Document:

Exhibit 10.1

 

EMPLOYMENT AGREEMENT

 

This sets forth the terms
of the Employment Agreement made as of January 1, 2021 between (i) COMMUNITY BANK SYSTEM, INC., a Delaware corporation and registered
bank holding company (“CBSI”), and COMMUNITY BANK, N.A., a national banking association (“CBNA”), both
having offices in DeWitt, New York (collectively, the “Employer”), and (ii) MARK E. TRYNISKI, an individual currently
residing at 1964 Penfold Way, Baldwinsville, New York (“Employee”). This Agreement is effective as of January 1, 2021
and supersedes the Employment Agreement between the parties dated as of January 1, 2018.

 

W I T N E S S E T H

 

IN CONSIDERATION of the
promises and mutual agreements and covenants contained herein, and other good and valuable consideration, the parties agree as
follows:

 

1.       Employment.

 

(a)       Term.
Employer shall continue to employ Employee, and Employee shall continue to serve, as President and Chief Executive Officer of Employer
for a term commencing on January 1, 2021 and ending on December 31, 2023 (“Period of Employment”), subject to termination
as provided in paragraph 3 hereof.

 

(b)       Salary.
During the Period of Employment, Employer shall pay Employee a base salary at an annual rate of not less than $861,492 (“Base
Salary”). Employee’s Base Salary shall be reviewed and adjusted in accordance with Employer’s regular payroll
practices for executive employees. Employee’s Base Salary is payable in accordance with Employer’s regular payroll
practices for executive employees.

 

(c)       Incentive
Compensation. During the Period of Employment, Employee shall be entitled to annual incentive compensation opportunities pursuant
to the terms of the Management Incentive Plan, which has been approved by the Board of Directors of Employer to cover Employee
and other key personnel of Employer, as well as other incentive plans that may be established by Employer. Upon termination of
Employee’s employment pursuant to subparagraph 3(a), 3(b), 3(c) or 6, Employee shall be entitled to a pro rata portion (based
on Employee’s complete months of active employment in the applicable year) of the annual incentive awards that are payable
with respect to the year during which the termination occurs or, if the annual awards for such year are not determinable at the
time of termination, then the immediately prior year’s awards shall be used to determine such pro rata portion. Any such
pro rata portion of an annual incentive award that becomes payable pursuant to the preceding sentence shall be paid at the time
and in the form determined in accordance with the applicable incentive award.

 

2.       Duties
during the Period of Employment. Employee shall have responsibility, subject to the control of Employer’s Board of Directors
for the supervision of all aspects of Employer’s business and operations, and the discharge of such other duties and responsibilities
to Employer, not inconsistent with such position, as may from time to time be reasonably assigned to Employee by Employer’s
Board of Directors. Employee shall report to Employer’s Board of Directors. Employee shall devote Employee’s best efforts
to the affairs of Employer, serve faithfully and to the best of Employee’s ability and devote all of Employee’s working
time and attention, knowledge, experience, energy and skill to the business of Employer, except that Employee may affiliate with
professional associations, and business, civic and charitable organizations; provided that such affiliations are not inconsistent
with and do not interfere with the performance of Employee’s duties under this Agreement. Consistent with CBSI’s Corporate
Governance Guidelines, Employee shall advise, and obtain the consent of, the Chair of the Board and Chair of the Nominating and
Corporate Governance Committee prior to accepting a position on another public company board of directors. Employee shall be appointed
to serve as a Director of Community Bank System, Inc. and Community Bank, NA, provided that such appointment and subsequent re-nomination
to serve as a Director shall be subject to (i) Employee being qualified to serve under applicable law, regulations, and the
Employer’s bylaws, and (ii) the exercise of the fiduciary duties of the Employer’s Board of Directors and nominating
committee of the Board of Directors. Employee shall serve on the Board of Directors of, or as an officer of Employer’s affiliates,
without additional compensation if requested to do so by the Board of Directors of Employer. Employee shall receive only the compensation
and other benefits described in this Agreement for Employee’s duties as a Director of Employer or any of its affiliates.

 

     

     

    

 

3.       Termination.
Employee’s employment by Employer shall be subject to termination as follows:

 

(a)       Expiration
of the Term. This Agreement shall terminate automatically at the expiration of the Period of Employment unless the parties
enter into a written agreement extending Employee’s employment, except for the continuing obligations of the parties as specified
hereunder.

 

(b)       Termination
Upon Death. This Agreement shall terminate upon Employee’s death. In the event this Agreement is terminated as a result
of Employee’s death, Employer shall continue payments of Employee’s Base Salary for a period of 90 days following Employee’s
death to the beneficiary designated by Employee on the “Beneficiary Designation Form” attached to this Agreement as
Appendix A. Any restrictions on shares of CBSI stock previously granted to Employee shall be waived as of the date of death, and
Employee’s beneficiary shall be free to dispose of any restricted stock previously granted to Employee by Employer. Additionally,
Employer shall treat as immediately exercisable all unexpired stock options issued by Employer and held by Employee that are not
exercisable or that have not been exercised, so as to permit Employee’s beneficiary to purchase the balance of CBSI stock
not yet purchased pursuant to said options until the end of the full exercise period provided in the original grant of the option
right, determined without regard to Employee’s death or termination of employment.

 

(c)       Termination
Upon Disability. Employer may terminate this Agreement upon Employee’s disability. For the purpose of this Agreement,
Employee’s inability to perform substantially all of Employee’s duties under this Agreement by reason of physical or
mental illness or injury for a period of 26 successive weeks (the “Disability Period”) shall constitute disability.
The determination of disability shall be made by a physician selected by Employer and a physician selected by Employee; provided,
however, that if the two physicians so selected shall disagree, the determination of disability shall be submitted to arbitration
in accordance with the rules of the American Arbitration Association and the decision of the arbitrator shall be binding and conclusive
on Employee and Employer. During the Disability Period, Employee shall be entitled to 100% of Employee’s Base Salary otherwise
payable during that period, reduced by all other Employer-provided income replacement benefits to which Employee may be entitled
for the Disability Period on account of such disability (including, but not limited to, benefits provided under any disability
insurance policy or program, workers’ compensation law, or any other benefit program or arrangement). Upon termination pursuant
to this disability provision, any restrictions on shares of CBSI stock previously granted to Employee shall be waived and Employee
shall be free to dispose of any restricted stock granted to Employee. Additionally, Employer shall treat as immediately exercisable
all unexpired stock options issued by Employer and held by Employee that are not exercisable or that have not been exercised, so
as to permit the Employee to purchase the balance of CBSI stock not yet purchased pursuant to said options until the end of the
full exercise period provided in the original grant of the option right, determined without regard to Employee’s disability
or termination of employment.

 

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(d)       Termination
for Cause. Employer may terminate Employee’s employment immediately for “cause” by written notice to Employee.
For purposes of this Agreement, a termination shall be for “cause” if the termination results from any of the following
events:

 

(i)       Employee’s
willful breach of any material provision of this Agreement, which breach Employee shall have failed to cure within thirty (30)
days following Employer’s written notice to Employee specifying the nature of the breach;

 

(ii)       Any
documented misconduct by Employee as an executive or director of Employer, or any subsidiary or affiliate of Employer for which
Employee is performing services hereunder, which is material and adverse to the interests, monetary or otherwise, of Employer or
any subsidiary or affiliate of Employer;

 

(iii)      Unreasonable
neglect or refusal to perform the duties assigned to Employee under or pursuant to this Agreement, unless cured within thirty
(30) days following Employer’s written notice to Employee specifying the nature of the neglect or refusal;

 

(iv)       Conviction
of a crime involving any act of dishonesty or moral turpitude, or the commission of a felony;

 

(v)       Adjudication
as a bankrupt, which adjudication has not been contested in good faith, unless bankruptcy is caused directly by Employer’s
unexcused failure to perform its obligations under this Agreement;

 

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(vi)      Documented
failure to follow the reasonable, written instructions of the Board of Directors of Employer, provided that the instructions do
not require Employee to engage in unlawful conduct; or

 

(vii)    A willful violation of a material rule or regulation of the Office of the Comptroller of the Currency or of any other
regulatory agency governing Employer or any subsidiary or affiliate of Employer.

 

Notwithstanding any other
term or provision of this Agreement to the contrary, if Employee’s employment is terminated for cause, Employee shall forfeit
all rights to payments and benefits otherwise provided pursuant to this Agreement; provided, however, that Base Salary shall be
paid through the date of termination.

 

(e)       Termination
For Reasons Other Than Cause. In the event Employer terminates Employee’s employment during the Period of Employment
or within 12 months following the expiration of the Period of Employment for reasons other than “cause” (as defined
in paragraph 3(d)), or in the event that Employee terminates his employment with Employer during the Period of Employment for “good
reason” (as defined in, and subject to the notice and right to cure provisions in, paragraph 6(d)), then Employee shall be
entitled to a severance benefit equal to the greater of (i) 200 percent of the sum of Employee’s annual Base Salary in effect
at the time of termination and the aggregate sum of all payments made to Employee during the 12 months preceding Employee’s
termination pursuant to the Management Incentive Plan (or equivalent successor plan), or (ii) amounts of Base Salary and expected
Management Incentive Plan (or equivalent successor plan) payments that otherwise would have been payable through the balance of
the unexpired term of this Agreement. Unless Employee is a “specified employee” (as determined in accordance with Internal
Revenue Code Section 409A), the benefit payable pursuant to this paragraph 3(e) shall be payable in equal biweekly installments
over the 12-month period that begins on the first day of the month following Employee’s termination. If Employee is a “specified
employee” (as determined in accordance with Internal Revenue Code Section 409A), then installment payments during the first
six months of the 12-month installment period shall be limited to the extent required by Internal Revenue Code Section 409A, any
unpaid installment amounts shall be paid immediately after such six-month period and installment payments due during the remaining
six months shall be paid as scheduled.

 

In addition to the
cash benefits described in the foregoing of this paragraph 3(e), Employer shall waive all restrictions on all CBSI stock previously
granted to Employee and permit Employee to dispose of any such restricted stock, as well as treat as immediately exercisable all
unexpired stock options held by Employee that are not exercisable or that have not been exercised, so as to permit Employee to
purchase the balance of CBSI stock not yet purchased pursuant to said options until the end of the full exercise period provided
in the original grant of the option right determined without regard to Employee’s termination of employment.

 

Notwithstanding the
foregoing, amounts payable under clauses (i) or (ii) of this paragraph 3(e) shall be reduced by any payments made to Employee under
paragraph 6(a)(i) of this Agreement. Payments under this paragraph 3(e) and payments under paragraph 6(a)(i) shall not be duplicated.

 

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(f)       Termination
by Employee Without Good Reason. Except in the case of Employee’s termination for good reason in accordance with paragraphs
3(e) and 6(d), Employee may elect to terminate this Agreement and Employee’s employment with Employer upon not less than
60 days prior written notice delivered to Employer, in which event Employee shall be entitled only to the compensation and benefits
Employee earned or accrued through the date of termination. Employer may appropriately adjust Employee’s authority, duties
and/or responsibilities upon notice of such termination, which notice shall constitute Employee’s consent to a change in
authority, duties and responsibilities.

 

4.       Fringe
Benefits.

 

(a)       Benefit
Plans. During the Period of Employment, Employee shall be eligible to participate in any employee pension benefit plans (as
that term is defined under Section 3(2) of the Employee Retirement Income Security Act of 1974, as amended), Employer-paid group
life insurance plans, medical plans, dental plans, long-term disability plans, business travel insurance programs and other fringe
benefit programs maintained by Employer for the benefit of (or which are applicable to) its executive employees. Participation
in any of Employer’s benefit plans and programs shall be based on, and subject to satisfaction of, the eligibility requirements
and other conditions of such plans and programs. Employer may require Employee to submit to an annual physical, to be performed
by a physician of his own choosing. Employee shall not be eligible to participate in Employer’s Severance Pay Plan maintained
for other employees not covered by employment agreements.

 

(b)       Expenses.
Upon submission to Employer of vouchers or other required documentation, Employee shall be reimbursed for (or Employer shall pay
directly) Employee’s actual out-of-pocket travel and other expenses reasonably incurred and paid by Employee in connection
with Employee’s duties hereunder. Reimbursable expenses must be submitted to the Compensation Committee of the Board of Directors
of Employer for review on no less than an annual basis.

 

(c)       Other
Benefits. During the Period of Employment, Employee also shall be entitled to receive the following benefits:

 

(i)        Paid
time-off of twenty-one (21) days each calendar year (with no carry-over of unused time to a subsequent year) and any holidays that
may be provided to all employees of Employer in accordance with Employer’s holiday policy;

 

(ii)       Reasonable
sick leave;

 

(iii)      Reimbursement
of membership fees and dues (but not personal expenses) for up to two club memberships and other appropriate professional associations,
subject to the approval of the Compensation Committee of the Board of Directors of Employer, the primary purpose of which memberships
shall be the promotion of Employer’s business interests. Reimbursements shall be made on or before the last day of Employee’s
taxable year following the taxable year in which the expense was incurred;

 

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(iv)      The
use of an Employer-owned automobile, the purchase and replacement of which shall be subject to the approval of the Compensation
Committee of the Board of Directors of Employer; and

 

(v)       The
use of an Employer-owned mobile telephone and the payment or reimbursement of all Employer-related business charges incurred in
connection with the use of such telephone.

 

(d)       Supplemental
Retirement Benefits. The terms and conditions for the payment of supplemental retirement benefits are set forth in a separate
written agreement between the parties.

 

5.       Restricted
Stock and Stock Options. Employer shall cause the Compensation Committee of the Board of Directors of Employer to review whether
Employee should be granted shares of restricted stock and/or options to purchase shares of common stock of CBSI. Such review may
be conducted pursuant to the terms of the Community Bank System, Inc. 2014 Long-Term Incentive Plan, a successor plan, or independently,
as the Compensation Committee shall determine. Reviews shall be conducted no less frequently than annually.

 

6.       Change
of Control.

 

(a)       If
Employee’s employment with Employer shall cease for any reason, including Employee’s voluntary termination for “good
reason” (as defined in paragraph 6(d) below), but not including Employee’s termination for “cause” (as
described in paragraph 3(d)) or Employee’s voluntary termination without “good reason”, within two years following
a “Change of Control” that occurs during the Period of Employment, then:

 

(i)       Employer
shall pay to the Employee the greater of (A) 300 percent of the sum of the annual Base Salary in effect at the time of Employee’s
termination and the aggregate sum of all payments made to Employee during the 12 months preceding Employee’s termination
pursuant to the Management Incentive Plan (or equivalent successor plan), or (B) amounts of Base Salary and expected payments under
the Management Incentive Plan (or equivalent successor plan) that otherwise would have been payable through the balance of the
unexpired term of this Agreement. Unless Employee is a “specified employee” (as determined in accordance with Internal
Revenue Code Section 409A), the amount determined pursuant to this paragraph 6(a)(i) shall be payable in equal biweekly installments
over the 12-month period that begins on the first day of the month following Employee’s termination. If Employee is a “specified
employee” (as determined in accordance with Internal Revenue Code Section 409A), then installment payments during the first
six months of the 12-month installment period shall be limited to the extent required by Internal Revenue Code Section 409A, any
unpaid installment amounts shall be paid immediately after such six-month period and installment payments due during the remaining
six months shall be paid as scheduled.

 

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(ii)      Employer
shall provide Employee with the cash equivalents of the benefits described in paragraph 4(a) for a period of 36 months following
Employee’s termination. Unless Employee is a “specified employee” (as determined in accordance with Internal
Revenue Code Section 409A), the cash equivalents payable pursuant to this subparagraph (ii) shall be payable in equal monthly installments
over the 36-month period that begins on the first day of the month following Employee’s separation from service. If Employee
is a “specified employee” (as determined in accordance with Internal Revenue Code Section 409A), then installment payments
during the first six months of the 36-month installment period shall be limited to the extent required by Internal Revenue Code
Section 409A, any unpaid installment amounts shall be paid immediately after such six-month period and installment payments due
during the remaining 30 months shall be paid as scheduled.

 

(iii)     Employer
shall treat as immediately exercisable all unexpired stock options issued by Employer and held by Employee that are not otherwise
exercisable or that have not been exercised so as to permit Employee to purchase the balance of CBSI stock not yet purchased pursuant
to said options until the end of the full exercise period provided in the original grant of the option right, determined without
regard to Employee’s termination of employment.

 

(iv)     Employer
shall waive all restrictions on any shares of CBSI stock granted to Employee and permit Employee to dispose of such stock.

 

(b)       Notwithstanding
any provision of this Agreement to the contrary, in the event that any payment or benefit received or to be received by the Employee
in connection with a Change of Control (whether pursuant to the terms of this Agreement or any other plan, arrangement or agreement)
(all such payments and benefits being hereinafter called “Total Benefits”) would be subject (in whole or part) to the
excise tax imposed pursuant to Internal Revenue Code Section 4999, then the cash severance payments provided in this Agreement
shall first be reduced, and the other payments and benefits hereunder shall thereafter be reduced, to the extent necessary so that
no portion of the Total Benefits will be subject to such excise tax, but only if (i) is greater than or equal to (ii), where (i)
equals the reduced amount of such Total Benefits minus the aggregate amount of federal, state and local income taxes on such reduced
Total Benefits, and (ii) equals the unreduced amount of such Total Benefits minus the sum of (A) the aggregate amount of federal,
state and local income taxes on such Total Benefits, and (B) the amount of excise tax to which the Employee would be subject in
respect of such unreduced Total Benefits.

 

(c)       For
purposes of this paragraph 6, a “Change of Control” shall be deemed to have occurred if:

 

(i)       any
 “person,” including a “group” as determined in accordance with the Section 13(d)(3) of the Securities Exchange
Act of 1934 (“Exchange Act”), is or becomes the beneficial owner, directly or indirectly, of securities of Employer
representing 30% or more of the combined voting power of Employer’s then outstanding securities;

 

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(ii)      as
a result of, or in connection with, any tender offer or exchange offer, merger or other business combination (a “Transaction”),
the persons who were directors of Employer before the Transaction shall cease to constitute a majority of the Board of Directors
of Employer or any successor to Employer;

 

(iii)     Employer
is merged or consolidated with another corporation and as a result of the merger or consolidation less than 70% of the outstanding
voting securities of the surviving or resulting corporation shall then be owned in the aggregate by the former stockholders of
Employer, other than (A) affiliates within the meaning of the Exchange Act, or (B) any party to the merger or consolidation;

 

(iv)     a
tender offer or exchange offer is made and consummated for the ownership of securities of Employer representing 30% or more of
the combined voting power of Employer’s then outstanding voting securities; or

 

(v)      Employer
transfers substantially all of its assets to another corporation, which is not controlled by Employer.

 

(d)       For
purposes of this paragraph 6, “good reason” shall mean action taken by Employer that results in:

 

(i)       An
involuntary and material adverse change in Employee’s authority, duties, responsibilities, or base compensation;

 

(ii)      An
involuntary and material relocation of the office from which Employee is expected to perform his duties; or

 

(iii)     A
material breach of this Agreement or any other agreement between the parties under which Employee provides services.

 

In all cases, Employee must provide notice
to Employer of the existence of a condition described in (i), (ii) or (iii) above within thirty (30) days of the initial existence
of the condition, upon the notice of which Employer shall have thirty (30) days thereafter in which to remedy the condition (and
not be required to pay or provide the severance benefit described in this paragraph 6). If the good reason condition is not remedied
within the 30-day remedy period, Employee shall receive the severance benefit described in this paragraph 6 only if Employee terminates
employment within ten business days following the expiration of the 30-day remedy period.

 

7.       Withholding.
Employer shall deduct and withhold from compensation and benefits provided under this Agreement all required income and employment
taxes and any other similar sums required by law to be withheld.

 

8.       Covenants.

 

(a)       Confidentiality.
Employee shall not, without the prior written consent of Employer, disclose or use in any way, either during his employment by
Employer or thereafter, except as required in the course of his employment by Employer, any confidential business or technical
information or trade secret acquired in the course of Employee’s employment by Employer. Employee acknowledges and agrees
that it would be difficult to fully compensate Employer for damages resulting from the breach or threatened breach of the foregoing
provision and, accordingly, that Employer shall be entitled to temporary preliminary injunctions and permanent injunctions to enforce
such provision. This provision with respect to injunctive relief shall not, however, diminish Employer’s right to claim and
recover damages. Employee covenants to use his best efforts to prevent the publication or disclosure of any trade secret or any
confidential information that is not in the public domain concerning the business or finances of Employer or Employer’s affiliates,
or any of its or their dealings, transactions or affairs which may come to Employee’s knowledge in the pursuance of his duties
or employment.

 

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(b)       No
Competition. Employee’s employment is subject to the condition that during the term of his employment hereunder and for
the period specified in paragraph 8(c) below, Employee shall not, directly or indirectly, own, manage, operate, control or participate
in the ownership, management, operation or control of, or be connected as an officer, employee, partner, director, individual proprietor,
lender, consultant or otherwise with, or have any financial interest in, or aid or assist anyone else in the conduct of, any entity
or business (a “Competitive Operation”) which competes in the banking industry or with any other business conducted
by Employer or by any group, affiliate, division or subsidiary of Employer, in the same counties of New York, Pennsylvania or any
other state in which the Employer or any such group, affiliate, division or subsidiary conducts business. Employee shall keep Employer
fully advised as to any activity, interest, or investment Employee may have in any way related to the banking industry. It is understood
and agreed that, for the purposes of the foregoing provisions of this paragraph, (i) no business shall be deemed to be a business
conducted by Employer or any group, division, affiliate or subsidiary of Employer unless 5% or more of Employer’s consolidated
gross sales or operating revenues is derived from, or 5% or more of Employer’s consolidated assets are devoted to, such business;
(ii) no business conducted by any entity by which Employee is employed or in which he is interested or with which he is connected
or associated shall be deemed competitive with any business conducted by Employer or any group, division, affiliate or subsidiary
of Employer unless it is one from which 2% or more of its consolidated gross sales or operating revenues is derived, or to which
2% or more of its consolidated assets are devoted; and (iii) no business which is conducted by Employer on the date of Employee’s
termination and which subsequently is sold by Employer shall, after such sale, be deemed to be a Competitive Operation within the
meaning of this paragraph. Ownership of not more than 5% of the voting stock of any publicly held corporation shall not constitute
a violation of this paragraph.

 

(c)       Non-Competition
Period. The “non-competition period” shall begin on January 1, 2021 and shall end twelve (12) months after Employee’s
termination of employment; provided, however, that the “non-competition period” shall end on the date Employee’s
employment ends in the event of Employee’s termination for “good reason” (as defined in paragraph 6(d)), or Employee’s
termination without “cause” (as defined in paragraph 3(d)).

 

(d)       Non-Solicitation.
While Employee is employed by Employer, and for a period of two years after Employee’s employment with Employer ends for
any reason, Employee shall not directly or indirectly solicit (other than on behalf of Employer) business or contracts for any
products or services of the type provided, developed or under development by Employer during Employee’s employment by Employer,
from or with (x) any person or entity which was a customer of Employer for such products or services as of, or within 12 months
prior to, the date of Employee’s termination of employment with Employer, or (y) any prospective customer which Employer
was soliciting as of, or within 12 months prior to, Employee’s termination. Additionally, while Employee is employed by Employer,
and for two years after Employee’s employment with the Employer ends for any reason, Employee will not directly or indirectly
contract with any such customer or prospective customer for any product or service of the type provided, developed or which was
under development by Employer during Employee’s employment with Employer. Employee will not at any time knowingly interfere
or attempt to interfere with any transaction, agreement or business relationship in which Employer was involved or was contemplating
during Employee’s employment with Employer, including but not limited to relationships with customers, prospective customers,
agents, contractors, vendors, service providers, and suppliers.

 

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(e)       Non-Recruitment.
While Employee is employed by Employer, and for a period of two years after Employee’s employment with Employer ends for
any reason, Employee shall not, directly or indirectly, solicit, recruit, or hire, or in any manner assist in the hiring, solicitation
or recruitment of any of individual who is or was an employee of Employer, or who otherwise provided services to Employer, within
12 months prior to the termination of Employee’s employment with Employer.

 

(f)       Termination
of Payments. Upon the breach by Employee of any covenant under this paragraph 8, Employer shall cease all payments to Employee
and may offset and/or recover from Employee immediately any and all amounts payable to Employee under this Agreement against any
damages to which Employer is legally entitled in addition to any and all other remedies available to Employer under the law or
in equity.

 

(g)       Resignation
as Director. In the event that Employee’s employment terminates for any reason, he shall be deemed to have immediately
tendered his resignation as a director on Employer’s (and any of Employer’s affiliates) Board of Directors, and such
Boards may accept such resignation in their discretion effective upon the termination date without further action by the Employee.

 

9.       Notices.
Any notice which may be given hereunder shall be sufficient if in writing and mailed by overnight mail, or by certified mail, return
receipt requested, to Employee at his residence and to Employer at 5790 Widewaters Parkway, Dewitt, New York 13214, or at such
other addresses as either Employee or Employer may, by similar notice, designate.

 

10.     Rules,
Regulations and Policies. Employee shall abide by and comply in all material respects with all of the rules, regulations,
and policies of Employer that may be in effect and amended from time to time, including without limitation (i) Employer’s
policy of strict adherence to, and compliance with, any and all requirements of the banking, securities, and antitrust laws and
regulations, (ii) Employer’s human resources, personnel and benefits policies, and (iii) to the extent applicable, Employer’s
Executive Equity Ownership Guidelines and claw-back policy.

 

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11.     No
Prior Restrictions. Employee affirms and represents that Employee is under no obligations to any former employer or other
third party which is in any way inconsistent with, or which imposes any restriction upon, the employment of Employee by Employer,
or Employee’s undertakings under this Agreement.

 

12.     Return
of Employer’s Property. After Employee has received notice of termination or at the end of the term hereof, whichever
first occurs, Employee shall promptly return to Employer all documents and other property in his possession belonging to Employer.

 

13.     Construction
and Severability. The invalidity of any one or more provisions of this Agreement or any part thereof, all of which are inserted
conditionally upon their being valid in law, shall not affect the validity of any other provisions to this Agreement; and in the
event that one or more provisions contained herein shall be invalid, as determined by a court of competent jurisdiction, the court
shall have authority to modify such provision in a manner that most closely reflects the intent of the parties and is valid.

 

14.     Internal
Revenue Code Section 409A. This Agreement shall be interpreted and applied in all circumstances in a manner that is consistent
with the intent of the parties that amounts earned and payable pursuant to this Agreement shall not be subject to the premature
income recognition or adverse tax provisions of Internal Revenue Code Section 409A. Accordingly, by way of example and not limitation,

 

(a)       distributions
of benefits payable following Employee’s termination of employment shall commence as of the date required by this Agreement
or, if later, the earliest date permitted by Internal Revenue Code Section 409A, (generally six months after termination, if Employee
is a “specified employee” within the meaning of Internal Revenue Code Section 409A);

 

(b)       the
phrase “termination of employment” (and similar terms and phrases) shall be construed to mean “separation from
service” within the meaning of Internal Revenue Code Section 409A;

 

(c)       the
right to receive installment payments pursuant to this Agreement shall be treated as a right to receive a series of separate and
distinct payments; and

 

(d)       to
the extent that any reimbursement or in-kind benefits are subject to the requirements of Internal Revenue Code Section 409A, (x)
the amount eligible for reimbursement or in-kind benefit in one calendar year will not affect the amount eligible for reimbursement
or in-kind benefit in any other calendar year (except that a plan providing medical or health benefits may impose a generally applicable
limit on the amount that may be reimbursed or paid), (y) the right to reimbursement or an in-kind benefit is not subject to liquidation
or exchange for another benefit, and (z) subject to any shorter time periods provided in this Agreement, any such reimbursement
of an expense or in-kind benefit must be made on or before the last day of the calendar year following the calendar year in which
the expense was incurred.

 

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15.     Governing
Law. This Agreement was executed and delivered in New York and shall be construed and governed in accordance with the
laws of the State of New York.

 

16.     Assignability
and Successors. This Agreement may not be assigned by Employee or Employer, except that this Agreement shall be binding upon
and shall inure to the benefit of the successor of Employer through merger or corporate reorganization. Any attempted assignment
in violation of this paragraph 16 shall be null and void and of no effect.

 

17.     Miscellaneous.

 

(a)       This
Agreement constitutes the entire understanding and agreement between the parties with respect to the subject matter hereof and
shall supersede all prior understandings and agreements, including the January 1, 2018 Employment Agreement between the parties
(which agreement expires/expired on December 31, 2020).

 

(b)       This
Agreement cannot be amended, modified, or supplemented in any respect, except by a subsequent written agreement entered into by
the parties hereto.

 

(c)       The
services to be performed by Employee are special and unique; it is agreed that any breach of this Agreement by Employee shall entitle
Employer (or any successor or assigns of Employer), in addition to any other legal remedies available to it, to apply to any court
of competent jurisdiction to enjoin such breach.

 

(d)       The
provisions of paragraphs 3(e), 6 and 8 hereof shall survive the termination of this Agreement.

 

18.     Counterparts.
This Agreement may be executed in counterparts (each of which need not be executed by each of the parties), which together shall
constitute one and the same instrument.

 

19.     Jurisdiction,
Venue and Fees. The jurisdiction of any proceeding between the parties arising out of, or with respect to, this Agreement shall
be in a court of competent jurisdiction in New York State, and venue shall be in Onondaga County. Each party shall be subject to
the personal jurisdiction of the courts of New York State. If Employee is the prevailing party in a proceeding to collect payments
due pursuant to this Agreement, Employer shall reimburse Employee for reasonable attorneys’ fees incurred by Employee in
connection with such proceeding. The foregoing right to reimbursement shall expire on the fifth anniversary of Employee’s
separation from employment with Employer.

 

[Signature page follows.]

 

    12 

     

    

 

The foregoing is established
by the following signatures of the parties.

 

	 	COMMUNITY
    BANK SYSTEM, INC.
	 	 
	 	By:	/s/
    Bernadette R. Barber
	 	 
	 	Its:	Senior Vice
    President and Chief HR Officer
	 	 
	 	Date:
    1/4/2021

 

	 	COMMUNITY BANK, N.A.
	 	 
	 	By:	/s/ Bernadette R. Barber
	 	 
	 	Its:	Senior Vice President and Chief HR Officer
	 	 
	 	Date: 1/4/2021
	 	 
	 	/s/ Mark E. Tryniski
	 	              MARK E. TRYNISKI
	 	 
	 	Date: 1/4/2021

 

    13Exhibit 10.2

 

EMPLOYMENT AGREEMENT 

 

This sets forth the terms of the Employment
Agreement between (i) COMMUNITY BANK SYSTEM, INC., a Delaware corporation and registered bank holding company (“CBSI”),
and COMMUNITY BANK, N.A., a national banking association (“CBNA”), both having offices located in Dewitt, New York
(collectively, the “Employer”), and (ii) JOSEPH E. SUTARIS, an individual currently residing at Manlius, New York
(“Employee”). This Agreement is effective as of January 1, 2021 and supersedes the Employment Agreement between the
parties that expires on December 31, 2020.

 

W I T N E S S E T H

 

IN CONSIDERATION of the
promises and mutual agreements and covenants contained herein, and other good and valuable consideration, the parties agree as
follows:

 

1.       Employment.

 

(a)       Term.
Employer shall employ Employee, and Employee shall serve, as Executive Vice President and Chief Financial Officer for CBSI and
CBNA for a term commencing on January 1, 2021 and ending on December 31, 2023 (“Period of Employment”), subject to
termination as provided in paragraph 3 hereof.

 

(b)       Salary.
During the Period of Employment, Employer shall pay Employee a base salary at an annual rate of not less than $408,000 (“Base
Salary”). Employee’s Base Salary shall be reviewed and adjusted in accordance with Employer’s regular payroll
practices for executive employees. Employee’s Base Salary is payable in accordance with Employer’s regular payroll
practices for executive employees.

 

(c)       Incentive
Compensation. During the Period of Employment, Employee shall be entitled to annual incentive compensation as a Tier 2 Executive
of Employer pursuant to the terms of the Management Incentive Plan, which has been approved by the Board of Directors of Employer
to cover Employee and other key personnel of Employer, as well as other incentive plans that may be established by Employer and
that are applicable to Employer’s executives of similar salary tier to Employee. Upon termination of Employee’s employment
pursuant to subparagraph 3(a), 3(b), 3(c) or 6, Employee shall be entitled to a pro rata portion (based on Employee’s complete
months of active employment in the applicable year) of the annual incentive awards that are payable with respect to the year during
which the termination occurs or, if the annual awards for such year are not determinable at the time of termination, then the immediately
prior year’s awards shall be used to determine such pro rata portion. Any such pro rata portion of an annual incentive award
that becomes payable pursuant to the preceding sentence shall be paid at the time and in the form determined in accordance with
the applicable incentive award.

 

    

     

    

 

2.       Duties
during the Period of Employment. As Employer’s Executive Vice President and Chief Financial Officer, Employee shall
have full responsibility, subject to the control of Employer’s President and Chief Executive Officer and/or the
authorized designee of Employer’s Board of Directors, for the supervision of all assigned aspects of Employer’s
business and operations, including all activities related to finance, accounting and investor relations, and the discharge of
such other duties and responsibilities to Employer, not inconsistent with such position, as may from time to time be
reasonably assigned to Employee by Employer’s President and Chief Executive Officer, or the authorized designee of
Employer’s Board of Directors. Employee shall report to Employer’s President and Chief Executive Officer.
Employee shall devote Employee’s best efforts to the affairs of Employer, serve faithfully and to the best of
Employee’s ability and devote all of Employee’s working time and attention, knowledge, experience, energy and
skill to the business of Employer, except that Employee may affiliate with professional associations, and business, civic and
charitable organizations, provided that such affiliations are not inconsistent with and do not interfere with the performance
of Employee’s duties under this Agreement. Employee shall serve on the Board of Directors of, or as an officer of
Employer’s affiliates, without additional compensation if requested to do so by the Board of Directors of Employer.
Employee shall receive only the compensation and other benefits described in this Agreement for Employee’s services to
affiliates of Employer.

 

3.       Termination.
Employee’s employment by Employer shall be subject to termination as follows:

 

(a)       Expiration
of the Term. This Agreement shall terminate automatically at the expiration of the Period of Employment unless the parties
enter into a written agreement extending Employee’s employment, except for the continuing obligations of the parties as specified
hereunder.

 

(b)      Termination
Upon Death. This Agreement shall terminate upon Employee’s death. In the event this Agreement is terminated as a result
of Employee’s death, Employer shall continue payments of Employee’s Base Salary for a period of 90 days following Employee’s
death to the beneficiary designated by Employee on the “Beneficiary Designation Form” attached to this Agreement as
Appendix A. Any restrictions on shares of CBSI stock previously granted to Employee shall be waived as of the date of death and
Employee’s beneficiary shall be free to dispose of any restricted stock previously granted to Employee by Employer. Additionally,
Employer shall treat as immediately exercisable all unexpired stock options issued by Employer and held by Employee that are not
exercisable or that have not been exercised, so as to permit Employee’s beneficiary to purchase the balance of CBSI stock
not yet purchased pursuant to said options until the end of the full exercise period provided in the original grant of the option
right, determined without regard to Employee’s death or termination of employment.

 

(c)      Termination
Upon Disability. Employer may terminate this Agreement upon Employee’s disability. For the purpose of this
Agreement, Employee’s inability to perform substantially all of Employee’s duties under this Agreement by reason
of physical or mental illness or injury for a period of 26 successive weeks (the “Disability Period”) shall
constitute disability. The determination of disability shall be made by a physician selected by Employer and a physician
selected by Employee; provided, however, that if the two physicians so selected shall disagree, the determination of
disability shall be submitted to arbitration in accordance with the rules of the American Arbitration Association and the
decision of the arbitrator shall be binding and conclusive on Employee and Employer. During the Disability Period, Employee
shall be entitled to 100% of Employee’s Base Salary otherwise payable during that period, reduced by all other
Employer-provided income replacement benefits to which Employee may be entitled for the Disability Period on account of such
disability (including, but not limited to, benefits provided under any disability insurance policy or program, workers’
compensation law, or any other benefit program or arrangement). Upon termination pursuant to this disability provision, any
restrictions on shares of CBSI stock previously granted to Employee shall be waived and Employee shall be free to dispose of
any restricted stock granted to Employee. Additionally, Employer shall treat as immediately exercisable all unexpired stock
options issued by Employer and held by Employee that are not exercisable or that have not been exercised, so as to permit the
Employee to purchase the balance of CBSI stock not yet purchased pursuant to said options until the end of the full exercise
period provided in the original grant of the option right, determined without regard to Employee’s disability or
termination of employment.

 

    2

     

    

 

(d)       Termination
for Cause. Employer may terminate Employee’s employment immediately for “cause” by written notice to Employee.
For purposes of this Agreement, a termination shall be for “cause” if the termination results from any of the following
events:

 

(i)       Employee’s
willful breach of any material provision of this Agreement, which breach Employee shall have failed to cure within thirty (30)
days following Employer’s written notice to Employee specifying the nature of the breach;

 

(ii)      Any
documented misconduct by Employee as an executive or director of Employer, or any subsidiary or affiliate of Employer for which
Employee is performing services hereunder, which is material and adverse to the interests, monetary or otherwise, of Employer or
any subsidiary or affiliate of Employer;

 

(iii)     Unreasonable
neglect or refusal to perform the duties assigned to Employee under or pursuant to this Agreement, unless cured within thirty (30)
days following Employer’s written notice to Employee specifying the nature of the neglect or refusal;

 

(iv)     Conviction
of a crime involving any act of dishonesty or moral turpitude, or the commission of a felony;

 

(v)      Adjudication
as a bankrupt, which adjudication has not been contested in good faith, unless bankruptcy is caused directly by Employer’s
unexcused failure to perform its obligations under this Agreement;

 

(vi)     Documented
failure to follow the reasonable, written instructions of the Board of Directors of Employer or Employer’s President and
Chief Executive Officer, provided that the instructions do not require Employee to engage in unlawful conduct; or

 

    3

     

    

 

(vii)    A
willful violation of a material rule or regulation of the Office of the Comptroller of the Currency or of any other regulatory
agency governing Employer or any subsidiary or affiliate of Employer.

 

Notwithstanding any other
term or provision of this Agreement to the contrary, if Employee’s employment is terminated for cause, Employee shall forfeit
all rights to payments and benefits otherwise provided pursuant to this Agreement; provided, however, that Base Salary shall be
paid through the date of termination.

 

(e)      Termination
For Reasons Other Than Cause. In the event Employer terminates Employee’s employment during the Period of Employment
or within 12 months following the expiration of the Period of Employment, for reasons other than “cause” (as defined
in paragraph 3(d)), or in the event that Employee terminates his employment with Employer during the Period of Employment for “good
reason” (as defined in, and subject to the notice and right to cure provisions in, paragraph 6(d)), then Employee shall be
entitled to a severance benefit equal to the greater of (i) 175 percent of the sum of Employee’s annual Base Salary in effect
at the time of termination and the aggregate sum of all payments made to Employee during the 12 months preceding Employee’s
termination pursuant to the Management Incentive Plan (or equivalent successor plan), or (ii) amounts of Base Salary and expected
Management Incentive Plan (or equivalent successor plan) payments that otherwise would have been payable through the balance of
the unexpired term of this Agreement. Unless Employee is a “specified employee” (as determined in accordance with Internal
Revenue Code Section 409A), the benefit payable pursuant to this paragraph 3(e) shall be payable in equal biweekly installments
over the 12 month period that begins on the first day of the month following Employee’s termination. If Employee is a “specified
employee” (as determined in accordance with Internal Revenue Code Section 409A), then installment payments during the first
six months of the 12 month installment period shall be limited to the extent required by Internal Revenue Code Section 409A, any
unpaid installment amounts shall be paid immediately after such six-month period and installment payments due during the remaining
six months shall be paid as scheduled.

 

In addition to the
cash benefits described in the foregoing of this paragraph 3(e), Employer shall: (iii) waive all restrictions on all CBSI stock
previously granted to Employee and permit Employee to dispose of any restricted stock; and (iv) treat as immediately exercisable
all unexpired stock options held by Employee that are not exercisable or that have not been exercised, so as to permit Employee
to purchase the balance of CBSI stock not yet purchased pursuant to said options until the end of the full exercise period provided
in the original grant of the option right determined without regard to Employee’s termination of employment.

 

Notwithstanding the
foregoing, amounts payable under clauses (i) or (ii) of this paragraph 3(e) shall be reduced by any payments made to Employee under
paragraph 6(a)(i) of this Agreement. Payments under this paragraph 3(e) and payments under paragraph 6(a)(i) shall not be duplicated.

 

    4

     

    

 

(f)       Termination
by Employee Without Good Reason. Except in the case of Employee’s termination for good reason in accordance with paragraphs
3(e) and 6(d), Employee may elect to terminate this Agreement and Employee’s employment with Employer upon not less than
60 days prior written notice delivered to Employer, in which event Employee shall be entitled only to the compensation and benefits
Employee earned or accrued through the date of termination. Employer may appropriately adjust Employee’s authority, duties
and/or responsibilities upon notice of such termination, which notice shall constitute Employee’s consent to a change in
authority, duties and responsibilities.

 

4.       Fringe
Benefits.

 

(a)       Benefit
Plans. During the Period of Employment, Employee shall be eligible to participate in any employee pension benefit plans (as
that term is defined under Section 3(2) of the Employee Retirement Income Security Act of 1974, as amended), Employer-paid group
life insurance plans, medical plans, dental plans, long-term disability plans, business travel insurance programs and other fringe
benefit programs maintained by Employer for the benefit of (or which are applicable to) its executive employees. Participation
in any of Employer’s benefit plans and programs shall be based on, and subject to satisfaction of, the eligibility requirements
and other conditions of such plans and programs. Employer may require Employee to submit to an annual physical, to be performed
by a physician of his own choosing. Employee shall not be eligible to participate in Employer’s Severance Pay Plan maintained
for other employees not covered by employment agreements.

 

(b)       Expenses.
Upon submission to Employer of vouchers or other required documentation, Employee shall be reimbursed for (or Employer shall pay
directly) Employee’s actual out-of-pocket travel and other expenses reasonably incurred and paid by Employee in connection
with Employee’s duties hereunder. Reimbursable expenses must be submitted to the President and Chief Executive Officer of
Employer, or the President and Chief Executive Officer’s designee, for review on no less than a quarterly basis.

 

(c)       Other
Benefits. During the Period of Employment, Employee also shall be entitled to receive the following benefits:

 

(i)       Paid
time-off of twenty-one (21) days each calendar year (with no carryover of unused time to a subsequent year) and any holidays that
may be provided to all employees of Employer in accordance with Employer’s holiday policy;

 

(ii)      Reasonable
sick leave;

 

(iii)     Reimbursement
of membership fees and dues (but not personal expenses) for up to two club memberships and other appropriate professional associations,
subject to the approval of the President and Chief Executive Officer of Employer, the primary purpose of which memberships shall
be the promotion of Employer’s business interests. Reimbursements shall be made on or before the last day of Employee’s
taxable year following the taxable year in which the expense was incurred;

 

    5

     

    

 

(iv)    The
use of an Employer-owned mobile telephone and the payment or reimbursement of all Employer related business charges incurred in
connection with the use of such telephone; and

 

(v)      At
Employer’s option, either (A) the use of an Employer-owned or Employer-leased automobile, the selection and replacement of
which shall be subject to the approval of the President and Chief Executive Officer of Employer, or (B) an automobile allowance
to provide for a reasonably similar benefit consistent with similarly-situated executive employees, as determined by the President
and Chief Executive Officer of Employer.

 

5.       Restricted
Stock and Stock Options. Employer shall cause the Compensation Committee of the Board of Directors of Employer to review whether
Employee should be granted shares of restricted stock and/or options to purchase shares of common stock of CBSI. Such review may
be conducted pursuant to the terms of the Community Bank System, Inc. 2014 Long-Term Incentive Plan, a successor plan, or independently,
as the Compensation Committee shall determine. Reviews shall be conducted no less frequently than annually.

 

6.       Change
of Control.

 

(a)       If
Employee’s employment with Employer shall cease for any reason, including Employee’s voluntary termination for “good
reason” (as defined in paragraph 6(d) below), but not including Employee’s termination for “cause” (as
described in paragraph 3(d)) or Employee’s voluntary termination without “good reason”, within two years following
a “Change of Control” that occurs during the Period of Employment, then:

 

(i)       Employer
shall pay to the Employee the greater of (A) 300 percent of the sum of the annual Base Salary in effect at the time of Employee’s
termination and the aggregate sum of all payments made to Employee during the 12 months preceding Employee’s termination
pursuant to the Management Incentive Plan (or equivalent successor plan), or (B) amounts of Base Salary and expected payments under
the Management Incentive Plan (or equivalent successor plan) that otherwise would have been payable through the balance of the
unexpired term of this Agreement. Unless Employee is a “specified employee” (as determined in accordance with Internal
Revenue Code Section 409A), the amount determined pursuant to this paragraph 6(a)(i) shall be payable in equal biweekly installments
over the 12-month period that begins on the first day of the month following Employee’s termination. If Employee is a “specified
employee” (as determined in accordance with Internal Revenue Code Section 409A), then installment payments during the first
six months of the 12-month installment period shall be limited to the extent required by Internal Revenue Code Section 409A, any
unpaid installment amounts shall be paid immediately after such six-month period and installment payments due during the remaining
six months shall be paid as scheduled.

 

(ii)      Employer
shall provide Employee with the cash equivalents of the benefits described in paragraph 4(a) for a period of 36 months
following Employee’s termination. Unless Employee is a “specified employee” (as determined in accordance
with Internal Revenue Code Section 409A), the cash equivalents payable pursuant to this subparagraph (ii) shall be payable in
equal monthly installments over the 36-month period that begins on the first day of the month following Employee’s
separation from service. If Employee is a “specified employee” (as determined in accordance with Internal Revenue
Code Section 409A), then installment payments during the first six months of the 36-month installment period shall be limited
to the extent required by Internal Revenue Code Section 409A, any unpaid installment amounts shall be paid immediately after
such six-month period and installment payments due during the remaining 30 months shall be paid as scheduled.

 

    6

     

    

 

(iii)     Employer
shall treat as immediately exercisable all unexpired stock options issued by Employer and held by Employee that are not otherwise
exercisable or that have not been exercised so as to permit Employee to purchase the balance of CBSI stock not yet purchased pursuant
to said options until the end of the full exercise period provided in the original grant of the option right, determined without
regard to Employee’s termination of employment.

 

(iv)       Employer
shall waive all restrictions on any shares of CBSI stock granted to Employee and permit Employee to dispose of such stock.

 

(b)       Notwithstanding
any provision of this Agreement to the contrary, in the event that any payment or benefit received or to be received by the Employee
in connection with a Change of Control (whether pursuant to the terms of this Agreement or any other plan, arrangement or agreement)(all
such payments and benefits being hereinafter called “Total Benefits”) would be subject (in whole or in part) to the
excise tax imposed pursuant to Internal Revenue Code Section 4999, then the cash severance payments provided in this Agreement
shall first be reduced, and the other payments and benefits hereunder shall thereafter be reduced, to the extent necessary so that
no portion of the Total Benefits will be subject to such excise tax, but only if (i) is greater than or equal to (ii), where (i)
equals the reduced amount of such Total Benefits minus the aggregate amount of federal, state and local income taxes on such reduced
Total Benefits, and (ii) equals the unreduced amount of such Total Benefits minus the sum of (A) the aggregate amount of federal,
state and local income taxes on such Total Benefits, and (B) the amount of excise tax to which the Employee would be subject in
respect of such unreduced Total Benefits.

 

(c)       For
purposes of this paragraph 6, a “Change of Control” shall be deemed to have occurred if:

 

(i)       any
 “person,” including a “group” as determined in accordance with the Section 13(d)(3) of the Securities Exchange
Act of 1934 (“Exchange Act”), is or becomes the beneficial owner, directly or indirectly, of securities of Employer
representing 30% or more of the combined voting power of Employer’s then outstanding securities;

 

(ii)      as
a result of, or in connection with, any tender offer or exchange offer, merger or other business combination (a “Transaction”),
the persons who were directors of Employer before the Transaction shall cease to constitute a majority of the Board of Directors
of Employer or any successor to Employer;

 

    7

     

    

 

(iii)     Employer
is merged or consolidated with another corporation and as a result of the merger or consolidation less than 70% of the outstanding
voting securities of the surviving or resulting corporation shall then be owned in the aggregate by the former stockholders of
Employer, other than (A) affiliates within the meaning of the Exchange Act, or (B) any party to the merger or consolidation;

 

(iv)     a
tender offer or exchange offer is made and consummated for the ownership of securities of Employer representing 30% or more of
the combined voting power of Employer’s then outstanding voting securities; or

 

(v)      Employer
transfers substantially all of its assets to another corporation, which is not controlled by Employer.

 

(d)       For
purposes of this paragraph 6, “good reason” shall mean action taken by Employer that results in:

 

(i)       An
involuntary and material adverse change in Employee’s authority, duties, responsibilities, or base compensation;

 

(ii)      An
involuntary and material relocation of the office from which Employee is expected to perform his duties; or

 

(iii)     A
material breach of this Agreement or any other agreement between the parties under which Employee provides services.

 

In all cases, Employee must provide notice
to Employer of the existence of a condition described in (i), (ii) or (iii) above within thirty (30) days of the initial existence
of the condition, upon the notice of which Employer shall have thirty (30) days thereafter in which to remedy the condition (and
not be required to pay or provide the severance benefit described in this paragraph 6). If the good reason condition is not remedied
within the 30-day remedy period, Employee shall receive the severance benefit described in this paragraph 6 only if Employee terminates
employment within ten business days following the expiration of the 30-day remedy period.

 

7.       Withholding.
Employer shall deduct and withhold from compensation and benefits provided under this Agreement all required income and employment
taxes and any other similar sums required by law to be withheld.

 

8.       Covenants.

 

(a)       Confidentiality.
Employee shall not, without the prior written consent of Employer, disclose or use in any way, either during his employment
by Employer or thereafter, except as required in the course of his employment by Employer, any confidential business or
technical information or trade secret acquired in the course of Employee’s employment by Employer. Employee
acknowledges and agrees that it would be difficult to fully compensate Employer for damages resulting from the breach or
threatened breach of the foregoing provision and, accordingly, that Employer shall be entitled to temporary preliminary
injunctions and permanent injunctions to enforce such provision. This provision with respect to injunctive relief shall not,
however, diminish Employer’s right to claim and recover damages. Employee covenants to use his best efforts to prevent
the publication or disclosure of any trade secret or any confidential information that is not in the public domain concerning
the business or finances of Employer or Employer’s affiliates, or any of its or their dealings, transactions or affairs
which may come to Employee’s knowledge in the pursuance of his duties or employment.

 

    8

     

    

 

(b)       No
Competition. Employee’s employment is subject to the condition that during the term of his employment hereunder and for
the period specified in paragraph 8(c) below, Employee shall not, directly or indirectly, own, manage, operate, control or participate
in the ownership, management, operation or control of, or be connected as an officer, employee, partner, director, individual proprietor,
lender, consultant or otherwise with, or have any financial interest in, or aid or assist anyone else in the conduct of, any entity
or business (a “Competitive Operation”) which competes in the banking industry or with any other business conducted
by Employer or by any group, affiliate, division or subsidiary of Employer, in the same counties of New York, Pennsylvania, Vermont,
Massachusetts or any other state in which the Employer or any such group, affiliate, division or subsidiary conducts business.
Employee shall keep Employer fully advised as to any activity, interest, or investment Employee may have in any way related to
the banking industry. It is understood and agreed that, for the purposes of the foregoing provisions of this paragraph, (i) no
business shall be deemed to be a business conducted by Employer or any group, division, affiliate or subsidiary of Employer unless
5% or more of Employer’s consolidated gross sales or operating revenues is derived from, or 5% or more of Employer’s
consolidated assets are devoted to, such business; (ii) no business conducted by any entity by which Employee is employed or in
which he is interested or with which he is connected or associated shall be deemed competitive with any business conducted by Employer
or any group, division, affiliate or subsidiary of Employer unless it is one from which 2% or more of its consolidated gross sales
or operating revenues is derived, or to which 2% or more of its consolidated assets are devoted; and (iii) no business which is
conducted by Employer on the date of Employee’s termination and which subsequently is sold by Employer shall, after such
sale, be deemed to be a Competitive Operation within the meaning of this paragraph. Ownership of not more than 5% of the voting
stock of any publicly held corporation shall not constitute a violation of this paragraph.

 

(c)       Non-Competition
Period. The “non-competition period” shall begin on January 1, 2021 and shall end twelve (12) months after the
Employee’s termination of employment; provided, however, that the “non-competition period” shall end on the
date Employee’s employment ends in the event of Employee’s termination for “good reason” (as defined in
paragraph 6(d)), or Employee’s termination without “cause” (as defined in paragraph 3(d)).

 

(d)       Non-Solicitation.
While Employee is employed by Employer, and for a period of two years after Employee’s employment with Employer ends
for any reason, Employee shall not directly or indirectly solicit (other than on behalf of Employer) business or contracts
for any products or services of the type provided, developed or under development by Employer during Employee’s
employment by Employer, from or with (x) any person or entity which was a customer of Employer for such products or services
as of, or within 12 months prior to, the date of Employee’s termination of employment with Employer, or (y) any
prospective customer which Employer was soliciting as of, or within 12 months prior to, Employee’s termination.
Additionally, while Employee is employed by Employer, and for two years after Employee’s employment with the Employer
ends for any reason, Employee will not directly or indirectly contract with any such customer or prospective customer for any
product or service of the type provided, developed or which was under development by Employer during Employee’s
employment with Employer. Employee will not at any time knowingly interfere or attempt to interfere with any transaction,
agreement or business relationship in which Employer was involved or was contemplating during Employee’s employment
with Employer, including but not limited to relationships with customers, prospective customers, agents, contractors,
vendors, service providers, and suppliers.

 

    9

     

    

 

(e)       Non-Recruitment.
While Employee is employed by Employer, and for a period of two years after Employee’s employment with Employer ends for
any reason, Employee shall not, directly or indirectly, solicit, recruit, or hire, or in any manner assist in the hiring, solicitation
or recruitment of any of individual who is or was an employee of Employer, or who otherwise provided services to Employer, within
12 months prior to the termination of Employee’s employment with Employer.

 

(f)       Termination
of Payments. Upon the breach by Employee of any covenant under this paragraph 8, Employer shall cease all payments to Employee
and may offset and/or recover from Employee immediately any and all amounts payable to Employee under this Agreement against any
damages to which Employer is legally entitled in addition to any and all other remedies available to Employer under the law or
in equity.

 

9.       Notices.
Any notice which may be given hereunder shall be sufficient if in writing and mailed by overnight mail, or by certified mail, return
receipt requested, to Employee at his residence and to Employer at 5790 Widewaters Parkway, Dewitt, New York 13214, or at such
other addresses as either Employee or Employer may, by similar notice, designate.

 

10.     Rules,
Regulations and Policies. Employee shall abide by and comply in all material respects with all of the rules, regulations, and
policies of Employer that may be in effect and amended from time to time, including without limitation (i) Employer’s policy
of strict adherence to, and compliance with, any and all requirements of the banking, securities, and antitrust laws and regulations,
(ii) Employer’s human resources, personnel and benefits policies, and (iii) to the extent applicable, Employer’s Executive
Equity Ownership Guidelines and claw-back policy.

 

11.     No
Prior Restrictions. Employee affirms and represents that Employee is under no obligations to any former employer or other third
party which is in any way inconsistent with, or which imposes any restriction upon, the employment of Employee by Employer, or
Employee’s undertakings under this Agreement.

 

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12.     Return
of Employer’s Property. After Employee has received notice of termination or at the end of the term hereof, whichever
first occurs, Employee shall promptly return to Employer all documents and other property in his possession belonging to Employer.

 

13.     Construction
and Severability. The invalidity of any one or more provisions of this Agreement or any part thereof, all of which are inserted
conditionally upon their being valid in law, shall not affect the validity of any other provisions to this Agreement; and, in the
event that one or more provisions contained herein shall be invalid, as determined by a court of competent jurisdiction, the court
shall have authority to modify such provision in a manner that most closely reflects the intent of the parties and is valid.

 

14.     Internal
Revenue Code Section 409A. This Agreement shall be interpreted and applied in all circumstances in a manner that is consistent
with the intent of the parties that amounts earned and payable pursuant to this Agreement shall not be subject to the premature
income recognition or adverse tax provisions of Internal Revenue Code Section 409A. Accordingly, by way of example and not limitation,

 

(a)       distributions
of benefits payable following Employee’s termination of employment shall commence as of the date required by this Agreement
or, if later, the earliest date permitted by Internal Revenue Code Section 409A, (generally six months after termination, if Employee
is a “specified employee” within the meaning of Internal Revenue Code Section 409A);

 

(b)       the
phrase “termination of employment” (and similar terms and phrases) shall be construed to mean “separation from
service” within the meaning of Internal Revenue Code Section 409A;

 

(c)       the
right to receive installment payments pursuant to this Agreement shall be treated as a right to receive a series of separate and
distinct payments; and

 

(d)       to
the extent that any reimbursement or in-kind benefits are subject to the requirements of Internal Revenue Code Section 409A, (x)
the amount eligible for reimbursement or in-kind benefit in one calendar year will not affect the amount eligible for reimbursement
or in-kind benefit in any other calendar year (except that a plan providing medical or health benefits may impose a generally applicable
limit on the amount that may be reimbursed or paid), (y) the right to reimbursement or an in-kind benefit is not subject to liquidation
or exchange for another benefit, and (z) subject to any shorter time periods provided in this Agreement, any such reimbursement
of an expense or in-kind benefit must be made on or before the last day of the calendar year following the calendar year in which
the expense was incurred.

 

15.     Governing
Law. This Agreement was executed and delivered in New York and shall be construed and governed in accordance with the laws
of the State of New York.

 

16.     Assignability
and Successors. This Agreement may not be assigned by Employee or Employer, except that this Agreement shall be binding
upon and shall inure to the benefit of the successor of Employer through merger or corporate reorganization. Any attempted
assignment in violation of this paragraph 16 shall be null and void and of no effect.

 

    	 	11	 

     

    

 

 

 17.     Miscellaneous.

 

(a)       This
Agreement constitutes the entire understanding and agreement between the parties with respect to the subject matter hereof and
shall supersede all prior understandings and agreements, including the Employment Agreement between the parties that expires on
December 31, 2020.

 

(b)       This
Agreement cannot be amended, modified, or supplemented in any respect, except by a subsequent written agreement entered into by
the parties hereto.

 

(c)       The
services to be performed by Employee are special and unique; it is agreed that any breach of this Agreement by Employee shall entitle
Employer (or any successor or assigns of Employer), in addition to any other legal remedies available to it, to apply to any court
of competent jurisdiction to enjoin such breach.

 

(d)       The
provisions of paragraphs 3(e), 6 and 8 hereof shall survive the termination of this Agreement.

 

18.     Counterparts.
This Agreement may be executed in counterparts (each of which need not be executed by each of the parties), which together shall
constitute one and the same instrument.

 

19.     Jurisdiction,
Venue and Fees. The jurisdiction of any proceeding between the parties arising out of, or with respect to, this Agreement shall
be in a court of competent jurisdiction in New York State, and venue shall be in Onondaga County. Each party shall be subject to
the personal jurisdiction of the courts of New York State. If Employee is the prevailing party in a proceeding to collect payments
due pursuant to this Agreement, Employer shall reimburse Employee for reasonable attorneys’ fees incurred by Employee in
connection with such proceeding. Reimbursement shall be made on or before the last day of Employee’s taxable year following
the taxable year in which the expense was incurred. The foregoing right of reimbursement shall expire on the fifth anniversary
of Employee’s separation of employment with Employer.

 

[Signature page follows.]

 

    	 	12	 

     

    

 

The foregoing is established
by the following signatures of the parties.

 

	 	COMMUNITY BANK SYSTEM, INC.
	 	 	 
	 	By:	/s/ Mark E. Tryniski
	 	 	Mark E. Tryniski
	 	 	President
and Chief Executive Officer
	 	 	 
	 	Date:	January 4, 2021

 

	 	COMMUNITY BANK, N.A.
	 	 	 
	 	By: 	/s/ Bernadette
R. Barber
	 	 	Bernadette R. Barber
	 	 	Senior Vice President and Chief
HR Officer
	 	 	 
	 	Date:	January 4, 2021

 

	 	 	/s/
Joseph E. Sutaris
	 	 	Joseph E.
Sutaris
	 	 	 
	 	Date:	January 4, 2021

 

    	 	13

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