Upland Software Inc
🔔 Watch stock
Assessment
Our Rating
A journalistic assessment by our editorial team at the time of the deep dive — it rates the company, not the entry point. Not investment advice and not a solicitation to buy or sell.
We found at least one documented issue that threatens the company itself — regardless of how the stock is currently valued.
Why this colour
Red here stands for documented substance findings, not for a fallen share price. Three of them sit openly in the filings: negative equity of $52.4 million as of March 31, 2026, interest coverage below one (operating income of about $10.5 million against roughly $17.8 million of interest expense over twelve months) and an Altman Z-score of minus 1.80. On top of that comes a capital structure in which $233.7 million of secured debt and a $135.1 million preferred claim rank ahead of the common, while 78 percent of the balance sheet consists of goodwill from old acquisitions. The business itself is not worthless — it generates cash, serves more than 1,100 customers without concentration risk and faces no near-term maturity. But the substance question is documented, and in case of doubt the more cautious grade applies. The decision is yours.
What the thesis turns on
Assessment: Opportunities & Risks
Upland Software is not a cheap software house but an equity stub sitting on a large pile of debt. The business works: $24.4 million of free cash flow in 2025, a first positive operating result and a cost base $44.5 million lighter. But revenue is shrinking for the third year ($216.9 million against $297.9 million in 2023), recurring revenue fell 26.5 percent in 2025, equity stands at minus $52.4 million, and ahead of the common sit $233.7 million of secured debt at 9.7 percent plus a $135.1 million preferred claim. The 0.4 reading therefore measures the residual, not the company: against enterprise value of about $350 million you pay fifteen times free cash flow. Not investment advice.
Cash generation and cost discipline
Despite three years of falling revenue the business throws off cash: $25.8 million of operating cash flow in 2025 and $24.4 million of free cash flow, plus $5.6 million and $5.5 million in the first quarter of 2026. Sales, research and administration were cut by $44.5 million combined in 2025, and operating income turned positive at $4.4 million (10-K 2025, 10-Q for Q1 2026).
A shrinking business
Revenue fell from $297.9 million (2023) through $274.8 million (2024) to $216.9 million (2025), and by another 23.5 percent to $48.7 million in the first quarter of 2026. Annualized recurring revenue dropped from $242.1 million to $165.9 million — down 26.5 percent in 2025 alone. The reported 96 percent net dollar retention excludes the sunsetting and divested businesses (10-K 2025).
Balance sheet and capital structure
As of March 31, 2026, equity of minus $52.4 million (December 31, 2022: plus $308.9 million) sits alongside $227.7 million of secured debt at carrying value and $130.6 million of preferred stock whose liquidation preference plus dividends is $135.1 million. Goodwill and intangibles make up 78 percent of total assets, and the Altman Z-score reads minus 1.80 (as of July 26, 2026).
Interest burden
The credit facility of July 25, 2025 cost 9.7 percent at March 31, 2026, up from 5.9 percent average cash interest a year earlier. In 2025, $20.4 million of the $44.9 million generated before interest went to the lenders (45 percent); in the first quarter of 2026 the share was already 51 percent. On a twelve-month view, operating income of about $10.5 million does not cover interest expense of about $17.8 million.
Portfolio unwind
The unwinding of the acquisition portfolio is underway but expensive: product lines were sold for $15.5 million in 2025, producing a $24.4 million loss and $9.7 million of expenses; part of the price is a $5.5 million promissory note that was reserved by $1.5 million on day one. It relieves the cost side and shrinks the revenue base at the same time (10-K 2025, Note 15).
Listing and personnel
The Nasdaq deficiency notice of April 7, 2026 has been resolved since July 2, 2026 — achieved through the 1-for-10 reverse split of June 17, 2026, whose ten-day window began on the day of the split. In parallel the auditor changed (March 9, 2026, Ernst & Young to KPMG) and the finance chief changed three times (retirement effective July 27, 2026, interim from July 6, 2026, successor from August 17, 2026) — in each case, according to the filings, without disagreement.
Worth Noting
Upland Software reached our research list through the in-house stock scanner: rank 8 of the U.S. selection in the P/FCF ranking with a ratio of 0.4 (544 hits in total, with the 25 strongest shown per market selection; as of July 26, 2026). These lists are recalculated daily, so the placement is a dated snapshot.
Mind the reverse split: on June 17, 2026 every ten shares became one. All share counts in the 2025 annual report and in the quarterly report for March 31, 2026 predate the split, while all price and market value figures postdate it. The preferred conversion price of $17.50 corresponds to $175.00 after the split.
Valuation figures are dated and evergreen: the market value of roughly $12.0 million (as of July 26, 2026) was checked against the share count from the quarterly report (29,363,201 shares as of April 29, 2026, divided by ten) and the price of $4.10; both routes give the same number. Analyses are evergreen; daily prices are not a reason to buy.
Stock Watch
This analysis is as of August 26, 2026. Stock Watch will tell you what's changed at UPLD since then.
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Price history
Chart
Interactive price chart (TradingView).
52-week range: 0.509 $ to 6.50 $ · Last price: 3.80 $ (As of: September 17, 2026)
Key figures
Key figures at a glance
Every figure we hold for this stock, grouped by topic. The question mark next to a label explains what the number means.
Basics
Performance
Technical Indicators
Calculated from the price history · as of 09/18/2026
Valuation
Profitability
Balance Sheet & Safety
Growth
Dividend
This stock currently pays no dividend.
Quality & Screener
Highlighted are things our editorial team noticed: green = stands out as strong, red = deserves a closer look. No single metric is a verdict on its own — always read it in context.
Comparison
Industry comparison
The stock alongside the largest companies in the same group. The median row is the middle value of the companies shown above — not of the whole industry.
Industry: Software - Application
| Company | Market cap ($B) | P/E | EV/EBITDA | Gross Margin % | EBIT Margin % | Sales Growth (Year) % | Perf. 1Y % |
|---|---|---|---|---|---|---|---|
| Upland Software Inc UPLD | 0.0 | – | 26.8 | 76.3 | – | -21.1 | -84.2 |
| Salesforce.com Inc CRM | 194.7 | 24.2 | 14.3 | 77.3 | 21.8 | 9.6 | 1.1 |
| Uber Technologies Inc UBER | 144.3 | 18.9 | 19.7 | 40.8 | 14.6 | 18.3 | -23.8 |
| ServiceNow Inc NOW | 138.5 | 82.3 | 40.2 | 74.8 | 13.3 | 20.9 | -27.2 |
| Snowflake Inc. SNOW | 115.4 | – | -76.6 | 67.0 | -22.2 | 29.2 | 55.3 |
| Automatic Data Processing Inc ADP | 108.8 | 25.1 | 16.4 | 48.7 | 30.2 | 7.1 | -3.0 |
| Adobe Systems Incorporated ADBE | 99.2 | 14.3 | 9.8 | 89.3 | 35.3 | 10.5 | -30.2 |
| Intuit Inc INTU | 86.0 | 20.0 | 12.2 | 81.0 | 47.0 | 15.6 | -52.2 |
| Datadog Inc DDOG | 84.3 | 631.8 | 268.8 | 79.5 | 0.8 | 27.7 | 75.8 |
| Median of companies shown | 108.8 | 24.2 | 16.4 | 76.3 | 18.2 | 15.6 | -23.8 |
Based on the most recently reported figures. Only stocks from the same trading venue are lined up, so the market caps are counted in one currency. Compare in a chart →
Fiscal years
Annual Figures
Fiscal years from the audited annual reports, oldest first. EBIT is the operating profit before interest and taxes; total assets are everything the company owns.
Revenue, operating income and net income per fiscal year $M
Revenue Operating income Net income
| Fiscal Year | Revenue ($M) | EBIT ($M) | Net Income ($M) | EPS ($) | Operating Cash Flow ($M) | Equity ($M) | Total Assets ($M) |
|---|---|---|---|---|---|---|---|
| 2016 | 75 | -9 | -14 | -8.20 | 4 | 59 | 151 |
| 2017 | 98 | -11 | -19 | -10.17 | 8 | 91 | 281 |
| 2018 | 150 | -5 | -10 | -4.98 | 7 | 88 | 484 |
| 2019 | 223 | -24 | -45 | -19.64 | 12 | 213 | 897 |
| 2020 | 292 | -24 | -51 | -19.23 | 36 | 307 | 1,011 |
| 2021 | 302 | -35 | -58 | -19.21 | 42 | 316 | 1,029 |
| 2022 | 317 | -40 | -68 | -21.70 | 30 | 421 | 1,113 |
| 2023 | 298 | -164 | -180 | -56.08 | 50 | 244 | 870 |
| 2024 | 275 | -102 | -113 | -40.57 | 24 | 105 | 530 |
| 2025 | 217 | 17 | -39 | -13.60 | 26 | 81 | 413 |
Quarters
Quarterly Figures
Each bar is one quarter, the last one is the most recent. Use the switch to step through the individual figures.
Revenue & Profit
Cash Flow
Balance Sheet
Margins
Per Share
Click the chart or tab into it, then use ← and → to step through the periods.
None of the selected stocks reports this metric. Pick another metric or switch between annual and quarterly.
· Total · per year
These companies report in different currencies — switch on “Indexed” or pick a margin for a fair comparison.
The figures could not be loaded right now.
Source: fundamental data
| Quarter | EPS (Earnings Per Share) | EPS YoY (%) | Sales ($M) | Sales YoY (%) | Net Margin (%) | OCF ($M) | FCF ($M) |
|---|---|---|---|---|---|---|---|
| 2024: Q4 | -1.17 | – | 68 | -5.80 | -5.00 | 9 | 9 |
| 2025: Q1 | -8.80 | – | 64 | -10.00 | -40.60 | 8 | 8 |
| 2025: Q2 | -4.44 | – | 53 | -23.00 | -24.40 | 3 | 3 |
| 2025: Q3 | -0.38 | – | 51 | -24.20 | -2.20 | 7 | 7 |
| 2025: Q4 | 0.37 | – | 49 | -27.50 | 2.20 | 7 | 7 |
| 2026: Q1 | -0.42 | – | 49 | -23.50 | -2.50 | 6 | 6 |
| 2026: Q2 | -12.53 | -182.20 | 49 | -8.10 | -71.90 | 5 | 5 |
What Do These Terms Mean?
- EPS (Earnings Per Share):
- Quarterly profit divided by the total share count — how much of the profit works out to a single share.
- YoY (Year over Year):
- Change versus the same quarter a year ago — this is how you compare without seasonal distortion (e.g. the holiday shopping season).
- Sales:
- All revenue for the quarter, before any costs are deducted — the top line of the income statement.
- Net Margin:
- What percentage of sales is left over as profit in the end. Negative means the company is posting a loss.
- OCF (Operating Cash Flow):
- The cash that actually flows into the till from the core business during the quarter — harder to dress up than book profit.
- FCF (Free Cash Flow):
- Operating cash flow minus capital expenditures — the money that's genuinely free to use, say for paying down debt, buybacks, or dividends.
Screening
Appears in These Scanners
This stock currently matches 3 of our scanner strategies — each hit links to the scanner.
Breakout & Setup
Momentum & Trend
Research
Only genuine hits from verified scanners count; pure ranking metrics (P/E, P/S, and similar, which just sort the whole universe) don't count as a hit. View all scanners
Outlook
Analysts & Price Target
Combined picture of the price targets and recommendations of every analyst covering the stock. Price targets are expectations for the next 12 months, not promises — and they often follow the price rather than predict it.
Distribution of Recommendations
Estimates by Fiscal Year
| Fiscal Year | EPS Estimate ($) | EPS Range ($) | Revenue Estimate ($M) | Expected Growth | Analysts |
|---|---|---|---|---|---|
| 12/31/2026 | 6.67 | 6.67 – 6.67 | 193 | -27.5% | 1 |
| 12/31/2027 | 6.34 | 5.66 – 7.01 | 194 | -5.0% | 2 |
Average of the analyst estimates for the coming fiscal years. The range shows how far the most optimistic and the most cautious estimate sit apart — the wider it is, the less certain the expectation.
Valuation
What is priced in?
Instead of guessing what the stock is worth, we turn the question around: what free cash flow growth has to happen for today’s market value to add up? The assumptions behind it can be moved.
With these assumptions (discount rate 10.0%, terminal growth 2.5%), no growth rate between -20.0% and 60.0% per year explains today’s market value — the reverse calculation yields no meaningful figure here.
| Free cash flow (last twelve months) | $24.7M |
|---|---|
| Market cap | $9.0M |
| Free cash flow in year ten | – |
| Terminal value as a share of market value | – |
For comparison: over the past five years free cash flow shrank by 6.6% per year.
It shows which assumption is built into today’s price, not whether that assumption will hold. Every assumption can be changed with the sliders; the figures move with them.
A simplified model calculation — not a forecast and not a recommendation.
AI classification
AI Rating
Upland beschreibt sich in Geschäfts- und Quartalsbericht selbst als Anbieter KI-gestützter Wissens- und Inhaltssoftware; die KI-Funktionen stecken in den Abo-Produkten und sind damit Umsatzquelle.
View the full file — quotes, sources, reviewed filings
„Upland is a leader in AI-powered knowledge and content management software. Our solutions help enterprises unlock critical knowledge, automate content workflows, and drive measurable ROI"
Upland ist ein führender Anbieter KI-gestützter Software für Wissens- und Inhaltsmanagement. Unsere Lösungen helfen Unternehmen, entscheidendes Wissen nutzbar zu machen, Inhalts-Abläufe zu automatisieren und eine messbare Rendite zu erzielen
10-K · 2026-03-03 · View SEC filing
„Features include AI-driven search, content recommendations, and workflow integrations aimed at improving information accessibility and operational efficiency."
Zu den Funktionen gehören KI-gestützte Suche, Inhaltsempfehlungen und Ablauf-Integrationen, die den Zugang zu Informationen und die betriebliche Effizienz verbessern sollen.
10-K · 2026-03-03 · View SEC filing
„Upland Software, Inc., together with its wholly owned subsidiaries (“Upland,” “we,” “us,” “our,” or the “Company”), a Delaware corporation headquartered in Austin, Texas, is a leader in AI-powered knowledge and content management software."
Upland Software, Inc. ist zusammen mit ihren hundertprozentigen Tochtergesellschaften eine Kapitalgesellschaft nach dem Recht von Delaware mit Sitz in Austin, Texas, und ein führender Anbieter KI-gestützter Software für Wissens- und Inhaltsmanagement.
10-Q · 2026-05-01 · View SEC filing
„We have created our own R&D Center of Excellence in India and use AI tools to internally boost development, testing, and overall employee efficiency."
Wir haben in Indien ein eigenes Entwicklungszentrum aufgebaut und setzen KI-Werkzeuge ein, um Entwicklung, Tests und die Effizienz der Mitarbeiter intern zu steigern.
10-K · 2026-03-03 · View SEC filing
Filings Reviewed: 10-Q 2026-05-01 · 10-Q 2025-11-06 · 10-Q 2025-07-31 · 10-Q 2025-05-12 · 10-K 2026-03-03 · 10-K 2025-03-12
Rated on July 26, 2026 · How the Rating Is Built
Growth
Growth Score
Ten checks against the annual reports — each one passed counts a point.
- Revenue grows by more than 15% a year over three years -11.9%
- More than 10% revenue growth is expected for the coming year 1.6%
- Share count grows by less than 3% a year -3.2%
- Revenue growth plus cash-flow margin add up to at least 40 ("Rule of 40") -9.8%
- Gross margin at 40% or higher and without meaningful erosion 62.4%
- Goodwill from acquisitions does not grow faster than revenue 62.8%
- Net debt below twice EBITDA 22.3 x EBITDA
- Operating cash flow covers the profits of the last three years 431 m
- Return on capital at 15% or higher, or up versus two years ago 5.2%
- Insiders hold at least 10% or are net buyers 28.2%
A criterion without figures counts neither as passed nor as failed; a score is only produced from 7 judgeable criteria upwards. Source: fundamental data. All ten criteria in detail
Quality check
AAQS
3/10The AAQS (AlleAktien Quality Score) checks 10 quality criteria on growth, profitability, and balance-sheet strength — per the methodology developed and published by AlleAktien, calculated by us from our own fundamental data. A stock counts as a quality stock from 9 out of 10 points. Where a company has a shorter listing history, we calculate over the fiscal years available (at least five).
- Sales growth 10Y > 5% 12.6%
- Exp. sales growth 3Y > 5% -5.4%
- EBIT growth 10Y > 5% –
- Exp. EBIT growth 3Y > 5% -5.4%
- Net debt < 4x EBIT 12.4x
- EBIT positive, 10Y straight 1
- Max. EBIT decline < 50% 0.0%
- Return on equity > 15% –
- ROCE > 15% 5.2%
- Expected return > 10% 251.7%
View stocks with the full AAQS score · Read the methodology at AlleAktien
Source: fundamental data
Insiders
Insider Transactions
Reportable transactions by officers and major shareholders from SEC Form 4 filings. "Other" includes things like stock grants and option exercises without a buy/sell character.
| Date | Person | Role | Type | Shares | Price | Value |
|---|---|---|---|---|---|---|
| Aug 17, 2026 | Simon Jennifer L. | Chief Financial Officer | Other | 30,000 | 0.00 | – |
| Aug 7, 2026 | Mattox Timothy | Director | Sell | 847 | 4.28 | 3,625 |
| Aug 6, 2026 | Mattox Timothy | Director | Sell | 1,000 | 4.27 | 4,270 |
| Aug 5, 2026 | Mattox Timothy | Director | Sell | 1,000 | 4.53 | 4,530 |
| Aug 4, 2026 | Mattox Timothy | Director | Sell | 1,000 | 4.33 | 4,330 |
| Aug 3, 2026 | Mattox Timothy | Director | Sell | 1,000 | 4.45 | 4,450 |
| Jul 31, 2026 | Mattox Timothy | Director | Sell | 1,000 | 4.48 | 4,480 |
The company
About the Company
Upland Software, Inc. bietet zusammen mit seinen Tochtergesellschaften KI-gestützte Software für Wissens- und Content-Management unter der Marke Upland in den USA, dem Vereinigten Königreich, Kanada und international an.
- Employees
- 760
- Headquarters
- Austin, TX
- Address
- 900 South Capital of Texas Highway, 78746 Austin, United States
- Phone
- 512 960 1010
- Website
- uplandsoftware.com
- IPO Date
- 11/06/2014
- ISIN
- US91544A2087
- Stock Split
- 1:10 on 06/17/2026
Management
| Name | Title | Birth Year |
|---|---|---|
| John T. McDonald J.D. | Founder & Chairman | 1963 |
| Daniel Doman | Chief Operating & Product Officer | 1981 |
| Sean Nathaniel | CEO & President | 1977 |
| Jennifer Simon CPA | CFO and Principal Financial & Accounting Officer | 1975 |
| Rick Rinewalt | Chief Technology Officer | – |
| Matthew H. Smith | General Counsel & Secretary | 1975 |
| Jen Verzal | Senior Vice President of Human Resources | – |
| Rochelle Delley | Chief Security Officer | – |
| Austin Woody | Chief Strategy Officer & GM | – |
| Amber Bennett | Senior Vice President of Finance | – |
Executives per the latest required filings; titles kept in their original language. Source: fundamental data.
Filings
Company Filings (8-K)
An 8-K is the filing a US company must use to disclose material events immediately — takeovers, changes at the top, major contracts or payment troubles, for instance. The links open the original document at the US Securities and Exchange Commission (SEC).
- 08/14/2026 Upland Software, Inc. (UPLD): Results of Operations and Financial Condition; Financial Statements and Exhibits SEC ↗
- 08/05/2026 Upland Software, Inc. (UPLD): Notice of Delisting or Failure to Satisfy a Continued Listing Rule or Standard; Transfer of Listing SEC ↗
- 07/21/2026 Upland Software, Inc. (UPLD): Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers: Compensatory Arrangements of Certain Officers; Regulation FD Disclosure; Financial Statements and Exhibits SEC ↗
- 07/08/2026 Upland Software, Inc. (UPLD): Other Events SEC ↗
- 07/07/2026 Upland Software, Inc. (UPLD): Departure of Directors or Certain Officers; Election of Directors; Appointment of Certain Officers: Compensatory Arrangements of Certain Officers SEC ↗
Data as of: September 17, 2026 · Source: fundamental data & SEC filings (annual and quarterly reports, 10-K/10-Q)
Note: pure fact-based analysis, not investment advice and not a solicitation to buy or sell. All figures without guarantee.