EXHIBIT 99.1

PROS HOLDINGS, INC. REPORTS FIRST QUARTER 2021 FINANCIAL RESULTS

HOUSTON – May 4, 2021 — PROS Holdings, Inc. (NYSE: PRO), a provider of AI-powered solutions that optimize selling in the digital economy, today announced financial results for the first quarter ended March 31, 2021.

“I’m incredibly proud of how our team executed in the first quarter,” stated CEO Andres Reiner. “We exceeded the high end of our guidance range across all metrics and welcomed some amazing new customers to the PROS family. We’re confident in our business and the momentum we’re seeing, and as a result, we’re happy to be able to provide annual guidance once again.”

First Quarter 2021 Financial Highlights

Key financial results for the first quarter 2021 are shown below. Throughout this press release, all dollar figures are in millions, except net loss per share. Unless otherwise noted, all results are on a reported basis and are compared with the prior-year period.

	GAAP			Non-GAAP
	Q1 2021	Q1 2020	Change	Q1 2021	Q1 2020	Change
Revenue:
Total Revenue	$61.4	$66.3	(7)%	n/a	n/a	n/a
Subscription Revenue	$42.6	$43.2	(1)%	n/a	n/a	n/a
Subscription and Maintenance Revenue	$52.3	$55.7	(6)%	n/a	n/a	n/a
Profitability:
Gross Profit	$34.9	$37.6	(7)%	$36.1	$39.1	(8)%
Operating Loss	$(20.6)	$(21.4)	$0.8	$(11.6)	$(13.1)	$1.5
Net Loss	$(22.0)	$(22.7)	$0.7	$(9.7)	$(9.8)	$0.1
Net Loss Per Share	$(0.50)	$(0.53)	$0.03	$(0.22)	$(0.23)	$0.01
Adjusted EBITDA	n/a	n/a	n/a	$(9.4)	$(11.4)	$2.1
Cash:
Net Cash Used in Operating Activities	$(4.4)	$(24.2)	$19.7	n/a	n/a	n/a
Free Cash Flow	n/a	n/a	n/a	$(4.6)	$(25.5)	$20.9

The attached table provides a summary of PROS results for the period, including a reconciliation of GAAP to non-GAAP metrics.

Recent Business Highlights

•Welcomed new customers that are adopting our digital selling technology such as Dedalus, Deluxe, Florida Water Products, and United Airlines, among others.

•Designated as one of the 2021 Best Workplaces in Texas by Great Place to Work, in recognition of PROS people first culture and commitment to creating an inclusive environment where employees can bring their authentic selves to work.

•Named inaugural winner of the 2021 Artificial Intelligence Excellence Award for Machine Learning, in recognition of our market-leading AI-powered digital selling innovations.

•Named a Microsoft Top 350 U.S. Partner by Redmond Channel Partner, placing PROS in the top 1% of Microsoft partners, continued proof of our successful partnership.

1

•Appointed Katrina Klier as Chief Marketing Officer to lead PROS global marketing strategy, responsible for fueling revenue growth by optimizing demand generation, increasing engagement, and amplifying brand visibility.

Financial Outlook

PROS currently anticipates the following based on an estimated 44.3 million basic weighted average shares outstanding for the second quarter of 2021 and a 22% non-GAAP estimated tax rate for the second quarter and a full year 2021.

	Q2 2021 Guidance	v. Q2 2020 at Mid-Point	Full Year 2021 Guidance	v. Prior Year at Mid-Point
Total Revenue	$61.0 to $62.0	(4)%	$250.5 to $253.5	—%
Subscription Revenue	$43.0 to $43.5	2%	$176.5 to $179.5	4%
ARR	n/a	n/a	$211.0 to $216.0	2%
Non-GAAP Loss Per Share	$(0.23) to $(0.21)	$(0.08)	n/a	n/a
Adjusted EBITDA	$(10.0) to $(9.0)	$(3.8)	$(36.0) to $(33.0)	$(6.9)
Free Cash Flow	n/a	n/a	$(39.0) to $(35.0)	$16.3

Conference Call

In conjunction with this announcement, PROS Holdings, Inc. will host a conference call on Thursday, May 4, 2021, at 4:45 p.m. ET to discuss the Company’s financial results and business outlook. To access this call, dial 1-877-407-9039 (toll-free) or 1-201-689-8470. The live and archived webcasts of this call can be accessed under the “Investor Relations” section of the Company’s website at www.pros.com.

A telephone replay will be available until Tuesday, May 18, 2021, at 1-844-512-2921 (toll-free) or 1-412-317-6671 using the pass code 13718107.

About PROS

PROS Holdings, Inc. (NYSE: PRO) provides AI solutions that optimize selling in the digital economy. PROS solutions make it possible for companies to price, configure and sell their products and services in an omnichannel environment with speed, precision and consistency. Our customers, who are leaders in their markets, benefit from decades of data science expertise infused into our industry solutions. To learn more, visit www.pros.com.

Forward-looking Statements

This press release contains forward-looking statements within the meaning of the Private Securities Litigation Reform Act of 1995, including statements about the business impact and duration of the coronavirus (COVID-19) pandemic; our financial outlook; expectations; ability to achieve future growth and profitability; management's confidence and optimism; positioning; customer successes; demand for our software solutions; pipeline; business expansion; revenue; subscription revenue; ARR; non-GAAP loss per share; adjusted EBITDA; free cash flow; shares outstanding and effective tax rate. The forward-looking statements contained in this press release are based upon our historical performance and our current plans, estimates and expectations and are not a representation that such plans, estimates or expectations will be achieved. Factors that could cause actual results to differ materially from those described herein include, among others, risks related to: (a) the impact of the COVID-19 pandemic, such as the scope and duration of the outbreak and timeframe for recovery of the travel industry, (b) cybersecurity, (c) increasing business from customers and maintaining subscription renewal rates, (d) managing our growth effectively, (e) disruptions from our third party data center, software, data, and other unrelated service providers, (f) implementing our solutions, (g) cloud operations, (h) intellectual property and third-party software, (i) acquiring and integrating businesses and/or technologies, (j) catastrophic events, (k) operating globally, including economic and commercial disruptions, (l) potential downturns in sales, (m) software innovation, (n) competition, (o) market acceptance of our software innovations, (p) maintaining our corporate culture, (q) personnel risks including loss of any key employees, (r) expanding and training our direct and indirect sales force, (s) evolving data privacy, cyber security and data localization laws, (t) our debt repayment obligations, (u) the timing of revenue recognition and cash flow from operations, (v) migrating customers to our latest cloud solutions, and (w) returning to profitability. Additional information relating to the risks and uncertainties affecting our business is contained in our filings with the SEC. These forward-looking statements represent our expectations as of the date hereof. Subsequent events

2

may cause these expectations to change, and PROS disclaims any obligations to update or alter these forward-looking statements in the future, whether as a result of new information, future events or otherwise.

Non-GAAP Financial Measures

PROS has provided in this release certain non-GAAP financial measures, including non-GAAP gross profit and margin, non-GAAP income (loss) from operations or non-GAAP operating loss, annual recurring revenue, adjusted EBITDA, free cash flow, non-GAAP subscription revenue, non-GAAP tax rate, non-GAAP net income (loss) or non-GAAP net loss, and diluted earnings (loss) per share or non-GAAP net loss per share. PROS uses these non-GAAP financial measures internally in analyzing its financial results and believes they are useful to investors, as a supplement to GAAP measures, in evaluating PROS’ ongoing operational performance and cloud transition. Non-GAAP gross margin can be compared to gross margin which can be calculated from the condensed consolidated statements of income (loss) by dividing gross profit by total revenue. Non-GAAP gross margin is similarly calculated but first adds back to gross profit the portion of certain of the non-GAAP adjustments described below attributable to cost of revenue. Non-GAAP subscription margin can be compared to subscription margin which can be calculated from the condensed consolidated statements of income (loss) by dividing subscription gross profit (subscription revenue minus subscription cost) by subscription revenue. Non-GAAP subscription margin is similarly calculated but first subtracts out from subscription cost the portion of certain of the non-GAAP adjustments described below attributable to cost of subscription. These items and amounts are presented in the Supplemental Schedule of Non-GAAP Financial Measures.

Non-GAAP financial measures should not be considered in isolation from, or as a substitute for, financial information prepared in accordance with GAAP. Investors are encouraged to review the reconciliation of these non-GAAP measures to their most directly comparable GAAP financial measure as detailed above. A reconciliation of GAAP to the non-GAAP financial measures has been provided in the tables included as part of this press release, and can be found, along with other financial information, in the investor relations portion of our website. PROS' use of non-GAAP financial measures may not be consistent with the presentations by similar companies in PROS' industry. PROS has also provided in this release certain forward-looking non-GAAP financial measures, including non-GAAP income (loss) from operations, annual recurring revenue, non-GAAP loss per share, adjusted EBITDA, free cash flow, non-GAAP tax rates, and calculated billings (collectively the "non-GAAP financial measures") as follows:

Non-GAAP income (loss) from operations: Non-GAAP income (loss) from operations excludes the impact of share-based compensation, amortization of acquisition-related intangibles and new headquarters noncash rent expense. Non-GAAP income (loss) from operations excludes the following items from non-GAAP estimates:

•Share-Based Compensation: Although share-based compensation is an important aspect of compensation for our employees and executives, our share-based compensation expense can vary because of changes in our stock price and market conditions at the time of grant, varying valuation methodologies, and the variety of award types. Since share-based compensation expense can vary for reasons that are generally unrelated to our performance during any particular period, we believe this could make it difficult for investors to compare our current financial results to previous and future periods. Therefore, we believe it is useful to exclude share-based compensation in order to better understand our business performance and allow investors to compare our operating results with peer companies.

•Amortization of Acquisition-Related Intangibles:  We view amortization of acquisition-related intangible assets, such as the amortization of the cost associated with an acquired company's research and development efforts, trade names, customer lists and customer relationships, as items arising from pre-acquisition activities determined at the time of an acquisition. While these intangible assets are continually evaluated for impairment, amortization of the cost of purchased intangibles is a static expense, one that is not typically affected by operations during any particular period.

•New Headquarters Noncash Rent Expense: Noncash rent expense is related to our new corporate headquarters and is incurred prior to occupation of this facility. These amounts are unrelated to our core performance during any particular period and we believe this could make it difficult for investors to compare our current financial results to previous and future periods. Therefore, we believe it is useful to exclude the noncash rent expense on the preoccupied new headquarters in order for investors to better understand our business performance and allow investors to compare our operating results with peer companies.

Non-GAAP loss per share: Non-GAAP net income (loss) excludes the items listed above as excluded from non-GAAP income (loss) from operations and also excludes amortization of debt discount and issuance costs and the taxes related to these items and the items excluded from non-GAAP income (loss) from operations. Estimates of non-GAAP loss per share are calculated by dividing estimates for non-GAAP loss by our estimate of shares outstanding for the future period. In addition to the items listed

3

above as excluded from non-GAAP income (loss) from operations, non-GAAP net income (loss) excludes the following items from non-GAAP estimates:

•Amortization of Debt Discount and Issuance Costs: Amortization of debt discount and issuance costs are related to our convertible notes. These amounts are unrelated to our core performance during any particular period, and therefore, we believe it is useful to exclude these amounts in order to better understand our business performance and allow investors to compare our results with peer companies.

•Taxes: We exclude the tax consequences associated with non-GAAP items to provide investors with a useful comparison of our operating results to prior periods and to our peer companies because such amounts can vary significantly. In the fourth quarter of 2014, we concluded that it is more likely than not that we will be unable to fully realize our deferred tax assets and accordingly, established a valuation allowance against those assets. The ongoing impact of the valuation allowance on our non-GAAP effective tax rate has been eliminated to allow investors to better understand our business performance and compare our operating results with peer companies.

Annual Recurring Revenue: Annual Recurring Revenue ("ARR") is used to assess the trajectory of our cloud business. ARR means, as of a specified date, the contracted recurring revenue, including contracts with a future start date, together with annualized overage fees incurred above contracted minimum transactions, and excluding perpetual and term license agreements recognized as license revenue in accordance with GAAP. ARR should be viewed independently of revenue and any other GAAP measure.

Non-GAAP Tax Rate: The estimated non-GAAP effective tax rate adjusts the tax effect to quantify the impact of the excluded non-GAAP items.

Adjusted EBITDA: Adjusted EBITDA is defined as GAAP net income (loss) before interest expense, provision for income taxes, depreciation and amortization, as adjusted to eliminate the effect of stock-based compensation cost, amortization of acquisition-related intangibles, depreciation and amortization, new headquarters noncash rent expense, debt extinguishment fees and capitalized internal-use software development costs. Adjusted EBITDA should not be considered as an alternative to net income (loss) as an indicator of our operating performance.

Free Cash Flow: Free cash flow is a non-GAAP financial measure which is defined as net cash provided by (used in) operating activities, less capital expenditures (excluding expenditures for PROS new headquarters), purchases of other (non-acquisition-related) intangible assets and capitalized internal-use software development costs.

Calculated Billings: Calculated billings is defined as total subscription, maintenance and support revenue plus the change in recurring deferred revenue in a given period.

These non-GAAP estimates are not measurements of financial performance prepared in accordance with GAAP, and we are unable to reconcile these forward-looking non-GAAP financial measures to their directly comparable GAAP financial measures because the information described above which is needed to complete a reconciliation is unavailable at this time without unreasonable effort.

Investor Contact:

PROS Investor Relations
Belinda Overdeput

713-335-5895

ir@pros.com

Media Contact:

Amanda Parrish

832-924-4731

aparrish@pros.com

4

PROS Holdings, Inc.

Condensed Consolidated Balance Sheets

(In thousands, except share and per share amounts)

(Unaudited)

	March 31, 2021		December 31, 2020
Assets:
Current assets:
Cash and cash equivalents	$	323,929	$	329,134
Trade and other receivables, net of allowance of $3,563 and $4,122, respectively	53,665		49,578
Deferred costs, current	5,883		5,941
Prepaid and other current assets	10,668		9,647
Total current assets	394,145		394,300
Property and equipment, net	35,629		36,504
Operating lease right-of-use assets	29,044		30,689
Deferred costs, noncurrent	11,735		12,544
Intangibles, net	7,467		8,341
Goodwill	49,563		50,044
Other assets, noncurrent	7,505		7,549
Total assets	$	535,088	$	539,971
Liabilities and Stockholders’ Equity:
Current liabilities:
Accounts payable and other liabilities	$	6,317	$	4,246
Accrued liabilities	16,734		13,065
Accrued payroll and other employee benefits	17,958		25,514
Operating lease liabilities, current	5,897		5,937
Deferred revenue, current	113,478		99,156
Total current liabilities	160,384		147,918
Deferred revenue, noncurrent	8,528		11,372
Convertible debt, net, noncurrent	287,169		218,028
Operating lease liabilities, noncurrent	42,529		44,099
Other liabilities, noncurrent	1,449		1,517
Total liabilities	500,059		422,934
Stockholders' equity:
Preferred stock, $0.001 par value, 5,000,000 shares authorized; none issued	—		—
Common stock, $0.001 par value, 75,000,000 shares authorized; 48,933,488  and 48,142,267 shares issued, respectively; 44,252,765 and 43,461,544 shares outstanding, respectively	49		48
Additional paid-in capital	518,338		589,040
Treasury stock, 4,680,723 common shares, at cost	(29,847)		(29,847)
Accumulated deficit	(449,472)		(438,773)
Accumulated other comprehensive loss	(4,039)		(3,431)
Total stockholders’ equity	35,029		117,037
Total liabilities and stockholders’ equity	$	535,088	$	539,971

5

PROS Holdings, Inc.

Condensed Consolidated Statements of Income (Loss)

(In thousands, except per share data)

(Unaudited) 

	Three Months Ended March 31,
	2021		2020
Revenue:
Subscription	$	42,648	$	43,170
Maintenance and support	9,674		12,523
Total subscription, maintenance and support	52,322		55,693
Services	9,056		10,618
Total revenue	61,378		66,311
Cost of revenue:
Subscription	13,801		12,864
Maintenance and support	2,258		2,790
Total cost of subscription, maintenance and support	16,059		15,654
Services	10,433		13,073
Total cost of revenue	26,492		28,727
Gross profit	34,886		37,584
Operating expenses:
Selling and marketing	21,564		24,920
Research and development	20,458		19,136
General and administrative	13,454		14,880
Loss from operations	(20,590)		(21,352)
Convertible debt interest and amortization	(1,576)		(2,062)
Other income, net	286		831
Loss before income tax provision	(21,880)		(22,583)
Income tax provision	149		152
Net loss	$	(22,029)	$	(22,735)
Net loss per share:
Basic and diluted	$	(0.50)	$	(0.53)
Weighted average number of shares:
Basic and diluted	44,245		43,102

6

PROS Holdings, Inc.

Condensed Consolidated Statements of Cash Flows

(In thousands)

(Unaudited)

	Three Months Ended March 31,
	2021		2020
Operating activities:
Net loss	$	(22,029)	$	(22,735)
Adjustments to reconcile net loss to net cash used in operating activities:
Depreciation and amortization	3,068		3,420
Amortization of debt discount and issuance costs	373		1,712
Share-based compensation	8,170		6,347
Provision for doubtful accounts	(559)		2,596
Changes in operating assets and liabilities:
Accounts and unbilled receivables	(3,610)		8,889
Deferred costs	867		763
Prepaid expenses and other assets	(395)		(701)
Operating lease right-of-use assets and liabilities	(173)		868
Accounts payable and other liabilities	2,012		579
Accrued liabilities	3,918		(3,840)
Accrued payroll and other employee benefits	(7,573)		(20,055)
Deferred revenue	11,502		(2,016)
Net cash used in operating activities	(4,429)		(24,173)
Investing activities:
Purchases of property and equipment	(1,300)		(10,993)
Capitalized internal-use software development costs	—		(412)
Purchase of equity securities	(501)		—
Net cash used in investing activities	(1,801)		(11,405)
Financing activities:
Proceeds from employee stock plans	1,596		1,364
Tax withholding related to net share settlement of stock awards	(352)		(20,172)
Net cash provided by (used in) financing activities	1,244		(18,808)
Effect of foreign currency rates on cash	(219)		91
Net change in cash and cash equivalents	(5,205)		(54,295)
Cash and cash equivalents:
Beginning of period	329,134		306,077
End of period	$	323,929	$	251,782

7

PROS Holdings, Inc.

Reconciliation of GAAP to Non-GAAP Financial Measures

(In thousands, except per share data)

(Unaudited)

We use these non-GAAP financial measures to assist in the management of the Company because we believe that this information provides a more consistent and complete understanding of the underlying results and trends of the ongoing business due to the uniqueness of these charges.

See breakdown of the reconciling line items on page 9.

		Three Months Ended March 31,						Year over Year
		2021			2020			% change
GAAP gross profit		$	34,886		$	37,584		(7)	%
	Non-GAAP adjustments:
	New headquarters noncash rent expense	—			162
	Amortization of acquisition-related intangibles	421			842
	Share-based compensation	826			524
Non-GAAP gross profit		$	36,133		$	39,112		(8)	%
Non-GAAP gross margin		58.9		%	59.0		%
GAAP loss from operations		$	(20,590)		$	(21,352)		(4)	%
	Non-GAAP adjustments:
	New headquarters noncash rent expense	—			555
	Amortization of acquisition-related intangibles	867			1,383
	Share-based compensation	8,170			6,347
	Total Non-GAAP adjustments	9,037			8,285
Non-GAAP loss from operations		$	(11,553)		$	(13,067)		(12)	%
Non-GAAP loss from operations % of total revenue		(18.8)		%	(19.7)		%
GAAP net loss		$	(22,029)		$	(22,735)		(3)	%
	Non-GAAP adjustments:
	Total Non-GAAP adjustments affecting loss from operations	9,037			8,285
	Amortization of debt discount and issuance costs	373			1,702
	Tax impact related to non-GAAP adjustments	2,895			2,923
Non-GAAP net loss		$	(9,724)		$	(9,825)		(1)	%
Non-GAAP diluted loss per share		$	(0.22)		$	(0.23)
Shares used in computing non-GAAP loss per share		44,245			43,102

8

PROS Holdings, Inc.

Supplemental Schedule of Non-GAAP Financial Measures

Increase (Decrease) in GAAP Amounts Reported

(In thousands)

(Unaudited)

		Three Months Ended March 31,
		2021		2020
Cost of Subscription Items
	New headquarters noncash rent expense	—		14
	Amortization of acquisition-related intangibles	408		683
	Share-based compensation	148		87
	Total cost of subscription items	$	556	$	784
Cost of Maintenance Items
	New headquarters noncash rent expense	—		26
	Amortization of acquisition-related intangibles	13		159
	Share-based compensation	104		66
	Total cost of maintenance items	$	117	$	251
Cost of Services Items
	New headquarters noncash rent expense	—		122
	Share-based compensation	574		371
	Total cost of services items	$	574	$	493
Sales and Marketing Items
	New headquarters noncash rent expense	—		104
	Amortization of acquisition-related intangibles	446		541
	Share-based compensation	2,224		1,866
	Total sales and marketing items	$	2,670	$	2,511
Research and Development Items
	New headquarters noncash rent expense	—		190
	Share-based compensation	1,826		1,507
	Total research and development items	$	1,826	$	1,697
General and Administrative Items
	New headquarters noncash rent expense	—		99
	Share-based compensation	3,294		2,450
	Total general and administrative items	$	3,294	$	2,549

9

PROS Holdings, Inc.

Supplemental Reconciliation of GAAP to Non-GAAP Financial Measures

(In thousands)

(Unaudited)

	Three Months Ended March 31,
	2021		2020
Adjusted EBITDA
GAAP Loss from Operations	$	(20,590)	$	(21,352)
Amortization of acquisition-related intangibles	867		1,383
New headquarters noncash rent expense	—		555
Share-based compensation	8,170		6,347
Depreciation and other amortization	2,201		2,037
Capitalized internal-use software development costs	—		(412)
Adjusted EBITDA	$	(9,352)	$	(11,442)
Net cash used in operating activities	$	(4,429)	$	(24,173)
Purchase of property and equipment (excluding new headquarters)	(203)		(957)
Capitalized internal-use software development costs	—		(412)
Free Cash Flow	$	(4,632)	$	(25,542)
Guidance
	Q2 2021 Guidance
	Low		High
Adjusted EBITDA
GAAP Loss from Operations	$	(22,200)	$	(21,200)
Amortization of acquisition-related intangibles	900		900
Share-based compensation	9,100		9,100
Depreciation and other amortization	2,200		2,200
Adjusted EBITDA	$	(10,000)	$	(9,000)
	Full Year 2021 Guidance
	Low		High
Adjusted EBITDA
GAAP Loss from Operations	$	(84,400)	$	(81,400)
Amortization of acquisition-related intangibles	3,400		3,400
Share-based compensation	36,700		36,700
Depreciation and other amortization	8,300		8,300
Adjusted EBITDA	$	(36,000)	$	(33,000)

10