SecProbe.io

June 9 , 2014

Via E -mail
John T. McDonald
Chief Executive Officer
Upland Software, Inc.
401 Congress Avenue, Suite 2950
Austin, TX  78701

Re: Upland Software, Inc.
Confidential Draft Registration Statement on Form S -1
Submitted May 13, 2014
CIK No . 0001 505155

Dear Mr. McDonald :

We have reviewed your draft registration statement  and have the following comments.  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 o ur comments apply to your facts and circumstances or do not
believe an amendment is appropriate, please tell us why in your response.

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

General

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

2. Please supplementally provide us with copies of all written co mmunications, as defined
in Rule 405 under the Securities Act, that you , or anyone authorized to do so on your
behalf , present to potential investors in reliance on Section 5(d) of the Securities Act,
whether or not they retain copies of the communications . Similarly, please
supplementally provide us with any research reports about you that are published or
distributed in reliance upon Section 2(a)(3) of the Securities Act of 1933 added by
Section 105(a) of the Jumpstart Our Business Startups Act by any bro ker or dealer that is
participating or will participate in your offering.

John T. McDonald
Upland Software, Inc.
June 9 , 2014
Page 2

 3. We will process your amendments without price ranges.  Since the price range you select
will affect disclosure in several sections of the filling, we will need sufficient time to
process your amendments once a price range is included and the material information
now appearing blank throughout the document has been provided.  Please understand that
the effect of the price range on disclosure throughout the document may cause us to ra ise
issues in areas on which we have not previously commented.

4. Please supplementally provide us with copies of any graphical materials or artwork you
intend to use in your prospectus.  Upon review of such materials, we may have further
comments.  See Que stion 101.02 of our Securities Act Forms Compliance and Disclosure
Interpretations, available on our website.

Prospectus Summary

Overview, page 1

5. Please provide support fo r the assertion that you are a “leading” provider of cloud -based
enterprise work  management software.  Also briefly describe in this section your “land -
and-expand go -to-market strategy.”

6. We note the risk factor disclosure on page 34 discussing the concentration of ownership
of your common stock among your existing officers, directors  and principal stockholders.
Disclose in the summary that your directors, executive officers and principal stockholders
will continue to have a substantial control over the company after the offering and
disclose the percentage of your voting power to be held by affiliates following the
offering.

7. With respect to all third -party statements in your prospectus —such as market data by
IDC—please provide us with the relevant portion of the industry research reports you
cite.  To expedite our review, please cl early mark each source to highlight the applicable
portion of the section containing the statistic, and cross -reference it to the appropriate
location in your prospectus.  Also, please tell us whether any of the reports were prepared
for you or in connecti on with the offering .

Key Metrics, page 10

8. Your reconciliation of adjusted EBITDA eliminates the impact of discontinued
operations and other expenses, before arriving at an EBITDA subtotal.  As such, it
appears that this subtotal does not meet the definition of EBITDA.  Please revise your
presentat ion accordingly or discontinue your presentation of such subtotal.  Further,
EBITDA should be disclosed as a Non -GAAP measure.  We note that you discuss
adjusted EBITDA but not EBITDA.

John T. McDonald
Upland Software, Inc.
June 9 , 2014
Page 3

 Risk Factors

“We rely on third -party software that is required for  the development…,” page 24

9. We note your statement that you rely on software licensed from or hosted by third parties
to offer your applications.  Please include in your business section a discussion of your
material license agreements and, to the extent you substantially depend on one or more
software licenses, please file any such license agreements as exhibits, or advise.  Refer to
Item 601(b)(10) of Regulation S -K.

“Sales of a substantial number of shares of our common stock…,” page 33

10. We note the disclosure in this risk factor and on page 120 that the representatives of the
underwriters may release the securities subject to the lock -up agreements any time with
or without notice.   To the extent any lock -up agreement relates to shares hel d by your
officers or directors, please explain how the above statement is consistent with the
requirements of FINRA Rule 5131(d)(2).   Additionally, please disclose whether there are
any agreements, understandings or intentions, tacit or explicit, to relea se any of the
securities from the lock -ups prior to the expiration of the corresponding period.   If so, or
if this constitutes a material risk, provide appropriate risk factor disclosure regarding the
discretionary power to release the securities subject t o the lock -up agreements.

Use of Proceeds, page 40

11. Although you do not have current specific plans for the net proceeds of this offering ,
consider disclosing the amount of proceeds that you plan to use to grow your business.
This section does not requir e disclosure of definitive plans and it is acceptable to provide
a quantitative discussion of preliminary plans.  Refer to Item 504 of Regulation S -K and
Instruction 7 to Item 504.  We note on page 78  you describe your growth strategy but do
not indicate i f it will be funded with offering proceeds.

Capitalization, page 41

12. The table presented on page 41 presents all the preferred stock within stockholders’
equity whereas your consolidated balance sheet on page F -3 presents the preferred stock
as temporar y equity.  Please reconcile these presentations.

Management’s Discussion and Results of Operations

Overview, page 49

13. Expand your overview  to provide insight into material opportunities, challenges and risks
facing the company, such as those presented by known material trends  and uncertainties,
as well as the actions management is taking to address these opportunities, challenges and
risks. See Item 303(a) of Regulation S -K and SEC Release No. 33 -8350. For example,

John T. McDonald
Upland Software, Inc.
June 9 , 2014
Page 4

 discuss the challenges and risks you face from your recent rapid growth and your plans to
expand your sales force and your overseas operations.  Your discussion of trends,
challeng es and uncertainties should provide insight into the extent to which reported
financial information is indicative of future results.

2013 Acquisitions, page 51

14. We note you acquired Clickability, Inc. , for $12.3 million .  Please provide your
significanc e evaluation based on the thresholds set forth in Rule 1 -02(w) of Regulation S -
X.  If significant, please revise your filing to provide the financial statements required by
Rule 3 -05 of Regulation S -X.

Components of Operating Results, page 53

15. You discuss the significant components that impact  cost of revenues and operating
expenses.  However, you do not quantify the relative percentages associated with each
cost component identified as having a material impact.  In this regard, please tell us what
consideration you gave to providing  greater insight into the relative significance of these
components along with a discussion of the variability of the significant cost components ,
included within cost of revenues and operating expenses , for each of the peri ods
presented.

Determination of the Fair Value of Stock -Based Compensation Grants , page 68

16. We note that your estimated stock volatility for 2013 declined significantly in comparison
to 2012.  Please describe the reasons for this decline.  Explain whether you changed your
comparable companies between these periods.  Tell us how you identified com parable
companies and explain how you considered that you were recently formed when making
this selection.

Common Stock Valuation Methodology , page 69

17. Please clarify whether the column labeled “Estimated Fair Value per Share” in your table
on page 70 r epresents the estimated fair value of your shares of common stock or your
stock options.  In this regard, the amounts do not agree with the discussion directly below
this table.  In addition, similar amounts and disclosures are provided in Footnote 9 on
page F-30.  Please advise.

Business Combinations and the Recoverability of Goodwill and Long -lived Intangible Assets ,
page 71

18. Your disclosure under this subheading indicates that you have one reporting unit.
However, your disclosure on page F -11 indic ates that you have two reporting units.
Please clarify this apparent inconsistency.

John T. McDonald
Upland Software, Inc.
June 9 , 2014
Page 5

 19. Please consider disclosing the percentage by which fair value exceeds the carrying value
of your goodwill.  In addition, please tell us the key assumptions used to dete rmine the
fair value of your reporting units.  Consider including a  discussion of the degree of
uncertainty associated with the key assumptions.   The discussion regarding uncertainty
should provide spe cifics to the extent possible  and description of potent ial events and/or
changes in circumstances that could reasonably be expected to negatively affect the key
assumptions.

20. We note that you recorded a $1.1 million impairment charge for trade name in 2013.
Please advise to which expense caption this charge w as recorded to.  In this regard, we
did not note any reference to this charge within your results of operations discussion.

Comparison of Fiscal Years Ended December 31, 2012 and 2013 , page 58

Revenue , page 58

21. While you discuss the factors that had an impact on revenues, please consider revising
your disclosures to quantify those factors that resulted in material posit ive or negative
fluctuations, on revenue, year over year.  For example, you indicate that the increase in
subscription and support revenu e during fiscal 2013 resulted primarily from the
acquisitions of FileBound and ComSci in fiscal 2013, as well as the inclusion of the full
year of ownership of our 2012 acquisitions.  However, you do not quantify the impact of
these items .  As such, it is unclear how that these disclosures provide sufficient detail for
an investor to gain an understanding of the relative impact that these underlying factors
had, and will continue to have,  on your results of operations. See Section III.B.4 of SEC
Release 33 -8350.

22. Based on your disclosures, it appears that your revenue growth is mostly due to
acquisitions.  Since your disclosures focus on the impact of the acquisitions, it’s not clear
whether you had any organic growth or deterioration in your existing opera tions.  In this
regard, please tell us what consideration you gave to providing disclosures that discuss
organic growth or deterioration of your existing business operations, for each of the years
presented.  Such disclosures would provide investors with a n understanding of continuing
operations and provide transparency into the growth trends of your core businesses,
including your ability to continue to generate organic growth in future periods.

Loan and Security Agreements, page 62

23. Please add a risk f actor disclosing that your obligations and those of your subsidiaries
under the loan agreements are secured by a security interest in substantially all of your
assets.

John T. McDonald
Upland Software, Inc.
June 9 , 2014
Page 6

 Business,  page 73

24. You state elsewhere that approximately 24% of your revenues was g enerated outside of
the United States in fiscal year 2013 and that foreign expansion is a core component of
your growth strategy.  Please tell us how you considered addressing your foreign
operations and international expansion plans in your business discu ssion.  In addition,
please provide the information required by Item 101(d) of Regulation S -K for each of
your last three fiscal years.  Alternatively, to the extent that the disclosed information
conforms to generally accepted accounting principles, you m ay include a cross -reference
with respect to the information provided in Note 16 to your financial statements.

Technology and Operations, page 83

25. We note that you currently serve your customers from eight third -party data center
hosting facilities.  Ple ase discuss your contractual arrangements with these centers in
your prospectus and file material agreements with your principal web hosting  providers
as exhibits  to the registration statement, or tell us why this is not required.  Refer to Item
601(b)(10) of Regulation S -K.

Intellectual Property and Proprietary Rights, page 85

26. Please revise to provi de a brief description of three patents that you own and  the d uration
and effect of the  patent s on your business.  Refer to  Item 101(c)(1)(iv) of Regulation S -K.

Management , page 86

27. Please disclose the names of the companies for which Mr. Hill worked as a consultant
from June 2007 to June 2012.  Also, we note the disclosure that prior to December 2011,
Mr. Wilson held various sales and management positions at Seagate Technology PLC
and Fujitsu Consumer Products of America.  Please revise to clearly identify Mr.
Wilson’s principal occupations and places of employment for the past five years.
Similarly, please clarify Mr. Sarracino’s dates of employment at Activant Capital and
Serent Ca pital.  Refer to Item 401(e)(1) of Regulation S -K.

Executive Compensation

Summary Compensation Table for Fiscal Year Ended December 31, 2013 , page 92

28. We note the disclosure in footnote five to the summary compensation table.  Please revise
to disclose  the “blended” rate used to convert Canadian dollars to U.S. dollars.  Refer to
Instruction 2 to Item 402(n) of Regulation S -K.

John T. McDonald
Upland Software, Inc.
June 9 , 2014
Page 7

 Notes to Consolidated Financial Statements

Note 2. Significant Accounting Policies
Revenue recognition, page F -12

29. We note  that in certain instances your professional services is not a separate unit of
accounting from your subscription services and as a result, you are recognizing the
implementation fees ratably over the contract life.   Please tell us your consideration for
recognizing these implementation fees over the estimated customer life based on the
guidance in footnote 39 of SAB Topic 13A.3.f.

30. We note that in certain instances your professional services are a separate unit of
accounting.  Please explain how such serv ices impacts the timing of revenue recognition
for the subscription term.  Indicate whether your customer can fully utilize their
subscription prior to the completion of the professional services.

31. Tell us and disclose how you determine whether an element or deliverable is a separate
unit of accounting (i.e., standalone value).

Comprehensive Loss, page F -16

32. You indicate that accumulated comprehensive loss as of December 31, 2012 and 2013
was due to foreign currency translation adjustments.   However, it appears that your
accumulated comprehensive loss resulted from net losses incurred for each of the periods
p