated in the
future, or a registration relating solely to a transaction on Form S-4 or similar forms that may be promulgated in the future. The Company may impose stop-transfer instructions and may stamp each certificate with a legend as substantially set
forth in Section 5(e) hereof with respect to the shares of common stock (or other securities) subject to the foregoing restriction until the end of such one hundred eighty (180) day (or other) period. The Holder agrees to execute a market
stand-off agreement with the underwriters in the offering in customary form consistent with the provisions of this section. 

11. Representations and Warranties of the Holder. By acceptance of this Warrant, the Holder represents and warrants to the Company
as follows: 
 (a) No Registration. The Holder understands that the Securities have not been, and
will not be, registered under the Securities Act by reason of a specific exemption from the registration provisions of the Securities Act, the availability of which depends upon, among other things, the bona fide nature of the investment
intent and the accuracy of the Holder’s representations as expressed herein or otherwise made pursuant hereto. 
 (b) Investment Intent. The Holder is acquiring the Securities for investment for its own account, not as a nominee or agent, and not with a view to, or for resale in connection with, any
distribution thereof. The Holder has no present intention of selling, granting any participation in, or otherwise distributing the Securities, nor does it have any contract, undertaking, agreement or arrangement for the same. 

(c) Investment Experience. The Holder has substantial experience in evaluating and investing in private
placement transactions of securities in companies similar to the Company, and has such knowledge and experience in financial or business matters so that it is capable of evaluating the merits and risks of its investment in the Company and protecting
its own interests. 
 (d) Speculative Nature of Investment. The Holder understands and acknowledges
that the Company has a limited financial and operating history and that its investment in the Company is highly speculative and involves substantial risks. The Holder can bear the economic risk of its investment and is able, without impairing its
financial condition, to hold the Securities for an indefinite period of time and to suffer a complete loss of its investment. 
 (e) Access to Data. The Holder has had an opportunity to ask questions of officers of the Company, which questions were answered to its satisfaction. The Holder believes that it has received
all the information that it considers necessary or appropriate for deciding whether to acquire the Securities. The Holder understands that any such discussions, as well as any information issued by the Company, were intended to describe certain
aspects of the Company’s business and prospects, but were not necessarily a thorough or exhaustive description. The Holder acknowledges that any business plans prepared by the Company have been, and continue to be, subject to change and that
any projections included in such business plans or otherwise are necessarily speculative in nature, and it can be expected that some or all of the assumptions underlying the projections will not materialize or will vary significantly from actual
results. 
 (f) Accredited Investor. The Holder is an “accredited investor” within the
meaning of Regulation D, Rule 501(a), promulgated by the Securities and Exchange Commission and agrees to submit to the Company such further assurances of such status as may be reasonably requested by the Company. 

  
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 (g) Residency. The residency of the Holder (or, in the case of
a partnership or corporation, such entity’s principal place of business) is correctly set forth on the signature page hereto. 
 (h) Restrictions on Resales. The Holder acknowledges that the Securities must be held indefinitely unless subsequently registered under the Securities Act or an exemption from such
registration is available. The Holder is aware of the provisions of Rule 144 promulgated under the Securities Act, which permit resale of shares purchased in a private placement subject to the satisfaction of certain conditions, which may
include, among other things, the availability of certain current public information about the Company; the resale occurring not less than a specified period after a party has purchased and paid for the security to be sold; the number of shares being
sold during any three-month period not exceeding specified limitations; the sale being effected through a “broker’s transaction,” a transaction directly with a “market maker” or a “riskless principal transaction”
(as those terms are defined in the Securities Act or the Securities Exchange Act of 1934, as amended, and the rules and regulations promulgated thereunder); and the filing of a Form 144 notice, if applicable. The Holder acknowledges and understands
that the Company may not be satisfying the current public information requirement of Rule 144 at the time the Holder wishes to sell the Securities and that, in such event, the Holder may be precluded from selling the Securities under
Rule 144 even if the other applicable requirements of Rule 144 have been satisfied. The Holder acknowledges that, in the event the applicable requirements of Rule 144 are not met, registration under the Securities Act or an exemption
from registration will be required for any disposition of the Securities. The Holder understands that, although Rule 144 is not exclusive, the Securities and Exchange Commission has expressed its opinion that persons proposing to sell
restricted securities received in a private offering other than in a registered offering or pursuant to Rule 144 will have a substantial burden of proof in establishing that an exemption from registration is available for such offers or sales
and that such persons and the brokers who participate in the transactions do so at their own risk. 
 (i)
No Public Market. The Holder understands and acknowledges that no public market now exists for any of the securities issued by the Company and that the Company has made no assurances that a public market will ever exist for the
Company’s securities. 
 12. Miscellaneous. 

(a) Amendments. Any provision of this Warrant may be amended, waived or modified only upon the written
consent of the Company and Holders (or their assigns) holding Notes representing a majority of the aggregate principal amount of all Notes then outstanding, including a representative of one of either the Camden Partners Entities or the Advent
International Entities (the “Majority-in-Interest”); provided, however, that no such amendment, waiver or consent shall, without the written consent of the affected Holder: (i) change the Exercise Price of
this Warrant, (ii) amend or waive Section 8(a) (Expiration of the Warrant) of this Warrant, or (iii) impose additional obligations on Holder, or limit rights granted to Holder, in a manner that does not similarly affect all
Holders. 
 (b) Waivers. No waiver of any single breach or default shall be deemed a waiver of any
other breach or default theretofore or thereafter occurring. 
 (c) Notices. All notices and other
communications required or permitted hereunder shall be in writing and shall be mailed by registered or certified mail, postage prepaid, sent by facsimile or electronic mail (if to the Holder) or otherwise delivered by hand, messenger or courier
service addressed: 
 (i) if to the Holder, to the Holder at the Holder’s address, facsimile number or
electronic mail address as shown in the Company’s records, as may be updated in accordance with the provisions hereof, or until any such Holder so furnishes an address, facsimile number or electronic mail

  
 - 10 -

 
address to the Company, then to and at the address, facsimile number or electronic mail address of the last holder of this Warrant for which the Company has contact information in its records; or

 (ii) if to the Company, to the attention of the Chief Executive Officer or Chief Financial Officer of the
Company at the Company’s address as shown on the signature page hereto, or at such other address as the Company shall have furnished to the Holder, with a copy to Wilson Sonsini Goodrich & Rosati, Professional Corporation, 650 Page
Mill Road, Palo Alto, CA 94304 Attn: David J. Segre. 
 Each such notice or other communication shall for
all purposes of this Warrant be treated as effective or having been given (i) if delivered by hand, messenger or courier service, when delivered, or (ii) if sent by mail, at the earlier of its receipt or 72 hours after the same has
been deposited in a regularly maintained receptacle for the deposit of the United States mail, addressed and mailed as aforesaid, or (iii) if sent by facsimile, upon confirmation of facsimile transfer or, if sent by electronic mail, upon
confirmation of delivery when directed to the relevant electronic mail address. In the event of any conflict between the Company’s books and records and this Warrant or any notice delivered hereunder, the Company’s books and records will
control absent fraud or error. 
 (d) Governing Law. This Warrant and all actions arising out of or
in connection with this Warrant shall be governed by and construed in accordance with the laws of the State of Delaware, without regard to the conflicts of law provisions of the State of Delaware, or of any other state. 

(e) Dispute Resolution. All disputes, claims, or controversies arising out of or relating to this Note that
are not resolved by mutual agreement shall be resolved solely and exclusively by binding arbitration to be conducted by the arbitration and mediation organization JAMS (“JAMS”) or its successor in accordance with Section 7(c)
of the Purchase Agreement. 
 (f) Titles and Subtitles. The titles and subtitles used in this
Warrant are used for convenience only and are not to be considered in construing or interpreting this Warrant. All references in this Warrant to sections, paragraphs and exhibits shall, unless otherwise provided, refer to sections and paragraphs
hereof and exhibits attached hereto. 
 (g) Severability. If any provision of this Warrant becomes
or is declared by a court of competent jurisdiction to be illegal, unenforceable or void, portions of such provision, or such provision in its entirety, to the extent necessary, shall be severed from this Warrant, and such illegal, unenforceable or
void provision shall be replaced with a valid and enforceable provision that will achieve, to the extent possible, the same economic, business and other purposes of the illegal, unenforceable or void provision. The balance of this Warrant shall be
enforceable in accordance with its terms. 
 (h) California Corporate Securities Law. THE SALE OF
THE SECURITIES THAT ARE THE SUBJECT OF THIS WARRANT HAS NOT BEEN QUALIFIED WITH THE COMMISSIONER OF CORPORATIONS OF THE STATE OF CALIFORNIA AND THE ISSUANCE OF SUCH SECURITIES OR THE PAYMENT OR RECEIPT OF ANY PART OF THE CONSIDERATION THEREFOR PRIOR
TO SUCH QUALIFICATION IS UNLAWFUL, UNLESS THE SALE OF SECURITIES IS EXEMPT FROM QUALIFICATION BY SECTION 25100, 25102, OR 25105 OF THE CALIFORNIA CORPORATIONS CODE. THE RIGHTS OF ALL PARTIES TO THIS WARRANT ARE EXPRESSLY CONDITIONED UPON THE
QUALIFICATION BEING OBTAINED, UNLESS THE SALE IS SO EXEMPT. 
 (i) Saturdays, Sundays and Holidays.
If the last or appointed day for the taking of any action or the expiration of any right required or granted herein shall be a Saturday, Sunday or U.S. federal 

  
 - 11 -

 
holiday, then such action may be taken or such right may be exercised on the next succeeding day that is not a Saturday, Sunday or U.S. federal holiday. 

(j) Rights and Obligations Survive Exercise of the Warrant. Except as otherwise provided herein, the rights
and obligations of the Company and the Holder under this Warrant shall survive exercise of this Warrant. 
 (k)
Entire Agreement. Except as expressly set forth herein, this Warrant (including the exhibits attached hereto and the other Transaction Documents) constitutes the entire agreement and understanding of the Company and the Holder with
respect to the subject matter hereof and supersede all prior agreements and understandings relating to the subject matter hereof. 
 (signature page follows) 

  
 - 12 -

 The Company and the Holder sign this Warrant as of the date stated on the first page.

  

			
	WAGEWORKS, INC.
		
	By:	 	 
		
	Name:	 	 
		
	Title:	 	 
		
	Address:	 	
	
	 WageWorks, Inc.

1100 Park Place, 4th Floor

San Mateo, CA 94403

 AGREED AND ACKNOWLEDGED, 
 [ — ] 

			
		
	By:	 	 
		
	Name:	 	 
		
	Title:	 	 

 Address: 

Fax number: 
 Email address: 

(Signature Page to Warrant to Purchase Shares of Series E-1 Preferred Stock of WageWorks, Inc.) 

  

 EXHIBIT A 

NOTICE OF EXERCISE 

TO: WAGEWORKS, INC. (the “Company”) 
 Attention: President 
  

	(1)	Exercise. The undersigned elects to purchase the following pursuant to the terms of the attached warrant: 

Number of shares: 
                                         
                                         
                                         
                              

Type of
security:                                       
                                         
                                         
                                    

 

	(2)	Method of Exercise. The undersigned elects to exercise the attached warrant pursuant to: 

 

	 	 ̈	A cash payment or cancellation of indebtedness, and tenders herewith payment of the purchase price for such shares in full, together with all applicable transfer taxes,
if any. 

  

	 	 ̈	The net issue exercise provisions of Section 2(b) of the attached warrant. 

 

	(3)	Conditional Exercise. Is this a conditional exercise pursuant to Section 2(e): 

 

	 	 ̈	Yes                    
 ̈       No 

 If
“Yes,” indicate the applicable condition: 
  

	
	 

  

	(4)	Stock Certificate. Please issue a certificate or certificates representing the shares in the name of: 

 

					
	  ̈
	  	The undersigned	  	
			
	  ̈
	  	Other—Name:	  	 
			
		  	Address:        	  	 
			
		  		  	 

  

	(5)	Unexercised Portion of the Warrant. Please issue a new warrant for the unexercised portion of the attached warrant in the name of: 

 

					
	  ̈
	  	The undersigned	  	
			
	  ̈
	  	Other—Name:	  	 
			
		  	Address:        	  	 
			
		  		  	 
			
	  ̈
	  	Not applicable	  	

  
 A-1

	(6)	Investment Intent. The undersigned represents and warrants that the aforesaid shares are being acquired for investment for its own account, not as a nominee or
agent, and not with a view to, or for resale in connection with, the distribution thereof, and that the undersigned has no present intention of selling, granting any participation in, or otherwise distributing the shares, nor does it have any
contract, undertaking, agreement or arrangement for the same, and all representations and warranties of the undersigned set forth in Section 11 of the attached warrant are true and correct as of the date hereof. 

 

	(7)	Investment Representation Statement and Market Stand-Off Agreement. The undersigned has executed, and delivers herewith, an Investment Representation Statement
and Market Stand-Off Agreement in a form substantially similar to the form attached to the warrant as Exhibit A-1. 

  

	(8)	Consent to Receipt of Electronic Notice. Subject to the limitations set forth in Delaware General Corporation Law §232(e), the undersigned consents to the
delivery of any notice to stockholders given by the Company under the Delaware General Corporation Law or the Company’s certificate of incorporation or bylaws by (i) facsimile telecommunication to the facsimile number provided below (or to
any other facsimile number for the undersigned in the Company’s records), (ii) electronic mail to the electronic mail address provided below (or to any other electronic mail address for the undersigned in the Company’s records),
(iii) posting on an electronic network together with separate notice to the undersigned of such specific posting or (iv) any other form of electronic transmission (as defined in the Delaware General Corporation Law) directed to the
undersigned. This consent may be revoked by the undersigned by written notice to the Company and may be deemed revoked in the circumstances specified in Delaware General Corporation Law §232. 

 

	
	  
	(Print name of the warrant holder)
	
	 
	(Signature)
	
	 
	(Name and title of signatory, if applicable)
	
	 
	(Date)
	
	 
	(Fax number)
	
	 
	(Email address)

(Signature page to the Notice of Exercise) 

  
 A-2

 EXHIBIT A-l 

INVESTMENT REPRESENTATION STATEMENT 
 AND 
 MARKET STAND-OFF AGREEMENT 

 

					
	INVESTOR:	 	 	 	 
			
	COMPANY:	 	WAGEWORKS, INC.	 	
		
	SECURITIES:	 	THE AMENDED AND RESTATED WARRANT ISSUED ON DECEMBER 28, 2009 AND AMENDED AND RESTATED AS OF JULY 30, 2010 (THE “WARRANT”) AND THE
SECURITIES ISSUED OR ISSUABLE UPON EXERCISE THEREOF (INCLUDING UPON SUBSEQUENT CONVERSION OF THOSE SECURITIES)
			
	DATE:	 	 	 	

 In connection with the purchase or acquisition of the above-listed Securities, the undersigned
Investor represents and warrants to, and agrees with, the Company as follows: 
 1. No Registration. The Investor
understands that the Securities have not been, and will not be, registered under the Securities Act of 1933, as amended (the “Securities Act”), by reason of a specific exemption from the registration provisions of the
Securities Act, the availability of which depends upon, among other things, the bona fide nature of the investment intent and the accuracy of the Investor’s representations as expressed herein or otherwise made pursuant hereto.

 2. Investment Intent. The Investor is acquiring the Securities for investment for its own account, not as a nominee or
agent, and not with a view to, or for resale in connection with, any distribution thereof. The Investor has no present intention of selling, granting any participation in, or otherwise distributing the Securities, nor does it have any contract,
undertaking, agreement or arrangement for the same. 
 3. Investment Experience. The Investor has substantial experience
in evaluating and investing in private placement transactions of securities in companies similar to the Company, and has such knowledge and experience in financial or business matters so that it is capable of evaluating the merits and risks of its
investment in the Company and protecting its own interests. 
 4. Speculative Nature of Investment. The Investor
understands and acknowledges that the Company has a limited financial and operating history and that its investment in the Company is highly speculative and involves substantial risks. The Investor can bear the economic risk of its investment and is
able, without impairing its financial condition, to hold the Securities for an indefinite period of time and to suffer a complete loss of its investment. 
 5. Access to Data. The Investor has had an opportunity to ask questions of officers of the Company, which questions were answered to its satisfaction. The Investor believes that it has received all
the information that it considers necessary or appropriate for deciding whether to acquire the Securities. The Investor understands that any such discussions, as well as any information issued by the Company, were intended to describe certain
aspects of the Company’s business and prospects, but were not necessarily a 

  
 A-1-1

 
thorough or exhaustive description. The Investor acknowledges that any business plans prepared by the Company have been, and continue to be, subject to change and that any projections included in
such business plans or otherwise are necessarily speculative in nature, and it can be expected that some or all of the assumptions underlying the projections will not materialize or will vary significantly from actual results. 

6. Accredited Investor. The Investor is an “accredited investor” within the meaning of Regulation D,
Rule 501(a), promulgated by the Securities and Exchange Commission and agrees to submit to the Company such further assurances of such status as may be reasonably requested by the Company. 

7. Residency. The residency of the Investor (or, in the case of a partnership or corporation, such entity’s principal place
of business) is correctly set forth on the signature page hereto. 
 8. Restrictions on Resales. The Investor
acknowledges that the Securities must be held indefinitely unless subsequently registered under the Securities Act or an exemption from such registration is available. The Investor is aware of the provisions of Rule 144 promulgated under the
Securities Act, which permit resale of shares purchased in a private placement subject to the satisfaction of certain conditions, which may include, among other things, the availability of certain current public information about the Company; the
resale occurring not less than a specified period after a party has purchased and paid for the security to be sold; the number of shares being sold during any three-month period not exceeding specified limitations; the sale being effected through a
“broker’s transaction,” a transaction directly with a “market maker” or a “riskless principal transaction” (as those terms are defined in the Securities Act or the Securities Exchange Act of 1934, as amended, and
the rules and regulations promulgated thereunder); and the filing of a Form 144 notice, if applicable. The Investor acknowledges and understands that the Company may not be satisfying the current public information requirement of Rule 144 at
the time the Investor wishes to sell the Securities and that, in such event, the Investor may be precluded from selling the Securities under Rule 144 even if the other applicable requirements of Rule 144 have been satisfied. The Investor
understands and acknowledges that, in the event the applicable requirements of Rule 144 are not met, registration under the Securities Act or an exemption from registration will be required for any disposition of the Securities. The Investor
understands that, although Rule 144 is not exclusive, the Securities and Exchange Commission has expressed its opinion that persons proposing to sell restricted securities received in a private offering other than in a registered offering or
pursuant to Rule 144 will have a substantial burden of proof in establishing that an exemption from registration is available for those offers or sales and that those persons and the brokers who participate in the transactions do so at their
own risk. 
 9. No Public Market. The Holder understands and acknowledges that no public market now exists for any of the
securities issued by the Company and that the Company has made no assurances that a public market will ever exist for the Company’s securities. 
 10. Market Stand-off. The Investor agrees that the Investor shall not sell or otherwise transfer, make any short sale of, grant any option for the purchase of, or enter into any hedging or similar
transaction with the same economic effect as a sale, of any common stock (or other securities) of the Company held by the Investor (other than those included in the registration) during the one hundred eighty (180) day period following the
effective date of the registration statement for the Company’s initial public offering filed under the Securities Act (or such other period as may be requested by the Company or an underwriter to accommodate regulatory restrictions on
(i) the publication or other distribution of research reports and (ii) analyst recommendations and opinions, including, but not limited to, the restrictions contained in NASD Rule 2711(f)(4) or NYSE Rule 472(f)(4), or any
successor provisions or amendments thereto). The obligations described in this section shall not apply to a registration relating solely to employee benefit plans on Form S-l or Form S-8 or similar forms that may be promulgated in the future, or a
registration relating solely to a transaction on Form S-4 or similar forms that may be promulgated in the future. The Company may impose stop-transfer instructions and may stamp each certificate with a legend with respect to the shares

  
 A-1-2

 
of common stock (or other securities) subject to the foregoing restriction until the end of such one hundred eighty (180) day (or other) period. The Investor agrees to execute a market
stand-off agreement with the relevant underwriters in customary form consistent with the provisions of this section. 

(signature page follows) 

  
 A-1-3

 The Investor is signing this Investment Representation Statement and Market Stand-Off
Agreement on the date first written above. 
  

	
	INVESTOR
	
	  
	(Print name of the investor)
	
	  
	(Signature)
	
	  
	(Name and title of signatory, if applicable)
	
	  
	(Street address)
	
	  
	(City, state and ZIP)

  
 A-1-4

 EXHIBIT B 
 ASSIGNMENT FORM 
  

					
	 ASSIGNOR:
	 	 
		
	COMPANY:	 	WAGEWORKS, INC.
		
	WARRANT:	 	THE AMENDED AND RESTATED WARRANT TO PURCHASE SHARES OF SERIES E-1 PREFERRED STOCK ISSUED ON DECEMBER 28, 2009 AND AMENDED AND RESTATED AS OF JULY 30, 2010
(THE “WARRANT”)
			
	DATE:	 	 	 	

  

	(1)	Assignment. The undersigned registered holder of the Warrant (“Assignor”) assigns and transfers to the assignee named below
(“Assignee”) all of the rights of Assignor under the Warrant, with respect to the number of shares set forth below: 

 

			
	Name of Assignee:	  	 
		
	Address of Assignee:	  	 
		
		  	 

 Number of Shares Assigned:
                                         
                                         
                                         
                          
 and does irrevocably constitute and appoint                      as attorney to make such
transfer on the books of WageWorks, Inc., maintained for the purpose, with full power of substitution in the premises. 
  

	(1)	Obligations of Assignee. Assignee agrees to take and hold the Warrant and any shares of stock to be issued upon exercise of the rights thereunder (and any shares
issuable upon conversion thereof) (the “Securities”) subject to, and to be bound by, the terms and conditions set forth in the Warrant to the same extent as if Assignee were the original holder thereof.

  

	(2)	Investment Intent. Assignee represents and warrants that the Securities are being acquired for investment for its own account, not as a nominee or agent, and not
with a view to, or for resale in connection with, the distribution thereof, and that Assignee has no present intention of selling, granting any participation in, or otherwise distributing the shares, nor does it have any contract, undertaking,
agreement or arrangement for the same, and all representations and warranties set forth in Section 11 of the Warrant are true and correct as to Assignee as of the date hereof. 

 

	(3)	Investment Representation Statement and Market Stand-Off Agreement. Assignee has executed, and delivers herewith, an Investment Representation Statement and
Market Stand-Off Agreement in a form substantially similar to the form attached to the Warrant as Exhibit A-1. 

  
 - 1 -

 Assignor and Assignee are signing this Assignment Form on the date first set forth above.

  

					
	ASSIGNOR	 		 	ASSIGNEE
			
	  	 		 	  
	(Print name of Assignor)	 		 	(Print name of Assignee)
			
	  	 		 	  
	(Signature of Assignor)	 		 	(Signature of Assignee)
			
	  	 		 	  
	(Print name of signatory, if applicable)	 		 	(Print name of signatory, if applicable)
			
	  	 		 	  
	(Print title of signatory, if applicable)	 		 	(Print title of signatory, if applicable)
			
	Address:	 		 	Address:
			
	  	 		 	  
			
	  	 		 	  

  
 - 2 -Warrant Agreement to Purchase Shares of Series C Preferred Stock

 Exhibit 4.7 
 THESE SECURITIES HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933 AS AMENDED, OR ANY STATE SECURITIES LAWS. THEY MAY NOT BE SOLD, OFFERED FOR SALE, PLEDGED, OR HYPOTHECATED IN THE ABSENCE OF AN
EFFECTIVE REGISTRATION STATEMENT RELATED THERETO OR AN OPINION OF COUNSEL (WHICH MAY BE COMPANY COUNSEL) REASONABLY SATISFACTORY TO THE COMPANY THAT SUCH REGISTRATION IS NOT REQUIRED UNDER THE SECURITIES ACT OF 1933 ACT AS AMENDED, OR ANY APPLICABLE
STATE SECURITIES LAWS. 
 WARRANT AGREEMENT 
 To Purchase Shares of the Series C Preferred Stock of 
 WageWorks, Inc.

 Dated as of May 23, 2005 (the “Effective Date”) 

WHEREAS, WageWorks, Inc., a Delaware corporation (the “Company”), has entered into a Senior Loan and Security Agreement
of even date herewith (the “Loan Agreement”) with Hercules Technology Growth Capital, Inc., a Maryland corporation (the “Warrantholder”); 
 WHEREAS, the Company desires to grant to Warrantholder, in consideration for, among other things, the financial accommodations provided for in the Loan Agreement, the right to purchase shares of its
Series C Preferred Stock pursuant to this Warrant Agreement (the “Agreement”); 
 NOW, THEREFORE, in
consideration of the Warrantholder executing and delivering the Loan Agreement and providing the financial accommodations contemplated therein, and in consideration of the mutual covenants and agreements contained herein, the Company and
Warrantholder agree as follows: 
 SECTION 1. GRANT OF THE RIGHT TO PURCHASE PREFERRED STOCK 

For value received, the Company hereby grants to the Warrantholder, and the Warrantholder is entitled, upon the terms and subject to the
conditions hereinafter set forth, to subscribe for and purchase, from the Company, 423,529 fully paid and non-assessable shares of the Preferred Stock (as defined below) at a purchase price of $4.25 per share (the “Exercise Price”).
The number and Exercise Price of such shares are subject to adjustment as provided in Section 8. As used herein, the following terms shall have the following meanings: 
 “Act” means the Securities Exchange Act of 1933, as amended. 

“Charter” means the Company’s Articles of Incorporation, Certificate of Incorporation or other constitutional
document, as may be amended from time to time. 
 “Common Stock” means the Company’s common stock;

 “Initial Public Offering” means the initial underwritten public offering of
the Company’s Common Stock pursuant to a registration statement under the Act, which public offering has been declared effective by the Securities and Exchange Commission (“SEC”); 

“Merger Event” means a merger or consolidation involving the Company in which the Company is not the surviving entity,
or in which the outstanding shares of the Company’s capital stock are otherwise converted into or exchanged for shares of capital of another entity. 
 “Preferred Stock” means the Series C Preferred Stock of the Company and any other stock into or for which the Series C Preferred Stock may be converted or exchanged, and upon
and after the occurrence of an event which results in the automatic or voluntary conversion, redemption or retirement of all (but not less than all) of the outstanding shares of such Preferred Stock, including, without limitation, the consummation
of an Initial Public Offering of the Common Stock in which such a conversion occurs, then from and after the date upon which such outstanding shares are so converted, redeemed or retired, “Preferred Stock” shall mean such Common Stock; and

 “Purchase Price” means, with respect to any exercise of this Agreement, an amount equal to the Exercise
Price as of the relevant time multiplied by the number of shares of Preferred Stock requested to be exercised under this Agreement pursuant to such exercise. 
 SECTION 2. TERM OF THE AGREEMENT. 
 Except as otherwise provided for herein,
the term of this Agreement and the right to purchase Preferred Stock as granted herein (the “Warrant”) shall commence on the Effective Date and shall be exercisable for a period ending upon the earliest to occur of (i) ten
(10) years from the Effective Date; or (ii) eighteen (18) months after the Initial Public Offering. 
 SECTION 3. EXERCISE OF
THE PURCHASE RIGHTS. 
 (a) Exercise. The purchase rights set forth in this Agreement are exercisable
by the Warrantholder, in whole or in part, at any time, or from time to time, prior to the expiration of the term set forth in Section 2, by surrendering this Agreement and tendering to the Company at its principal office a notice of exercise
in the form attached hereto as Exhibit I (the “Notice of Exercise”), duly completed and executed. Promptly upon such surrender and receipt of the Notice of Exercise and the payment of the Purchase Price in accordance with the
terms set forth below, and in no event later than five (5) business days thereafter, the Company shall issue to the Warrantholder a certificate for the number of shares of Preferred Stock purchased and shall execute the acknowledgment of
exercise in the form attached hereto as Exhibit II (the “Acknowledgment of Exercise”) indicating the number of shares which remain subject to future purchases, if any. 

The Purchase Price may be paid at the Warrantholder’s election either (i) by cash or check, or (ii) by surrender of all or
a portion of the Warrant for shares of Preferred Stock to be exercised under this Agreement and, if applicable, an amended Agreement representing the remaining number of shares purchasable hereunder, as determined below (“Net
Issuance”). If the Warrantholder elects the Net Issuance method, the Company will issue Preferred Stock in accordance with the following formula: 

  
 2. 

											
		 	X = Y(A–B)	 		 		 		  	
		 	A	 		 		 		  	

  

			
	Where: X = the number of shares of Preferred Stock to be issued to the Warrantholder.
		
	 Y =
	 	the number of shares of Preferred Stock requested to be exercised under this Agreement.
		
	A =	 	the fair market value of one (1) share of Preferred Stock at the time of issuance of such shares of Preferred Stock.
		
	B =	 	the Exercise Price.

 For purposes of the
above calculation, current fair market value of Preferred Stock shall mean with respect to each share of Preferred Stock: 
 (i) if the exercise is in connection with an Initial Public Offering, and if the Company’s Registration Statement relating to such Initial Public Offering has been declared effective by the SEC, then
the fair market value per share shall be the product of (x) the initial “Price to Public” of the Common Stock specified in the final prospectus with respect to the offering and (y) the number of shares of Common Stock into which
each share of Preferred Stock is convertible at the time of such exercise; 
 (ii) if the exercise is after, and
not in connection with an Initial Public Offering, and: 
 (A) if the Common Stock is traded on a securities
exchange, the fair market value shall be deemed to be the product of (x) the average of the closing prices over a five (5) trading day period ending three days before the day the current fair market value of the securities is being
determined and (y) the number of shares of Common Stock into which each share of Preferred Stock is convertible at the time of such exercise; or 
 (B) if the Common Stock is actively traded over-the-counter, the fair market value shall be deemed to be the product of (x) the average of the closing bid and asked prices quoted on the NASDAQ system
(or similar system) over the five (5) trading day period ending three days before the day the current fair market value of the securities is being determined and (y) the number of shares of Common Stock into which each share of Preferred
Stock is convertible at the time of such exercise; 
 (iii) if at any time the Common Stock is not listed on any
securities exchange or quoted in the NASDAQ National Market or the over-the-counter market, the current fair market value of Preferred Stock shall be the product of (x) the highest price per share which the Company could obtain from a willing
buyer (not a current employee or director) for shares of Common Stock sold by the Company, from authorized but unissued shares, as determined in good faith by its Board of Directors and (y) the number of shares of Common Stock into which each
share of Preferred Stock is convertible at the time of such exercise, unless the Company shall become subject to a Merger Event pursuant to which the Company is not the surviving party, in which case the fair market value of Preferred Stock shall he
deemed to be the per share 

  
 3. 

 
value received by the holders of the Company’s Preferred Stock on a common equivalent basis pursuant to such Merger Event. 

Upon partial exercise by either cash or Net Issuance, the Company shall promptly issue an amended Agreement representing the remaining
number of shares purchasable hereunder. All other terms and conditions of such amended Agreement shall be identical to those contained herein, including, but not limited to the Effective Date hereof. 

(b) Exercise Prior to Expiration. To the extent this Agreement is not previously exercised as to all Preferred
Stock subject hereto, and if the fair market value of one share of the Preferred Stock is greater than the Exercise Price then in effect, this Agreement shall be deemed automatically exercised pursuant to Net Issuance under Section 3(a) (even
if not surrendered) immediately before its expiration. For purposes of such automatic exercise, the fair market value of one share of the Preferred Stock upon such expiration shall be determined pursuant to Section 3(a). To the extent this
Agreement or any portion thereof is deemed automatically exercised pursuant to this Section 3(b), the Company agrees to promptly notify the Warrantholder of the number of shares of Preferred Stock, if any, the Warrantholder is to receive by
reason of such automatic exercise. 
 SECTION 4. RESERVATION OF SHARES. 

During the term of this Agreement, the Company will at all times have authorized and reserved a sufficient number of shares of its
Preferred Stock to provide for the exercise of the rights to purchase Preferred Stock as provided for herein, and shall have authorized and reserved a sufficient number of shares of its Common Stock to provide for the conversion of the Preferred
Shares available hereunder. Warrantholder acknowledges that upon issuance hereof an amendment to the Charter increasing the authorized shares of Series C Preferred Stock has not been filed as of the Effective Date. Company will file such
amendment within 30 days of the Effective Date. 
 SECTION 5. NO FRACTIONAL SHARES OR SCRIP. 

No fractional shares or scrip representing fractional shares shall be issued upon the exercise of this Agreement, but in lieu of such
fractional shares the Company shall make a cash payment therefor upon the basis of the Exercise Price then in effect. 
 SECTION 6. NO RIGHTS
AS SHAREHOLDER 
 This Agreement does not entitle the Warrantholder to any voting rights or other rights as a shareholder of
the Company prior to the exercise of this Agreement. 
 SECTION 7. WARRANTHOLDER REGISTRY. 

The Company shall maintain a registry showing the name and address of the registered holder of this Agreement. Warrantholder’s
initial address, for purposes of such registry, is set forth below Warrantholder’s signature on this Agreement. Warrantholder may change such address by giving written notice of such changed address to the Company. 

  
 4. 

 SECTION 8. ADJUSTMENT RIGHTS. 

The Exercise Price and the number of shares of Preferred Stock purchasable hereunder are subject to adjustment, as follows: 

(a) Merger Event. If at any time there shall be Merger Event, then, as a part of such Merger Event, lawful
provision shall be made so that the Warrantholder shall thereafter be entitled to receive, upon exercise of this Agreement, the number of shares of preferred stock or other securities or property of the successor corporation resulting from such
Merger Event that would have been issuable if Warrantholder had exercised this Agreement immediately prior to the Merger Event. In any such case, appropriate adjustment (as determined in good faith by the Company’s Board of Directors) shall be
made in the application of the provisions of this Agreement with respect to the rights and interests of the Warrantholder after the Merger Event to the end that the provisions of this Agreement (including adjustments of the Exercise Price and number
of shares of Preferred Stock purchasable) shall be applicable in their entirety, and to the greatest extent practicable. Without limiting the foregoing, in connection with any Merger Event, upon the closing thereof, the successor or surviving entity
shall assume the obligations of this Agreement. 
 (b) Reclassification of Shares. Except as set forth in
Section 8, if the Company at any time shall, by combination, reclassification, exchange or subdivision of securities or otherwise, change any of the securities as to which purchase rights under this Agreement exist into the same or a different
number of securities of any other class or classes, this Agreement shall thereafter represent the right to acquire such number and kind of securities as would have been issuable as the result of such change with respect to the securities which were
subject to the purchase rights under this Agreement immediately prior to such combination, reclassification, exchange, subdivision or other change. 
 (c) Subdivision or Combination of Shares. If the Company at any time shall combine or subdivide its Preferred Stock, (i) in the case of a subdivision, the Exercise Price shall be
proportionately decreased, and the number of shares of Preferred Stock issuable upon exercise of this Agreement shall be proportionately increased, or (ii) in the case of a combination, the Exercise Price shall be proportionately increased, and
the number of shares of Preferred Stock issuable upon the exercise of this Agreement shall be proportionately decreased. 
 (d) Stock Dividends. If the Company at any time while this Warrant is outstanding and unexpired shall: 
 (i) pay a dividend with respect to the Preferred Stock payable in Preferred Stock, then the Exercise Price shall be adjusted, from and after the date of determination of shareholders entitled to receive
such dividend or distribution, to that price determined by multiplying the Exercise Price in effect immediately prior to such date of determination by a fraction (A) the numerator of which shall be the total number of shares of Preferred Stock
outstanding immediately prior to such dividend or distribution, and (B) the denominator of which shall be the total number of shares of Preferred Stock outstanding immediately after such dividend or distribution; or 

  
 5. 

 (ii) make any other distribution with respect to Preferred Stock (or stock
into which the Preferred Stock is convertible), except any distribution specifically provided for in any other clause of this Section 8, then, in each such case, provision shall be made by the Company such that the Warrantholder shall receive
upon exercise or conversion of this Warrant a proportionate share of any such distribution as though it were the holder of the Preferred Stock (or other stock for which the Preferred Stock is convertible) as of the record date fixed for the
determination of the shareholders of the Company entitled to receive such distribution. 
 (e) Antidilution
Rights. Additional antidilution rights applicable to the Preferred Stock purchasable hereunder are as set forth in the Company’s Charter and shall be applicable with respect to the Preferred Stock issuable hereunder. No restatement,
amendment, modification or waiver of the Charter shall impair or reduce the antidilution rights applicable as of the date hereof to the Preferred Stock issuable upon exercise of this Warrant in a manner that treats the Warrantholder in a more
adverse and substantially dissimilar manner to other holders of the same series of the company’s Preferred Stock. For the avoidance of doubt, there shall be no duplicate anti-dilution adjustment pursuant to this subsection (e), the forgoing
subsection (d) and the Company’s Charter. 
 (f) Notice of Adjustments. If (i) the Company
shall declare any dividend or distribution upon its Preferred Stock, whether in stock, cash, property or other securities (other than any stock split or stock dividend for which adjustment is made pursuant to Section 8(c) above); (ii) the
Company shall offer for subscription prorata to the holders of Preferred Stock or other convertible stock any additional shares of stock of any class or other rights; (iii) there shall be any Merger Event; (iv) there shall be an Initial
Public Offering; (v) the Company shall sell, lease, license or otherwise transfer all or substantially all of its assets; or (vi) there shall be any voluntary dissolution, liquidation or winding up of the Company; then, in connection with
each such event, the Company shall send to the Warrantholder: (A) at least ten (10) business days’ prior written notice of the date on which the books of the Company shall close or a record shall be taken for such dividend,
distribution, subscription rights (specifying the date on which the holders of Preferred Stock shall be entitled thereto) or for determining rights to vote in respect of such Merger Event, dissolution, liquidation or winding up; (B) in the case
of any such Merger Event, sale, lease, license or other transfer of all or substantially all assets, dissolution, liquidation or winding up, at least ten (10) business days’ prior written notice of the anticipated date when the same shall
take place (and specifying the anticipated date on which the holders of Preferred Stock shall be entitled to exchange their Preferred Stock for securities or other property deliverable upon such Merger Event, dissolution, liquidation or winding up);
and (C) in the case of an Initial Public Offering, the Company shall give the Warrantholder at least ten (10) business days’ written notice prior to the anticipated effective date thereof. 

Each such written notice shall set forth, in reasonable detail to the extent then available, (i) the event requiring the notice, and
(ii) if any adjustment is required to be made, (A) the amount of such adjustment, (B) the method by which such adjustment was calculated, (C) the adjusted Exercise Price (if the Exercise Price has been adjusted), and (D) the
number of shares subject to purchase hereunder after giving effect to such adjustment, and shall be given by first class mail, postage prepaid, or by reputable overnight courier with all charges prepaid, addressed to the Warrantholder at the address
for Warrantholder set forth in the registry referred to in Section 7. 

  
 6. 

 SECTION 9. REPRESENTATIONS, WARRANTIES AND COVENANTS OF THE COMPANY. 

The Company represents and warrants to the Warrantholder as of the Effective Date as follows: 

(a) Reservation of Preferred Stock. Subject to the filing of an amended Charter with respect to the increase in the
authorized shares of Series C Preferred Stock, the Preferred Stock issuable upon exercise of the Warrantholder’s rights has been duly and validly reserved and, when issued in accordance with the provisions of this Agreement, will be
validly issued, filly paid and non-assessable, and will be free of any taxes, liens, charges or encumbrances of any nature whatsoever; provided, that the Preferred Stock issuable pursuant to this Agreement may be subject to restrictions on transfer
under state and/or federal securities laws and is subject to the terms of the Charter. The Company has made available to the Warrantholder true, correct and complete copies of its Charter and current bylaws. The issuance of certificates for shares
of Preferred Stock upon exercise of this Agreement shall be made without charge to the Warrantholder for any issuance tax in respect thereof or other cost incurred by the Company in connection with such exercise and the related issuance of shares of
Preferred Stock; provided, that the Company shall not be required to pay any tax which may be payable in respect of any transfer and the issuance and delivery of any certificate in a name other than that of the Warrantholder. 

(b) Due Authority. The execution and delivery by the Company of this Agreement and the performance of all
obligations of the Company hereunder, including the issuance to Warrantholder of the right to acquire the shares of Preferred Stock and the Common Stock into which it may be converted, have been duly authorized by all necessary corporate action on
the part of the Company. This Agreement: (1) is not inconsistent with the Company’s Charter or current bylaws; (2) does not contravene any law or governmental rule, regulation or order applicable to it; and (3) does not and will
not contravene any provision of, or constitute a default under, any indenture, mortgage, contract or other instrument to which it is a party or by which it is bound. This Agreement constitutes a legal, valid and binding agreement of the Company,
enforceable in accordance with its terms subject to applicable bankruptcy, insolvency, reorganization or other similar laws generally affecting the enforcement of the rights of creditors and subject to general principles of equity. 

(c) Consents and Approvals. No consent or approval of, giving of notice to, registration with, or taking of any
other action in respect of any state, federal or other governmental authority or agency is required with respect to the execution, delivery and performance by the Company of its obligations under this Agreement, except for the filing of notices
pursuant to Regulation D under the Act and any filing required by applicable state securities law, which filings will be effective by the time required thereby. 

(d) Issued Securities. All issued and outstanding shares of Common Stock and Preferred Stock of the Company have
been duly authorized and validly issued and are fully paid and nonassessable. All outstanding shares of Common Stock and Preferred Stock were issued in material compliance with all federal and state securities laws. In addition, as of the date
immediately preceding the date of this Agreement: 

  
 7. 

 (i) The authorized capital of the Company consists of (A) 34,401,854
shares of Common Stock, of which 1,795,750 shares are issued and outstanding, and (B) 23,541,743 shares of preferred stock, of which (i) 50,000 shares have been designated Series A Preferred Stock, all of which are issued and
outstanding, and are convertible into 85,208 shares of Common Stock, (ii) 1,725,796 shares have been designated Series A-1 Preferred Stock, all of which are issued and outstanding, and are convertible into 5,075,871 shares of Common Stock,
(iii) 1,013,395 shares have been designated Series A-2 Preferred Stock, of which 998,668 are issued and outstanding, and are convertible into 1,701,887 shares of Common Stock, (iv) 14,870,179 shares have been designated Series B
Preferred Stock, all of which are issued and outstanding, and are convertible into 14,870,179 shares of Common Stock and (v) 5,882,373 shares have been designated Series C Preferred Stock, of which 5,882,353 are issued and outstanding, and
are convertible into 5,882,353 shares of Common Stock. 
 (ii) The Company has reserved 4,665,488 shares of
Common Stock for issuance under its Stock Option Plan(s), under which 4,256,901 options are outstanding. Except for rights of first refusal and conversion rights in favor of preferred stockholders, outstanding warrants to purchase 10,208 shares of
the Company’s Common Stock and outstanding warrants to purchase 14,727 shares of the Company’s Series A-2 Preferred Stock, there are no other options, warrants, conversion privileges or other rights presently outstanding to purchase
or otherwise acquire any authorized but unissued shares of the Company’s capital stock. 
 (e) In accordance
with the Company’s Charter, no shareholder of the Company (other than preferred stockholders) has preemptive rights to purchase new issuances of the Company’s capital stock. 

(f) Insurance. The Company has in full force and effect directors’ and officers’ liability insurance
policies, with extended coverage, insuring against such losses and risks, and in such amounts, as are customary for corporations engaged in a similar business and similarly situated and as otherwise may be required pursuant to the terms of any other
contract or agreement. 
 (g) Exempt Transaction. Subject to the accuracy of the Warrantholder’s
representations in Section 10, the issuance of the Preferred Stock upon exercise of this Agreement, and the issuance of the Common Stock upon conversion of the Preferred Stock, will each constitute a transaction exempt from (i) the
registration requirements of Section 5 of the Act, in reliance upon Section 4(2) thereof, and (ii) the qualification requirements of the applicable state securities laws. 

(h) Compliance with Rule 144. If the Warrantholder proposes to sell Preferred Stock issuable upon the exercise
of this Agreement, or the Common Stock into which it is convertible, in compliance with Rule 144 promulgated by the SEC, then, upon Warrantholder’s written request to the Company, the Company shall furnish to the Warrantholder, within ten
days after receipt of such request, a written statement confirming the Company’s compliance with the filing requirements of the SEC as set forth in such Rule, as such Rule may be amended from time to time. 

  
 8. 

 SECTION 10. REPRESENTATIONS AND COVENANTS OF THE WARRANTHOLDER. 

This Agreement has been entered into by the Company in reliance upon the following representations and covenants of the Warrantholder:

 (a) Investment Purpose. This Agreement and the right to acquire the Preferred Stock issuable upon
exercise of the Warrantholder’s rights contained herein or the Common Stock into which the Preferred Stock is convertible are and will be acquired for investment and not with a view to the sale or distribution of any part thereof, and the
Warrantholder has no present intention of selling or engaging in any public distribution of the same except pursuant to a registration or exemption. 
 (b) Private Issue. The Warrantholder understands (i) that the issuance of the Warrants and the Preferred Stock issuable upon exercise of this Agreement and the Common Stock into which the
Preferred Stock is convertible are not registered under the Act or qualified under applicable state securities laws on the ground that the issuance contemplated by this Agreement will be exempt from the registration and qualifications requirements
thereof, and (ii) that the Company’s reliance on such exemption is predicated on the representations set forth in this Section 10. 
 (c) Disposition of Warrantholder’s Rights. In no event will the Warrantholder make a disposition of any of this Agreement or its rights to acquire Preferred Stock or Preferred Stock issuable
upon exercise of such rights or the Common Stock into which such Preferred Stock is convertible unless and until (i) it shall have notified the Company of the proposed disposition, and (ii) if requested by the Company, it shall have
furnished the Company with an opinion of counsel (which counsel may either be inside or outside counsel to the Warrantholder) satisfactory to the Company and its counsel to the effect that (A) appropriate action necessary for compliance with
the Act has been taken, or (B) an exemption from the registration requirements of the Act is available. Notwithstanding the foregoing, the restrictions imposed upon the transferability of any of its rights to acquire Preferred Stock or
Preferred Stock issuable on the exercise of such rights do not apply to transfers from the beneficial owner of any of the aforementioned securities to its nominee or from such nominee to its beneficial owner, and shall terminate as to any particular
share of Preferred Stock when (1) such security shall have been effectively registered under the Act and sold by the holder thereof in accordance with such registration or (2) such security shall have been sold without registration in
compliance with Rule 144 under the Act, or (3) a letter shall have been issued to the Warrantholder at its request by the staff of the SEC or a ruling shall have been issued to the Warrantholder at its request by the SEC stating that no
action shall be recommended by such staff or taken by the SEC, as the case may be, if such security is transferred without registration under the Act in accordance with the conditions set forth in such letter or ruling and such letter or ruling
specifies that no subsequent restrictions on transfer are required. Whenever the restrictions imposed hereunder shall terminate, as hereinabove provided, the Warrantholder or holder of a share of Preferred Stock then outstanding as to which such
restrictions have terminated shall be entitled to receive from the Company, without expense to such holder, one or more new certificates for this Agreement or for such shares of Preferred Stock not bearing any restrictive legend (except with respect
to Section 3(e)). 
 (d) Financial Risk. The Warrantholder has such knowledge and experience in
financial and business matters as to be capable of evaluating the merits and risks of its 

  
 9. 

 
investment, and has the ability to bear the economic risks of its investment. 
 (e) Risk of No Registration. The Warrantholder understands that if the Company does not register with the SEC pursuant to Section 12 of the Securities Exchange Act of 1934 (the “1934
Act”), or file reports pursuant to Section 15(d) of the 1934 Act, or if a registration statement covering the securities under the Act is not in effect when it desires to sell (i) the rights to purchase Preferred Stock pursuant to
this Agreement or (ii) the Preferred Stock issuable upon exercise of the right to purchase or (iii) the Common Stock into which such Preferred Stock is convertible, it may be required to hold such securities for an indefinite period. The
Warrantholder also understands that any sale of (A) its rights hereunder to purchase Preferred Stock, (B) Preferred Stock issued or issuable hereunder or (C) Common Stock into which such Preferred Stock is convertible which might be
made by it in reliance upon Rule 144 under the Act may be made only in accordance with the terms and conditions of that Rule. 
 (f) Accredited Investor. Warrantholder is an “accredited investor” within the meaning of the Securities and Exchange Rule 501 of Regulation D, as presently in effect.

 SECTION 11. TRANSFERS. 
 Subject to the terms and conditions contained in Section 10, this Agreement and all rights hereunder are transferable in whole or in part by the Warrantholder and any successor transferee, provided,
that, prior to an Initial Public Offering, in no event shall the number of transfers of the rights and interests in this Agreement exceed three (3) transfers. The transfer shall be recorded on the books of the Company upon receipt by the
Company of a notice of transfer in the form attached hereto as Exhibit III (the “Transfer Notice”) and surrender of this Warrant, at its principal offices and the payment to the Company of all transfer taxes and other
governmental charges imposed on such transfer. 
 SECTION 12. MISCELLANEOUS. 

(a) Effective Date. The provisions of this Agreement shall be construed and shall be given effect in all respects
as if it had been executed and delivered by the Company on the date hereof. This Agreement shall be binding upon any successors or assigns of the Company and Warrantholder. 

(b) Remedies. In the event of any default hereunder, the non-defaulting party may proceed to protect and enforce
its rights either by suit in equity and/or by action at law, including but not limited to an action for damages as a result of any such default, and/or an action for specific performance for any default where Warrantholder will not have an adequate
remedy at law and where damages will not be readily ascertainable. The Company expressly agrees that it shall not oppose an application by the Warrantholder or any other person entitled to the benefit of this Agreement requiring specific performance
of any or all provisions hereof or enjoining the Company from continuing to commit any such breach of this Agreement. In no event shall either party be liable for any special, consequential, incidental, punitive or indirect damages, including
without limitation, for any loss of profit for breach of this Agreement. 
 (c) No Impairment of Rights.
The Company will not, by amendment of its Charter or through any other means, avoid or seek to avoid the observance or performance of any 

  
 10.

 
of the terms of this Agreement, but will at all times in good faith assist in the carrying out of all such terms and in the taking of all such actions as may be necessary or appropriate in order
to protect the rights of the Warrantholder against impairment. 
 (d) Additional Documents. The Company,
shall provide the Warrantholder with such accounts or reports as the Company may provide to its Preferred Stockholders (in their capacity as such) which Warrantholder may from time to time reasonably request. Warrantholder shall at all times keep
confidential and not divulge, furnish or make accessible to anyone any confidential information, knowledge or data concerning or relating to the business or financial affairs of the Company to which the Warrantholder has been or shall become privy
pursuant hereto which is not otherwise publicly available, provided, however, that Warrantholder may share such information with permitted transferees so long as they agree to observe the confidentiality restrictions of this Section 12(d).

 (e) Attorney’s Fees. In any litigation, arbitration or court proceeding between the Company and
the Warrantholder relating hereto, the prevailing party shall be entitled to attorneys’ fees and expenses and all costs of proceedings incurred in enforcing this Agreement. For the purposes of this Section 12(e), attorneys’ fees shall
include without limitation fees incurred in connection with the following: (i) contempt proceedings; (ii) discovery; (iii) any motion, proceeding or other activity of any kind in connection with an insolvency proceeding;
(iv) garnishment, levy, and debtor and third party examinations; and (v) post-judgment motions and proceedings of any kind, including without limitation any activity taken to collect or enforce any judgment. 

(f) Severability. in the event any one or more of the provisions of this Agreement shall for any reason be held
invalid, illegal or unenforceable, the remaining provisions of this Agreement shall be unimpaired, and the invalid, illegal or unenforceable provision shall be replaced by a mutually acceptable valid, legal and enforceable provision, which comes
closest to the intention of the parties underlying the invalid, illegal or unenforceable provision. 
 (g)
Notices. Except as otherwise provided herein, any notice, demand, request, consent, approval, declaration, service of process or other communication that is required, contemplated, or permitted under this Agreement or with respect to the
subject matter hereof shall be in writing, and shall be deemed to have been validly served, given, delivered, and received upon the earlier of: (i) the first business day after transmission by facsimile or hand delivery or deposit with an
overnight express service or overnight mail delivery service; or (ii) the third calendar day after deposit in the United States mails, with proper first class postage prepaid (provided, that any surrender of this Agreement shall not be deemed
received until Company’s actual receipt thereof), and shall be addressed to the party to be notified as follows: 
  

	 	(i)	If to Warrantholder: 

 HERCULES
TECHNOLOGY GROWTH CAPITAL, INC. 
 Legal Department 
 Attention: Chief Legal Officer 
 525 University Avenue 

Suite 700 

  
 11.

 Palo Alto, CA 9430 

Facsimile: 650-473-9194 
 Telephone: 650-813-6200 
 With a copy to: 

HERCULES TECHNOLOGY GROWTH CAPITAL, INC. 
 Attention: Manuel Henriquez 
 525 University Avenue Suite 700 

Palo Alto, CA 94301 
 Facsimile: 650-81306211 
 Telephone: 650-813-6200 

 

	 	(ii)	If to the Company: 

 WAGEWORKS,
INC. 
 Attention: Dickson Leung, General Counsel 
 Two Water Park Drive, Suite 250 
 San Mateo, CA 94403 

Facsimile: 650- 

Telephone: 650-577-5200 
 With a copy to: 
 MORGAN LEWIS & BOCKIUS LLP 

Attention: John Larson One Market 
 Spear Street Tower 
 San Francisco, CA 94105 

Facsimile: 415-442-1000 
 Telephone: 415-442-1001 
 or to such other address as each party may designate for itself by like
notice. Any communication to Company that is otherwise valid under this Section shall be effective even if such communication is not delivered to Company’s counsel. 

(h) Entire Agreement; Amendments. This Agreement constitute the entire agreement and understanding of the parties
hereto in respect of the subject matter hereof, and supersede and replace in their entirety any prior proposals, term sheets, letters, negotiations or other documents or agreements, whether written or oral, with respect to the subject matter hereof
(including Warrantholder’s proposal letter dated March 23, 2005). None of the terms of this Agreement may be amended except by an instrument executed by each of the parties hereto. 

(i) Headings. The various headings in this Agreement are inserted for convenience only and shall not affect the
meaning or interpretation of this Agreement or any provisions hereof. 

  
 12.

 (j) Advice of Counsel. Each of the parties represents to each other
party hereto that it has discussed (or had an opportunity to discuss) with its counsel this Agreement and, specifically, the provisions of Sections 12(n), 12(o) and 12(p). 

(k) No Strict Construction. The parties hereto have participated jointly in the negotiation and drafting of this
Agreement. In the event an ambiguity or question of intent or interpretation arises, this Agreement shall be construed as if drafted jointly by the parties hereto and no presumption or burden of proof shall arise favoring or disfavoring any party by
virtue of the authorship of any provisions of this Agreement. 
 (l) No Waiver. No omission or delay by
Warrantholder at any time to enforce any right or remedy reserved to it, or to require performance of any of the terms, covenants or provisions hereof by the Company at any time designated, shall be a waiver of any such right or remedy to which
Warrantholder is entitled, nor shall it in any way affect the right of Warrantholder to enforce such provisions thereafter. 
 (m) Survival. All agreements, representations and warranties contained in this Agreement or in any document delivered pursuant hereto shall be for the benefit of Warrantholder and shall survive the
execution and delivery of this Agreement and the indemnity provisions hereof shall survive the expiration or other termination of this Agreement. 
 (n) Governing Law. This Agreement have been negotiated and delivered to Warrantholder in the State of California, and shall have been accepted by Warrantholder in the State of California. Delivery
of Preferred Stock (or Common Stock issuable upon conversion of such Preferred Stock) to Warrantholder by the Company under this Agreement is due in the State of California. This Agreement shall be governed by, and construed and enforced in
accordance with, the laws of the State of California, excluding conflict of laws principles that would cause the application of laws of any other jurisdiction. 
 (o) Consent to Jurisdiction and Venue. All judicial proceedings arising in or under or related to this Agreement may be brought in any state or federal court of competent jurisdiction located in
the State of California. By execution and delivery of this Agreement, each party hereto generally and unconditionally: (a) consents to personal jurisdiction in Santa Clara County, State of California; (b) waives any objection as to
jurisdiction or venue in Santa Clara County, State of California; (c) agrees not to assert any defense based on lack of jurisdiction or venue in the aforesaid courts; and (d) irrevocably agrees to be bound by any judgment rendered thereby
in connection with this Agreement. Service of process on any party hereto in any action arising out of or relating to this Agreement shall be effective if given in accordance with the requirements for notice set forth in Section 12(g), and
shall be deemed effective and received as set forth in Section 12(g). Nothing herein shall affect the right to serve process in any other manner permitted by law or shall limit the right of either party to bring proceedings in the courts of any
other jurisdiction. 
 (p) Mutual Waiver of Jury Trial. Because disputes arising in connection with
complex financial transactions are most quickly and economically resolved by an experienced and expert person and the parties wish applicable state and federal laws to apply (rather than arbitration rules), the parties desire that their disputes be
resolved by a judge applying such applicable laws. EACH OF THE COMPANY AND WARRANTHOLDER 

  
 13.

 
SPECIFICALLY WAIVES ANY RIGHT IT MAY HAVE TO TRIAL BY JURY OF ANY CAUSE OF ACTION, CLAIM, CROSS-CLAIM, COUNTERCLAIM, THIRD PARTY CLAIM OR ANY OTHER CLAIM IN RESPECT HEREOF (COLLECTIVELY,
“CLAIMS”) ASSERTED BY THE COMPANY AGAINST WARRANTHOLDER OR ITS ASSIGNEE OR BY WARRANTHOLDER OR ITS ASSIGNEE AGAINST THE COMPANY. This waiver extends to all such Claims, including Claims that involve Persons other than Borrower and Lender;
Claims that arise out of or are in any way connected to the relationship between the Company and Warrantholder; and any Claims for damages, breach of contract, specific performance, or any equitable or legal relief of any kind, arising out of this
Agreement. 
 (q) Counterparts. This Agreement and any amendments, waivers, consents or supplements hereto
may be executed in any number of counterparts, and by different parties hereto in separate counterparts, each of which when so delivered shall be deemed an original, but all of which counterparts shall constitute but one and the same instrument.

 (r) Specific Performance. The parties hereto hereby declare that it is impossible to measure in money
the damages which will accrue to Warrantholder by reason of the Company’s failure to perform any of the obligations under this Agreement and agree that the terms of this Agreement shall be specifically enforceable by Warrantholder. If
Warrantholder institutes any action or proceeding to specifically enforce the provisions hereof, any person against whom such action or proceeding is brought hereby waives the claim or defense therein that Warrantholder has an adequate remedy at
law, and such person shall not offer in any such action or proceeding the claim or defense that such remedy at law exists. 

[Remainder of Page Intentionally Left Blank] 

  
 14.

 IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed by its
officers thereunto duly authorized as of the Effective Date. 
  

									
	 COMPANY:
	 		 	WAGEWORKS, INC.
					
		 		 		 	By:	 	/s/ Illegible
					
		 		 		 	Title:	 	 
			
	WARRANTHOLDER:	 		 	HERCULES TECHNOLOGY GROWTH CAPITAL, INC.
					
		 		 		 	By:	 	/s/ Illegible
					
		 		 		 	Title:	 	Chief Legal Officer

  
 SIGNATURE
PAGE TO WARRANT AGREEMENT 

 EXHIBIT I 
 NOTICE OF EXERCISE 
  

	To:	WageWorks, Inc. 

  

	(1)	The undersigned Warrantholder hereby elects to purchase [            ] shares of the Series C
Preferred Stock of WageWorks, Inc., pursuant to the terms of the Agreement dated the 23rd day of May, 2005 (the “Agreement”) between WageWorks, Inc. and the Warrantholder, and [CASH PAYMENT: tenders herewith payment of the Purchase
Price in full, together with all applicable transfer taxes, if any.] [NET ISSUANCE: elects pursuant to Section 3(a) of the Agreement to effect a Net Issuance.] 

 

	(2)	In exercising its rights to purchase the Series C Preferred Stock of WageWorks, Inc., the undersigned hereby confirms and acknowledges the investment
representations and warranties made in Section 10 of the Agreement. 

  

	(3)	Please issue a certificate or certificates representing said shares of Series C Preferred Stock in the name of the undersigned or in such other name as is
specified below. 

  

	
	  
	(Name)
	
	  
	(Address)

  

									
			
	WARRANTHOLDER:	 		 	HERCULES TECHNOLOGY GROWTH CAPITAL, INC.
				
		 		 		 	 
					
		 		 		 		 	

  
 16.

 EXHIBIT II 
 ACKNOWLEDGMENT OF EXERCISE 
 The undersigned
[                                       
             ], hereby acknowledge receipt of the “Notice of Exercise” from Hercules Technology Growth Capital, Inc., to purchase
[            ] shares of the Series C Preferred Stock of WageWorks, Inc., pursuant to the terms of the Agreement, and further acknowledges that
[            ] shares remain subject to purchase under the terms of the Agreement. 
  

									
	 COMPANY:
	 		 	WAGEWORKS, INC.
					
		 		 		 	By:	 	 
					
		 		 		 	Title:	 	 
					
		 		 		 	Date:	 	 

  
 17.

 EXHIBIT III 
 TRANSFER NOTICE 
 (To transfer or assign the foregoing Agreement execute this form and
supply required information. Do not use this form to purchase shares.) 
 FOR VALUE RECEIVED, the foregoing Agreement and all rights evidenced
thereby are hereby transferred and assigned to 

											
	  	  	 
	  	  	 
	(Please Print)	  		  	
			
	whose address is 	 	 	  	
		
	 	  	
					
		 	Dated:	 	 	  		  	
					
		 	Holder’s Signature: 	  	 	  		  	
					
		 	Holder’s Address:	  	 	  		  	
				
		 	 	  		  	

							
			
	Signature Guaranteed: 	  	 	  	

 NOTE: The signature to this Transfer Notice must correspond with the name as it appears on the face of the
Agreement, without alteration or enlargement or any change whatever. Officers of corporations and those acting in a fiduciary or other representative capacity should file proper evidence of authority to assign the foregoing Agreement. 

By its acceptance of the Agreement, each assignee shall be deemed to have made to the Company the representations and warranties set forth in
Section 10 of the Agreement. 

  
 18.

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