Is Upland Software (UPLD) the Ridiculously Cheap Stock to Invest In? A Cramer-esque Take
16min read 
If you’re scanning for dirt-cheap stocks that Wall Street has overlooked, Upland Software (UPLD) is flashing a “Buy on the Dips” signal—but only if you’ve got a stomach for volatility and a belief in turnarounds. Let’s break down the numbers and see if this cloud-software play is a steal or a trap.
The Valuation Numbers: Red Flags and Green Lights
Upland’s Enterprise Value (EV) of $420 million is just 1.5x trailing revenue ($275 million), which sounds cheap. The Forward P/E of 2.93 is also tantalizingly low in a sector where peers like SPS Commerce trade at 75x earnings. But here’s the catch: those valuations are built on negative EBITDA (-$46 million) and net losses. The trailing P/E is a negative -0.37, meaning the company hasn’t turned a profit over the past year.
On the bright side, its Price-to-Book ratio of 0.59 suggests it’s trading at a discount to its balance sheet value—though that’s skewed by a negative book value per share (-$0.65) due to accumulated debt. Meanwhile, the EV/FCF of 18x isn’t alarming given it generated $23 million in free cash flow last year.
The Bull Case: Margins and Customers Are Turning
Analysts are starting to take notice. In Q1 2025, Upland added 155 new customers, a 16% sequential jump, and saw gross margins hit 74%—up 170 basis points year-over-year. This isn’t just fluff; it’s the first quarter of organic revenue growth (0.3% YoY) in years.
“The margin improvements are real,” says one analyst. “They’re cutting costs and finally seeing the benefits of their cloud transition.” With 41 major customer expansions in Q1—the most since 2022—there’s hope Upland can stabilize its revenue slide.
The Bear Case: Revenue Still Sags, Debt Hangs Overhead
But here’s the problem: revenue keeps shrinking. Q1 2025 revenue of $70.7 million was down 13% YoY, and the company cut its 2025 guidance to $269–$282 million—a 7.5% midpoint drop from prior forecasts. Adjusted EBITDA hit a seven-year low, and the $292 million in debt looms large against a $62 million market cap.
“The stock is a penny-stock gamble,” warns a skeptic. “They need a revenue miracle to justify even the $3.75 price target.”
What the Analysts Are Saying
- Consensus Rating: Hold (but with a Buy tilt in April 2025 as margin wins spark optimism).
- Price Target: $13 (a 0% near-term upside but a 500% leap from April lows).
- Risk Factors: Debt load, reliance on a handful of industries (healthcare/finance), and a -1.05 Altman Z-Score (bankruptcy watchlist).
The Bottom Line: A Speculative Play for the Bold
Upland is the definition of a “value trap” right now. The $420 million EV is dirt-cheap on paper, but the company needs to reverse its revenue slide fast. If management can stabilize customer retention and leverage its cloud tools (like its $13 price target suggests), this could be a steal. But with shares at $2.19 and technicals screaming “Strong Sell,” it’s a high-risk bet.
Action Alert: Only buy UPLD if you’re a trader with a 12–18-month horizon, a tolerance for volatility, and faith in management’s turnaround. For the rest? Wait for revenue growth to materialize.
In the end, Upland isn’t “ridiculously cheap”—it’s a speculative gamble. Roll the dice? Maybe. But remember: even the best turnaround stories can crater.
Disclosure: This analysis is for informational purposes only. Always consult a financial advisor before making investment decisions.
