Document:

EX-10.10

 Exhibit 10.10 

EXECUTIVE EMPLOYMENT AGREEMENT 

This Executive Employment Agreement (the “Agreement”) is made and entered into effective as of the 15th day of September, 2017 (the
“Effective Date”), by and between Pluralsight, LLC (the “Company”) and Joseph DiBartolomeo (“Executive”). 

RECITALS 
 Employee
desires to be or is currently employed by the Company as an at-will employee. The Company desires to employ or continue employing Executive and Executive desires to be employed or continue to be employed by the Company on the terms and conditions
set forth herein. 
 This Agreement, together with the Confidentiality, Intellectual Property Assignment and Non-Solicitation Agreement (the
“Confidentiality Agreement”) executed by Executive concurrently herewith and the terms of which are incorporated herein by this reference, shall govern the terms and conditions of employment between the Executive and the Company. As of the
Effective Date, this Agreement and the Confidentiality Agreement shall supersede and negate all previous agreements between the Company and Executive except as expressly set forth herein. 

AGREEMENT 
 NOW THEREFORE,
in consideration of the foregoing, and in consideration of the mutual covenants and agreements set forth in this Agreement, the Company and Executive hereby mutually covenant and agree as set forth below. 

1. Employment. The Company hereby agrees to employ Executive in the position of Chief Revenue Officer, and Executive hereby
accepts employment with the Company, upon the terms and conditions set forth herein. 
 2. Term. Executive shall be
employed by the Company from the Effective Date until Executive’s employment with the Company is terminated in accordance with Section 7 below (the “Term”). 

3. Duties. 
 3.1
General Duties. Executive will have and perform those duties and responsibilities which are appropriate and customary to the position held by Executive and assigned or delegated to Executive from time to time by the Company’s CEO (the
“CEO”). The CEO may, in its sole discretion, alter, modify, or change Executive’s duties, offices, positions, responsibilities and obligations set forth in this Agreement at any time. 

3.2 Performance. To the best of Executive’s ability and experience, Executive will at all times loyally and conscientiously perform
all duties, and discharge all responsibilities and obligations, required of and from Executive pursuant to the terms hereof and to the reasonable satisfaction of the Company. During the Term of this Agreement, Executive will be a

 
full-time employee of the Company and will devote substantially all of his or her business time, energy, skill, and attention to the business of the Company, and the Company will be entitled to
all of the benefits and profits arising from or incident to all such work, services, and advice of Executive rendered to the Company. Executive shall faithfully adhere to, and execute, and fulfill all lawful policies established from time to time by
the Company as well as all applicable federal, state, and local laws and regulations relating to the business of the Company and its associated operations. 

3.3 Undivided Attention. During the Term, Executive agrees not to perform services for any other person, business, or entity unrelated
to the Company, whether as an employee, independent contractor, or otherwise without the prior written consent of the CEO; it being understood that the CEO’s consent is likely to be granted where the services are in the nature of engaging in
non-profit charitable/ civic activities or serving as an advisor or director to companies that do not compete with the business of the Company, provided that such pursuits or activities do not materially interfere with the services required to be
rendered to the Company hereunder; provided, however, that nothing in this Agreement shall prohibit Executive’s pursuit of personal investment opportunities, provided that such pursuit does not interfere with the services required to be
rendered to the Company hereunder, is consistent with the Company’s policies regarding conflicts of interest, including without limitation Section 8 hereof, and does not in any way violate or infringe the covenants set forth in this
Agreement or the Confidentiality Agreement. 
 4. Compensation and Related Matters. 

4.1 Base Salary. In consideration for services rendered to the Company as provided herein, the Company will pay to Executive a base
salary at a rate of $350,000.00 per annum, payable in accordance with the Company’s standard payroll practices in effect from time to time (the “Base Salary”). The Base Salary may be increased or decreased from time to time in
accordance with normal business practices of the Company. 
 4.2 Bonus. During the term of this Agreement, Executive shall be eligible
to participate in any annual bonus plan made available by the Company to its employees generally, which plan may be modified, amended or terminated at any time, in the Company’s discretion. Individual goals and performance assessment, and
discretionary bonus payments, if any, will be determined by the Company’s CEO or Board of Directors (the “Board”). If Executive’s employment with the Company terminates for any reason, Executive shall not be entitled to any
portion of the bonus applicable to the year in which Executive was terminated or for any calendar year thereafter. 
 4.3 Expenses.
Executive will be entitled to receive prompt reimbursement for all reasonable expenses incurred by Executive in performing services hereunder, including expenses of travel while away from home on business in the service of the Company, provided that
all expenses are incurred, documented, and accounted for in accordance with the policies and procedures as are established from time to time by the Company. 

 4.4 Executive Benefit Plans. During the term of this Agreement, Executive is entitled to
participate in any employee benefit plans that may be made available by the Company to its employees generally, including, but not limited to, cafeteria plans and health, life, dental, or other insurance plans as may be in effect and/or modified
from time to time and in accordance with and subject to the qualification requirements and the terms, conditions, and limitations established from time to time for individual participation in such plans. 

4.5 Paid Leave. Executive will be eligible to receive paid leave for vacation and/or sick leave consistent with policies adopted by the
Company from time to time. Executive also will be entitled to all paid holidays given by the Company to its employees generally. Scheduling and use of paid leave and, if applicable, accrual of and compensation for unused paid leave, will be subject
to the Company’s policies and procedures, as modified from time to time. 
 4.6 Employee Perquisites. During the term of this
Agreement, Executive is entitled to participate in any employee perquisites that may be made available by the Company to its employees generally, including but not limited to (i) gym and wellness reimbursement of up to $50 per month;
(ii) snacks, drinks and other food policies as may be in effect from time to time; and (iii) tuition reimbursement in pre-approved courses at pre-approved locations of up to $1,500 per semester or $3,000 per year. All perquisites and
reimbursements referenced in this Section 4.6 are subject to change or discontinuation at any time in accordance with the normal business practices of the Company. 

4.7 Deductions; Taxes. The Company shall have the right to deduct from the compensation due to Executive under this Agreement any and
all sums required for Social Security, Medicare and other income withholding taxes and for any other federal, state, or local tax or charge which may be hereafter enacted or required by law as a charge on compensation of Executive. Neither the
Company, nor any of its subsidiaries, affiliates, members, officers, managers, employees, or agents (a) has made any representation, assurance or guarantee to Executive regarding the tax treatment of any compensation to be paid to Executive
hereunder; or (b) shall have any obligation or liability to indemnify, gross-up or reimburse Executive for, or hold him or her harmless against, any taxes or tax-related penalties or interest applicable to compensation earned by Executive under
this Agreement or otherwise, including without limitation any taxes incurred under Internal Revenue Code (the “Code”) Sections 409A or 4999. 

4.8 Corporate Housing. The Company will provide a housing reimbursement of up to $2,500 per month. 

5. Incentive Units. Nothing in this Agreement shall alter, limit, or void the respective rights and obligations of the parties
with regard to any grant of incentive units to Executive under any Pluralsight Holdings, LLC Incentive Unit Offer Letter (the “Incentive Unit Offer Letter”). 

6. Conflict of Interest. Executive will not become involved in a situation which reasonably might create or appear to create a
conflict of interest, including but not limited to being connected directly or indirectly with any business (as owner, officer, director, manager, participant, licensee, consultant, shareholder, or the recipient of wages) which is involved with any
aspect of Executive’s duties or which is in direct or indirect competition with the Company. Executive will report immediately any circumstances or situations arising in the future that might involve Executive or appear to involve Executive in
a conflict of interest, including without limitation the reporting of gifts, entertainment, or any other personal favors given to or received from anyone with whom the Company has or is likely to have any business dealings which go beyond common
courtesies usually associated with accepted business practices. 

 7. Termination. The employment of Executive hereunder shall be “at will”
and may be terminated at any time, for any or no reason, by either the Company or Executive on thirty (30) days’ written notice to the other party. Notwithstanding the foregoing, (i) the Company may terminate Executive’s
employment immediately and without prior notice for Cause (as defined below) or at the Company’s sole discretion by providing Executive with pay in lieu of the 30-day notice period; and (ii) the Executive may terminate the employment
immediate and without prior notice for Good Reason (as defined below) and satisfaction of the criteria set forth in the definition of Good Reason. In the event Executive terminates this Agreement for any reason other than immediately for Good Cause,
then during the 30-day notice period, the Company may in its sole discretion terminate Executive’s employment at any time, in which case all obligations of the Company to Executive shall cease except as set forth in Section 9 below.

 8. Certain Defined Terms. For purposes of this Agreement: 

8.1 “Cause” shall mean (i) Executive’s willful conduct that is materially injurious to the Company or any of its affiliates
(whether monetary or otherwise) or the commission of any other material act or omission involving dishonesty with respect to the Company; (ii) Executive’s conviction of a felony or of a misdemeanor involving a crime of moral turpitude;
(iii) Executive’s fraud, embezzlement, or misappropriation of any money, assets, or other property of the Company; (iv) Executive’s insubordination or other willful refusal to comply with any lawful request of the Board,
including without limitation failure to cooperate in any investigation conducted and/or undertaken by the Company that has reasonable and legitimate objectives; (v) Executive’s material breach of any of his or her obligations, duties, or
agreements to the Company, including without limitation this Agreement or the Confidentiality Agreement, which breach cannot be cured or, if capable of being cured, is not cured within thirty (30) days after receipt of written notice of the
need to cure from the CEO, CFO or General Counsel acting under the authority of the Board); (vi) Executive’s death; and/or (vii) Executive’s Disability (as defined below). 

8.2 “Disability” shall mean any physical or mental incapacitation that results in Executive’s inability to perform substantially
all of his or her duties and responsibilities for the Company for a total of ninety (90) consecutive working days, as determined in accordance with the Family and Medical Leave Act, or an aggregate of one hundred eighty (180) working days
during any twelve-month period, as determined by the CFO in his or her good faith judgment. 
 8.3 “Good Reason” shall mean
(i) a material adverse change in Executive’s job duties or authorities, including demotion or change in line of reporting, without Executive’s advance written consent; (ii) a reduction in the Base Salary without Executive’s
advance written consent; and/or (iii) the Company’s material breach of this Agreement. Notwithstanding the foregoing, any act or failure to act by the Company shall not be deemed material unless the Company has failed to cure such act or
failure to act within thirty (30) days of the date that the Company is provided written notice by Executive stating in reasonable detail the grounds for Executive’s determination of such act or failure to act, and Executive resigns from
employment within thirty (30) days after the expiration of the Company’s cure period. 

 9. Effect of Termination. 

9.1 Continuing Obligations. In the event Executive’s employment is terminated for any reason, all obligations of the Company and
Executive under this Agreement shall cease, except that the terms of Section 10 and any other provision which by its terms is so intended shall survive such termination. Upon such termination, Executive or his or her estate (in the event of
Executive’s death) shall be entitled to receive any applicable compensation, benefits, and reimbursements set forth in Section 4 through the date of termination. Executive acknowledges that upon termination of Executive’s employment,
Executive is entitled to no other compensation, severance, or other benefits other than those specifically set forth in this Agreement and in the Incentive Unit Offer Letter. 

9.2 Termination Without Cause / For Good Reason. If the Company terminates this Agreement without Cause, or if Executive terminates this
Agreement for Good Reason, then subject to Executive’s execution and delivery to the Company within a time period specified by the Company after Executive’s effective date of termination (“Termination Date”) of a separation
agreement and release of all claims (“Separation Agreement”) in a form acceptable to the Company and Executive’s non-revocation of such Separation Agreement: (i) the Company shall pay Executive severance pay in an amount equal to
$200,000.00, less applicable withholdings (“Severance Payment”); and (ii) if Executive properly elects continuation coverage under the Company’s group medical insurance plan pursuant to Sections 601 through 607 of the Employee
Retirement Income Security Act of 1974, as amended (“COBRA”), the Company will pay that percentage of the premium for such medical plan coverage which the Company bears for similarly situated active Company employees and their enrolled
family members immediately prior to the Termination Date through the earlier of (a) six (6) months from the Termination Date; (b) the date Executive first becomes eligible for coverage under any group health plan maintained by another
employer of Executive or his or her spouse; or (c) the date such COBRA continuation coverage otherwise terminates as to Executive under the provisions of the Company’s group medical insurance plan (“COBRA Coverage”). Except as
otherwise provided below, the Severance Payment shall be payable in equal periodic installments in accordance with the Company’s payroll practices and subject to withholding taxes on each regular payroll date of the Company commencing on the
applicable Severance Commencement Date and continuing through the six month anniversary thereof (the “Severance Period”). The applicable Severance Commencement Date shall be the first regularly scheduled Company payroll date that is at
least 45 days after the Executive’s Termination Date. Collectively, the Severance Payment and COBRA Coverage shall be referred to herein as the “Severance Benefits.” 

9.2.1 Notwithstanding the foregoing, Executive shall be entitled to Severance Benefits in accordance with this Section 9.2 only so long
as Executive has not breached any of the provisions of the Separation Agreement, the Confidentiality Agreement, or Section 10 of this Agreement. 

 9.2.2 Notwithstanding the foregoing, if any equity securities of the Company or of any direct or
indirect entity that is an affiliate of the Company is “publicly traded” within the meaning of Code Section 409A(a)(2)(B) and Executive is a “specified employee” (as defined in Treasury Regulation Section 1.409A-1(i))
at the time this Agreement is terminated, then subject to Section 9.2.3 below, any Severance Payments otherwise payable to Executive during the first six months and one day following the date of his or her separation from service pursuant to
this Section 9.2.2 shall be deferred until the date that is six months and one day following such separation from service, and if such payments are required to be so deferred, the first payment shall be in an amount equal to the total amount to
which Executive would otherwise have been entitled to during the period following the date of termination if the deferral had not been required, less any portion of the Executive’s premium the Company paid on his or her behalf for COBRA
coverage as set forth above. 
 9.2.3 Notwithstanding Section 9.2.2, any portion of the Severance Payments payable hereunder that do
not exceed two times the lesser of (i) the sum of Executive’s annualized compensation based on the Executive’s annual rate of pay for the year immediately preceding the year of termination (or for the year of termination if
Executive’s employment with Company commenced in the year of termination), adjusted for any increase in pay that was expected to continue indefinitely if the termination had not occurred and (ii) the Code Section 401(a)(17) limit
applicable in the year of termination, shall be treated as separate benefits and payments for purposes of Code Section 409A, shall not be subject to the six-month and one-day delay rule in Section 9.2.2, and shall be paid as otherwise
provided in Section 9.2 
 9.2.4 Notwithstanding the foregoing, the Severance Payment payable pursuant to this Section 9.2 shall
be reduced by the amount of any compensation Executive earns with respect to any other employment during the Severance Period; provided that Executive shall have no duty or obligation to seek other employment during the Severance Period or otherwise
mitigate damages hereunder. Notwithstanding any other provision of this Agreement, if, following the termination of his or her employment, Executive is entitled to payments or other benefits under this Section 9.2, but the Company later
determines that Cause with respect to Executive exists or existed on, prior to, or after such termination of Executive, then (i) Executive shall not be entitled to any Severance Benefits pursuant to this Section 9.2, (ii) any and all
Severance Benefits pursuant to this Section 9.2 shall cease, and (iii) any Separation Payments previously paid to Executive shall be returned immediately to the Company by Executive. 

9.2.5 The Severance Benefits shall not constitute, and are not intended to constitute, an employee welfare benefit plan, a welfare plan, an
employee pension benefit plan, a pension plan or any other plan under the Employee Retirement Income Security Act of 1974, as amended, 29 U.S.C. §§ 1001 et seq. (ERISA). 

9.3 Termination With Cause / Without Good Reason. If the Company terminates this Agreement for Cause or if Executive terminates this
Agreement without Good Reason, then the Company shall pay Executive only his or her Base Salary due and owing through the date of termination of employment and shall have no obligation to pay any further sums to Executive other than Executive’s
business expenses that shall be reimbursed in accordance with Section 4.3 above or as otherwise required under the Incentive Unit Offer Letter. 

 9.4 Return of Company Property. Upon ceasing employment with the Company for any reason,
Executive shall immediately return to the Company, and Executive shall have absolutely no right to use, any equipment and/or tangible property entrusted to Executive by the Company. 

10. Restrictive Covenants. 

10.1 Acknowledgment. Executive acknowledges that (i) the Company has spent substantial time, effort, and money to develop the
Company’s goodwill; recruitment and training of personnel, customer, author, and supplier relations; Confidential Information (as that term is defined in the Confidentiality Agreement); and its worldwide business in the educational technology
and online software development training industry (the “Training Industry”); (ii) the Company’s customers, suppliers, authors, and independent contractors are and shall remain the sole and exclusive customers, suppliers, authors,
and independent contractors of the Company; (iii) any new business or improvement in customer, supplier, author, or independent contractor relations attributable to Executive during Executive’s employment is for the sole benefit of the
Company; (iv) the Company has and will continue to make a significant investment in the training and education of Executive, regardless of job title and department; (v) Executive will render services to the Company that are special,
unique, and extraordinary; (vi) Executive’s efforts will contribute to the goodwill of the Company; and (vii) Executive has the means to support Executive and Executive’s dependents other than by engaging in the Training Industry
as restricted herein. 
 10.2 Covenant Period. For purposes of this Agreement, the term “Covenant Period” shall be defined
as beginning on the earlier of the date of Executive’s acceptance of an offer of employment with the Company or the Effective Date of this Agreement and continuing for one (1) year from the date of termination of Executive’s
employment with the Company, whether Executive retires, resigns, quits, is fired or discharged, or otherwise ceases employment with the Company. 

10.3 Covenant Not to Compete. As a material term of this Agreement and to protect the goodwill, the Confidential Information, and the
business of the Company, Executive agrees that during the Term of this Agreement, Executive does not, and will not, have any relationship with any customer, supplier, or independent contractor of the Company that is independent of Executive’s
role as an Executive of the Company, unless the Company has given its prior written consent. Executive further agrees that during the Covenant Period, Executive shall not, anywhere in the world which engages in the Training Industry, either
individually or on behalf of or with any Person, directly or indirectly (a) compete with or against the Company or engage in any aspect of the Training Business in competition with the Company; (b) directly or indirectly own, manage,
operate, control, be employed by, or provide management or consulting services to any individual, firm, corporation, entity, or organization (each, a “Person”) (other than the Company, or any affiliate of the Company, or as a stockholder
of less than 5% of the equities of a publicly traded corporation) that competes with, or is a competitor of, the Company (“Competing Person”); (c) discuss the possibility of employment or other relationship with any Competing Person;
(d) render or provide any services to or for any Competing Person; or (e) discuss or otherwise deal with any customer, supplier, or independent contractor of the Company regarding the extent or nature of the present or future business of
any customer, supplier, or independent contractor with the Company. 

 10.4 Reformation. The Company intends to restrict Executive under this Agreement only to
the extent necessary for the protection of the Company’s legitimate business interests. The Company and Executive agree that the scope, duration, and geographic area provisions are reasonable. In the event a court of competent jurisdiction
concludes that any provision of this Agreement is too restrictive, such provision(s) shall nevertheless be valid and enforceable to the fullest extent permitted by such court, and such provision(s) shall be reformed to the maximum scope, time, or
geographic limitations determined appropriate by such court. 
 10.5 Remedies. The Company and Executive intend that the covenants of
Executive are separate and independent of any covenants of the Company in this Agreement or elsewhere, and any breach by the Company shall not justify or excuse any breach by Executive. In the event of an actual or threatened breach of this
Section 10, Executive specifically acknowledges that the Company will suffer irreparable damage and other damages beyond those that can be calculated, for which the Company has no adequate remedy at law. Executive therefore acknowledges that
the Company shall be entitled to ex parte injunctive relief, both preliminary and permanent, immediately and permanently restraining Executive from such continuing or threatened breach. Executive hereby expressly waives any and all right to prior
notice or to security in connection with temporary injunctive relief on behalf of the Company and to security in connection with permanent injunctive relief on behalf of the Company. Executive shall also remain liable for any damages sustained by
reason of any actual or threatened breach by Executive of Sections 10. The exercise of one or more of the rights or remedies provided by this Agreement or otherwise shall not preclude the exercise of any other rights also provided. 

11. Rights of Other Persons. Executive shall not disclose to the Company, or use in the performance of his or her work or
responsibilities for the Company, any proprietary or confidential information, any trade secret, or any other intellectual property of (a) Executive, (b) any former employer of Executive, or (c) any other Person, unless the Company
has received written authorization from Executive or such former employer or other Person and the Company has instructed Executive in writing to do so. The provisions of this Section 11 are not intended to create any rights as an intended or
third-party beneficiary for any third party. 
 12. Executive’s Representations and Warranties. Executive
acknowledges, represents and warrants that the Recitals above are true and correct, and that Executive has read and understands the terms of this Agreement and has had the opportunity, if Executive so desires, to consult with independent legal
counsel. Executive further warrants and represents that Executive’s employment with the Company will not conflict with or be constrained by any prior employment or consulting agreement with any other Person, including but not limited to any
prior employer. 
 13. Subpoena; Court Order; Other Legal Requirement. If Executive is requested, under the terms of a subpoena
or order or other compulsory instrument issued by or under the authority of a court or arbitrator(s) of competent jurisdiction or by a governmental agency, or is advised in writing by counsel for any such party that there is otherwise a legal
obligation to 

 
disclose (i) all or any part of the Confidential Information, (ii) the fact that the Confidential Information has been made available to Executive, or (iii) any of the terms,
conditions, or other facts with respect to Executive’s employment with the Company or the services provided by Executive to the Company, Executive agrees to, at the Company’s expense: (1) provide the Company with prompt written notice
of the existence, terms, and circumstances surrounding such request or requirement; (2) consult with the Company on the advisability of taking steps to resist or narrow that request; (3) if disclosure of Confidential Information is
required, furnish only such portion of the Confidential Information as Executive is advised in writing by Executive’s counsel is legally required to be disclosed; and (4) cooperate with the Company, at the request of the Company and at the
Company’s expense, in its efforts to obtain an order excusing the Confidential Information from disclosure, or an order or other reliable assurance that confidential treatment will be accorded to that portion of the Confidential Information
that is required to be disclosed. 
 14. Post-Employment Cooperation. During Executive’s employment and for a period of
two (2) years after the termination of Executive’s employment with the Company for any reason, Executive, in good faith and using diligent efforts, shall reasonably cooperate and assist the Company, at the Company’s sole cost and
expense, in any dispute, controversy, or litigation in which the Company may be involved (excluding any such proceeding in which Executive is an adverse party), including without limitation Executive’s participation in any court, arbitration,
or other proceedings, the giving of testimony, the signing of affidavits or declarations, or such other reasonable cooperation and assistance as the Company or counsel for the Company may reasonably request. 

15. Miscellaneous. 

15.1 Severability. In the event that a court of competent jurisdiction determines that any portion of this Agreement is in violation of
any statute or public policy, then only the portions of this Agreement which violate such statute or public policy shall be stricken. All portions of this Agreement which do not violate any statute or public policy shall continue in full force and
effect. Further, any court order striking any portion of this Agreement shall modify the stricken terms to give as much effect as possible to the intentions of the parties under this Agreement. 

15.2 Notices. Any notice required by this Agreement shall either be hand-delivered or sent by registered or certified mail, return
receipt requested, to Executive’s residence or business address last known to the Company and to the Company’s regular business address last known to Executive or to such other address as a party may specify to the other in writing. Mailed
notices shall be deemed delivered three days after the date of mailing. 
 15.3 New Employer Notification. Following the termination
of this Agreement, Executive expressly consents to allow the Company to notify Executive’s subsequent employer(s) about the Company’s rights and Executive’s obligations under this Agreement. 

 15.4 Governing Law and Mandatory Venue. This Agreement shall be governed by the laws of
the State of Utah without regard to any conflict of law provisions. All claims or disputes arising hereunder or in any way relating to Executive’s employment with the Company shall be subject to the exclusive jurisdiction of the state or
federal courts situated in Salt Lake County, State of Utah, and each party hereby submits himself/herself/itself to the personal jurisdiction and mandatory venue of such courts. If any party violates this provision and files suit in another forum,
the other party shall be entitled to anti-suit injunctive relief in the state and federal courts situated in Salt Lake County, State of Utah, enjoining the action in the improper forum. 

15.5 Successors and Assigns. The rights and obligations of the Company under this Agreement shall inure to the benefit of and shall be
binding upon the successors and assigns of the Company. Executive agrees that this includes, but is not limited to, Section 10. This Agreement is for the unique personal services of Executive, and Executive shall not be entitled to assign any
of Executive’s rights or obligations hereunder. 
 15.6 Entire Agreement; Amendment. This Agreement constitutes the entire
agreement and understanding between the parties with respect to the subject matter hereof, and except as expressly stated herein, supersedes all prior agreements and understandings with respect thereto. Notwithstanding any Utah statutory or common
law to the contrary, this Agreement can be amended or modified only in a writing signed by Executive and the CFO, whether or not a claimed modification is supported by separate consideration. 

15.7 No Waiver. No waiver by either party at any time of any breach by the other party of, or compliance with, any condition or
provision of this Agreement to be performed by the other party shall be deemed a waiver of similar or dissimilar provisions or conditions at the same time or any prior or subsequent time. 

15.8 Headings. The headings herein contained are for reference only and shall not affect the meaning or interpretation of any provision
of this Agreement. 
 15.9 Counterparts. This Agreement may be executed in one or more counterparts, each of which shall be deemed to
be an original but all of which together will constitute one and the same instrument. Facsimile, PDF or other electronically delivered copies of signature pages to this Agreement shall be treated between the parties as original signatures for all
purposes. 
 15.10 Attorneys’ Fees. Notwithstanding any Utah statutory or common law to the contrary, in the event of any action
at law or in equity, whether relating to this Agreement or to Executive’s employment with the Company or the termination thereof, each party shall pay its/his/her own attorney’s fees incurred in prosecuting or defending any such action and
hereby waives any right to seek attorney’s fees from the other party hereto. 
 15.11 Code Section 409A. To the extent any
payments under this Agreement are subject to the provisions of Code Section 409A, it is intended that the Agreement will comply fully with and meet all the requirements of Code Section 409A. Notwithstanding anything in this Agreement to
the contrary, the Employee acknowledges and agrees that neither the Company nor its subsidiaries, affiliates, owners, directors, managers, officers or other agents makes or has made any representation, warranty, covenant or commitment to the
Employee 

 
regarding the tax treatment of any compensation or other benefits provided to the Employee, including without limitation any representation, warranty, covenant or commitment relating to Code
Section 409A. Neither the Company, nor its subsidiaries, affiliates, owners, directors, managers, officers or other agents, shall have any obligation or liability to reimburse or indemnify the Employee for, or hold the Employee harmless
against, any taxes imposed on the Employee under the Code or otherwise. 
 16. Waiver of Trial by Jury. The Company and
Executive hereby irrevocably waive any and all constitutional, statutory, and other rights to a trial by jury in any and all actions or proceedings arising from or in any related to this Agreement or to Executive’s employment with the Company,
including without limitation claims for breach of express or implied contract, discrimination, termination in violation of public policy, whistleblowing, defamation, and emotional distress. 

 IN WITNESS WHEREOF, the parties have executed this Agreement as of the Effective Date. 

 

			
	THE COMPANY:
	
	Pluralsight, LLC

 
			
		
	By:	 	 /s/ Aaron Skonnard

			
	Name: Aaron Skonnard
	Its: Chief Executive Officer
	
	EXECUTIVE:
	
	 /s/ Joseph DiBartolomeo

	Joseph DiBartolomeoEX-10.11

 Exhibit 10.11 

PLURALSIGHT HOLDINGS, LLC 

May 30, 2016 
 Gary Crittenden 

Dear Mr. Crittenden: 
 This letter agreement
(this “Agreement”) confirms our understanding that Pluralsight Holdings, LLC, a Delaware limited liability company (the “Company”, “we”, or “us”), has engaged you to act in the capacity and to provide the
services to the Company as set forth below, upon the terms and conditions set Forth below. For your information, the controlling instrument with respect to the business, activities and governance of the Company is the Amended and Restated Limited
Liability Company Agreement of Pluralsight Holdings, LLC dated as of March 14, 2016, as amended, modified, or supplemented from time to time, a copy of which has been provided to you (the “LLC Agreement”). Capitalized terms used in
this Agreement and not otherwise defined herein shall have the meanings as set forth in the LLC Agreement. 
 1. Capacity; Services.
You shall be a member of the Board of Managers (the “Board”) of the Company with the authority and duties as set forth in the LLC Agreement and as are normally associated with that position. 

2. Unit Award. As consideration for your service as a member of the Board, the Company will award or grant to you 209,000 Incentive
Units (representing approximately 0.20%, in total, of the aggregate outstanding Units of the Company on a fully-diluted basis as of the date hereof). The Incentive Units will be subject to the terms and conditions of the LLC Agreement, the
Pluralsight Holdings, LLC Incentive Unit Plan dated as of May 24, 2013, as amended, modified, or supplemented from time to time, and an Incentive Unit Offer Letter between you and the Company (the “Offer Letter”). We anticipate that
the strike price for your Incentive Units (as set forth in the Offer Letter) will be an amount equal to $9.42 per Incentive Unit and your applicable “Catch-up Amount” (as defined in the LLC
Agreement) is $4.27 per Incentive Unit, subject to review and confirmation from our tax, legal, and accounting representatives, and subject to Board approval. Additionally, we anticipate that your units will vest over the course of three years on a
quarterly basis, beginning on July 1, 2016 (all as further set forth in the Offer Letter). 
 3. Reimbursement of Expenses. The
Company agrees to reimburse you for reasonable out-of-pocket expenses incurred by you for attendance at each meeting of the Board and for such additional reasonable out-of-pocket expenses incurred by you on behalf of the Company in connection with the services provided pursuant to this Agreement as are approved in advance by the Company.
Reimbursement of out-of-pocket expenses will be paid promptly by the Company after receipt of reasonable documentation covering such expenses. 

 

 4. Information; Confidentiality. 

(a) The Company understands and agrees that in performing the services hereunder you will use and rely upon the information provided by the
Company and its advisors and that you do not assume responsibility for independent verification of any information, whether publicly available or otherwise furnished to you concerning the Company including, without limitation, any financial
information, forecasts or projections, considered in connection with the rendering of your services. Accordingly, you shall he entitled to assume and rely upon the accuracy and completeness of all such information and are not required to conduct a
physical inspection of any of the properties or assets, or to prepare or obtain any independent evaluation or appraisal of any of the assets or liabilities of the Company (except to the extent required to satisfy your fiduciary responsibilities).

 (b) During the term of this Agreement, you will have access to and become acquainted with confidential information of the Company and/or
any of its subsidiaries, including among other things customer relationships, processes, and compilations of information, records and specifications, which are owned by the Company or any of its subsidiaries. You shall not use or disclose any of the
Company’s or any of its subsidiaries confidential information in any way that is detrimental to the interests of the Company or any of its subsidiaries, directly or indirectly, either during or after the term of this Agreement, except as
required in the course of this Agreement. You agree to use reasonable efforts to ensure that your employees, agents, and representatives similarly maintain the confidentiality of such proprietary and confidential information of the Company and its
subsidiaries. 
 5. Indemnity. The Company agrees to indemnify and hold you harmless to the full extent allowed by law and as set
forth in the LLC Agreement against all expense, liability, and loss (including attorneys’ fees, judgments, fines, excise taxes or penalties and amounts paid in settlement) reasonably incurred by you in connection with your engagement hereunder;
provided, however, there shall be excluded from such indemnification any such expense, liability, and loss (a) for acts or omissions involving actual fraud or willful misconduct or (b) with respect to any transaction from which you derived
improper personal benefit. 
 6. Term. Your services hereunder and the term of this Agreement may be terminated at any time
(a) by you, upon written notice to the Company, or (b) by the Members of the Company, as provided in the LLC Agreement. 
 7.
Notice. All notices, requests, consents, claims, demands, waivers and other communications hereunder shall be in writing and shall be deemed to have been given: (a) when delivered by hand (with written confirmation of receipt);
(b) when received by the addressee if sent by a nationally recognized overnight courier (receipt requested); (c) on the date sent by facsimile or e-mail of a PDF document (with confirmation of
transmission) if sent during normal business hours of the recipient, and on the next Business Day if sent after normal business hours of the recipient; or (d) on the third day after the date mailed, by certified or registered mail, return
receipt requested, postage prepaid. Such communications must be sent to the respective parties at the addresses indicated below (or at such other address for a party as shall be specified in a notice given in accordance with this Section 7).

  
 -2- 

 If to you: 

Gary Crittenden 
 If to the
Company: 
 Pluralsight Holdings, LLC 

182 North Union Avenue 

Farmington, Utah 84025 

Attention: Legal Counsel 
 8.
Independent Contractor. In providing the services hereunder, you are acting as an independent contractor and it is expressly understood and agreed that this Agreement is not intended to create, and does not create, any partnership, agency,
joint venture or similar relationship and that no party has the right or ability to contract for or on behalf of any other party or to effect any transaction for the account of any other party. Nothing herein shall be construed to an
employee/employer relationship. Neither party hereto shall have any express or implied right or authority to assume or create any obligations on behalf of or in the name of the other party or to bind the other party to any contract, agreement or
undertaking with any third party. Nothing in this Agreement shall be deemed or construed to enlarge your fiduciary duties and responsibilities, if any, including without limitation in your capacity as a member of the Board. 

9. Entire Agreement; Amendment and Modification; Waiver. This Agreement constitutes the entire agreement between the parties hereto with
regard to the subject matter hereof, superseding all prior understandings and agreements whether written or oral. This Agreement may only be amended, modified or supplemented by an agreement in writing signed by each party hereto. No waiver by any
party of any of the provisions hereof shall be effective unless explicitly set forth in writing and signed by the party so waiving. Except as otherwise set forth in this Agreement, no failure to exercise, or delay in exercising, any rights, remedy,
power or privilege arising from this Agreement shall operate or be construed as a waiver thereof, nor shall any single or partial exercise of any right, remedy, power or privilege hereunder preclude any other or further exercise thereof or the
exercise of any other right, remedy, power or privilege. 
 10. Successors and Assigns. This Agreement shall be binding upon and inure
to the benefit of the parties and their respective successors and assigns. However, neither this Agreement nor any of the rights of the parties hereunder may otherwise be transferred or assigned by any party hereto, except that if the Company shall
merge or consolidate with or into, or sell or otherwise transfer substantially all its assets to, another company which assumes the Company’s obligations under this Agreement, the Company may assign its rights hereunder to that company. Any
attempted transfer or assignment in violation of this Section 10 shall be void. 

  
 -3- 

 11. Legal Matters. 

(a) Governing Law. This Agreement will be governed by the internal laws of the State of Delaware without giving effect to any choice or
conflict of law provision or rule. 
 (b) Jurisdiction. Any legal suit, action or proceeding arising out of or based upon or relating
to this Agreement or the transactions contemplated hereby shall be instituted in the federal courts of the United States of America or the courts of the State of Utah in each case located in the City of Salt Lake and County of Salt Lake, and each
party irrevocably submits to the exclusive jurisdiction of such courts in any such suit, action or proceeding. Service of process, summons, notice or other document by certified mail in accordance with Section 7 shall be effective service of
process for any suit, action or other proceeding brought in any such court. The parties irrevocably and unconditionally waive any objection to the laying of venue of any suit, action or proceeding in such courts and irrevocably waive and agree not
to plead or claim in any such court that any such suit, action or proceeding brought in any such court has been brought in an inconvenient forum. 

(c) Waiver of Trial by Jury. Each party acknowledges and agrees that any controversy that may arise under this Agreement is likely to
involve complicated and difficult issues and, therefore, each such party irrevocably and unconditionally waives any right it may have to a trial by jury in respect of any legal action arising out of or relating to this Agreement or the transactions
contemplated hereby. Each party to this Agreement certifies and acknowledges that (i) no representative of any other party has represented, expressly or otherwise, that such other party would not seek to enforce the foregoing waiver in the
event of a legal action, (ii) such party has considered the implications of this waiver, (iii) such party makes this waiver voluntarily, and (iv) such party has been induced to enter into this Agreement by, among other things, the
mutual waivers and certifications in this Section 11(e). 
 (d) Equitable Remedies. The parties agree that irreparable damage
would occur if any provision of this Agreement were not performed in accordance with the terms hereof and that the parties shall be entitled to equitable relief, including injunctive relief or specific performance of the terms hereof, in addition to
any other remedy to which they are entitled at law or in equity. 
 (e) Fees and Costs. In the event that any party institutes any
legal suit, action or proceeding against the other party to enforce the covenants contained in this Agreement (or obtain any other remedy in respect of any breach or this Agreement) or otherwise arising out of or relating to this Agreement, the
prevailing party in the suit, action or proceeding shall be entitled to receive in addition to all other damages to which it may be entitled, the costs incurred by such party in conducting the suit, action or proceeding, including reasonable
attorneys’ fees and expenses and court costs. 
 12. Counterparts. This Agreement may be executed in counterparts, each of which
shall be deemed an original, but all of which together shall be deemed to be one and the same agreement. A signed copy of this Agreement delivered by facsimile, e-mail or other means of electronic transmission
shall be deemed to have the same legal effect as delivery of an original signed copy of this Agreement. 

  
 -4- 

 13. No Strict Construction. The parties to this Agreement have participated jointly in the
negotiation and drafting of this Agreement. In the event an ambiguity or question of intent or interpretation arises, this Agreement will be construed as if drafted jointly by the parties, and no presumption or burden of proof will arise favoring or
disfavoring any party by virtue of the authorship of any of the provisions of this Agreement. 
 [Signature Page Follows] 

  
 -5- 

 Please confirm that the foregoing correctly sets forth our agreement with respect to the subject matter hereof by
signing and returning to the undersigned a copy of this Letter. 
  

			
	Pluralsight Holdings, LLC

			
		
	By:	 	 /s/ Aaron Skonnard

			
	Name: Aaron Skonnard
	Its: President/Chief Executive Officer

 The foregoing Letter is accepted and agreed to as of the date first set forth above. 

 

	
	 /s/ Gary Crittenden

	Gary Crittenden, an individual

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