Document:

Exhibit 4.2

  

INCORPORATED UNDER THE LAWS OF THE

STATE OF MARYLAND

 

	 	 	 
	
        NUMBER

        B-
	ESQUIRE FINANCIAL HOLDINGS, INC.

                                                                                New York, New York
	SHARES
	 	 	 

 

FULLY
PAID AND NON-ASSESSABLE

SERIES B NON-VOTING PREFERRED STOCK, PAR
VALUE $0.01 PER SHARE

 

THIS CERTIFIES that ________________________________________
is the

 

registered holder of ___________________________________________
Shares

 

transferable only on the books the Corporation
by the holder hereof, in person or by Attorney, upon surrender of this Certificate properly endorsed.

 

IN WITNESS WHEREOF,
the said Corporation has caused this certificate to be signed by its duly authorized officers and its Corporate Seal to be hereunto
affixed.

 

This _______________ day of ________________
A.D.__________

 

	By:	 	 	[SEAL]	By:	 
	 	Andrew C. Sagliocca, President	 	 	 	Eric Bader, Secretary

 

     

     

    

 

For value received,
_______________________________________________hereby sell, assign and transfer unto

 

_________________________________________________________________________________Shares

 

represented by the within Certificate,
and do hereby irrevocably constitute and

 

appoint ________________________________________________________________ Attorney
to transfer the said

 

Shares on the books of the within
named Corporation with full power of substitution in the premises.

 

Dated, _______________________________

 

	In the presence of	 	Signature:
	 	 	 
	 	 	 

 

NOTICE: THE SIGNATURE OF THIS
ASSIGNMENT MUST CORRESPOND WITH THE NAME AS WRITTEN UPON THE FACE OF THE CERTIFICATE, IN EVERY PARTICULAR, WITHOUT ALTERATION OR
ENLARGEMENT, OR ANY CHANGE WHATSOEVER.

 

The securities
represented by this certificate have not been registered under the Securities Act of 1933, as amended (the “Act”),
or registered or qualified under the securities laws of any state. The holder of the securities cannot make any sale, assignment
or other transfer of any such securities except pursuant to an offering of such securities duly registered under the Act and registered
or qualified under any applicable state securities laws, or under such other circumstances as, in the opinion of counsel for (or
counsel satisfactory to) EQUIRE FINANCIAL HOLDINGS, iNC., shall not, at the time, require registration under the Act and/or registration
or qualification under any applicable state securities lawsExhibit 10.1

 

ESQUIRE FINANCIAL HOLDINGS, INC.

320 Old Country Road, Suite 101

Garden City, New York 11530

 

December
23, 2014

 

CJA
Private Equity Financial Restructuring Master Fund I, LP

c/o
Gapstow Capital Partners

654
Madison Avenue, Suite 601

New
York, NY 10065

 

		Re:	Investor Rights

 

Ladies and Gentlemen:

 

This letter will confirm
our agreement that pursuant to and effective as of your purchase of capital stock of Esquire Financial Holdings, Inc. (the “Company”),
a Delaware corporation and parent company of Esquire Bank (the “Bank”), CJA Private Equity Financial Restructuring
Master Fund I, LP, a Cayman Islands limited partnership (the “Investor”), shall be entitled to the following
contractual rights, in addition to any other rights specifically provided to the Investor pursuant to that certain Subscription
Agreement dated as of December 23, 2014 by and between the Company and the Investor, including any amendments or supplements thereto,
and such other agreements, instruments and certificates delivered in connection therewith (collectively, the “Subscription
Documents”):

 

1.           Right
to Designate Board Member. Effective on and after the first anniversary of the date hereof, as long as the Investor, together
with its affiliates (as such term is defined under the Home Owners’ Loan Act of 1933, as amended (“HOLA”)
(“Affiliates”), beneficially owns at least 4.0% of the total outstanding capital stock of the Company, and subject
to any required approvals or non-objections of the Board of Governors of the Federal Reserve System (whether acting directly or
through the Federal Reserve Bank of New York in such reserve bank’s regulatory capacity), the Federal Deposit Insurance Corporation,
the Office of the Comptroller of the Currency and/or any other regulatory body having jurisdiction over the Company or the Bank
(collectively, the “Regulators”), the Company shall use its reasonable best efforts, subject to the fiduciary
duties of the directors of the Company, to cause one person nominated by the Investor to be elected to serve on the Board of Directors
of the Company, and any direct or indirect subsidiary thereof, including the Bank (collectively, the “Board”),
which efforts shall include, without limitation, if consistent with the fiduciary duties of the directors of the Company, soliciting
proxies for the Investor’s nominee in the same manner as it does for the Company’s other nominees. Any director nominated
by the Investor pursuant to this paragraph 1 shall be entitled to indemnification rights in his or her capacity as a member of
the Board in a manner no less favorable as provided to other members of the Board. The Board representative of the Investor shall
receive compensation from the Company equal in form and value to compensation paid to other Board members generally (such compensation
to be paid as directed by the Investor), it being understood that certain Board members may receive different compensation

 

     

     

    

 

for services as chairman,
lead director or a committee chairman. In the event the Investor designates as its Board representative an individual who is not
an employee of the Investor or any of its Affiliates, the Company shall, in negotiation with the Investor, provide such individual
with reasonable stock incentive compensation as the Company customarily offers to other independent, outside directors, if any.
To facilitate the in-person attendance of the Board representative of the Investor (as a member of the Board pursuant to this paragraph
1 or as an observer pursuant to paragraph 2 below), the Company shall reimburse the Investor for all reasonable travel expenses
of such representative promptly upon receiving documentation thereof reasonably acceptable to the Company.

 

2.           Board
Observer Rights. If the Investor is not represented on the Board (including during such time as regulatory approval of the
person nominated by the Investor as its Board representative is pending), as long as the Investor (together with its Affiliates)
beneficially owns at least 4.0% of the total outstanding capital stock of the Company, the Company shall allow a representative
of the Investor to attend all meetings of the Board in a non-voting observer capacity and, in this respect, shall give such representative
copies of all notices, minutes, consents and other materials that it provides to its directors at the same time and in the same
manner as provided to such directors; provided, however, that (i) such representative shall agree,
in writing, to hold in confidence and trust all information so provided; (ii) the representative may be excluded from access to
any material or meeting or portion thereof if the Board determines in good faith, upon advice of counsel, that access to such material
or attendance at such meeting would adversely affect the attorney-client privilege between the Company or the Bank and its counsel
or would conflict with applicable banking laws or regulations or if such material or meeting relates to relations or negotiations
with the Investor or require the consent or non-objection of any Regulator; and (iii) such observer shall be excluded from all
“executive sessions” of the Board if any other persons who are not members of the Board, other than counsel to the
Company, are also excluded. For the avoidance of doubt, such representative shall not have access to any “confidential supervisory
information” (as such term or relevant similar term is defined under the regulations of any Regulator).

 

3.           Terms
of Agreements with Other Investors. The Company represents and warrants that it has not entered into, and does not currently
intend to enter into, any agreement with any other investor who is not currently a stockholder of the Company or that provides
rights to such investor related to its investment in capital stock of the Company, other than any such agreement as to which it
has provided a copy to the Investor.  If, during the eighteen-month period immediately after the date hereof, the Company
enters into any such agreement with a party that agrees to purchase capital stock issued by the Company, then the Company shall
promptly provide a copy of any such agreement to the Investor, and any terms of such agreement that are more favorable to such
investor than the terms of the Subscription Documents shall be added and incorporated into this letter agreement, unless the Investor
provides written notice to the Company that it elects to waive its rights to any such additional or modified terms.

 

4.           Capital
Structure.

 

(a)           Preemptive
Rights. If, following the consummation of the transactions contemplated by the Subscription Documents, and while the Investor
(together with its

 

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Affiliates) beneficially
owns at least 4.0% of the total outstanding capital stock of the Company, the Company authorizes the issuance or sale of any securities,
comparable or identical to the securities issued in this offering pursuant to the Subscription Documents, the Investor shall be
entitled, in its sole discretion, to purchase shares of the Company’s capital stock such that the Investor would maintain
its percentage ownership interest in the Company’s capital stock on a fully-diluted basis, subject to compliance with the
applicable requirements of the Regulators. With respect to such rights described above (the “Preemptive Rights”),
the Company shall give written notice of such proposed issuance or sale (including the terms and conditions thereof) to the Investor
at least thirty (30) days prior to the anticipated issuance or sale date, and the Investor shall have twenty (20) days from the
receipt thereof to provide the Company with notice of the exercise of its Preemptive Rights with respect to such issuance or sale.
The Preemptive Rights described herein (A) will terminate upon the registration of the Company’s common stock, par value
$0.01 per share (“Common Stock”) on NASDAQ, NYSE or other national securities exchange, (B) shall not apply
in a transaction approved by the Board that results in a Change of Control (as defined below), (C) shall not apply to the issuance
of Common Stock, or options to purchase the same, pursuant to the Company Stock Plans (as defined in the Subscription Documents)
and (D) shall not apply to shares of Common Stock, or options to purchase the same, issued to employees or directors of, or consultants
or advisors to, the Company or any Company Subsidiary (as defined in the Subscription Documents) pursuant to a plan, agreement
or arrangement approved by the Board (each such issuances described in clauses (B) through (D) above, an “Excluded Issuance”);
provided, however, that in all cases, (1) the aggregate ownership percentage of the Investor and its
Affiliates of any class of voting securities of the Company shall not exceed 9.95% (or 4.95%, if so elected by the Investor) and
(2) the total equity ownership in the Company by the Investor and its Affiliates shall not exceed 24.95% of the Company’s
total issued and outstanding capital stock. For purposes of this letter agreement a “Change of Control” means
the acquisition by any person (including a group of related persons within the meaning of Rule 13d-2 of the Securities Exchange
Act of 1934, as amended) of (1) more than fifty percent (50%) of the outstanding capital stock of the Company, (2) all or substantially
all of the assets of the Company (including the sale of more than two-thirds (2/3) of the capital stock held by the Company in
the Bank) or (3) a merger of the Company with or into any person, or of any person with or into the Company, immediately after
which the shareholders of the Company (as measured immediately prior to completion of the transaction) own less than a majority
of the combined capital stock or membership interests of the surviving entity.

 

(b)          Avoidance
of Control. Notwithstanding anything to the contrary in this letter agreement, neither the Company nor any Company Subsidiary
(as defined in the Subscription Documents) shall take any action (including any redemption, repurchase, or recapitalization of
common stock, or securities or rights, options or warrants to purchase common stock, or securities of any type whatsoever that
are, or may become, convertible into or exchangeable into or exercisable for common stock in each case, where the Investor is not
given the right to participate in such redemption, repurchase or recapitalization to the extent of the Investor’s pro rata
proportion) that would: (i) cause the Investor’s equity of the Company (together with equity owned by the Investor’s
Affiliates) to exceed 24.95% of the Company’s total equity; or (ii) cause the Investor’s ownership of any class of
voting securities of the Company (together with the ownership by the Investor’s Affiliates of voting securities of the Company)
to exceed 9.95% (or 4.95%, if so elected by the Investor), in each case without the

 

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prior written consent
of the Investor (which consent shall not be unreasonably withheld), or to increase to an amount that would constitute “control”
under the HOLA or any rules or regulations promulgated thereunder (or any successor provisions) or otherwise cause the Investor
to “control” the Company under and for purposes of the HOLA or any rules or regulations promulgated thereunder (or
any successor provisions). Notwithstanding anything to the contrary in this letter agreement, the Investor (together with its Affiliates)
shall not have the ability to own or control (A) more than 24.95% of the Company’s total equity or (B) in excess of 9.95%
(or 4.95%, if so elected by the Investor) of any class of voting securities of the Company. In the event either the Company or
the Investor breaches its obligations under this paragraph 4(b) or believes that it is reasonably likely to breach such an obligation,
it shall promptly notify the other party hereto and shall cooperate in good faith with such party to modify ownership or make other
arrangements or take any other action, in each case, as is necessary to cure or avoid such breach.

 

(c)          Dilutive
Issuances. In the event the Company shall, at any time during the six-month period following the date hereof (provided
that during such period the Investor, together with its Affiliates, beneficially owns at least 4.0% of the total outstanding capital
stock of the Company), issue, sell or exchange any shares of Company Stock (other than in an Excluded Issuance) for a consideration
per share less than $12.50 per share (the consideration for any such issuance, the “Dilutive Price”, and any
such issuance, sale or exchange, a “Dilutive Transaction”), then and thereafter successively upon the consummation
of any Dilutive Transaction, the Company shall issue and deliver to the Investor certificates representing such number of additional
shares of Company Stock in an amount such that, when added to the number of shares issued to the Investor on the date hereof, the
Investor has received an aggregate number of shares equal to the amount the Investor would have received if the Investor had purchased
shares at a per share purchase price equal to the Dilutive Price for an aggregate purchase price equal to the aggregate purchase
price paid for such shares pursuant to the Subscription Documents. The Investor may elect to receive such shares in the form of
the Company’s Series B Non-Voting Preferred Stock (“Non-Voting Preferred Stock”). In all cases (i) the
shares of Common Stock held by the Investor will be limited to 9.95% (or 4.95%, if the Investor so elects) of the Company’s
total issued and outstanding shares of Common Stock (inclusive of all shares owned the Investor, including any that may have been
acquired outside of the purchase effected by way of the Subscription Documents), which, as of the date hereof, is the only class
of voting securities of the Company, and (ii) the Investor’s total equity ownership in the Company will be limited to 24.95%
of the Company’s total issued and outstanding capital stock (inclusive of all shares owned by the Investor, including any
that may have been acquired outside of the purchase effected by way of the Subscription Documents).

 

(d)          Exchange
Rights. In the event the Investor acquires in excess of 4.95% of the voting securities held by all stockholders of the
Company on a fully-diluted basis, the Investor shall have the right, but not the obligation, from time to time, in its sole discretion
but subject to the conditions set forth below, to exchange any shares of Common Stock held by the Investor for shares of the Non-Voting
Preferred Stock in order to reduce its ownership of voting Common Stock to 4.95% of the voting securities held by all stockholders
of the Company on a fully-diluted basis. The shares of Non-Voting Preferred Stock shall be issued and authorized by the Company
prior to the closing of the transactions contemplated by the Subscription Documents and shall have such rights, powers and preferences
as set forth in a Certificate of

 

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Designations of Series
B Non-Voting Preferred Stock substantially in the form attached as Exhibit A hereto. Any shares of Non-Voting Preferred
Stock received by the Investor or any Affiliate of the Investor pursuant to this paragraph shall not be convertible by the Investor
or any Affiliate of the Investor into shares of Common Stock, and any such shares shall be subject to restrictions set forth in
the Certificate of Designations of Series B Non-Voting Preferred Stock, including restrictions on transfer contained therein that
are intended to have such shares qualify as non-voting shares under the applicable requirements and policies of the Regulators.
In the event the Investor’s exercise of the exchange right set forth herein would cause any other stockholder of the Company
to own or control either (i) 25% or more of any class of voting securities of the Company or (ii) 25% or more of the total equity
of the Company, the Investor shall (A) refrain from exercising such right and (B) work together with the Company and such other
stockholder in good faith in order to manage such other stockholder’s ownership limitations for the purpose of allowing the
Investor to exercise such right; provided, however, that the Investor shall only be required to refrain
from exercising such right if the Company and such other stockholder also use good faith efforts to manage such ownership limitations
for such purpose.

 

(e)          Transferee
Exchange Rights. Any transferee of the Investor’s shares of Non-Voting Preferred Stock shall have the right to exchange
any shares of Non-Voting Preferred Stock held by such person for shares of Common Stock on a one-to-one basis; provided,
however, that neither the Investor nor any Affiliate of the Investor shall have or shall exercise such right. Any
such exchange shall be effected by way of an Exchange Agreement in form and substance substantially as set forth on Exhibit
B hereto. Notwithstanding the foregoing, the Company may deny such exchange to the extent it would be inconsistent with,
or in violation of, the requirements of any Regulator with respect to the restrictions on the transfer of the Non-Voting Preferred
Stock that are required in order to preserve the non-voting classification for regulatory purposes of the Non-Voting Preferred
Stock. Any such denial shall be imposed by the transmittal by the Company of written notice to such holder specifying in reasonable
detail the reason for such denial. Such notice may be dispatched by first class mail, by electronic transmission, or by any other
means reasonably designed and in good faith intended to provide prompt delivery to an executive officer (or equivalent) of, or
legal counsel to, such holder.

 

5.           Registration
Rights. In addition to, and not exclusive of, any other registration rights granted to the Investor pursuant to the Subscription
Documents, the Investor shall be entitled to exercise “piggyback” registration rights to participate in the registration
of shares pursuant to all registration statements proposed to be filed by the Company (except for the registration of securities
(a) to be offered pursuant to an employee benefit plan on Form S-8 or pursuant to a registration made on Form S-4 or any successor
forms then in effect or (b) in a transaction relating solely to the sale of debt or convertible debt instruments). The rights
and obligations of the Investor and the Company in respect of such registration rights shall be set forth in a Registration Rights
Agreement in form and substance substantially as set forth on Exhibit C hereto.

 

6.           Regulatory
Approval. The Company and the Investor shall cooperate to obtain the appropriate approvals from the Regulators in accordance
with this letter agreement and the Subscription Documents. If necessary, the Investor shall agree to certain passivity commitments

 

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imposed by the Regulators,
provided, that the terms and conditions of such commitments are customary and are not deemed by the Investor (in
its sole discretion) to be unreasonable and provided, further, that the Investor shall not be required to
agree to any restrictions, conditions or commitments imposed or otherwise required by any Regulator that are determined by the
Investor (in its sole discretion) to be unduly burdensome.

 

7.           Miscellaneous.
The validity, construction and interpretation of this letter agreement and the rights and duties of the parties hereunder shall
be governed by and construed in accordance with laws of the State of Delaware without regard to its conflicts of laws provisions.
This letter agreement (together with the Subscription Documents) constitutes the entire agreement among the parties hereto, and
supersedes any and all prior representations, agreements and understandings, whether written or oral, with respect to the subject
matter hereof. This letter agreement shall not be modified, amended or waived, in whole or in part, except by written agreement
of both parties. The provisions hereof shall be binding upon, and shall inure to the benefit of, the parties hereto and their successors
and assigns. Each of the parties hereto shall, at the request of the other party, execute, deliver and acknowledge without any
consideration, such additional documents, instruments or certificates or do or cause to be done such other things as are reasonably
necessary or desirable to make effective the agreements and transactions contemplated by this letter agreement. This letter agreement
may be executed and delivered (including by facsimile or other electronic transmission) in multiple counterparts, each of which
shall constitute an original and all of which together shall be deemed to be one and the same instrument.

 

[Remainder of page intentionally left
blank. Signature page follows.]

 

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	 	Very truly yours,
	 	 
	 	Esquire Financial Holdings, Inc.
	 	 	 
	 	By:	/s/ Andrew C. Sagliocca
	 	Name:	Andrew C. Sagliocca
	 	Title:	President and Chief Executive Officer

 

******************************************************

 

ACKNOWLEDGED AND AGREED:

 

CJA PRIVATE EQUITY
FINANCIAL

RESTRUCTURING MASTER
FUND I, LP

 

		By:	CJA Private Equity Financial Restructuring

GP I, Ltd, its General Partner

 

By: Christopher J. Acito & Associates

GP, LLC, its Managing Member

 

	By: 	/s/ Christopher J. Acito	 
	Name:  	Christopher J. Acito	 
	Title:  	Managing Member	 

 

[Signature Page to Investor Rights Letter
Agreement]

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