Document:

EX-4.4

 Exhibit 4.4 

EXECUTION COPY 
 THE SECURITIES
REPRESENTED HEREBY HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”) AND MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED, ASSIGNED, PLEDGED OR HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER THE ACT OR
UNLESS THE COMPANY HAS RECEIVED AN OPINION OF COUNSEL SATISFACTORY TO THE COMPANY AND ITS COUNSEL THAT SUCH REGISTRATION IS NOT REQUIRED. 

THE SECURITIES REPRESENTED HEREBY ARE SUBJECT TO A LOCK-UP PERIOD OF UP TO 180 DAYS AFTER THE EFFECTIVE DATE OF THE ISSUER’S REGISTRATION
STATEMENT FILED UNDER THE ACT, AS AMENDED, AS SET FORTH IN AN AGREEMENT BETWEEN THE COMPANY AND THE ORIGINAL HOLDER OF THE SHARES, A COPY OF WHICH MAY BE OBTAINED AT THE COMPANY’S PRINCIPAL OFFICE. SUCH LOCK-UP PERIOD IS BINDING ON TRANSFEREES
OF THESE SHARES. 
 WARRANT TO PURCHASE PREFERRED STOCK 
  

			
	 Company:
	  	 PHREESIA, INC., a Delaware corporation

	 Number of Shares:
	  	 489,605 Shares of Junior Convertible Preferred Stock, par value $0.01 per share (“Junior Preferred”), and
358,244 Shares of Redeemable Preferred Stock, par value $0.01 per share (“Redeemable Preferred” and together with the Junior Preferred, the “Preferred Stock”) (Subject to Article 1.1.2 and Article
1.6)

	 Classes of Stock:
	  	 Junior Preferred and Redeemable Preferred (Subject to Article 1.6)

	 Initial Exercise Price:
	  	 $0.01 per unit (as defined below)

	 Issue Date:
	  	 February 25, 2015 (originally issued on September 5, 2013)

	 Expiration Date:
	  	 September 5, 2020 (Subject to Article 4.1)

 THIS WARRANT CERTIFIES THAT, in consideration of the payment of $1.00 and for other good and
valuable consideration, Escalate Capital Partners SBIC I, L.P., or its permitted assignee (“Holder”) is entitled to purchase the number of units of fully paid and nonassessable shares of Preferred Stock (the
“Shares”) of Phreesia, Inc., a Delaware corporation (the “Company”), at the initial exercise price per unit of Shares (in aggregate, the “Warrant Price”) all as set forth above and as adjusted
pursuant to Article 2 of this Warrant, subject to the provisions and upon the terms and conditions set forth in this Warrant. This Warrant amends and restates the Warrant to Purchase Preferred Stock issued by the Company to the holder of this
warrant on September 5, 2013 (the “Prior Warrant”) in connection with the recapitalization of the Corporation’s Series D Preferred Stock, which was consummated on October 14, 2014 through the Restated Charter (as
defined below), and this Warrant supersedes the Prior Warrant in its entirety which shall have no further force and effect. 
 As used
herein, a “unit” of Shares shall be equal to one (1) share of Junior Preferred and 0.7317 shares of Redeemable Preferred; provided, that if and to the extent the number of shares of Redeemable Preferred associated with a share of
Junior Preferred are automatically extinguished and cancelled pursuant to the terms of the Restated Charter, a “unit” of Shares shall be adjusted in accordance with the terms of the Restated Charter. “Restated Charter” shall mean
the Fifth Amended and Restated Certificate of Incorporation of the Company, as amended and/or restated from time to time. 
 ARTICLE
1.     EXERCISE. 
 1.1       Exercise of Warrant. 

 1.1.1     Exercisability. Subject to Article
1.1.2, the purchase rights represented by this Warrant are exercisable by Holder in whole or in part, at any time, or from time to time, on or before the Expiration Date set forth above, in the manner set forth in Article 1.2 below. 

1.1.2     Vesting. Notwithstanding the foregoing, this Warrant shall vest and be exercisable by
Holder (pursuant to Article 1.1.1) only with respect to the number of units set forth in the following vesting schedule: 

(i)       279,773 of the units shall vest and be immediately exercisable
on September 5, 2013; and 
 (ii)       69,944 of the units shall
vest and be immediately exercisable upon the date each One Million Dollars ($1,000,000) of Incremental Advances (as defined in the Loan and Security Agreement, dated as of September 5, 2013, by and between Holder and Company (as amended,
restated, supplemented or otherwise modified from time to time, the “Loan Agreement”; capitalized terms used but not otherwise defined herein shall have the meanings set forth in the Loan Agreement), is advanced by Holder to the
Company, with a pro rata basis increase in such number of vested units if the incremental amount over $1,000,000 of any Incremental Advance is other than a whole multiple of $1,000,000. Thus, and by way of example, an Incremental Advance in the
aggregate principal amount of One Million Five Hundred Thousand Dollars ($1,500,000) would result in three-fourteenths (3/14) of the units vesting and becoming immediately exercisable. 

1.2       Method of Exercise. Holder may exercise this Warrant by delivering this Warrant
and a duly executed Notice of Exercise or Exchange in substantially the form attached as Appendix 1 to the principal office of the Company (or such other appropriate location as Holder is instructed by the Company); provided, that subject to
Section 2.6, (i) Shares may only be purchased pursuant to the exercise of whole units and (ii) this Warrant shall not be exercisable for a number of Shares of Junior Preferred and Redeemable Preferred in any other ratio. Unless Holder
is exercising the exchange right set forth in Article 1.3, Holder shall also deliver to the Company a check, wire transfer (to an account designated by the Company) or other form of payment acceptable to the Company for the aggregate Warrant
Price for the units being purchased. 
 1.3       Exchange Right. In lieu of exercising
this Warrant as specified in Article 1.2, if the Fair Market Value of one unit is greater than the Warrant Price, Holder may from time to time exchange this Warrant, in whole or in part, by surrendering this Warrant at the principal office of
the Company (or such other appropriate location as Holder is instructed by the Company) together with a duly completed Notice of Exercise or Exchange for a number of Shares determined by dividing (a) the aggregate Fair Market Value of the
Shares (in whole units) or other securities otherwise issuable upon exercise of this Warrant or for which this Warrant shall become exercisable pursuant to the Restated Charter minus the aggregate Warrant Price of such whole units by (b) the
Fair Market Value of one unit. The Fair Market Value of the Shares shall be determined pursuant to Article 1.4. 

1.4       Fair Market Value. For purposes of this Warrant, “Fair Market Value”
shall be determined as follows: 
 1.4.1     If Holder elects to exchange this Warrant in connection
with the closing of Company’s initial underwritten public offering of its securities to the general public (the “IPO”) pursuant to an effective registration statement filed by the Company under the Securities Act of 1933, as
amended (the “Act”) and if the Company’s registration statement relating to such IPO has been declared effective 

  
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 by the Securities and Exchange Commission (the “SEC”), the Fair Market Value of
a Share shall be the initial price to the public of such Share specified in the final prospectus with respect to such IPO. 

1.4.2     If the Shares are traded regularly on a national securities exchange, the Fair Market Value of
such Shares shall be the average closing prices of such Shares (or the closing price of the Company’s stock into which the Shares are convertible multiplied by the number of shares of the Company stock into which such Share is convertible)
reported on such exchange for the ten (10) business days immediately prior to the date Holder delivers its Notice of Exercise or Exchange to the Company. 

1.4.3     If Holder elects to exchange this Warrant in connection with an Acquisition, the Fair Market
Value of the Shares shall be the greater of (x) the price per share which each share of Junior Preferred and/or Redeemable Preferred is entitled to receive in such Acquisition multiplied by the number of Shares, and (y) the price per share
which each share of the Company’s stock into which each Share is convertible is entitled to receive in such Acquisition multiplied by the number of applicable Shares. 

1.4.4     In all other cases, the Board of Directors of the Company in its reasonable good faith judgment
shall determine the fair market value of the Shares (or the Company’s stock into which the Shares are convertible multiplied by the number of shares of the Company stock into which a Share is convertible) as of the close of business on the
business day immediately prior to the date Holder delivers its Notice of Exercise or Exchange to the Company. 

1.5       Delivery of Certificate and New Warrant. Promptly after Holder exercises or
exchanges this Warrant and, if applicable, the Company receives payment of the aggregate Warrant Price, the Company shall deliver to Holder certificates for the Shares acquired and, if this Warrant has not been fully exercised or exchanged and has
not expired, a new Warrant representing the Shares not so acquired. 
 1.6      
Reserved. 
 1.7       Replacement of Warrants. On 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 affidavit of loss and 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 Holder’s expense shall execute and deliver, in lieu of this Warrant, a new Warrant of like tenor. 

1.8       Treatment of Warrant Upon Acquisition. 

1.8.1     Acquisition. For the purpose of this Warrant, “Acquisition” means any sale,
exclusive license, or other disposition of all or substantially all of the equity, securities or assets of the Company, or any reorganization, consolidation, or merger of the Company where the holders of the Company’s outstanding voting
securities immediately prior to the transaction beneficially own less than 50% of the outstanding voting securities of the Company or the successor or surviving entity, as applicable, immediately after the transaction; provided, that none of the
following shall be considered an Acquisition: (A) a merger or consolidation affected exclusively for the purpose of changing the domicile of the Company or (B) any transaction or series of transactions principally for bona fide equity
financing purposes in which cash is received by the Company or any successor or indebtedness of the Company is canceled or converted or a combination thereof. The Company will provide Holder at least five (5) business days’ prior notice of
the estimated closing for any Acquisition. 
 1.8.2     Assumption of Warrant. If upon the
closing of any Acquisition the successor or surviving entity expressly assumes the obligations of the Company pursuant to this Warrant, then from 

  
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and after the closing of such Acquisition, this Warrant shall be exercisable for the same securities, cash and property as would be payable for the Shares issuable upon exercise or exchange of
the unexercised portion of this Warrant as if such Shares were outstanding on the record date for, or the closing of, the Acquisition. The Warrant Price shall be adjusted accordingly, as necessary. 

1.8.3     Nonassumption. If upon the closing of any Acquisition, Holder has not otherwise
exercised or exchanged this Warrant in full, then Holder, by written notice to the Company received prior to the closing of such Acquisition, may elect to (a) deem this Warrant to have been automatically exchanged for Shares pursuant to
Article 1.3 and thereafter Holder shall participate in the Acquisition as a holder of Shares on the same terms as other holders of the same class of securities of the Company or (b) require the successor or surviving entity or the
Company, if the successor or surviving entity does not assume the obligations of this Warrant pursuant to Article 1.8.2, to purchase this Warrant upon the closing of the Acquisition, subject to the same terms as other holders of the same
class of securities of the Company participating in the Acquisition as if the Warrant were exercised and Holder held the Shares prior to the Acquisition, for an amount equal to the pro rata portion of the aggregate consideration Holder would have
received in consideration for the Shares issued upon exercise of this Warrant in connection with the Acquisition had Holder exercised this Warrant immediately prior to the record date for determining such consideration to the security holders, minus
the aggregate Warrant Price for such Shares. 
 1.9       Conditional Exercise, Exchange or
Sale. The exercise, exchange or sale of this Warrant may at the election of Holder be contingent upon the Company’s IPO or the closing of an Acquisition or other transaction involving the Company, in which case, upon the Holder electing to
exercise, exchange, or sell this Warrant once the conditions have been met, such exercise, exchange or sale shall be deemed to be effective immediately prior to or upon the commencement of the Company’s IPO or the closing of the Acquisition or
other transaction involving the Company, as applicable. 
 ARTICLE 2.     ADJUSTMENTS TO THE SHARES. 

2.1       Stock Dividends, Splits, Etc. If the Company declares or pays after the Issue
Date a dividend on its Preferred Stock payable in preferred stock, common stock, or other securities of the Company or subdivides the outstanding Preferred Stock into a greater amount of Junior Preferred and/or Redeemable Preferred, then upon
exercise or exchange of this Warrant, for each Share acquired, Holder shall receive, without cost to Holder, the total number and kind of securities to which Holder would have been entitled had Holder owned the Shares of record as of the date the
dividend or subdivision occurred. 
 2.2       Reclassification, Exchange or
Substitution. Upon any reclassification, exchange, substitution, or other event that results in a change of the number and/or class of the securities issuable upon exercise or conversion of this Warrant, Holder shall be entitled to receive, upon
exercise or exchange of this Warrant, the number and kind of securities and property that Holder would have received for the Shares if this Warrant had been exercised or exchanged immediately before such reclassification, exchange, substitution, or
other event and Holder had continued to hold such Shares until after such event. The Company or its successor shall promptly issue to Holder a new Warrant for such new securities or other property issuable upon exercise or conversion of this Warrant
as a result of such reclassification, exchange, substitution, or other event that results in a change to the number and/or class of securities issuable upon exercise or conversion of this Warrant. The new Warrant shall provide for adjustments which
shall be as nearly equivalent as may be practicable to the adjustments provided for in this Article 2 including, without limitation, adjustments to the Warrant Price and to the number of securities or property issuable upon exercise of the new
Warrant. The provisions of this Article 2.2 shall similarly apply to successive reclassifications, exchanges, substitutions, or other events. 

  
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 2.3       Adjustments for Combinations, Etc.
If the outstanding shares of Preferred Stock are combined or consolidated, by reclassification or otherwise, into a lesser number of shares, the number of Shares shall be proportionately decreased. If the outstanding shares of Preferred Stock are
split or multiplied, by reclassification or otherwise, into a greater number of Shares, the Warrant Price shall be proportionally decreased. 

2.4       No Impairment. The Company shall not, by amendment of its certificate of
incorporation or through a reorganization, transfer of assets, consolidation, merger, dissolution, issue, or sale of securities or any other voluntary action, avoid or seek to avoid the observance or performance of any of the terms to be observed or
performed under this Warrant by the Company, but shall at all times in good faith assist in carrying out all the provisions of this Article 2 and in taking all such action as may be necessary or appropriate to protect Holder’s rights
under this Article against impairment. Notwithstanding the foregoing, no waiver or amendment to any provision of the Company’s certificate of incorporation, bylaws, or of any provision of the Company’s Fourth Amended and Restated Investor
Rights Agreement, by and between the Company and the Purchasers listed as party thereto, dated as of October 14, 2014, as amended from time to time (the “IRA”) and a copy of which is attached hereto as Exhibit A, shall
be deemed to have impaired Holder’s rights if such amendments or waivers do not affect Holder in a manner materially different than such amendments or waivers generally effect the holders of Preferred Stock. 

2.5       Certificate as to Adjustments. Upon each adjustment of the Warrant Price, the
Company at its expense shall promptly compute such adjustment, and furnish Holder with a certificate of its Chief Financial Officer or other appropriate officer setting forth such adjustment and the facts upon which such adjustment is based. The
Company shall, upon written request, furnish Holder a certificate setting forth the Warrant Price in effect upon the date thereof and the series of adjustments leading to such Warrant Price. 

2.6       Fractional Shares. No fractional Shares shall be issuable upon exercise or
conversion of the Warrant and the number of Shares to be issued shall be rounded down to the nearest whole Share. If a fractional share interest of Redeemable Preferred arises upon any exercise or conversion of the Warrant, the Company shall
eliminate such fractional share interest by paying Holder the amount computed by multiplying the fractional interest times $1. If a fractional share interest of Junior Preferred arises upon any exercise or conversion of the Warrant, the Company
shall eliminate such fractional share interest by paying Holder the amount computed by multiplying the fractional interest times the Fair Market Value, as determined in accordance with Section 1.4, of a full Share of Junior Preferred. 

ARTICLE 3.     REPRESENTATIONS AND COVENANTS. 

3.1       Representations and Warranties of the Company. The Company hereby represents
and warrants to the Holder as follows: 
 3.1.1     All Shares which may be issued upon the exercise or
exchange of this Warrant, together with any shares of common stock issuable upon conversion of the Shares, shall, upon issuance, be duly authorized, validly issued, fully paid and nonassessable, and free of any liens and encumbrances except for
restrictions on transfer provided for herein, in the IRA, or under applicable federal and state securities laws. 

3.1.2     The Company’s capitalization table attached to this Warrant as Schedule A is a
complete and correct summary of the Company’s capitalization in all material respects as of the Issue Date. 

  
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 3.2       Notice of Certain Events. If the
Company proposes at any time (a) to declare any dividend or distribution upon its preferred stock or common stock, whether in cash, property, stock, or other securities and whether or not a regular cash dividend; (b) to offer for
subscription pro rata to holders of any class or series of its stock any additional shares of stock of any class or series or other rights (other than pursuant to contractual pre-emptive rights, including any rights of first offer contained in the
IRA as in effect on the date hereof); (c) to effect any reclassification or recapitalization of common stock or preferred stock; or (d) to merge or consolidate with or into any other corporation, or sell, lease, license, or convey all or
substantially all of its assets, or to liquidate, dissolve or wind up, then, in connection with each such event, the Company shall give Holder (1) at least ten (10) days prior written notice of the date on which a record will be taken for
such dividend, distribution, or subscription rights (and specifying the date on which the holders of common stock or preferred stock will be entitled thereto) or for determining rights to vote, if any, in respect of the matters referred to in
(a) and (b) above; and (2) in the case of the matters referred to in (c) and (d) above at least ten (10) days prior written notice of the date when the same will take place (and specifying
the date on which such holders will be entitled to exchange their common stock or preferred stock for securities or other property deliverable upon the occurrence of such event). 

3.3       Information Rights. During the term of this Warrant, Holder shall be entitled
to the inspection rights contained in Section 4.2 of the IRA and the information rights contained in Section 4.3 of the IRA as in effect on the date of this Warrant, as if Holder were a “Purchaser” under the IRA
with the requisite Share holdings to be entitled to such rights. In addition, but without duplication, so long as the Holder holds this Warrant and/or any of the Shares, the Company shall deliver to the Holder, (a) promptly after mailing,
copies of all communiques to all holders of Shares, (b) to the extent updated, within thirty (30) days of the last day of each fiscal quarter, a detailed fully diluted capitalization table for the Company as of the end of such fiscal
quarter, (c) within 180 days after the end of each fiscal year of the Company, the annual audited financial statements of the Company certified by independent public accountants of recognized standing, (d) within thirty (30) days
after the end of each calendar month, the Company’s monthly, unaudited financial statements, (e) within thirty (30) days after any amendment, revision, alteration or other modification of the Restated Charter, bylaws, or other
applicable formation and governing documents, a copy thereof; and (f) as soon as available, but in any event within thirty (30) days after the Company receives copies of any 409A valuation reports or other documents that value any
compensation, equity award, bonus, benefit plan or any other arrangement that could be deemed deferred compensation within the meaning of Section 409A of the Internal Revenue Code of 1986, as amended. The rights set forth in this
Article 3.3 shall terminate and be of no further force or effect upon the earlier to occur of (i) the closing of the Company’s IPO, (ii) the closing of an Acquisition, or (iii) the Company becoming subject to the
periodic reporting requirements of Section 12(g) or 15(d) of the Securities Exchange Act of 1934, as amended. 

3.4       Reservation of Shares. The Company shall at all times reserve and keep
available out of its authorized but unissued capital stock, solely for the purpose of issuance upon the exercise or exchange of this Warrant, the maximum number of Shares issuable upon exercise of this Warrant and the maximum number of shares of
common stock issuable upon conversion of the Shares. 
 3.5       No Stockholder
Rights. Except as provided in this Warrant, Holder will not have any rights as a stockholder of the Company until exercise of this Warrant. 

3.6       Representations and Warranties of Holder. The Holder hereby represents,
warrants and covenants to the Company as follows: 
 3.6.1     Purchase for Own Account. This
Warrant and the securities to be acquired upon exercise of this Warrant by the Holder will be acquired for investment for the Holder’s account, not as a 

  
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nominee or agent, and not with a view to the public resale or distribution within the meaning of the Act. Holder also represents that the Holder has not been formed for the specific purpose of
acquiring this Warrant or the Shares. 
 3.6.2     Disclosure of Information. The Holder has
received or has had full access to all the information it considers necessary or appropriate to make an informed investment decision with respect to the acquisition of this Warrant and its underlying securities. The Holder further has had an
opportunity to ask questions and receive answers from the Company regarding the terms and conditions of the offering of this Warrant and its underlying securities and to request additional information necessary to verify any information furnished to
the Holder or to which the Holder has access. 
 3.6.3     Investment Experience. The Holder
understands that the purchase of this Warrant and its underlying securities involves substantial risk. The Holder has experience as an investor in securities of companies in the development stage and acknowledges that the Holder can bear the
economic risk of such Holder’s investment in this Warrant and its underlying securities and has such knowledge and experience in financial or business matters that the Holder is capable of evaluating the merits and risks of its investment in
this Warrant and its underlying securities and/or has a preexisting personal or business relationship with the Company and certain of its officers, directors or controlling persons of a nature and duration that enables the Holder to be aw are of the
character, business acumen and financial circumstances of such persons. 
 3.6.4     Accredited
Investor Status. The Holder is an “accredited investor” within the meaning of Regulation D promulgated under the Act. 

3.6.5     The Act. The Holder understands that this Warrant and the Shares issuable upon exercise
or conversion hereof have not been registered under the Act in reliance upon a specific exemption therefrom, which exemption depends upon, among other things, the bona fide nature of the Holder’s investment intent as expressed herein. The
Holder understands that this Warrant and the Shares issued upon any exercise, conversion or exchange hereof must be held indefinitely unless subsequently registered under the Act and qualified under applicable state securities laws, or unless one or
more exemptions from such registration and qualification are otherwise available. 
 3.6.6    
Market Stand-Off Agreement. Holder hereby agrees that if the Company and managing underwriter so request and if and only so long as all officers, directors and holders of more than one percent (1%) of the Company’s common stock are
subject to the same agreements, during the period commencing on the effective date of the registration statement relating to the Company’s IPO and ending on the date specified by the Company and the managing underwriter (such period not to
exceed one hundred eighty (180) days) it will not, without the prior written consent of such managing underwriter, (i) lend, offer, pledge, sell, contract to sell, sell any option or contract to purchase, purchase any option or contract to
sell, grant any option, right or warrant to purchase, or otherwise transfer or dispose of, directly or indirectly, any shares of common stock or any securities convertible into or exercisable or exchangeable for common stock (whether such shares or
any such securities are then owned by the Holder or are thereafter acquired), or (ii) enter into any swap or other arrangement that transfers to another, in whole or in part, any of the economic consequences of ownership of the common stock,
whether any such transaction described in clause (i) or (ii) above is to be settled by delivery of common stock or such other securities, in cash or otherwise. The underwriters in connection with the Company’s IPO are
intended third party beneficiaries of this Article 3.6.6 and shall have the right, power and authority to enforce the provisions hereof as though they were a party hereto. In order to enforce the foregoing covenant, the Company may impose
stop-transfer instructions with respect to the registrable securities of each Holder until the end of such period. 

  
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 3.7       Registration Rights. The Company
agrees that the Shares or, if the Shares are convertible into common stock of the Company, such common stock, shall have certain “piggyback” and “S-3” registration rights in parity with Purchasers pursuant to and as set forth in
the IRA. The provisions set forth in the IRA relating to the above in effect as of the Issue Date may not be amended, modified or waived without the Holder’s prior written consent unless such amendment, modification or waiver affects the rights
associated with the Shares in the same manner as such amendment, modification, or waiver affects the rights associated with all other shares of the same series and class as the Shares granted to the Holder. 

3.8       Compliance with Rule 144. At the written request of the Holder, any time after
the Company is subject to the reporting requirements of the Securities Exchange Act of 1934, as amended, and to the extent that the Holder proposes to sell Preferred Stock issuable upon the exercise of this Warrant in compliance with Rule 144
promulgated by the SEC, the Company shall furnish to the Holder, within thirty (30) days after receipt of such request, a written statement as to whether the Company is then in compliance with the filing requirements of the SEC as set forth in
such Rule, as such Rule may be amended from time to time. 
 ARTICLE 4.     MISCELLANEOUS. 

4.1       Term. This Warrant is exercisable in whole or in part, at any time and from
time to time on or before the Expiration Date set forth above. If the Company completes its IPO within the one-year period immediately prior to the Expiration Date, the Expiration Date shall automatically be extended until the first anniversary of
the effective date of the Company’s IPO. If this Warrant has not been exercised prior to the Expiration Date and the Fair Market Value of one unit of Shares as of the Expiration Date (determined in accordance with Article 1.4) is greater
than the Warrant Price, this Warrant shall be deemed to have been automatically exercised on the Expiration Date by “cashless” exercise pursuant to Article 1.3. 

4.2       Legends. In addition to any other legends required by the Company’s
Bylaws, the IRA, and any other agreements, this Warrant and the Shares shall be imprinted with a legend in substantially the following form: THE SECURITIES REPRESENTED HEREBY HAVE NOT BEEN REGISTERED 

UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”) AND MAY NOT BE OFFERED, SOLD OR OTHERWISE TRANSFERRED,
ASSIGNED, PLEDGED OR HYPOTHECATED UNLESS AND UNTIL REGISTERED UNDER THE ACT OR UNLESS THE COMPANY HAS RECEIVED AN OPINION OF COUNSEL SATISFACTORY TO THE COMPANY AND ITS COUNSEL THAT SUCH REGISTRATION IS NOT REQUIRED. 

THE SECURITIES REPRESENTED HEREBY ARE SUBJECT TO A LOCK-UP PERIOD OF UP TO 180 DAYS AFTER THE EFFECTIVE DATE OF THE
ISSUER’S REGISTRATION STATEMENT FILED UNDER THE ACT, AS AMENDED, AS SET FORTH IN AN AGREEMENT BETWEEN THE COMPANY AND THE ORIGINAL HOLDER OF THE SHARES, A COPY OF WHICH MAY BE OBTAINED AT THE COMPANY’S PRINCIPAL OFFICE. SUCH LOCK-UP PERIOD
IS BINDING ON TRANSFEREES OF THESE SHARES. 
 4.3       Compliance with Securities Laws on
Transfer. This Warrant and the Shares issuable upon exercise of this Warrant may not be transferred or assigned in whole or in part without compliance with, or an applicable exemption from, applicable federal and state securities laws by the
transferor and 

  
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 the transferee (including, without limitation, the delivery of investment representation letters
and legal opinions reasonably acceptable to the Company, as reasonably requested by the Company). 

4.4       Transfer Procedure. Subject to the provisions of Article 4.3, Holder may
transfer all or part of this Warrant or the Shares issuable upon exercise of this Warrant (or the securities issuable, directly or indirectly, upon conversion of the Shares, if any) by giving the Company notice of the portion of the Warrant being
transferred setting forth the name, address and taxpayer identification number of the transferee and surrendering this Warrant to the Company for reissuance to the transferee(s) (and Holder, if applicable) (which reissuance, for the avoidance of
doubt, shall be in whole units of Shares); provided, however, that Holder may transfer all or part of this Warrant to its affiliates at any time with prior written notice to the Company, and such affiliate shall then be entitled to all
the rights of Holder under this Warrant and any related agreements, and the Company shall cooperate fully in ensuring that any stock issued upon exercise of this Warrant is issued in the name of the affiliate that exercises the Warrant. The terms
and conditions of this Warrant shall inure to the benefit of, and be binding upon, the Company and the holders hereof and their respective permitted successors and assigns. 

4.5       Notices. All notices and other communications from the Company to the Holder,
or vice versa, shall be deemed delivered and effective when given personally or mailed by first-class registered or certified mail, postage prepaid, at such address as may have been furnished to the Company or the Holder, as the case may be, in
writing by the Company or such Holder from time to time. Effective upon receipt of the fully executed Warrant, notices to the Holder shall be addressed as follows until the Company receives notice of a change of address in connection with a transfer
or otherwise: 
  

			
		  	 Escalate Capital Partners SBIC I, L.P.

		  	 300 West Sixth Street

		  	 Suite 2300

		  	 Austin, Texas 78701

		  	 Attention: Tony Schell

		  	 Phone: 512.651.2105

		  	 Fax: 512.651.2101

		  	 Email: tony@escalatecapital.com

		
	 And to:
	  	
		
		  	 Escalate Capital Partners

		  	 1901 S. Bascom Avenue, Suite 1030

		  	 Campbell, California 95008

		  	 Attention: Simon James

		  	 Phone: 408.200.0097

		  	 Fax: 408.200.0099

		  	 Email: simon@escalatecapital.com

  
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	 with a copy (which shall not constitute notice) to:

 

		 	 McGuire Woods LLP

		 	 2000 McKinney Avenue, Suite 1400

		 	 Dallas, Texas 75201

		 	 Attn: David McLean, Esq.

		 	 Phone: 214.932.6401

		 	 Fax: 214.932.6499

		 	 Email: dpmclean@mcguirewoods.com

  

			
	 Notice to the Company shall be addressed as follows until the Holder receives notice of a
change in address:

		
		 	 Phreesia, Inc.

		 	 432 Park Avenue South, 12th Floor

		 	 New York, NY 10016

		 	 Attention: Chief Financial Officer

		 	 Phone: 212.863.9455

		 	 Email: taltier@phreesia.com

		
	 with a copy to:
	 	
		
		 	 Goodwin Procter LLP

		 	 53 State Street

		 	 Boston, MA 02109

		 	 Attention: John J. Egan III, Esq.

		 	 Phone: 617.570.1514

		 	 Fax: 617.321.4742

		 	 Email: jegan@goodwinprocter.com

 4.6       Waiver. This Warrant and any term hereof may be
amended, changed, waived, discharged or terminated only by an instrument in writing signed by the party against which enforcement of such amendment, change, waiver, discharge or termination is sought. 

4.7       Attorneys’ Fees. In the event of any dispute between the parties
concerning the terms and provisions of this Warrant, the party prevailing in such dispute shall be entitled to collect from the other party all costs incurred in such dispute, including reasonable attorneys’ fees. 

4.8       Governing Law. This Warrant shall be governed by and construed in accordance
with the laws of the State of Delaware, without giving effect to its principles regarding conflicts of law. 

4.9       Counterparts. This Warrant may be executed in counterparts, including by
facsimile or e-mail, all of which together shall constitute one and the same agreement. 
 [Signature page follows.] 

  
 10 

 The Company has caused this Warrant to be duly executed and delivered as of the
Issue Date specified above. 
  

			
	 PREESIA, INC.,

	 a Delaware corporation

		
	 By:
	 	 /s/ Chaim Indig

	 Name:
	 	 Chaim Indig

	 Title:
	 	 CEO

  
 [SIGNATURE
PAGE TO WARRANT TO PURCHASE PREFERRED STOCK] 

 AGREED AND ACCEPTED: 

ESCALATE CAPITAL PARTNERS SBIC I, L.P., 

a Delaware limited partnership 
  

			
	 By:
	 	Escalate SBIC Capital Management, LLC,
		 	 its general partner

		
	 By:
	 	 /s/ Ross Cockrell

	 Name:
	 	 Ross Cockrell

	 Title:
	 	 Member

  
 [SIGNATURE
PAGE TO WARRANT TO PURCHASE PREFERRED STOCK] 

 APPENDIX 1 

NOTICE OF EXERCISE 
 ARTICLE 1.
    The undersigned hereby elects to (check applicable blank below): 
  

					
	
                       
   
	 	               
	 	purchase                     units of Shares of Junior Convertible Preferred Stock and Redeemable Preferred Stock of
PHREESIA, INC. pursuant to the terms of the attached Warrant, and tenders herewith payment of the Warrant Price of such Shares in full: or
			
		 	             
	 	exchange the attached Warrant for Shares in the manner specified in the Warrant. This exchange is exercised with respect to             of the units covered by the
Warrant.

 ARTICLE 2.     Please issue a certificate or certificates representing said shares in the
name of the undersigned or in such other name as is specified below: 
  

					
		 	  

	
                       
   
	 	 Attn:
	 	
                       
         

		 	  

		 	  

		
		 	Or Registered Assignee

 ARTICLE 3.     The undersigned represents it is acquiring the Shares solely for its own
account and not as a nominee for any other party and not with a view toward the resale or distribution thereof except in compliance with applicable securities laws. 

                        or
Registered Assignee 
  

	
	  

(Signature)

	
	  
 (Date)

 SCHEDULE A 

(attached)EX-4.5

 Exhibit 4.5 

THIS WARRANT AND THE SHARES ISSUABLE HEREUNDER HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE
“ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AS SET FORTH IN SECTIONS 5.3 AND 5.4 BELOW, MAY NOT BE OFFERED, SOLD, PLEDGED OR OTHERWISE TRANSFERRED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND LAWS OR, IN THE
OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER, SUCH OFFER, SALE, PLEDGE OR OTHER TRANSFER IS EXEMPT FROM SUCH REGISTRATION. 

WARRANT TO PURCHASE STOCK 

Company: Phreesia, Inc., a Delaware corporation  

Number of Shares: As set forth in Paragraph A below  

Type/Series of Stock: Common Stock, $0.01 par value per share  

Warrant Price: As set forth in Paragraph A below  

Issue Date: October 22, 2015 

Expiration Date: October 21, 2025 See also Section 5.1(b). 

Credit Facility: This Warrant to Purchase Stock (“Warrant”) is issued in connection with that
certain Fifth Loan Modification Agreement, of even date herewith, to that certain Loan and Security Agreement dated June 6, 2012, between Silicon Valley Bank and the Company, as amended (collectively, and as may be further amended and/or
modified and in effect from time to time, the “Loan Agreement”). 
 THIS WARRANT CERTIFIES THAT, for
good and valuable consideration, SILICON VALLEY BANK (together with any successor or permitted assignee or transferee of this Warrant or of any shares issued upon exercise hereof, “Holder”) is entitled to purchase the number
of fully paid and non-assessable shares of the above-stated Type/Series of Stock (the “Class”) of the above-named company (the
“Company”) as determined pursuant to Paragraph A below, at the Warrant Price (as defined below), subject to the provisions and upon the terms and conditions set forth in this Warrant. Reference is made to
Section 5.4 of this Warrant whereby Silicon Valley Bank shall transfer this Warrant to its parent company, SVB Financial Group. 

A.      Warrant Price; Number of Shares. 

(1)        Warrant Price. The purchase price per Share hereunder (the
“Warrant Price”) shall be: (a) if, on or before December 15, 2015, the Company shall receive, and its Board of Directors shall approve and adopt, a new valuation of the Company’s common stock
conducted for purposes of its compliance with Section 409A of the Internal Revenue Code of 1986, as amended, the fair market value of a share of the Class as reported therein; or (b) if, for any reason or no reason, the Company shall
not have received, and/or its Board of Directors shall not have approved and adopted, such a new 409A valuation on or before December 15, 2015, or if, prior to such receipt, approval and adoption of such new 409A valuation on or before such
date, there shall be an Acquisition (as hereinafter defined), IPO (as hereinafter defined) or any other event described in Section 3.2 below, then the “Warrant Price” shall be $0.92 (as such number may be adjusted from time to time
from and after the Issue Date hereof in accordance with the provisions of this Warrant as if such number were the Warrant Price) from and after such date or as of immediately prior to the closing of the Acquisition, the effectiveness of the
registration statement filed in connection with the IPO or the effective date of such Section 3.2 event (or the record date thereof if the Company shall establish a record date for determining shareholders entitled 

 to participate in such event), as the case may be; and in all cases subject to adjustment
thereafter from time to time in accordance with the provisions of this Warrant. 
 (2)     Number of
Shares. The number of shares of the Class for which this Warrant shall be exercisable shall equal (a) $337,500, divided by (b) the Warrant Price as and when first determined pursuant to Paragraph A(l) above, subject to adjustment
thereafter from time to time in accordance with the provisions of this Warrant (the “Shares”). 

SECTION 1. EXERCISE. 

1.1     Method of Exercise. Holder may at any time and from time to time exercise this Warrant, in
whole or in part, by delivering to the Company the original of this Warrant together with a duly executed Notice of Exercise in substantially the form attached hereto as Appendix 1 and, unless Holder is exercising this Warrant pursuant to a cashless
exercise set forth in Section 1.2, a check, wire transfer of same-day funds (to an account designated by the Company), or other form of payment acceptable to the Company for the aggregate Warrant Price
for the Shares being purchased. 
 1.2     Cashless Exercise. On any exercise of this Warrant,
in lieu of payment of the aggregate Warrant Price in the manner as specified in Section 1.1 above, but otherwise in accordance with the requirements of Section 1.1, Holder may elect to receive Shares equal to the value of this Warrant, or
portion hereof as to which this Warrant is being exercised. Thereupon, the Company shall issue to the Holder such number of fully paid and non-assessable Shares as are 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 with respect to which this Warrant is being exercised (inclusive of the Shares
surrendered to the Company in payment of the aggregate Warrant Price); 

  

	 	A =	 the Fair Market Value (as determined pursuant to Section 1.3 below) of one Share; and

 B =     the Warrant Price. 

1.3     Fair Market Value. If shares of the Class are then traded or quoted on a nationally
recognized securities exchange, inter-dealer quotation system or over-the-counter market (a “Trading Market”), the fair market value of a Share
shall be the closing price or last sale price of a share of the Class reported for the Business Day immediately before the date on which Holder delivers this Warrant together with its Notice of Exercise to the Company. If shares of the
Class are not then traded in a Trading Market, the Board of Directors of the Company shall determine the fair market value of a Share in its reasonable good faith judgment. 

1.4     Delivery of Certificate and New Warrant. Within a reasonable time after Holder exercises
this Warrant in the manner set forth in Section 1.1 or 1.2 above, the Company shall deliver to 
  

  
 2 

 Holder a certificate representing the Shares issued to Holder upon such exercise and, if this
Warrant has not been fully exercised and has not expired, a new warrant of like tenor representing the Shares not so acquired. 

1.5     Replacement of Warrant. On 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, substance and amount to the Company or, in the case of mutilation, on
surrender of this Warrant to the Company for cancellation, the Company shall, within a reasonable time, execute and deliver to Holder, in lieu of this Warrant, a new warrant of like tenor and amount. 

1.6     Treatment of Warrant Upon Acquisition of Company. 

(a)     Acquisition. For the purpose of this Warrant,
“Acquisition” means any transaction or series of related transactions involving: (i) the sale, lease, exclusive license, or other disposition of all or substantially all of the assets of the
Company (ii) any merger or consolidation of the Company into or with another person or entity (other than a merger or consolidation effected exclusively to change the Company’s domicile), or any other corporate reorganization, in which the
stockholders of the Company in their capacity as such immediately prior to such merger, consolidation or reorganization, own less than a majority of the Company’s (or the surviving or successor entity’s) outstanding voting power
immediately after such merger, consolidation or reorganization (or, if such Company stockholders beneficially own a majority of the outstanding voting power of the surviving or successor entity as of immediately after such merger, consolidation or
reorganization, such surviving or successor entity is not the Company); or (iii) any sale or other transfer by the stockholders of the Company of shares representing at least a majority of the Company’s then-total outstanding combined
voting power. 
 (b)     Treatment of Warrant at Acquisition. In the event of an Acquisition in
which the consideration to be received by the Company’s stockholders consists solely of cash, solely of Marketable Securities or a combination of cash and Marketable Securities (a “Cash/Public Acquisition”), and the fair
market value of one Share as determined in accordance with Section 1.3 above would be greater than the Warrant Price in effect on such date immediately prior to such Cash/Public Acquisition, and Holder has not exercised this Warrant pursuant to
Section 1.1 above as to all Shares, then this Warrant shall automatically be deemed to be Cashless Exercised pursuant to Section 1.2 above as to all Shares effective immediately prior to and contingent upon the consummation of a
Cash/Public Acquisition. In connection with such Cashless Exercise, Holder shall be deemed to have restated each of the representations and warranties in Section 4 of the Warrant as of the date thereof and the Company shall promptly notify the
Holder of the number of Shares (or such other securities) issued upon exercise. In the event of a Cash/Public Acquisition where the fair market value of one Share as determined in accordance with Section 1.3 above would be less than the Warrant
Price in effect immediately prior to such Cash/Public Acquisition, then this Warrant will expire immediately prior to the consummation of such Cash/Public Acquisition. 

(c)     Upon the closing of any Acquisition other than a Cash/Public Acquisition, the acquiring,
surviving or successor entity shall assume the obligations of this Warrant, and this Warrant shall thereafter be exercisable for the same securities and/or other property as would have been paid for the Shares issuable upon exercise of the
unexercised portion of this Warrant as if such Shares were outstanding on and as of the closing of such Acquisition, subject to further adjustment from time to time in accordance with the provisions of this Warrant. 

  
 3 

 (d)     As used in this Warrant, “Marketable
Securities” means securities meeting all of the following requirements: (i) the issuer thereof is then subject to the reporting requirements of Section 13 or Section 15(d) of the Securities Exchange Act of 1934, as
amended (the “Exchange Act”), and is then current in its filing of all required reports and other information under the Act and the Exchange Act; (ii) the class and series of shares or other security of the issuer that
would be received by Holder in connection with the Acquisition were Holder to exercise this Warrant on or prior to the closing thereof is then traded in a Trading Market, and (iii) following the closing of such Acquisition, Holder would not be
restricted from publicly re-selling all of the issuer’s shares and/or other securities that would be received by Holder in such Acquisition were Holder to exercise this Warrant in full on or prior to the
closing of such Acquisition, except to the extent that any such restriction (x) arises solely under federal or state securities laws, rules or regulations, and (y) does not extend beyond six (6) months from the closing of such
Acquisition. 
 1.7     Certain Agreements. Upon any exercise of this Warrant, Holder shall,
solely with respect to the Shares issued upon such exercise or conversion, join and become a “Purchaser” party to (a) that certain the Fourth Amended and Restated Right of First Refusal and
Co-Sale Agreement dated as of October 14, 2014, as amended and in effect from time to time, and (b) that certain Fourth Amended and Restated Stockholders’ Voting Agreement dated as of
October 14, 2014, as amended and in effect from time to time (the “Investor Agreements”), to the extent that such agreements are then by their terms still in force and effect. 

SECTION 2. ADJUSTMENTS TO THE SHARES AND WARRANT PRICE. 

2.1     Stock Dividends, Splits, Etc. If the Company declares or pays a dividend or distribution
on the outstanding shares of the Class payable in additional shares of the Class or other securities or property (other than cash), then upon exercise of this Warrant, for each Share acquired, Holder shall receive, without additional cost
to Holder, the total number and kind of securities and property which Holder would have received had Holder owned the Shares of record as of the date the dividend or distribution occurred. If the Company subdivides the outstanding shares of the
Class by reclassification or otherwise into a greater number of shares, the number of Shares purchasable hereunder shall be proportionately increased and the Warrant Price shall be proportionately decreased. If the outstanding shares of the
Class are combined or consolidated, by reclassification or otherwise, into a lesser number of shares, the Warrant Price shall be proportionately increased and the number of Shares shall be proportionately decreased. 

2.2     Reclassification, Exchange, Combinations or Substitution. Upon any event whereby all of
the outstanding shares of the Class are reclassified, exchanged, combined, substituted, or replaced for, into, with or by Company securities of a different class and/or series, then from and after the consummation of such event, this Warrant
will be exercisable for the number, class and series of Company securities that Holder would have received had the Shares been outstanding on and as of the consummation of such event, and subject to further adjustment thereafter from time to time in
accordance with the provisions of this Warrant. The provisions of this Section 2.2 shall similarly apply to successive reclassifications, exchanges, combinations, substitutions, replacements or other similar events. 

2.3     No Fractional Share. No fractional Share shall be issuable upon exercise of this Warrant
and the number of Shares to be issued shall be rounded down to the nearest whole Share. If a fractional Share interest arises upon any exercise of the Warrant, the Company shall eliminate such 

  
 4 

 fractional Share interest by paying Holder in cash the amount computed by multiplying the
fractional interest by (i) the fair market value (as determined in accordance with Section 1.3 above) of a full Share, less (ii) the then-effective Warrant Price. 

2.4     Notice/Certificate as to Adjustments. Upon each adjustment of the Warrant Price,
Class and/or number of Shares, the Company, at the Company’s expense, shall notify Holder in writing within a reasonable time setting forth the adjustments to the Warrant Price, Class and/or number of Shares and facts upon which such
adjustment is based. The Company shall, upon written request from Holder, furnish Holder with a certificate of its Chief Financial Officer, including computations of such adjustment and the Warrant Price, Class and number of Shares in effect
upon the date of such adjustment. 
 SECTION 3. REPRESENTATIONS AND COVENANTS OF THE COMPANY. 

3.1     Representations and Warranties. The Company represents and warrants to, and agrees with,
the Holder as follows: 
 (a) $0.92 is not greater than the fair market value of a share of the Class as determined by
the most recently completed valuation as of the date hereof, approved by the Company’s Board of Directors, of the Company’s stock for purposes of its compliance with Section 409A of the Internal Revenue Code of 1986, as amended. 

(b)     All Shares which may be issued upon the exercise of this Warrant shall, upon issuance, be duly
authorized, validly issued, fully paid and non-assessable, and free of any liens and encumbrances except for restrictions on transfer provided for herein, under the Investor Agreements (to the extent that
Holder is then subject thereto in accordance with Section 1.7 above) or under applicable federal and state securities laws. The Company covenants that it shall at all times cause to be reserved and kept available out of its authorized and
unissued capital stock such number of shares of the Class and other securities as will be sufficient to permit the exercise in full of this Warrant. 

(c)     The Company’s capitalization table attached hereto as Schedule 1 is true and complete, in
all material respects, as of the Issue Date. 
 3.2     Notice of Certain Events. If the Company
proposes at any time to: 
 (a) declare any dividend or distribution upon the outstanding shares of the Class, whether in
cash, property, stock, or other securities and whether or not a regular cash dividend; 
 (b) offer for subscription or
sale pro rata to the holders of the outstanding shares of the Class any additional shares of any class or series of the Company’s stock (other than pursuant to contractual pre-emptive rights); 

(c) effect any reclassification, exchange, combination, substitution, reorganization or recapitalization of the outstanding
shares of the Class; 
 (d) effect an Acquisition or to liquidate, dissolve or wind up; or 

(e) effect its initial, underwritten offering and sale of its securities to the public pursuant to an effective registration
statement under the Act (the “IPO”); 

  
 5 

 
then, in connection with each such event, the Company shall give Holder: 

(1) in the case of the matters referred to in (a) and (b) above, at least seven (7) Business Days
prior written notice of the earlier to occur of the effective date thereof or the date on which a record will be taken for such dividend, distribution, or subscription rights (and specifying the date on which the holders of outstanding shares of the
Class will be entitled thereto) or for determining rights to vote, if any; 
 (2) in the case of the
matters referred to in (c) and (d) above at least seven (7) Business Days prior written notice of the date when the same will take place (and specifying the date on which the holders of outstanding shares of the Class will be entitled
to exchange their shares for the securities or other property deliverable upon the occurrence of such event and such reasonable information as Holder may reasonably require regarding the treatment of this Warrant in connection with such event giving
rise to the notice); and 
 (3) with respect to the IPO, at least seven (7) Business Days prior
written notice of the date on which the Company proposes to file its registration statement in connection therewith. 
 The Company will
also provide information requested by Holder that is reasonably necessary to enable Holder to comply with Holder’s accounting or reporting requirements. 

SECTION 4. REPRESENTATIONS AND COVENANTS OF THE HOLDER. 

The Holder represents and warrants to the Company as follows: 

4.1         Purchase for Own Account. This Warrant and the Shares to be
acquired upon exercise of this Warrant by Holder are being acquired for investment for Holder’s account, not as a nominee or agent, and not with a view to the public resale or distribution within the meaning of the Act. Holder also represents
that it has not been formed for the specific purpose of acquiring this Warrant or the Shares. 

4.2         Disclosure of Information. Holder is aware of the Company’s
business affairs and financial condition and has received or has had full access to all the information it considers necessary or appropriate to make an informed investment decision with respect to the acquisition of this Warrant and its underlying
securities. Holder further has had an opportunity to ask questions and receive answers from the Company regarding the terms and conditions of the offering of this Warrant and its underlying securities and to obtain additional information (to the
extent the Company possessed such information or could acquire it without unreasonable effort or expense) necessary to verify any information furnished to Holder or to which Holder has access. 

4.3         Investment Experience. Holder understands that the purchase of
this Warrant and its underlying securities involves substantial risk. Holder has experience as an investor in securities of companies in the development stage and acknowledges that Holder can bear the economic risk of such Holder’s investment
in this Warrant and its underlying securities and has such knowledge and experience in financial or business matters that Holder is capable of evaluating the merits and risks of its investment in this Warrant and its underlying securities and/or has
a preexisting personal or business relationship with the Company and certain of its officers, directors or controlling persons of a nature and 

  
 6 

 duration that enables Holder to be aware of the character, business acumen and financial
circumstances of such persons. 
 4.4         Accredited Investor Status.
Holder is an “accredited investor” within the meaning of Regulation D promulgated under the Act. 

4.5         The Act. Holder understands that this Warrant and the Shares
issuable upon exercise hereof have not been registered under the Act in reliance upon a specific exemption therefrom, which exemption depends upon, among other things, the bona fide nature of the Holder’s investment intent as expressed herein.
Holder understands that this Warrant and the Shares issued upon any exercise hereof must be held indefinitely unless subsequently registered under the Act and qualified under applicable state securities laws, or unless exemption from such
registration and qualification are otherwise available. Holder is aware of the provisions of Rule 144 promulgated under the Act. 

4.6         No Shareholder Rights. Without limiting any provision of this
Warrant, Holder agrees that as a Holder of this Warrant it will not have any rights (including, without limitation, voting rights) as a shareholder of the Company with respect to the Shares issuable hereunder unless and until the exercise of this
Warrant, and then only with respect to the Shares issued on such exercise. 
 SECTION 5. MISCELLANEOUS. 

5.1         Term; Automatic Cashless Exercise Upon Expiration. 

(a)         Term. Subject to the provisions of Section 1.6 above, this
Warrant is exercisable in whole or in part at any time and from time to time on or before 6:00 PM, Pacific time, on the Expiration Date and shall be void thereafter. 

(b)         Automatic Cashless Exercise upon Expiration. In the event that,
upon the Expiration Date, the fair market value of one Share as determined in accordance with Section 1.3 above is greater than the Warrant Price in effect on such date, then this Warrant shall automatically be deemed on and as of such date to
be exercised pursuant to Section 1.2 above as to all Shares for which it shall not previously have been exercised, and the Company shall, within a reasonable time, deliver a certificate representing the Shares issued upon such exercise to
Holder. 
 5.2         Legends. Each certificate evidencing Shares shall be
imprinted with a legend in substantially the following form: 
 THE SHARES EVIDENCED BY THIS CERTIFICATE
HAVE NOT BEEN REGISTERED UNDER THE SECURITIES ACT OF 1933, AS AMENDED (THE “ACT”), OR THE SECURITIES LAWS OF ANY STATE AND, EXCEPT AS SET FORTH IN THAT CERTAIN WARRANT TO PURCHASE STOCK ISSUED BY THE ISSUER TO SILICON VALLEY
BANK DATED OCTOBER 22, 2015, MAY NOT BE OFFERED, SOLD, PLEDGED OR OTHERWISE TRANSFERRED UNLESS AND UNTIL REGISTERED UNDER SAID ACT AND LAWS OR, IN THE OPINION OF LEGAL COUNSEL IN FORM AND SUBSTANCE SATISFACTORY TO THE ISSUER, SUCH OFFER, SALE,
PLEDGE OR OTHER TRANSFER IS EXEMPT FROM SUCH REGISTRATION. 

  
 7 

 5.3     Compliance with Securities Laws on Transfer.
This Warrant and the Shares issued upon exercise of this Warrant may not be transferred or assigned in whole or in part except in compliance with applicable federal and state securities laws by the transferor and the transferee (including, without
limitation, the delivery of investment representation letters and legal opinions reasonably satisfactory to the Company, as reasonably requested by the Company). The Company shall not require Holder to provide an opinion of counsel if the transfer
is to SVB Financial Group (Silicon Valley Bank’s parent company) or any other affiliate of Holder, provided that any such transferee is an “accredited investor” as defined in Regulation D promulgated under the Act. Additionally, the
Company shall also not require an opinion of counsel if there is no material question as to the availability of Rule 144 promulgated under the Act. 

5.4     Transfer Procedure. After receipt by Silicon Valley Bank of the executed Warrant, Silicon
Valley Bank will transfer all of this Warrant to its parent company, SVB Financial Group. By its acceptance of this Warrant, SVB Financial Group hereby makes to the Company each of the representations and warranties set forth in Section 4
hereof and agrees to be bound by all of the terms and conditions of this Warrant as if the original Holder hereof. Subject to the provisions of Section 5.3 and upon providing the Company with written notice, SVB Financial Group and any
subsequent Holder may transfer all or part of this Warrant or the Shares issued upon exercise of this Warrant to any transferee, provided, however, in connection with any such transfer, SVB Financial Group or any subsequent Holder will give the
Company notice of the portion of the Warrant and/or Shares being transferred with the name, address and taxpayer identification number of the transferee and Holder will surrender this Warrant to the Company for reissuance to the transferee(s) (and
Holder if applicable); and provided further, that any subsequent transferee other than SVB Financial Group shall agree in writing with the Company to be bound by all of the terms and conditions of this Warrant; and provided further, that the
transfer of any Shares issued on exercise hereof shall be subject to the provisions of the Investor Agreements (to the extent that Holder is then subject thereto in accordance with Section 1.7 above). Notwithstanding any contrary provision
herein, at all times prior to the IPO, Holder may not, without the Company’s prior written consent, transfer this Warrant or any portion hereof, or any Shares issued upon any exercise hereof, to any person or entity who directly competes with
the Company, except in connection with an Acquisition of the Company by such a direct competitor. 

5.5     Notices. All notices and other communications hereunder from the Company to the Holder, or
vice versa, shall be deemed delivered and effective (i) when given personally, (ii) on the third (3rd) Business Day after being mailed by first-class registered or certified mail,
postage prepaid, (iii) upon actual receipt if given by facsimile or electronic mail and such receipt is confirmed in writing by the recipient, or (iv) on the first Business Day following delivery to a reliable overnight courier service,
courier fee prepaid, in any case at such address as may have been furnished to the Company or Holder, as the case may be, in writing by the Company or such Holder from time to time in accordance with the provisions of this Section 5.5. All
notices to Holder shall be addressed as follows until the Company receives notice of a change of address in connection with a transfer or otherwise: 

SVB Financial Group 

Attn: Treasury Department 

3003 Tasman Drive, HC 215 

Santa Clara, CA 95054 

Telephone: (408) 654-7400 

Facsimile: (408) 988-8317 

Email address: derivatives@svb.com 

  
 8 

 Notice to the Company shall be addressed as follows until Holder receives notice
of a change in address: 
 Phreesia, Inc. 

Attn: Chief Financial Officer 

432 Park Avenue South, 12th Floor 

New York, NY 10016 

Telephone: 

Facsimile: 

Email: 

With a copy (which shall not constitute notice) to: 

Goodwin Procter LLP 

Attn: John Egan 

Exchange Place 

Boston, MA 02109 

Telephone: 617-570-1514 

Facsimile: 617-570-1231 

Email: jegan@goodwinprocter.com 

5.6     Waiver. This Warrant and any term hereof may be changed, waived, discharged or terminated
(either generally or in a particular instance and either retroactively or prospectively) only by an instrument in writing signed by the party against which enforcement of such change, waiver, discharge or termination is sought. 

5.7     Attorneys’ Fees. In the event of any dispute between the parties concerning the terms
and provisions of this Warrant, the party prevailing in such dispute shall be entitled to collect from the other party all costs incurred in such dispute, including reasonable attorneys’ fees. 

5.8     Counterparts; Facsimile/Electronic Signatures. This Warrant may be executed in
counterparts, all of which together shall constitute one and the same agreement. Any signature page delivered electronically or by facsimile shall be binding to the same extent as an original signature page with regards to any agreement subject to
the terms hereof or any amendment thereto. 
 5.9     Governing Law. This Warrant shall be
governed by and construed in accordance with the laws of the State of California, without giving effect to its principles regarding conflicts of law. 

5.10     Headings. The headings in this Warrant are for purposes of reference only and shall not
limit or otherwise affect the meaning of any provision of this Warrant. 
 5.11     Business
Days. “Business Day” is any day that is not a Saturday, Sunday or a day on which Silicon Valley Bank is closed. 

[Remainder of page left blank intentionally] 

[Signature page follows] 

  
 9 

 IN WITNESS WHEREOF, the parties have caused this Warrant to Purchase Stock to be
executed by their duly authorized representatives effective as of the Issue Date written above. 
 “COMPANY” 

PHREESIA, INC. 
  

			
	 By:
	 	 /s/ Chaim Indig

		
	 Name:
	 	 Chaim Indig

	 Title:
	 	 (Print)

President & CEO

“HOLDER” 
 SILICON
VALLEY BANK 
  

			
	 By:
	 	 /s/ Lauren Cole

		
	 Name:
	 	 Lauren Cole

	 Title:
	 	 (Print)
 Vice
President

  
 10 

 APPENDIX 1 

NOTICE OF EXERCISE 

1.         The undersigned Holder hereby exercises its right to
purchase                         shares of the
Common/Series                 Preferred [circle one] Stock
of                                 (the “Company”) in
accordance with the attached Warrant To Purchase Stock, and tenders payment of the aggregate Warrant Price for such shares as follows: 
  

	 	[    ]	         check in the amount of $
                     payable to order of the Company enclosed herewith 

 

	 	[    ]	         Wire transfer of immediately available funds to the
Company’s account 

  

	 	[    ]	         Cashless Exercise pursuant to Section 1.2 of the
Warrant 

  

	 	[    ]	         Other
[Describe]                                       
                                         
             

2.         Please issue a certificate or certificates representing the Shares in the
name specified below: 
  

					
		  	  
	  	
		  	 Holder’s Name
	  	
			
		  	  
	  	
		  		  	
		  	  
	  	
		  	 (Address)
	  	

  

3.         By its execution below and for the benefit of the Company, Holder hereby
restates each of the representations and warranties in Section 4 of the Warrant to Purchase Stock as of the date hereof. 
  

					
	 HOLDER:
	 	
	
                       
             
	 	

 
					
			
	 By:
	 	  
	 	

 
					
			
	 Name:
	 	  
	 	

 
					
			
	 Title:
	 	  
	 	

 
					
			
	 (Date):
	 	  
	 	

  
 Appendix 1 

 SCHEDULE 1  

Company Capitalization Table 

See attached 

  
 Schedule 1

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