Upland Software (UPLD) falls 53.9% as billings decline and revenue outlook weakens

Upland Software (UPLD) has dropped 53.9% over the six months ended May 15, 2026, trading at $0.81 after weaker quarterly results and concerns over demand, customer retention and sales efficiency. The company reported Q1 billings of $47.81 million, while billings averaged a 25.1% year-over-year decline over the past four quarters. Analysts expect revenue to fall 2.2% over the next 12 months, signaling continued pressure despite a slower decline than its two-year trend. Upland’s customer acquisition cost payback period was negative in the latest quarter, indicating sales and marketing spending exceeded incremental revenue gains. The stock trades at 0.1 times forward price-to-sales, but the low valuation reflects weak fundamentals and competitive pressure.