Comprehensive Stock Comparison
Compare Asana, Inc. (ASAN) vs Upland Software, Inc. (UPLD) Stock
Analyze side-by-side fundamentals, valuation, growth, and profitability to decide which stock is the better buy.
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Quick Verdict
| Category | Winner | Why |
|---|---|---|
| Growth | ASAN | 10.9% revenue growth vs UPLD's -7.7% |
| Value | UPLD | Better valuation composite |
| Quality / Margins | UPLD | -18.4% net margin vs ASAN's -28.3% |
| Stability / Safety | UPLD | Beta 1.43 vs ASAN's 1.70 |
| Dividends | Tie | Neither pays a meaningful dividend |
| Momentum (1Y) | ASAN | -63.1% vs UPLD's -72.2% |
| Efficiency (ROA) | UPLD | -10.6% ROA vs ASAN's -26.1%, ROIC -18.5% vs -58.9% |
Who Each Stock Is For
Income & stability
Growth exposure
Long-term compounding (10Y)
Sleep-well-at-night portfolio
Defensive / Recession hedge
Business Model
What each company does and how it makes money
Asana operates a cloud-based work management platform that helps teams organize, track, and manage their work—from daily tasks to strategic initiatives. It generates revenue primarily through subscription fees for its SaaS platform, with tiered pricing for individuals, teams, and enterprise customers. The company benefits from strong network effects within organizations and a user-friendly interface that drives adoption and reduces switching costs.
Upland Software is a cloud-based enterprise work management software provider offering applications for marketing, sales, contact center, project management, and other business functions. It generates revenue primarily through subscription fees for its software-as-a-service products—supplemented by professional services like implementation and training—with the majority coming from recurring subscriptions. The company's competitive advantage lies in its integrated family of applications that address multiple enterprise needs through a unified platform, creating cross-selling opportunities and reducing customer churn.
Revenue Breakdown by Segment
How each company's revenue is distributed across its business units
Segment breakdown not available.
Financial Metrics Comparison
Side-by-side fundamentals across 2 stocks. BestLagging
Financial Scorecard
UPLD leads in 3 of 6 categories (Financial Metrics, Valuation Metrics). ASAN leads in 1 (Total Returns). 1 tied.
Financial Metrics (TTM)
ASAN is the larger business by revenue, generating $774M annually — 3.3x UPLD's $236M. UPLD is the more profitable business, keeping -18.4% of every revenue dollar as net income compared to ASAN's -28.3%. On growth, ASAN holds the edge at +9.3% YoY revenue growth, suggesting stronger near-term business momentum.
| Metric | ASANAsana, Inc. | UPLDUpland Software, … |
|---|---|---|
| RevenueTrailing 12 months | $774M | $236M |
| EBITDAEarnings before interest/tax | -$175M | $33M |
| Net IncomeAfter-tax profit | -$219M | -$43M |
| Free Cash FlowCash after capex | $72M | $26M |
| Gross MarginGross profit ÷ Revenue | +89.5% | +73.2% |
| Operating MarginEBIT ÷ Revenue | -25.4% | -2.0% |
| Net MarginNet income ÷ Revenue | -28.3% | -18.4% |
| FCF MarginFCF ÷ Revenue | +9.4% | +11.1% |
| Rev. Growth (YoY)Latest quarter vs prior year | +9.3% | -24.2% |
| EPS Growth (YoY)Latest quarter vs prior year | -16.0% | +18.2% |
Valuation Metrics
| Metric | ASANAsana, Inc. | UPLDUpland Software, … |
|---|---|---|
| Market CapShares × price | $1.7B | $26M |
| Enterprise ValueMkt cap + debt − cash | $1.7B | $261M |
| Trailing P/EPrice ÷ TTM EPS | -6.40x | -0.21x |
| Forward P/EPrice ÷ next-FY EPS est. | 27.68x | — |
| PEG RatioP/E ÷ EPS growth rate | — | — |
| EV / EBITDAEnterprise value multiple | — | — |
| Price / SalesMarket cap ÷ Revenue | 2.28x | 0.09x |
| Price / BookPrice ÷ Book value/share | 7.16x | 0.23x |
| Price / FCFMarket cap ÷ FCF | 176.73x | 1.09x |
Profitability & Efficiency
UPLD delivers a -64.6% return on equity — every $100 of shareholder capital generates $-65 in annual profit, vs $-116 for ASAN. ASAN carries lower financial leverage with a 1.18x debt-to-equity ratio, signaling a more conservative balance sheet compared to UPLD's 2.78x. On the Piotroski fundamental quality scale (0–9), UPLD scores 7/9 vs ASAN's 3/9, reflecting strong financial health.
| Metric | ASANAsana, Inc. | UPLDUpland Software, … |
|---|---|---|
| ROE (TTM)Return on equity | -116.3% | -64.6% |
| ROA (TTM)Return on assets | -26.1% | -10.6% |
| ROICReturn on invested capital | -58.9% | -18.5% |
| ROCEReturn on capital employed | -49.8% | -17.8% |
| Piotroski ScoreFundamental quality 0–9 | 3 | 7 |
| Debt / EquityFinancial leverage | 1.18x | 2.78x |
| Net DebtTotal debt minus cash | $84M | $236M |
| Cash & Equiv.Liquid assets | $185M | $56M |
| Total DebtShort + long-term debt | $268M | $292M |
| Interest CoverageEBIT ÷ Interest expense | -65.67x | -2.94x |
Total Returns (with DRIP)
A $10,000 investment in ASAN five years ago would be worth $1,920 today (with dividends reinvested), compared to $175 for UPLD. Over the past 12 months, ASAN leads with a -63.1% total return vs UPLD's -72.2%. The 3-year compound annual growth rate (CAGR) favors ASAN at -21.7% vs UPLD's -46.6% — a key indicator of consistent wealth creation.
| Metric | ASANAsana, Inc. | UPLDUpland Software, … |
|---|---|---|
| YTD ReturnYear-to-date | -45.2% | -41.1% |
| 1-Year ReturnPast 12 months | -63.1% | -72.2% |
| 3-Year ReturnCumulative with dividends | -52.0% | -84.7% |
| 5-Year ReturnCumulative with dividends | -80.8% | -98.3% |
| 10-Year ReturnCumulative with dividends | -75.3% | -85.8% |
| CAGR (3Y)Annualised 3-year return | -21.7% | -46.6% |
Risk & Volatility
UPLD is the less volatile stock with a 1.43 beta — it tends to amplify market swings less than ASAN's 1.70 beta. A beta below 1.0 means the stock typically moves less than the S&P 500. ASAN currently trades 36.3% from its 52-week high vs UPLD's 22.6% drawdown — a narrower gap to the peak suggests stronger recent price momentum.
| Metric | ASANAsana, Inc. | UPLDUpland Software, … |
|---|---|---|
| Beta (5Y)Sensitivity to S&P 500 | 1.70x | 1.43x |
| 52-Week HighHighest price in past year | $19.56 | $3.91 |
| 52-Week LowLowest price in past year | $6.51 | $0.88 |
| % of 52W HighCurrent price vs 52-week peak | +36.3% | +22.6% |
| RSI (14)Momentum oscillator 0–100 | 30.3 | 22.6 |
| Avg Volume (50D)Average daily shares traded | 3.8M | 146K |
Analyst Outlook
| Metric | ASANAsana, Inc. | UPLDUpland Software, … |
|---|---|---|
| Analyst RatingConsensus buy/hold/sell | Buy | — |
| Price TargetConsensus 12-month target | $13.29 | — |
| # AnalystsCovering analysts | 18 | — |
| Dividend YieldAnnual dividend ÷ price | — | — |
| Dividend StreakConsecutive years of raises | — | — |
| Dividend / ShareAnnual DPS | — | — |
| Buyback YieldShare repurchases ÷ mkt cap | +4.7% | +43.0% |
Historical Charts
Charts are rendered on first load. Hover for details.
Chart 1Total Return — 5 Years (Rebased to 100)
| Stock | Sep 20 | Feb 26 | Change |
|---|---|---|---|
| Asana, Inc. (ASAN) | 100 | 34.41 | -65.6% |
| Upland Software, In… (UPLD) | 100 | 3.34 | -96.7% |
Asana, Inc. (ASAN) returned -81% over 5 years vs Upland Software, In… (UPLD)'s -98%.
Chart 2Revenue Growth — 10 Years
| Stock | 2016 | 2025 | Change |
|---|---|---|---|
| Asana, Inc. (ASAN) | $77M | $724M | +842.9% |
| Upland Software, In… (UPLD) | $75M | $275M | +267.5% |
Chart 3Net Margin Trend — 10 Years
| Stock | 2016 | 2025 | Change |
|---|---|---|---|
| Asana, Inc. (ASAN) | -66.3% | -35.3% | +46.8% |
| Upland Software, In… (UPLD) | -18.1% | -41.0% | -127.0% |
Chart 4EPS Growth — 10 Years
| Stock | 2016 | 2025 | Change |
|---|---|---|---|
| Asana, Inc. (ASAN) | -0.34 | -1.11 | -226.5% |
| Upland Software, In… (UPLD) | -0.82 | -4.26 | -419.5% |
Chart 5Free Cash Flow — 5 Years
Asana, Inc. generated $9M FCF in 2025 (+106% vs 2021). Upland Software, Inc. generated $23M FCF in 2024 (-43% vs 2021).
ASAN vs UPLD: Frequently Asked Questions
7 questions · data-driven answers · updated daily
01Is ASAN or UPLD a better buy right now?
Analysts rate Asana, Inc. (ASAN) a "Buy" — based on 18 analyst ratings — the highest consensus in this comparison. The "better buy" depends entirely on your goals: growth investors should weight revenue trajectory, value investors should weight P/E and PEG, and income investors should weight dividend yield and streak.
02Which is the better long-term investment — ASAN or UPLD?
Over the past 5 years, Asana, Inc. (ASAN) delivered a total return of -80.8%, compared to -98.3% for Upland Software, Inc. (UPLD). A $10,000 investment in ASAN five years ago would be worth approximately $2K today (assuming dividends reinvested). Over 10 years, the gap is even starker: ASAN returned -75.3% versus UPLD's -85.8%. Past returns do not guarantee future results, and the stock with the higher historical return may already have its best growth priced in.
03Which is safer — ASAN or UPLD?
By beta (market sensitivity over 5 years), Upland Software, Inc. (UPLD) is the lower-risk stock at 1.43β versus Asana, Inc.'s 1.70β — meaning ASAN is approximately 18% more volatile than UPLD relative to the S&P 500. On balance sheet safety, Asana, Inc. (ASAN) carries a lower debt/equity ratio of 118% versus 3% for Upland Software, Inc. — giving it more financial flexibility in a downturn.
04Which has better profit margins — ASAN or UPLD?
Asana, Inc. (ASAN) is the more profitable company, earning -35.3% net margin versus -41.0% for Upland Software, Inc. — meaning it keeps -35.3% of every revenue dollar as bottom-line profit. Operating margin tells a similar story: ASAN leads at -36.8% versus -37.2% for UPLD. At the gross margin level — before operating expenses — ASAN leads at 89.3%, reflecting greater pricing power or product mix advantage. Stronger margins indicate durable pricing power, lower cost of revenue, or higher mix of software/services. They are one of the clearest signs of business quality.
05Which pays a better dividend — ASAN or UPLD?
None of the stocks in this comparison currently pay a material dividend. All are effectively zero-yield and should be held for capital appreciation rather than income.
06Is ASAN or UPLD better for a retirement portfolio?
For long-horizon retirement investors, Upland Software, Inc. (UPLD) is the stronger choice — it scores higher on the combination of lower volatility, dividend reliability, and long-term compounding. Asana, Inc. (ASAN) carries a higher beta of 1.70 — meaning larger drawdowns in market downturns, which matters significantly when you cannot wait years for a recovery. Both have compounded well over 10 years (UPLD: -85.8%, ASAN: -75.3%), confirming both are viable long-term holds — but the lower-volatility option typically results in less emotional selling during corrections. Retirement portfolios generally favour predictability over maximum returns. Consult a financial advisor before making allocation decisions.
07What are the main differences between ASAN and UPLD?
Both stocks operate in the Technology sector, making this a peer-level intra-sector comparison — the same macro tailwinds and headwinds will affect both. These fundamental differences mean investors should not choose between them on a single metric — the "better stock" depends entirely on which of these characteristics aligns with your investment strategy.
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