EX-10.1



 Exhibit 10.1 

RESTRICTED STOCK AWARD AGREEMENT 

CEO MARKET-BASED VESTING 

PAYCOM SOFTWARE, INC. 

2014 LONG-TERM INCENTIVE PLAN 

1. Grant of Award. Pursuant to the Paycom Software, Inc. 2014 Long-Term Incentive Plan (the “Plan”) for
Employees, Contractors, and Outside Directors of Paycom Software, Inc., a Delaware corporation (the “Company”), the Company grants to 
  

					
		 	 Chad Richison
	 	
		 	(the “Participant”)	 	

 an Award of Restricted Stock in accordance with Section 6.4 of the Plan. The number of shares of Common Stock awarded under
this Restricted Stock Award Agreement (this “Agreement”) is
                    (                ) shares (the
“Awarded Shares”). The “Date of Grant” of this Award is [             ], 2016. 

2. Subject to Plan; Definitions. 

a. This Agreement is subject to the terms and conditions of the Plan, and the terms of the Plan shall control to the extent not
otherwise inconsistent with the provisions of this Agreement. To the extent the terms of the Plan are inconsistent with the provisions of the Agreement, this Agreement shall control. This Agreement is subject to any rules promulgated pursuant to the
Plan by the Board or the Committee and communicated to the Participant in writing. 
 b. The capitalized terms used herein
that are defined in the Plan shall have the same meanings assigned to them in the Plan; provided, that the following terms shall have the meanings set forth below: 

i. “Appraised Value” means the value ascribed to a share of the subject Equity Securities as set forth
in the most recent written appraisal previously issued by an independent Person selected by the audit committee of the Company nationally recognized as having experience in providing investment banking or similar appraisal or valuation services and
with expertise generally in the valuation of securities; provided, that it being understood that neither the Board nor the audit committee shall have any obligation to obtain any such appraisal more than once per calendar year. 

ii. “Cause” shall have the meaning set forth in that certain Executive Employment Agreement, entered
into on December 30, 2013, by and between the Participant and the Company. 
 iii. “Equity
Securities” means, as applicable, (a) any capital stock, membership interests or other share capital, (b) any securities directly or indirectly convertible into or exchangeable for any capital stock, membership interests or other share
capital or containing any profit participation features, (c) any rights or options directly or indirectly to subscribe for or to purchase any capital stock, membership interests, other share capital or securities containing any profit participation
features or to 







 
subscribe for or to purchase any securities directly or indirectly convertible into or exchangeable for any capital stock, membership interests, other share capital or securities containing any
profit participation features, (d) any share appreciation rights, phantom share rights or other similar rights, or (e) any Equity Securities as defined in clauses (a) through (d) above issued or issuable with respect to the securities referred to in
clauses (a) through (d) above in connection with a combination of shares, recapitalization, merger, consolidation or other reorganization. 

iv. “Equity Securities Value Per Share” means, for any class or series of Equity Securities of the
Company, for any date, the price determined by the first of the following clauses that applies: (a) if such Equity Securities are then listed or quoted on a Trading Market, the arithmetic average of the VWAP of a share of such Equity Securities
on each of the twenty (20) consecutive Trading Days immediately preceding such date; (b) if the Equity Securities are not then listed or quoted for trading on a Trading Market and if prices for such Equity Securities are then reported on the
OTC Bulletin Board (or a similar organization or agency succeeding to its functions of reporting prices), the arithmetic average of the closing bid price per share of the Common Stock so reported on each of the twenty (20) consecutive Trading Days
immediately preceding such date; or (c) in all other cases, the Appraised Value of a share of such Equity Securities. 

v. “SEC” means the Securities and Exchange Commission. 

vi. “TEV Threshold” means $2.65 billion. 

vii. “Total Enterprise Value” means the sum of: (i) the product of (A) the Equity Securities
Value Per Share of a share of Common Stock not subject to vesting or other restrictions multiplied by (B) the number of outstanding shares of Common Stock, less (y) the number of outstanding shares of Restricted Stock or Other Awards of shares
of Common Stock without vesting restrictions, in each case, issued after the date of this Agreement (including outstanding shares of Common Stock resulting from the vesting of such Restricted Stock), and less (z) the number of shares of Common Stock
issued by the Company after the date of this Agreement in connection with any merger, consolidation, share exchange or other transaction in which, in each case, the Company acquires voting securities of another Person or all or any portion of
another Person’s assets; (ii) for each other class or series of Equity Securities of the Company, if any, the product of (A) Equity Securities Value Per Share for such class or series of such Equity Securities of the Company multiplied by (B)
the number of shares of such class or series of such Equity Securities of the Company, less (y) the number of shares of such class or series of such Equity Securities issued under the Plan (or otherwise issued for compensatory purposes) after the
date of this Agreement, and less (z) the number of shares of such class or series of such Equity Securities issued by the Company after the date of this Agreement in connection with any merger, consolidation, share exchange or other transaction in
which, in each case, the Company acquires the voting securities of another Person or all or any portion of another Person’s assets; and (iii) the principal amount of all outstanding funded indebtedness of the Company less the aggregate
amount of cash and cash equivalents of the Company (exclusive of funds held on behalf of clients). 
 viii.
“Trading Day” means each Monday, Tuesday, Wednesday, Thursday and Friday, other than any day on which securities are not traded on the applicable Trading Market or in the applicable securities market. 

  
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 ix. “Trading Market” means the primary securities
exchange on which the Common Stock is listed or quoted for trading on the date in question. 
 x.
“VWAP” means the daily volume weighted average price of a share of the Common Stock for such date on the Trading Market on which the Common Stock is then listed or quoted for trading as reported by Bloomberg L.P. (or
successor thereto) using its “Volume at Price” function (based on a Trading Day from 9:30 a.m. (New York City time) to 4:00 p.m. (New York City time)). 

3. Vesting. Except as specifically provided in this Agreement and subject to certain restrictions and conditions set forth in the
Plan, the Awarded Shares shall vest as follows: one hundred percent (100%) of the Awarded Shares shall vest on the first date, if any, that the Total Enterprise Value equals or exceeds the TEV Threshold, provided that, such date occurs on or before
the sixth (6th) anniversary of the Date of Grant, and provided further that the Participant is employed by (or if the Participant is a Contractor or an Outside Director, is providing services to)
the Company or a Subsidiary on that date. 
 Notwithstanding the foregoing, all Awarded Shares not previously vested shall immediately become vested in full
upon a Termination of Service as a result of the Participant’s death or Total and Permanent Disability. In addition, in the event that (i) a Change in Control occurs, and (ii) this Agreement is not assumed by the surviving corporation or its
parent, or the surviving corporation or its parent does not substitute its own restricted shares, then immediately prior to the effective date of such Change in Control, all Awarded Shares not previously vested shall thereupon immediately become
fully vested. 
 Notwithstanding anything herein to the contrary, in the event of the Participant’s Termination of Service by the Company without
Cause, the unvested Awarded Shares shall remain outstanding for a period of one (1) year following such Termination of Service (but no later than the sixth (6th) anniversary of the Date of Grant)
and shall remain eligible for vesting in accordance with this Section 3; provided, that any Awarded Shares that do not become vested within the one (1) year period immediately following such Termination of Service shall be immediately
forfeited and shall cease to be outstanding. 
 4. Forfeiture of Awarded Shares. Except as otherwise provided in Section
3, Awarded Shares that are not vested in accordance with Section 3 shall be forfeited on the earlier of (i) the sixth (6th) anniversary of the Date of Grant, or (ii)
the date of the Participant’s Termination of Service. Upon forfeiture, all of the Participant’s rights with respect to the forfeited Awarded Shares shall cease and terminate, without any further obligations on the part of the Company. 

5. Restrictions on Awarded Shares. Subject to the provisions of the Plan and the terms of this Agreement, from the Date of Grant
until the date the Awarded Shares are vested in accordance with Section 3 and are no longer subject to forfeiture in accordance with Section 4 (the “Restriction Period”),
the Participant shall not be permitted to sell, transfer, pledge, hypothecate, margin, assign or otherwise encumber any of the Awarded Shares. Except for these limitations, the Committee may in its sole discretion, remove any or all of the
restrictions on such Awarded Shares whenever it may determine that, by reason of changes in applicable laws or changes in circumstances after the date of this Agreement, such action is appropriate. 

  
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 6. Legend. The following legend shall be placed on all certificates issued
representing Awarded Shares: 
 On the face of the certificate: 

“Transfer of this stock is restricted in accordance with conditions printed on the reverse of this certificate.” 

On the reverse: 
 “The
shares of stock evidenced by this certificate are subject to and transferable only in accordance with that certain Paycom Software, Inc. 2014 Long-Term Incentive Plan, a copy of which is on file at the principal office of the Company in Oklahoma
City, Oklahoma. No transfer or pledge of the shares evidenced hereby may be made except in accordance with and subject to the provisions of said Plan. By acceptance of this certificate, any holder, transferee or pledgee hereof agrees to be
bound by all of the provisions of said Plan.” 
 The following legend shall be inserted on a certificate evidencing Common Stock issued
under the Plan if the shares were not issued in a transaction registered under the applicable federal and state securities laws: 

“Shares of stock represented by this certificate have been acquired by the holder for investment and not for resale, transfer or
distribution, have been issued pursuant to exemptions from the registration requirements of applicable state and federal securities laws, and may not be offered for sale, sold or transferred other than pursuant to effective registration under such
laws, or in transactions otherwise in compliance with such laws, and upon evidence satisfactory to the Company of compliance with such laws, as to which the Company may rely upon an opinion of counsel satisfactory to the Company.” 

All Awarded Shares owned by the Participant shall be subject to the terms of this Agreement and shall be represented by a certificate or
certificates bearing the foregoing legend. 
 7. Delivery of Certificates; Registration of Shares. The Company shall deliver
certificates for the Awarded Shares to the Participant or shall register the Awarded Shares in the Participant’s name, free of restriction under this Agreement, promptly after, and only after, the Restriction Period has expired without
forfeiture pursuant to Section 4. In connection with any issuance of a certificate for Restricted Stock, the Participant shall endorse such certificate in blank or execute a stock power in a form satisfactory to the
Company in blank and deliver such certificate and executed stock power to the Company. 
 8. Rights of a Stockholder. Except as
provided in Section 4 and Section 5 above, the Participant shall have, with respect to his Awarded Shares, all of the rights of a stockholder of the Company, including the right to vote the shares, and the right to
receive any dividends thereon, subject to the provisions of this Section 8. Any stock dividends paid with respect to Awarded Shares shall at all times be treated as Awarded Shares and shall be subject to all restrictions placed on
such Awarded Shares; any such stock dividends paid with respect to such Awarded Shares shall vest as the related Awarded Shares become vested. Any cash dividends paid with respect to unvested Awarded Shares shall at all times be subject to the
provisions of this Agreement (including the vesting and forfeiture provisions 

  
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set forth above); any such cash dividends paid with respect to such unvested Awarded Shares shall vest as such Awarded Shares become vested, and shall be paid to the Participant on the date the
Awarded Shares to which such cash dividends relate become vested.
 9. Voting. The Participant, as record holder of the Awarded
Shares, has the exclusive right to vote, or consent with respect to, such Awarded Shares until such time as the Awarded Shares are transferred in accordance with this Agreement; provided that this Section 9 shall not
create any voting right where the holders of such Awarded Shares otherwise have no such right. 
 10. Adjustment to Number of Awarded
Shares. The number of Awarded Shares shall be subject to adjustment in accordance with Articles 11-13 of the Plan. 
 11.
Specific Performance. The parties acknowledge that remedies at law will be inadequate remedies for breach of this Agreement and consequently agree that this Agreement shall be enforceable by specific performance. The remedy of
specific performance shall be cumulative of all of the rights and remedies at law or in equity of the parties under this Agreement. 
 12.
Participant’s Representations. Notwithstanding any of the provisions hereof, the Participant hereby agrees that he or she will not acquire any Awarded Shares, and that the Company will not be obligated to issue any Awarded Shares to
the Participant hereunder, if the issuance of such shares shall constitute a violation by the Participant or the Company of any provision of any law or regulation of any governmental authority. Any determination in this connection by the
Company shall be final, binding, and conclusive. The rights and obligations of the Company and the rights and obligations of the Participant are subject to all Applicable Laws, rules, and regulations. 

13. Investment Representation. Unless the Awarded Shares are issued in a transaction registered under applicable federal and state
securities laws, by his or her execution hereof, the Participant represents and warrants to the Company that all Common Stock which may be purchased and or received hereunder will be acquired by the Participant for investment purposes for his or her
own account and not with any intent for resale or distribution in violation of federal or state securities laws. Unless the Common Stock is issued to him or her in a transaction registered under the applicable federal and state securities laws,
all certificates issued with respect to the Common Stock shall bear an appropriate restrictive investment legend and shall be held indefinitely, unless they are subsequently registered under the applicable federal and state securities laws or the
Participant obtains an opinion of counsel, in form and substance satisfactory to the Company and its counsel, that such registration is not required. 

14. Participant’s Acknowledgments. The Participant acknowledges that a copy of the Plan has been made available for his
review by the Company, and represents that he is familiar with the terms and provisions thereof, and hereby accepts this Award subject to all the terms and provisions thereof. The Participant hereby agrees to accept as binding, conclusive, and
final all decisions or interpretations of the Committee or the Board, as appropriate, upon any questions arising under the Plan or this Agreement. 

15. Law Governing. This Agreement shall be governed by, construed, and enforced in accordance with the laws of the State of
Delaware (excluding any conflict of laws rule or principle of Delaware law that might refer the governance, construction, or interpretation of this agreement to the laws of another state). 

16. No Right to Continue Service or Employment. Nothing herein shall be construed to confer upon the Participant the right to
continue in the employ or to provide services to the Company or any Subsidiary, whether as an Employee or as a Contractor or as an Outside Director, or interfere with or restrict in any way the right of the Company or any Subsidiary to discharge the
Participant as an Employee, Contractor, or Outside Director at any time. 

  
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 17. Legal Construction. In the event that any one or more of the terms, provisions,
or agreements that are contained in this Agreement shall be held by a court of competent jurisdiction to be invalid, illegal, or unenforceable in any respect for any reason, the invalid, illegal, or unenforceable term, provision, or agreement shall
not affect any other term, provision, or agreement that is contained in this Agreement and this Agreement shall be construed in all respects as if the invalid, illegal, or unenforceable term, provision, or agreement had never been contained herein.

 18. Covenants and Agreements as Independent Agreements. Each of the covenants and agreements that are set forth in this
Agreement shall be construed as a covenant and agreement independent of any other provision of this Agreement. The existence of any claim or cause of action of the Participant against the Company, whether predicated on this Agreement or
otherwise, shall not constitute a defense to the enforcement by the Company of the covenants and agreements that are set forth in this Agreement. 

19. Entire Agreement. This Agreement together with the Plan supersede any and all other prior understandings and agreements,
either oral or in writing, between the parties with respect to the subject matter hereof and constitute the sole and only agreements between the parties with respect to the said subject matter. All prior negotiations and agreements between the
parties with respect to the subject matter hereof are merged into this Agreement. Each party to this Agreement acknowledges that no representations, inducements, promises, or agreements, orally or otherwise, have been made by any party or by
anyone acting on behalf of any party, which are not embodied in this Agreement or the Plan and that any agreement, statement or promise that is not contained in this Agreement or the Plan shall not be valid or binding or of any force or effect. 

20. Parties Bound. The terms, provisions, and agreements that are contained in this Agreement shall apply to, be binding upon, and
inure to the benefit of the parties and their respective heirs, executors, administrators, legal representatives, and permitted successors and assigns, subject to the limitation on assignment expressly set forth herein. No person shall be
permitted to acquire any Awarded Shares without first executing and delivering an agreement in the form satisfactory to the Company making such person or entity subject to the restrictions on transfer contained herein. 

21. Modification. No change or modification of this Agreement shall be valid or binding upon the parties unless the change or
modification is in writing and signed by the parties. Notwithstanding the preceding sentence, the Company may amend the Plan to the extent permitted by the Plan. 

22. Headings. The headings that are used in this Agreement are used for reference and convenience purposes only and do not
constitute substantive matters to be considered in construing the terms and provisions of this Agreement. 
 23. Gender and
Number. Words of any gender used in this Agreement shall be held and construed to include any other gender, and words in the singular number shall be held to include the plural, and vice versa, unless the context requires otherwise. 

  
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 24. Notice. Any notice required or permitted to be delivered hereunder shall be
deemed to be delivered only when actually received by the Company or by the Participant, as the case may be, at the addresses set forth below, or at such other addresses as they have theretofore specified by written notice delivered in accordance
herewith: 
 a. Notice to the Company shall be addressed and delivered as follows: 

Paycom Software, Inc. 
 7501 W.
Memorial Rd. 
 Oklahoma City, OK 73142 

Attn: Chief Financial Officer 

b. Notice to the Participant shall be addressed and delivered as set forth on the signature page. 

25. Tax Requirements. The Participant is hereby advised to consult immediately with his or her own tax advisor regarding the
tax consequences of this Agreement, the method and timing for filing an election to include this Agreement in income under Section 83(b) of the Code, and the tax consequences of such election. By execution of
this Agreement, the Participant agrees that if the Participant makes such an election, the Participant shall provide the Company with written notice of such election in accordance with the regulations promulgated under Section 83(b) of the
Code. The Company or, if applicable, any Subsidiary (for purposes of this Section 25, the term “Company” shall be deemed to include any applicable Subsidiary), shall have the right to deduct from all amounts
paid in cash or other form in connection with the Plan, any Federal, state, local, or other taxes required by law to be withheld in connection with this Award. The Company may, in its sole discretion, also require the Participant receiving shares of
Common Stock issued under the Plan to pay the Company the amount of any taxes that the Company is required to withhold in connection with the Participant’s income arising with respect to this Award. Such payments shall be required to be made
when requested by Company and may be required to be made prior to the delivery of any certificate representing shares of Common Stock. Such payment may be made (i) by the delivery of cash to the Company in an amount that equals or exceeds (to avoid
the issuance of fractional shares under (iii) below) the required tax withholding obligations of the Company; (ii) if the Company, in its sole discretion, so consents in writing, the actual delivery by the Participant to the Company of shares of
Common Stock, other than (A) Restricted Stock, or (B) Common Stock that the Participant has acquired from the Company within six (6) months prior thereto, which shares so delivered have an aggregate Fair Market Value that equals or exceeds (to avoid
the issuance of fractional shares under (iii) below) the required tax withholding payment; (iii) if the Company, in its sole discretion, so consents in writing, the Company’s withholding of a number of shares to be delivered upon the vesting of
this Award, which shares so withheld have an aggregate Fair Market Value that equals (but does not exceed) the required tax withholding payment; or (iv) any combination of (i), (ii), or (iii). The Company may, in its sole discretion, withhold
any such taxes from any other cash remuneration otherwise paid by the Company to the Participant. 
 * * * * * * * * * * 

[Remainder of Page Intentionally Left Blank. 

Signature Page Follows] 

  
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 IN WITNESS WHEREOF, the Company has caused this Agreement to be executed by its duly authorized
officer, and the Participant, to evidence his or her consent and approval of all the terms hereof, has duly executed this Agreement, as of the date specified in Section 1 hereof. 

 

			
	 COMPANY:

	
	 Paycom Software, Inc.

		
	 By:
	 	  

	 Name:
	 	  

	 Title:
	 	  




 

			
	 PARTICIPANT:

	
	  

	 Signature

		
	 Name:
	 	 Chad Richison

	Address:	 	  

		 	  



 Signature Page to Restricted Stock Award Agreement – 

CEO Market-Based Vesting