SecProbe.io

August 7, 2014

Via E -mail
John T. McDonald
Chief Executive Officer
Upland Software, Inc.
401 Congress Avenue, Suite 1850
Austin, TX  78701

Re: Upland Software, Inc.
Amendment No. 1 to the Draft Registration Statement on Form S -1
Submitted July 22, 2014
CIK No . 0001 505155

Dear Mr. McDonald :

We have reviewed your amended draft registration statement  and have the following
comments.  References to prior comments are to those in our letter dated June 9, 2014.  In some
of our comments, we may ask you to provide us with information so we may better understand
your disclosure.

Please respond to this letter by providing the requested information and either submitting
an amended draft  registration statement or  publicly  filing your registration statement on
EDGAR.  If you do not believe our comments apply to your facts and circumstances or do not
believe an amendment is appropriate, please tell us why in your response.

After reviewin g the information you provide in response to these  comments  and your
amended draft registration statement or filed registration statement,  we may have  additional
comments.

Prospectus Summary

Company Overview, page 1

1. We note your response to prior comment 1.  We do not believe that you have provided
sufficient quantitative data to support the claim that you are a leading provider of cloud -
based enterprise work management software.”  Please remove this claim or advise.

The Upland Approach, page 3

2. We note the claim in the first sentence of this section that your software is “award -
winning.”  Pl ease provide support and context for this claim by disclosing in the filing the
awards that your software has won and discussing the process for each award, such as

John T. McDonald
Upland Software, Inc .
August 7, 2014
Page 2

 whether your products were independently chosen or nominated for each award or if you
appli ed for consideration, if you paid to  compete for the award, the criteria used in
conferring the award, the number of companies considered for the award and the number
of awards  made.

Use of Proceeds, page 39

3. We note that you intend to use some portion of the offering proceeds to repay outstanding
and accrued interest under your loan and security agreements with Comerica Bank.
Please disclose in this section the interest rate and maturity of your debt.  Refer to
Instruction 4 to Item 504 of Regulation S -K.

Management’s Discussion and Analysis of Financial Condition and Results of Operations, page
48

Comparison of Fiscal Quarters Ended March 31, 2013 and 2014, page 57

4. You indicate that discussing organic growth or decay would not be meaningful to
investors, as you disclose that you have achieved significant growth since inception,
primarily as a result of your acquisition strategy.   However, based on your disclosures on
page 57, growth related to acquisitions appears to exceed total subscription an d support
revenues.   In this regard, please clarify whether or not there was a corresponding decrease
in the revenues of your existing subscription and support operations.   If so, discussing the
reasons for the apparent deterioration in your existing busin ess operations, whether
temporary or permanent, would provide investors with an understanding of your
continuing operations and provide transparency into the growth trends of your core
businesses.   As such, please consider revising your filing accordingly.

Research and Development, page 58

5. We note that in January 2014, you issued 11,000,000 shares of common stock in
connection with an amendment of a technology services agreement with a related party,
and recognized a noncash charge of $11.2 million.   In this regard, please tell us the nature
of and timeline of events associated with the amendment to the technology and services
agreement.

Notes to Consolidated Financial Statements

Note 2. Significant Accounting Policies

Revenue recognition, page F -12

6. You indicate that subscription services have standalone value as such services are often
sold separately. Furthermore, you indicate that when determining whether
implementation and other professional services have standalone value apart from the

John T. McDonald
Upland Software, Inc .
August 7, 2014
Page 3

 subscripti on services, you consider various factors including the availability of the
services from other vendors.   Please clarify for us whether the available services provided
from other vendors involve implementation services related to your specific products, or
general implementation services for others in the industry.

General

7. Please update your financial statement to comply with the requirements set forth in Rule
3-12 of Regulation S -X.

If you intend to respond to these comments with an amended dr aft registration statement ,
please submit it and any associated correspondence in accordance with the guidance we provide
in the Division’s October 11 , 2012 announcement on the SEC website at
http://www.sec.gov/divisions/corpfin/cfannouncements/drsfilingprocedures101512.htm .

You may contact Juan Migone , Senior Staff Accountant,  at (202) 551 -3312  or Stephen
Krikorian, Accounting Branch Chief, at (202) 551 -3488  if you have questions regarding
comments on the financial statements and re lated matters.  Please contact Matthew Crispino,
Staff Attorney,  at (202) 551 -3456 or me at (202) 55 1-3457 with any other questions.

        Sincerely,

        /s/ Maryse Mills -Apenteng

       Maryse Mills -Apenteng
       Special Counsel

cc: Via E-mail
 Brian K. Beard, Esq.
 Wilson Sonsini Goodrich & Rosati