Document:

EX-10.1

 Exhibit 10.1 

FIRST AMENDMENT TO STOCKHOLDERS’ AGREEMENT 

This First Amendment to Stockholders’ Agreement (this “First Amendment”) is entered as of April 27, 2015, among
CUMULUS MEDIA INC., a Delaware corporation (the “Company”); and CRESTVIEW RADIO INVESTORS, LLC (“Crestview Stockholder”). 

RECITALS 
 WHEREAS, the
parties hereto, along with certain other stockholders of the Company, are parties to that certain Stockholders’ Agreement dated as of September 16, 2011 (the “Stockholders’ Agreement”); 

WHEREAS, the Company has confirmed that Crestview Stockholder holds the number of shares of Common Stock of the Company necessary to approve
and effect, together with the approval of the Company, the amendments provided for herein to the Stockholders’ Agreement, and Crestview Stockholder and the Company desire to modify certain terms of the Stockholders’ Agreement in accordance
with the terms hereof; 
 WHEREAS, this First Amendment, once executed by the Company and Crestview Stockholder shall be incorporated into
the Stockholders’ Agreement and shall have the same force and effect as if it were part of the original Stockholders’ Agreement; and 

WHEREAS, capitalized terms used but not defined in this First Amendment have the respective meanings set forth in the Stockholders’
Agreement. 
 NOW, THEREFORE, in consideration of the premises, and of the representations, warranties, covenants and agreements set forth
herein, the parties agree upon the amendments to the Stockholders’ Agreement set for below: 
  

	 	1.	The final paragraph of Section 2.1(b) is deleted and replaced in its entirety with: 

“The rights of the Stockholders to designate nominees for election to the Board set forth in this Section 2.1(b) are
personal to each Stockholder and may not be exercised by any Transferee, except such rights may be exercised by the applicable Transferee (if and to the extent assigned to such Transferee by the transferring Stockholder) in the event (x) a
Stockholder no longer holds any Common Stock but its Affiliates continue to hold Common Stock transferred by such Stockholder to such Affiliates (whether directly or by Transfers through other Affiliates of such Stockholder), and such rights have
not been terminated pursuant to Section 2.1(e), or (y) a Transferee and its Affiliates acquires by Transfer from a Stockholder (whether directly or by Transfers through other Affiliates of such Stockholder) in a Transfer not prohibited
under Section 3.5 a number of shares of Common Stock in excess of those specifically indicated in Section 2.1(e) in respect of the transferring Stockholder necessary for such Stockholder to maintain such right. The provisions of
Section 2.1(e) will continue to apply to any Transferee described in this Section 2.1(b).” 

	 	2.	Section 2.1(c) is deleted and replaced in its entirety with: 

 “(c)
Chairman. Jeffrey Marcus has been appointed by the Directors of the Company to serve as the Chairman of the Board (who shall not be an officer of the Company), effective as of the date of the First Amendment to this Agreement. For so long as
Crestview Stockholder is the largest stockholder of the Company, Crestview Stockholder will have the right to have one of its designees who is nominated and elected to the Board appointed by the Directors to serve as the Chairman of the Board. In
the event that a vacancy is created at any time by the death, disability, resignation or removal of the Person serving as Chairman of the Board, the Stockholders shall use their reasonable best efforts to cause the Directors to approve any such
other designee of Crestview Stockholder who is nominated and elected to the Board to serve as the Chairman of the Board. Any such designee must qualify as an Independent Director. This right of Crestview Stockholder to have one of its designees who
is nominated and elected to the Board appointed by the Directors to serve as Chairman of the Board is personal to Crestview Stockholder and may not be exercised by any Transferee, except in the event Crestview Stockholder no longer holds any Common
Stock but its Affiliates continue to hold Common Stock transferred by Crestview Stockholder to such Affiliates (whether directly or by Transfers through other Affiliates of such Stockholder), and such right of Crestview Stockholder to designate at
least one nominee for election to the Board has not been terminated pursuant to Section 2.1(e), then this right of Crestview Stockholder may be exercised by such Affiliates of Crestview Stockholder to which such Common Stock was transferred.
Further, this right of Crestview Stockholder to have one of its designees who is nominated and elected to the Board appointed by the Directors to serve as Chairman of the Board shall terminate when the rights of Crestview Stockholder to designate
any nominee for election to the Board have been terminated pursuant to Section 2.1(e).” 
  

	 	3.	In Section 2.2, “lead director” is deleted and replaced with “Chairman”. 

  

	 	4.	In Section 3.2(a), “Prior to the seven (7) year anniversary of the Closing” is deleted and replaced with “Prior to the eight (8) year anniversary of the Closing,”. 

 

	 	5.	Section 3.2(b) is deleted and replaced in its entirety with: 

 “(b)
Notwithstanding anything in Section 3.2(a) to the contrary, Crestview Stockholder will be permitted to (i) exercise the Crestview Class A Warrants and (ii) directly or indirectly, acquire, agree to acquire or make a
proposal to acquire (or publicly announce or otherwise disclose an intention to propose to acquire) beneficial ownership of a number of shares that would not cause Crestview Stockholder to beneficially own more than 75,000,000 shares of Common Stock
(in addition to the shares underlying the Crestview Class A Warrants), as such number may be proportionately adjusted for stock splits, reverse stock splits and the like after the date of this Agreement.” 

	 	6.	In Section 3.5, the phrase “ten percent (10%)” is deleted and replaced with “twenty-five percent (25%)”, and there is added to the end of such Section the following: 

“Prior to the consummation of a Transfer by a Stockholder that is not an Excluded Transfer, as a condition thereto, the
applicable Transferee shall agree in writing to be bound by the terms of this Agreement (if not already bound hereby) to the same extent as the Transferring Stockholder is bound hereunder, and the applicable Transferee shall be entitled to the
benefits of the terms of this Agreement to the same extent as the Transferring Stockholder is entitled hereunder (including, as applicable, any rights assigned by the Transferring Stockholder to the applicable Transferee in accordance with
Section 2.1(b)), and shall become a Stockholder (and, if applicable, Significant Stockholder) hereunder, prior to giving effect to such Transfer, if and only if, immediately following the consummation of such Transfer to such proposed
Transferee, such Person would have (together with its Affiliates and all members of any Group that includes such Person) beneficial ownership of ten percent (10%) or more of the outstanding shares of Common Stock.” 

 

	 	7.	In Section 4.5, “lead director” is deleted, and replaced with “Chairman of the Board”. 

 IN WITNESS WHEREOF, the parties hereto have caused this First Amendment to be executed effective
as of the date set forth in the first paragraph hereof. 
  

			
	CUMULUS MEDIA INC.
		
	By:		/s/ Richard S. Denning
	Name:		Richard S. Denning
	Title:		Senior Vice President
	
	CRESTVIEW RADIO INVESTORS, LLC
		
	By:		/s/ Jeffrey A. Marcus
	Name:		Jeffrey A. Marcus
	Title:		Managing DirectorEX-10.2

 Exhibit 10.2 

FIRST AMENDMENT TO EMPLOYMENT AGREEMENT 

This First Amendment to Employment Agreement (“First Amendment”), is made by and between Lewis W. Dickey, Jr. (“Employee”)
and Cumulus Media Inc. (“Company”) on the 28th day of April, 2015 (the “Amendment Effective Date”). 
 WHEREAS,
Employee and Company are parties to that certain Employment Agreement dated November 29, 2011 (“Agreement”); 

WHEREAS, the Parties wish to extend and modify the terms of the Agreement in accordance with the terms hereof; and 

WHEREAS, this First Amendment, once executed by the Parties, shall be incorporated into the Agreement and shall have the same force and
effect as if it were part of the original Agreement between the Parties. 
 NOW THEREFORE, the Parties in consideration of the mutual
promises set forth herein, hereby agree as follows: 
  

	 	1.	The first sentence of Section 2 of the Agreement is deleted in its entirety and the following is inserted in lieu thereof: 

“The Executive’s employment under the terms and conditions of this Agreement shall commence on the Effective Date and shall
continue until December 31, 2018 (the “Initial Term”).” 
  

	 	2.	Section 3(a) of the Agreement is deleted in its entirety and the following is inserted in lieu thereof: 

“During the Term, the Executive shall, pursuant to the terms of this Agreement, serve as the Chief Executive Officer and President of
the Company, and shall report directly to the Board of Directors of the Company (the “Board”).” 
  

	 	3.	The reference to Chairman in Section 3(b) of the Agreement is hereby deleted. 

  

	 	4.	Section 6(c)(i), clause (A) of the Agreement is deleted in its entirety and replaced with the following: 

“(A) three (3) (the “Severance Multiple”) and”. 

 

	 	5.	Section 6(c)(iii) of the Agreement is deleted in its entirety and replaced with the following: 

“100% of any unvested Equity Awards shall become immediately and fully vested.” 

	 	6.	In connection with and conditional upon the effectiveness of this First Amendment, the provisions of Section 8 of each Nonqualified Stock Option Agreement under which Employee holds options exercisable for shares
of Class A Common Stock of the Company pursuant to the Company’s 2011 Equity Incentive Plan shall be amended to delete clauses (a) - (e) in their entirety and replace with the following: 

 

	 	“(a)	the date of Optionee’s Termination for Cause; 

  

	 	(b)	ninety (90) calendar days following Optionee’s Resignation Without Good Reason; or 

  

	 	(c)	ten (10) years from the Date of Grant.” 

 Further, in connection with and
conditional upon effectiveness of this First Amendment, such Section 8 of each such Nonqualified Stock Option Agreement is amended to add thereto : 

“For purposes of this Agreement, “Resignation Without Good Reason” shall mean the termination of the Optionee’s employment
with the Company or any Subsidiary by resignation by the Optionee without “Good Reason”, as that term is defined in that certain Employment Agreement by and between the Company and the Optionee, dated as of November 29, 2011, as
amended.” 
 All capitalized terms used herein, unless given specific definitions in this First Amendment shall have the definition
ascribed to such terms in the Agreement. 
 Except as expressly amended hereby, the Agreement shall remain in full force and effect in
accordance with its terms. 
 This First Amendment may be executed in any number of counterparts, each of which when taken together shall
constitute one and the same original instrument. 
 IN WITNESS WHEREOF, the parties hereto, intending to be legally bound, have executed
this First Amendment the day and year indicated herein. 
  

									
	COMPANY				EMPLOYEE
			
	Cumulus Media Inc.				Lewis W. Dickey, Jr.
				
	By:		/s/ Richard S. Denning				/s/ Lewis W. Dickey, Jr.
	Name:		Richard S. Denning						
	Title:		Senior Vice President

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