14 years of historical data (2012–2025) · Technology · Software - Application
Percentile shows where the current value sits in 30-year historical distribution. Sparklines show 5-year trend.
Price-based multiples — how expensive the stock is relative to earnings, sales, book value, and cash flow
Upland Software, Inc. currently has a negative P/E ratio, indicating the company is operating at a loss on a trailing-twelve-month basis. On a free-cash-flow basis, the stock trades at 1.2x P/FCF, 81% below the 5-year average of 6.1x.
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Market Cap | $29M | $41M | $121M | $136M | $225M | $544M | $1.2B | $825M | $543M | $399M | $147M |
| Enterprise Value | $234M | $247M | $356M | $380M | $499M | $883M | $1.5B | $1.2B | $806M | $488M | $167M |
| P/E Ratio → | -0.62 | — | — | — | — | — | — | — | — | — | — |
| P/S Ratio | 0.13 | 0.19 | 0.44 | 0.46 | 0.71 | 1.80 | 4.19 | 3.71 | 3.62 | 4.07 | 1.97 |
| P/B Ratio | 0.34 | 0.51 | 1.15 | 0.56 | 0.53 | 1.72 | 3.99 | 3.88 | 6.16 | 4.36 | 2.50 |
| P/FCF | 1.17 | 1.67 | 5.16 | 2.78 | 7.72 | 13.38 | 35.63 | 79.78 | 84.72 | 54.89 | 52.71 |
| P/OCF | 1.11 | 1.59 | 4.98 | 2.72 | 7.50 | 13.02 | 34.31 | 68.31 | 73.94 | 51.68 | 38.05 |
P/E links to full P/E history page with 30-year chart
Enterprise-value multiples — capital-structure-neutral measures of total business value
Upland Software, Inc.'s enterprise value stands at 4.8x EBITDA, 83% below its 5-year average of 28.3x. The Technology sector median is 17.5x, placing the stock at a 72% discount on an enterprise-value basis.
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| EV / Revenue | — | 1.14 | 1.30 | 1.27 | 1.57 | 2.92 | 5.16 | 5.32 | 5.38 | 4.98 | 2.23 |
| EV / EBITDA | 4.81 | 5.06 | — | — | 31.37 | 48.38 | 64.47 | 114.72 | 48.44 | 626.74 | 131.18 |
| EV / EBIT | 14.10 | 14.85 | — | — | — | — | — | — | — | — | — |
| EV / FCF | — | 10.09 | 15.25 | 7.79 | 17.15 | 21.74 | 43.88 | 114.44 | 125.73 | 67.12 | 59.56 |
Margins and return-on-capital ratios measuring operating efficiency
Upland Software, Inc. earns an operating margin of 7.7%. Operating margins have expanded from -55.0% to 7.7% over the past 3 years, signaling improving operational efficiency. A negative ROE of -41.9% indicates the company is currently destroying shareholder equity. ROIC of 4.0% represents below-average returns on invested capital.
Full margin charts and quarterly trend are on the Earnings History page
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Gross Margin | 62.4% | 62.4% | 70.5% | 67.6% | 67.3% | 67.1% | 66.3% | 69.0% | 67.6% | 65.6% | 63.1% |
| Operating Margin | 7.7% | 7.7% | -37.2% | -55.0% | -12.7% | -11.5% | -8.2% | -10.9% | -3.1% | -11.4% | -11.4% |
| Net Profit Margin | -17.9% | -17.9% | -41.0% | -60.4% | -21.6% | -19.3% | -17.6% | -20.4% | -6.6% | -19.1% | -18.1% |
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| ROE | -41.9% | -41.9% | -64.6% | -54.1% | -18.6% | -18.7% | -19.7% | -30.1% | -11.1% | -24.9% | -22.7% |
| ROA | -8.3% | -8.3% | -16.1% | -18.1% | -6.4% | -5.7% | -5.4% | -6.6% | -2.6% | -8.7% | -9.9% |
| ROIC | 4.0% | 4.0% | -18.5% | -20.8% | -4.5% | -4.2% | -3.1% | -4.0% | -1.3% | -6.5% | -8.9% |
| ROCE | 4.6% | 4.6% | -17.8% | -19.3% | -4.4% | -3.9% | -2.9% | -4.2% | -1.6% | -7.0% | -8.6% |
Solvency and debt-coverage ratios — lower is generally safer
Upland Software, Inc. carries a Debt/EBITDA ratio of 4.8x, which is highly leveraged (65% above the sector average of 2.9x). Net debt stands at $206M ($235M total debt minus $29M cash). Interest coverage of just 1.1x is concerning — the company has limited headroom to absorb earnings volatility before struggling with debt service.
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Debt / Equity | 2.91 | 2.91 | 2.78 | 1.97 | 1.24 | 1.67 | 1.74 | 2.51 | 3.17 | 1.22 | 0.81 |
| Debt / EBITDA | 4.82 | 4.82 | — | — | 32.86 | 28.97 | 22.84 | 51.72 | 16.81 | 142.86 | 37.74 |
| Net Debt / Equity | — | 2.55 | 2.24 | 1.00 | 0.65 | 1.07 | 0.92 | 1.68 | 2.98 | 0.97 | 0.32 |
| Net Debt / EBITDA | 4.22 | 4.22 | — | — | 17.24 | 18.60 | 12.13 | 34.75 | 15.80 | 114.16 | 15.10 |
| Debt / FCF | — | 8.42 | 10.08 | 5.01 | 9.43 | 8.36 | 8.26 | 34.67 | 41.02 | 12.23 | 6.85 |
| Interest Coverage | 1.05 | 1.05 | -11.32 | -8.76 | -1.41 | -1.10 | -0.76 | -1.34 | -0.59 | -1.65 | -3.53 |
Short-term solvency ratios and asset-utilisation metrics
The current ratio of 0.80x is below 1.0, meaning current liabilities exceed current assets. The current ratio has declined from 2.30x to 0.80x over the past 3 years.
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Current Ratio | 0.80 | 0.80 | 0.98 | 2.30 | 2.12 | 1.68 | 2.62 | 1.85 | 0.61 | 0.69 | 1.19 |
| Quick Ratio | 0.80 | 0.80 | 0.98 | 2.30 | 2.05 | 1.68 | 2.57 | 1.85 | 0.59 | 0.69 | 1.19 |
| Cash Ratio | 0.31 | 0.31 | 0.47 | 1.81 | 1.64 | 1.21 | 2.06 | 1.35 | 0.16 | 0.30 | 0.72 |
| Asset Turnover | — | 0.52 | 0.52 | 0.34 | 0.28 | 0.29 | 0.29 | 0.25 | 0.31 | 0.35 | 0.50 |
| Inventory Turnover | — | — | — | — | 9.46 | — | 17.02 | — | 18.45 | — | — |
| Days Sales Outstanding | — | 52.87 | 56.92 | 55.44 | 60.86 | 66.83 | 61.34 | 91.89 | 108.45 | 98.76 | 74.47 |
Earnings, FCF, buyback, and dividend yields — total returns to shareholders
Upland Software, Inc. returns 0.5% to shareholders annually primarily through share buybacks.
Full dividend history and growth charts are on the Dividend History page
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Dividend Yield | — | — | — | — | — | — | — | — | — | — | — |
| Payout Ratio | — | — | — | — | — | — | — | — | — | — | — |
| Metric | TTM | FY 2025 | FY 2024 | FY 2023 | FY 2022 | FY 2021 | FY 2020 | FY 2019 | FY 2018 | FY 2017 | FY 2016 |
|---|---|---|---|---|---|---|---|---|---|---|---|
| Earnings Yield | — | — | — | — | — | — | — | — | — | — | — |
| FCF Yield | 85.7% | 59.7% | 19.4% | 35.9% | 13.0% | 7.5% | 2.8% | 1.3% | 1.2% | 1.8% | 1.9% |
| Buyback Yield | 0.5% | 0.3% | 9.1% | 10.4% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.3% |
| Total Shareholder Yield | 0.5% | 0.3% | 9.1% | 10.4% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.0% | 0.3% |
| Shares Outstanding | — | $29M | $28M | $32M | $32M | $30M | $27M | $23M | $20M | $18M | $16M |
Compare UPLD with 10 similar companies in its peer group
| Company | Market Cap | P/E | EV/EBITDA | P/FCF | Gross Margin | Op Margin | ROE | ROIC | Debt/EBITDA |
|---|---|---|---|---|---|---|---|---|---|
| $29M | -0.6 | 4.8 | 1.2 | 62.4% | 7.7% | -41.9% | 4.0% | 4.8 | |
| $2B | -37.9 | — | 45.1 | 57.8% | -12.1% | -13.3% | -8.6% | — | |
| $13B | 284.1 | 69.2 | 17.8 | 83.8% | 0.4% | 2.3% | 0.4% | 2.8 | |
| $9B | 39.9 | 28.7 | 22.7 | 55.7% | 26.1% | 71.7% | 236.8% | 0.4 | |
| $6B | 27.1 | 14.3 | 17.3 | 68.8% | 19.1% | 20.0% | 26.2% | 0.5 | |
| $2B | -24.6 | — | 78.9 | 77.5% | -11.0% | -9.6% | -6.0% | — | |
| $142M | -2.7 | — | — | 75.0% | -12.3% | — | — | — | |
| $7B | -92.0 | — | 48.6 | 76.1% | -15.7% | -8.6% | -8.0% | — | |
| $2B | 23.2 | 11.3 | 14.0 | 64.2% | 15.7% | 10.2% | 12.2% | 0.1 | |
| $2B | -18.5 | — | 37.3 | 67.1% | -19.6% | -23.9% | -20.5% | — | |
| $3B | 17.5 | 13.5 | 11.0 | 82.8% | 33.2% | 38.2% | 47.5% | 0.4 | |
| Technology Median | — | 27.7 | 17.5 | 19.2 | 48.5% | -0.6% | 2.4% | 2.9% | 2.9 |
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Includes 30+ ratios · 14 years · Updated daily
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Start ComparisonQuick answers to the most common questions about buying UPLD stock.
Upland Software, Inc.'s current P/E ratio is -0.6x. This places it at the 50th percentile of its historical range.
Upland Software, Inc.'s current EV/EBITDA is 4.8x. This enterprise value multiple compares the company's total value (equity + debt - cash) to its EBITDA. The historical average is 39.5x.
Upland Software, Inc.'s return on equity (ROE) is -41.9%. The historical average is -29.1%.
Based on historical data, Upland Software, Inc. is trading at a P/E of -0.6x. This is at the 50th percentile of its historical P/E range. Compare with industry peers and growth rates for a complete picture.
Upland Software, Inc. has 62.4% gross margin and 7.7% operating margin.
Upland Software, Inc.'s Debt/EBITDA ratio is 4.8x, indicating high leverage. A ratio above 4x may signal elevated financial risk.