Upland Software (UPLD) AI Stock Analysis

• Market Cap: $80.56M
• Dividend Yield: N/A
• Average Volume (3M): 725.41K
• Price to Earnings (P/E): ―
• Beta (1Y): 2.02
• Revenue Growth: -12.09%
• EPS Growth: 62.51%
• Country: US
• Employees: 998
• Sector: Technology
• Sector Strength: 86
• Industry: Software - Application
• EPS (TTM): 0.15
• Shares Outstanding: 28,772,095
• 10 Day Avg. Volume: 1,497,838
• 30 Day Avg. Volume: 725,413
• PEG Ratio: N/A
• Price to Book (P/B): N/A
• Price to Sales (P/S): N/A
• P/FCF Ratio: N/A
• Enterprise Value/Market Cap: 4.95
• Enterprise Value/Revenue: 1.58
• Enterprise Value/Gross Profit: 2.21
• Enterprise Value/Ebitda: 166.85
• 1Y Price Target: $4.00
• Price Target Upside: 47.06% Upside
• Rating Consensus: Strong Buy
• Number of Analyst Covering: 4

• Rating: 54 Neutral
• Price Target: $2.50 ▼(-8.09% Downside)

Upland Software's overall stock score reflects significant financial challenges, with declining revenues and high leverage posing risks. However, positive momentum in technical analysis and strategic financial moves, such as debt refinancing and investment in AI, provide some optimism. The earnings call highlighted improvements in EBITDA margins and growth prospects, but valuation concerns persist due to ongoing losses.

Positive Factors

Business Strategy

Upland has predominantly divested and sunset their front-office solutions, improving margins and adding visibility around growth.

Debt Management

The recent debt refinance eliminates any immediate cash concerns, which is expected to attract new interest.

Financial Performance

Upland is poised to deliver over $20 million of annual free cash flow, which supports a premium to the current valuation.

Negative Factors

Revenue Impact

Upland divested another product line, Mobile Messaging, which was guided to negatively impact revenue by $25mm.

Revenue Trends

Revenue declines are expected to extend into future years on divestitures and sunset revenue.

Upland Software Business Overview & Revenue Model

Company Description

Upland Software, Inc. provides cloud-based enterprise work management software in the United States, the United Kingdom, Canada, and internationally. It offers a family of software applications under the Upland brand in the areas of marketing, sales, contact center, project management, information technology, business operations, and human resources and legal. The company also provides professional services, such as implementation, data extraction, integration and configuration, and training services, as well as customer support services. It serves large global corporations, various government agencies, and small and medium-sized businesses, as well as financial, consulting, technology, manufacturing, media, telecommunication, political, healthcare, life sciences, retail and hospitality, and non-profit industries through direct and indirect sales organizations. The company was formerly known as Silverback Enterprise Group, Inc. and changed its name to Upland Software, Inc. in November 2013. Upland Software, Inc. was incorporated in 2010 and is headquartered in Austin, Texas.

How the Company Makes Money

Upland Software generates revenue primarily through a subscription-based model, offering its software solutions on a recurring basis to businesses. This model allows the company to secure consistent, predictable revenue streams from its customer base. Key revenue streams include subscription fees for its cloud-based applications, which are typically charged on a monthly or annual basis. Additionally, Upland earns revenue from professional services, such as implementation and consulting, which help clients effectively deploy and utilize their software solutions. The company also benefits from upselling and cross-selling opportunities within its existing customer base, expanding the use of its products. Strategic partnerships with other technology providers and integrations with various platforms further enhance Upland's offerings, contributing to its overall earnings growth.

Upland Software Financial Statement Overview

Summary

Upland Software is experiencing financial difficulties with declining revenues and persistent losses. The company has a high leverage ratio and negative return on equity, indicating financial instability. While there is some positive cash flow from operations, it is insufficient to cover net losses.

Income Statement

Upland Software's income statement reveals a challenging financial situation. The company has experienced declining revenue over the TTM period with a negative revenue growth rate of -5.96%. The gross profit margin remains relatively strong at 71.78%, indicating efficient cost management. However, the net profit margin is deeply negative at -18.07%, reflecting significant losses. The EBIT and EBITDA margins are also negative, suggesting operational inefficiencies and high fixed costs.

Balance Sheet

The balance sheet indicates a high level of leverage with a debt-to-equity ratio of 3.09, which poses a risk in terms of financial stability. The return on equity is negative, highlighting the company's inability to generate profits from shareholders' investments. The equity ratio is low, suggesting a heavy reliance on debt financing. Overall, the balance sheet reflects financial vulnerability and potential liquidity concerns.

Cash Flow

The cash flow statement shows a decline in free cash flow growth by -9.66% in the TTM period, which is concerning. However, the operating cash flow to net income ratio of 0.28 indicates that the company is generating positive cash flow from operations, albeit not sufficient to cover net losses. The free cash flow to net income ratio is relatively high at 0.94, suggesting some level of cash flow efficiency despite the net losses.

Breakdown	TTM	Dec 2024	Dec 2023	Dec 2022	Dec 2021	Dec 2020
Income Statement
Total Revenue	251.76M	274.79M	297.85M	317.30M	302.02M	291.78M
Gross Profit	180.71M	193.70M	201.49M	213.56M	202.56M	193.33M
EBITDA	2.39M	-46.17M	-96.99M	15.14M	18.00M	22.04M
Net Income	-45.49M	-112.73M	-179.87M	-68.41M	-58.21M	-51.22M
Balance Sheet
Total Assets	441.72M	529.52M	870.02M	1.11B	1.03B	1.01B
Cash, Cash Equivalents and Short-Term Investments	41.01M	56.43M	236.56M	248.65M	189.16M	250.03M
Total Debt	258.67M	291.96M	480.62M	523.13M	528.65M	533.30M
Total Liabilities	357.99M	424.60M	626.09M	692.30M	712.72M	704.61M
Stockholders Equity	83.73M	104.92M	243.93M	421.16M	316.29M	306.62M
Cash Flow
Free Cash Flow	23.76M	23.36M	48.72M	29.11M	40.62M	34.30M
Operating Cash Flow	25.24M	24.24M	49.94M	29.98M	41.74M	35.62M
Investing Cash Flow	7.58M	-882.00K	-1.22M	-63.22M	-93.53M	-68.97M
Financing Cash Flow	-224.27M	-202.31M	-61.38M	94.15M	-8.18M	107.90M

Upland Software Technical Analysis

• Technical Analysis Sentiment: Positive
• Last Price: 2.72
• 50DMA: Positive
• 100DMA: Positive
• 200DMA: Negative
• MACD: Negative
• RSI: Neutral
• STOCH: Neutral

Evaluating momentum and price trends is crucial in stock analysis to make informed investment decisions. For UPLD, the sentiment is Positive. The current price of 2.72 is above the 20-day moving average (MA) of 2.39, above the 50-day MA of 2.15, and below the 200-day MA of 2.99, indicating a neutral trend. The MACD of 0.21 indicates Negative momentum. The RSI at 60.09 is Neutral, neither overbought nor oversold. The STOCH value of 29.75 is Neutral, not indicating any strong overbought or oversold conditions. Overall, these indicators collectively point to a Positive sentiment for UPLD.

Upland Software Peers Comparison

Name	Overall Rating	Market Cap	P/E Ratio	ROE	Dividend Yield	Revenue Growth	EPS Growth
Sector *	61 Neutral	$35.09B	8.26	-10.57%	1.90%	8.56%	-9.51%
RSSS	59 Neutral	$103.22M	―	-30.88%	―	14.85%	-460.91%
UPLD	54 Neutral	$80.56M	―	-208.78%	―	-12.09%	62.51%
DUOT	51 Neutral	$124.25M	―	-274.34%	―	172.93%	34.97%
LPSN	44 Neutral	$90.05M	―	-137.76%	―	-24.89%	-72.84%
TROO	―	$110.27M	―		―	―	―
PSQH	48 Neutral	$73.92M	―	-269.26%	―	93.83%	23.31%

Upland Software Corporate Events

Upland Software Secures New $240 Million Loan Agreement

On July 25, 2025, Upland Software entered into a Credit Agreement with Sound Point Capital, establishing a new $240 million senior secured term loan and a $30 million revolving credit facility, both maturing in 2031. This refinancing enhances Upland’s financial flexibility, allowing further investment in their AI-powered solutions and supporting long-term growth, as stated by CEO Jack McDonald.

Upland Software Announces Leadership Transition Plans

Karen Cummings, President and COO of Upland Software, will retire on July 31, 2025, with no disagreements cited. Daniel Doman will assume the role of Chief Product and Operating Officer on August 1, 2025, while CEO John T. McDonald will also take on the role of President.

Upland Software Holds Annual Meeting, Elects Directors

On June 4, 2025, Upland Software held its Annual Meeting at its Austin, Texas offices, where stockholders voted on key proposals. The meeting saw the election of three Class II directors, the ratification of Ernst & Young, LLP as the independent auditor for the fiscal year ending December 31, 2025, and the approval of executive compensation on an advisory basis. These decisions reflect the company’s ongoing governance and operational strategies, impacting its leadership structure and financial oversight.