Upland Software

UPLD

Software - Application · Technology

Winston Score

Winston is serious

Below-average fundamentals — multiple weak pillars.

Data as of Aug 23, 2026 · filings through Jun 30, 2026

How the score breaks down

Quality

Mixed

Growth

Mixed

Cash Flow

Mixed

Stability

Weak

Valuation

Data not available

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Winston Score History

The full picture

Upland Software makes cloud-based software tools that help businesses run more smoothly. Its products cover things like project management, customer messaging, document handling, and sales support. The company sells to mid-sized and large businesses across many industries, and it has built its portfolio mainly by acquiring smaller software companies over the years.

Upland earns most of its revenue through subscriptions, where customers pay a recurring fee to use its software. It operates primarily in North America but also has customers in Europe and other regions, generating roughly $300 million in annual revenue. The company's main challenge is that it competes against much larger software vendors, and its growth-through-acquisition strategy has left it carrying significant debt, which limits financial flexibility and remains a key risk going forward.

Growth Profile

For growth stock investors

When traditional metrics don't capture the full picture, these are the signals growth stock investors use instead.

Revenue Growth

-7.9% YoY

YoY Growth Rate

Revenue declining

EPS Growth

-145.7% YoY

YoY Growth Rate

Earnings declining

Insider Activity

26.5%ownership

→ Flat

Insider ownership roughly steady over the past year

Cash Position

Cash flow positive

$32M cash & investments

Quarterly Free Cash Flow

↓ Burn rate worsening

Company generates more cash than it spends — no dilution risk from fundraising

Revenue declining

Upland Software's revenue is actually shrinking. In a growth stock, that removes the core investment thesis. The low Winston Score here may be warranted — unless there's a turnaround story.

The Winston Score above measures business quality today. Growth stocks often score lower because they invest in the future rather than maximising current profits. These metrics show what matters most for evaluating that future.

Score breakdown

Every number that matters to educated investors.

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Quality

Profit per sale

Gross Margin

76.3%

Premium pricing power — 76.3% gross margin

Profit after running costs

Operating Margin

-60.4%

Losing money on operations — -60.4%

Return on the money invested

ROCE

-4.5%

Weak — -4.5% return on capital

Negative ROIC means the business is losing money on every dollar invested in it.

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Growth

Sales growth

Sales YoY

-21.5%

Shrinking sales (-21.5% YoY)

Profit growth

EPS YoY

N/A

—

Data not available

How steady the profit is

EPS Consistency

6/8 quarters

Earnings grew in most of the last 8 quarters

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Cash Flow

Profit that turns into cash

Cash Conversion

N/A

Data not available

Spare cash per sale

FCF Margin

12.5%

Converts sales into free cash efficiently (12.5%)

FCF margin between 10% and 20%. Every $100 in sales becomes $10 to $20 in real cash.

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Stability

What it owes vs what it owns

Debt / Equity

5.34

Heavy debt load (5.34)

Covers its interest

Interest Cover

N/A

Data not available

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Valuation

Price vs profit

P/E Ratio (TTM)

N/M

no trend

Negative earnings — P/E not meaningful

Cheaper or dearer next year

P/E vs Forward

N/A

not available

Data not available

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Dividends

Not applicable for this business.

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