Upland Software

UPLD

Software - Application · Technology

Price

$5.38

+0.08 (+1.51%)

Market Cap

$15.8M

Winston Score

Winston is serious

Below-average fundamentals — multiple weak pillars.

Share count falling — buybacks

−5.5% over 4y

The company has reduced its share count over this period, returning value to shareholders through buybacks.

Diluted shares outstanding: 3.0M (2021) → 2.9M (2025)

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.

Winston Score History

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

-23.5% YoY

YoY Growth Rate

Revenue declining

EPS Growth

+90.7% YoY

YoY Growth Rate

EPS growth accelerating

R&D Spend

$37M/ year

↓ Declining (-23% vs prior year)

16.8% of revenue

In line with sector average (15%)

R&D spend declining — could signal cost-cutting or efficiency

Insider Activity

26.5%ownership

→ Flat

Insiders holding steady — not selling despite ability to

Cash Position

Cash flow positive

$30M 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.

Each metric is explained in plain language so you know exactly what you're looking at. Start your free trial now.

Quality

Gross Margin

75.5%

Premium pricing power — 75.5% gross margin

Operating Margin

10.4%

Modest — 10.4% operating margin

ROCE

1.7%

Weak — 1.7% return on capital

ROIC between 0% and 5%. They earn a few cents back per dollar invested in the business.

Full breakdown available with your free trial

See every metric, trend, and what it means for this stock.

Try free

Growth

Sales YoY

-24.6%

Shrinking sales (-24.6% YoY)

EPS YoY

N/A

—

Data not available

EPS Consistency

0/8 quarters

Earnings rarely grow — volatile business

Full breakdown available with your free trial

See every metric, trend, and what it means for this stock.

Try free

Cash Flow

Cash Conversion

N/A

Data not available

FCF Margin

10.9%

Modest free cash flow (10.9%)

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

Full breakdown available with your free trial

See every metric, trend, and what it means for this stock.

Try free

Stability

Debt / Equity

2.91

Heavy debt load (2.91)

Interest Cover

0.64x

Dangerous — barely covers interest (0.6x)

Interest coverage below 1. Their profits don't cover the interest bill.

Full breakdown available with your free trial

See every metric, trend, and what it means for this stock.

Try free

Valuation

P/E Ratio (TTM)

N/M

—

Negative earnings — P/E not meaningful

P/E vs Forward

N/A

not available

Data not available

Full breakdown available with your free trial

See every metric, trend, and what it means for this stock.

Try free

Dividends

Not applicable for this business.

🔒 See full fundamentals and if they are improving or declining — click here for your free trial now.

Start free trial