Upland Software (UPLD) AI Stock Analysis

• Market Cap: $16.10M
• Dividend Yield: N/A
• Average Volume (3M): 145.13K
• Price to Earnings (P/E): 9.3
• Beta (1Y): 2.01
• Revenue Growth: -15.54%
• EPS Growth: 61.46%
• Country: US
• Employees: 998
• Sector: Technology
• Sector Strength: 88
• Industry: Software - Application
• EPS (TTM): 0.24
• Shares Outstanding: 29,118,177
• 10 Day Avg. Volume: 148,481
• 30 Day Avg. Volume: 145,125
• PEG Ratio: 0.02
• Price to Book (P/B): 0.51
• Price to Sales (P/S): 0.19
• P/FCF Ratio: 1.67
• Enterprise Value/Market Cap: 21.80
• Enterprise Value/Revenue: 1.62
• Enterprise Value/Gross Profit: 2.16
• Enterprise Value/Ebitda: 88.56
• 1Y Price Target: $3.75
• Price Target Upside: 202.42% Upside
• Rating Consensus: Moderate Buy
• Number of Analyst Covering: 2
• EPS Forecast (FY): 0.76
• Revenue Forecast (FY): $200.10M

• Rating: 42 Neutral
• Price Target: $0.50 ▼(-59.76% Downside)
• Action: Reiterated Date: 03/11/26
• Date: Action: Reiterated 03/11/26

The score is held down primarily by weak technicals (sharp downtrend with bearish momentum) and fundamental pressure from declining revenue and a leveraged balance sheet. These are partially offset by consistently positive free cash flow and earnings-call emphasis on margin expansion and cash generation, with valuation (low P/E) providing only modest support.

Positive Factors

Consistent positive free cash flow

Sustained positive free cash flow provides durable liquidity to fund operations, pay down debt, and invest in AI product development without reliance on equity raises. Over 2–6 months this underpins financial flexibility despite accounting losses and supports execution of strategic initiatives.

Sustained margin expansion and strong adjusted EBITDA

Material margin improvement reflects durable operating leverage and cost discipline, allowing the company to retain cash from each incremental dollar of revenue. Continued margin focus can sustain profitability and free cash flow even if revenue growth is modest, supporting long-term viability.

AI-focused product strategy and market validation

Concentrating revenue in AI-enabled knowledge and content management positions Upland in a structural growth market. Recognition (G2 badges, industry guides) and new customer wins support differentiated product-market fit, enhancing long-term upsell and renewal potential across enterprise accounts.

Negative Factors

Revenue declines driven by divestitures

Divestitures materially reduce the recurring revenue base and scale, creating a smaller top-line to leverage fixed costs and invest in growth. Over the medium term this raises the burden on remaining products to deliver organic expansion and makes achieving prior growth trajectories harder.

Elevated leverage and weakened equity

High leverage limits strategic flexibility, increases interest exposure, and constrains M&A or investment capacity. With equity base reduced by cumulative losses, the balance sheet is vulnerable to revenue setbacks and raises refinancing risk over the next several quarters if cash generation weakens.

Modest organic growth and execution risk

Low organic growth targets and recent weak bookings indicate a meaningful execution challenge in converting pipeline into durable revenue. Over 2–6 months this constrains top-line momentum, increases pressure on cost cuts to drive results, and risks underutilizing product investments.

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 primarily makes money by selling subscriptions to its cloud-based software products (SaaS), typically contracted on a recurring basis (e.g., annual or multi-year agreements) and priced based on factors such as number of users/seats, usage/volume, or the scope of features/modules purchased (exact pricing mechanics vary by product and are not uniformly disclosed). In addition to subscription revenue, the company generates revenue from related services such as implementation, onboarding/configuration, training, and customer support/professional services tied to deploying and optimizing its software. A smaller portion of revenue may come from maintenance or support associated with any on-premises or term-based licenses where applicable; if present, these arrangements generally produce recurring support/maintenance fees rather than one-time license sales. Revenue is influenced by renewals and expansions within the installed customer base (upsells/cross-sells across its product portfolio) as well as new customer acquisition. The company also sells through a mix of direct sales and partner/third-party channels (specific partner identities and contribution levels are not consistently detailed publicly), with partner ecosystems potentially supporting lead generation, implementation, and co-selling for certain products.

Upland Software Financial Statement Overview

Summary

Results are pressured by shrinking revenue and ongoing net losses, and the balance sheet is a key risk with elevated leverage and declining equity. Offsetting this, cash generation is consistently positive (TTM operating cash flow and free cash flow), supporting operations and debt reduction, and losses have narrowed versus 2024.

Income Statement

Revenue has been shrinking across recent periods (TTM (Trailing-Twelve-Months) down ~7.9% after modest declines in 2023–2024), signaling pressure on the top line. Profitability is mixed: gross margin remains strong (TTM ~73%), but the company is still loss-making (TTM net margin ~-18%). The latest TTM shows a notable improvement versus 2024 (losses narrowed materially and EBIT moved closer to breakeven), but the overall earnings profile remains weak and inconsistent.

Balance Sheet

Leverage remains elevated with substantial debt (TTM total debt ~$235M) relative to equity (~$81M), limiting financial flexibility. While total debt has come down meaningfully from 2022–2023 levels, equity has also declined over time, reflecting cumulative losses and weakening capitalization. Returns on equity are deeply negative (TTM), highlighting that shareholders are not currently earning an adequate return and the balance sheet remains a key risk area.

Cash Flow

Cash generation is a relative bright spot: the company produced positive operating cash flow and free cash flow in every period shown, including TTM (operating cash flow ~$25.8M; free cash flow ~$24.4M). Free cash flow has been slightly down year over year in TTM, but overall cash conversion remains solid given ongoing accounting losses, helping support debt reduction and ongoing operations. The main weakness is that cash flow has not shown consistent growth recently.

Breakdown	Dec 2025	Dec 2024	Dec 2023	Dec 2022	Dec 2021
Income Statement
Total Revenue	216.88M	274.79M	297.85M	317.30M	302.02M
Gross Profit	135.27M	193.70M	201.49M	213.56M	202.56M
EBITDA	48.76M	-46.17M	-91.70M	15.14M	18.00M
Net Income	-38.90M	-112.73M	-179.87M	-68.41M	-58.21M
Balance Sheet
Total Assets	413.18M	529.52M	870.02M	1.11B	1.03B
Cash, Cash Equivalents and Short-Term Investments	29.40M	56.43M	236.56M	248.65M	189.16M
Total Debt	364.27M	291.96M	480.62M	523.13M	528.65M
Total Liabilities	332.47M	424.60M	626.09M	692.30M	712.72M
Stockholders Equity	80.71M	104.92M	243.93M	421.16M	316.29M
Cash Flow
Free Cash Flow	24.45M	23.36M	48.72M	29.11M	40.62M
Operating Cash Flow	25.80M	24.24M	49.94M	29.98M	41.74M
Investing Cash Flow	8.80M	-882.00K	-1.22M	-63.22M	-93.53M
Financing Cash Flow	-63.45M	-202.31M	-61.38M	94.15M	-8.18M

Upland Software Technical Analysis

• Technical Analysis Sentiment: Negative
• Last Price: 1.24
• 50DMA: Negative
• 100DMA: Negative
• 200DMA: Negative
• MACD: Positive
• RSI: Positive
• STOCH: Positive

Evaluating momentum and price trends is crucial in stock analysis to make informed investment decisions. For UPLD, the sentiment is Negative. The current price of 1.24 is above the 20-day moving average (MA) of 0.77, above the 50-day MA of 1.12, and below the 200-day MA of 1.82, indicating a bearish trend. The MACD of -0.18 indicates Positive momentum. The RSI at 16.24 is Positive, neither overbought nor oversold. The STOCH value of 12.29 is Positive, not indicating any strong overbought or oversold conditions. Overall, these indicators collectively point to a Negative 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	$37.18B	12.37	-10.20%	1.83%	8.50%	-7.62%
YXT	49 Neutral	$36.11M	-2.82	-89.60%	―	―	―
LPSN	44 Neutral	$32.30M	-0.45	132.32%	―	-23.03%	-107.34%
NXTT	44 Neutral	$10.69M	-0.91	74.86%	―	259.01%	-61.05%
RDZN	44 Neutral	$93.24M	-5.19	<0.01%	―	3.42%	93.90%
PHUN	43 Neutral	$35.13M	-5.76	-11.63%	―	―	―
UPLD	42 Neutral	$16.10M	9.34	-76.27%	―	-15.54%	61.46%

Upland Software Corporate Events

Upland Software Announces CEO Transition to Sean Nathaniel

Upland Software announced that founder Jack McDonald, who has served as chairman and chief executive officer since establishing the company in 2010, notified the board on February 21, 2026, of his decision to retire as CEO effective April 30, 2026, while remaining chairman. His transition agreement cancels his existing performance stock units in favor of new restricted stock units and keeps him available for up to 24 months to support leadership transition, with the company emphasizing that his departure is not due to any disagreement over operations or policies.

On February 21, 2026, the board appointed former Upland executive Sean Nathaniel, currently president and CEO of DryvIQ, as chief executive officer effective May 1, 2026, with a compensation package that includes salary, bonus eligibility, time-based restricted stock units, and performance-based stock awards. Nathaniel, who helped lead Upland through its 2014 IPO and has deep experience in AI and enterprise content, is expected to steer the company’s next phase of AI-driven growth, reinforcing its strategic focus on serving as a core intelligence layer for large enterprises’ data and content ecosystems.

The most recent analyst rating on (UPLD) stock is a Hold with a $1.50 price target. To see the full list of analyst forecasts on Upland Software stock, see the UPLD Stock Forecast page.