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Side-by-side financial comparison of OCTAVE SPECIALTY GROUP INC (OSG) and Upland Software, Inc. (UPLD). Click either name above to swap in a different company.
OCTAVE SPECIALTY GROUP INC is the larger business by last-quarter revenue ($66.9M vs $49.3M, roughly 1.4× Upland Software, Inc.). On growth, OCTAVE SPECIALTY GROUP INC posted the faster year-over-year revenue change (2.6% vs -27.5%). Over the past eight quarters, OCTAVE SPECIALTY GROUP INC's revenue compounded faster (16.2% CAGR vs -16.5%).
Octave Specialty Group Inc. is a specialty insurance holding company that provides tailored property and casualty insurance products. Its core business focuses on excess and surplus lines, catering to commercial and individual clients across primary North American markets with customized risk coverage solutions.
Upland Software, Inc. is a global provider of cloud-based enterprise work management solutions. It offers products covering project portfolio management, customer engagement, IT service management, and financial automation, serving businesses of all sizes across North America, Europe, and Asia-Pacific in tech, healthcare, and professional services sectors.
OSG vs UPLD — Head-to-Head
Income Statement — Q4 FY2025 vs Q4 FY2025
| Metric | | |
|---|---|---|
| Revenue | $66.9M | $49.3M |
| Net Profit | $-29.7M | — |
| Gross Margin | — | 76.5% |
| Operating Margin | -76.7% | 14.5% |
| Net Margin | -73.8% | — |
| Revenue YoY | 2.6% | -27.5% |
| Net Profit YoY | -41.7% | — |
| EPS (diluted) | $-0.82 | $0.01 |
Green = leading value per metric. Periods may differ when fiscal calendars don't align.
8-Quarter Revenue & Profit Trend
Side-by-side quarterly history. Quarters aligned by calendar period so offset fiscal years line up.
| Q4 25 | $66.9M | $49.3M | ||
| Q3 25 | $66.6M | $50.5M | ||
| Q2 25 | $55.0M | $53.4M | ||
| Q1 25 | $62.8M | $63.7M | ||
| Q4 24 | $65.2M | $68.0M | ||
| Q3 24 | $70.0M | $66.7M | ||
| Q2 24 | $51.0M | $69.3M | ||
| Q1 24 | $49.6M | $70.7M |
| Q4 25 | $-29.7M | — | ||
| Q3 25 | $-112.6M | $-1.1M | ||
| Q2 25 | $-72.7M | $-13.0M | ||
| Q1 25 | $-44.7M | $-25.8M | ||
| Q4 24 | $-20.9M | — | ||
| Q3 24 | $-27.5M | $-1.7M | ||
| Q2 24 | $-750.0K | $-11.4M | ||
| Q1 24 | $20.8M | $-96.1M |
| Q4 25 | — | 76.5% | ||
| Q3 25 | — | 76.9% | ||
| Q2 25 | — | 74.8% | ||
| Q1 25 | — | 71.6% | ||
| Q4 24 | — | 70.8% | ||
| Q3 24 | — | 70.5% | ||
| Q2 24 | — | 70.5% | ||
| Q1 24 | — | 70.2% |
| Q4 25 | -76.7% | 14.5% | ||
| Q3 25 | -48.2% | 10.6% | ||
| Q2 25 | -41.8% | -13.2% | ||
| Q1 25 | -24.1% | -1.7% | ||
| Q4 24 | -55.5% | -2.9% | ||
| Q3 24 | -29.7% | -5.0% | ||
| Q2 24 | -28.9% | -7.7% | ||
| Q1 24 | -6.5% | -129.6% |
| Q4 25 | -73.8% | — | ||
| Q3 25 | -169.1% | -2.2% | ||
| Q2 25 | -132.3% | -24.4% | ||
| Q1 25 | -71.3% | -40.6% | ||
| Q4 24 | -55.1% | — | ||
| Q3 24 | -39.3% | -2.6% | ||
| Q2 24 | -1.5% | -16.5% | ||
| Q1 24 | 41.9% | -135.9% |
| Q4 25 | $-0.82 | $0.01 | ||
| Q3 25 | $-2.35 | $-0.09 | ||
| Q2 25 | $-1.54 | $-0.51 | ||
| Q1 25 | $-1.22 | $-0.97 | ||
| Q4 24 | $-11.75 | $-0.30 | ||
| Q3 24 | $-0.63 | $-0.12 | ||
| Q2 24 | $-0.02 | $-0.47 | ||
| Q1 24 | $0.44 | $-3.37 |
Balance Sheet & Financial Strength
Snapshot of each company's liquidity, leverage and book value from the latest quarter.
| Metric | | |
|---|---|---|
| Cash + ST InvestmentsLiquidity on hand | $146.4M | $29.4M |
| Total DebtLower is stronger | $117.6M | $232.4M |
| Stockholders' EquityBook value | $715.8M | $-48.4M |
| Total Assets | $2.2B | $413.2M |
| Debt / EquityLower = less leverage | 0.16× | — |
8-quarter trend — quarters aligned by calendar period.
| Q4 25 | $146.4M | $29.4M | ||
| Q3 25 | $27.5M | $22.8M | ||
| Q2 25 | $22.5M | $41.0M | ||
| Q1 25 | $34.1M | $33.7M | ||
| Q4 24 | $157.2M | $56.4M | ||
| Q3 24 | $40.8M | $59.7M | ||
| Q2 24 | $14.6M | $232.4M | ||
| Q1 24 | $13.8M | $231.6M |
| Q4 25 | $117.6M | $232.4M | ||
| Q3 25 | — | — | ||
| Q2 25 | — | — | ||
| Q1 25 | — | — | ||
| Q4 24 | $0 | $290.2M | ||
| Q3 24 | $518.0M | — | ||
| Q2 24 | $515.0M | — | ||
| Q1 24 | $512.0M | — |
| Q4 25 | $715.8M | $-48.4M | ||
| Q3 25 | $843.4M | $-47.3M | ||
| Q2 25 | $859.8M | $-42.4M | ||
| Q1 25 | $852.2M | $-37.8M | ||
| Q4 24 | $798.4M | $-18.3M | ||
| Q3 24 | $1.5B | $907.0K | ||
| Q2 24 | $1.4B | $6.5M | ||
| Q1 24 | $1.4B | $20.1M |
| Q4 25 | $2.2B | $413.2M | ||
| Q3 25 | $2.1B | $409.1M | ||
| Q2 25 | $8.5B | $441.7M | ||
| Q1 25 | $8.3B | $457.0M | ||
| Q4 24 | $8.1B | $529.5M | ||
| Q3 24 | $9.3B | $554.9M | ||
| Q2 24 | $8.2B | $739.9M | ||
| Q1 24 | $8.4B | $754.9M |
| Q4 25 | 0.16× | — | ||
| Q3 25 | — | — | ||
| Q2 25 | — | — | ||
| Q1 25 | — | — | ||
| Q4 24 | 0.00× | — | ||
| Q3 24 | 0.35× | — | ||
| Q2 24 | 0.38× | — | ||
| Q1 24 | 0.38× | — |
Cash Flow & Capital Efficiency
How much cash each business actually produces after reinvestment. Cash flow is harder to manipulate than net income.
| Metric | | |
|---|---|---|
| Operating Cash FlowLast quarter | $-52.3M | $7.3M |
| Free Cash FlowOCF − Capex | — | $7.2M |
| FCF MarginFCF / Revenue | — | 14.7% |
| Capex IntensityCapex / Revenue | — | 0.2% |
| Cash ConversionOCF / Net Profit | — | — |
| TTM Free Cash FlowTrailing 4 quarters | — | $24.4M |
8-quarter trend — quarters aligned by calendar period.
| Q4 25 | $-52.3M | $7.3M | ||
| Q3 25 | $-41.2M | $6.9M | ||
| Q2 25 | $2.1M | $3.3M | ||
| Q1 25 | $-12.6M | $8.3M | ||
| Q4 24 | $762.0K | $9.3M | ||
| Q3 24 | $48.9M | $4.3M | ||
| Q2 24 | $20.4M | $5.5M | ||
| Q1 24 | $7.1M | $5.1M |
| Q4 25 | — | $7.2M | ||
| Q3 25 | — | $6.7M | ||
| Q2 25 | — | $2.7M | ||
| Q1 25 | — | $7.9M | ||
| Q4 24 | — | $9.0M | ||
| Q3 24 | — | $4.2M | ||
| Q2 24 | — | $5.2M | ||
| Q1 24 | — | $4.9M |
| Q4 25 | — | 14.7% | ||
| Q3 25 | — | 13.2% | ||
| Q2 25 | — | 5.0% | ||
| Q1 25 | — | 12.4% | ||
| Q4 24 | — | 13.3% | ||
| Q3 24 | — | 6.3% | ||
| Q2 24 | — | 7.5% | ||
| Q1 24 | — | 7.0% |
| Q4 25 | — | 0.2% | ||
| Q3 25 | — | 0.4% | ||
| Q2 25 | — | 1.2% | ||
| Q1 25 | — | 0.7% | ||
| Q4 24 | — | 0.5% | ||
| Q3 24 | — | 0.2% | ||
| Q2 24 | — | 0.4% | ||
| Q1 24 | — | 0.3% |
| Q4 25 | — | — | ||
| Q3 25 | — | — | ||
| Q2 25 | — | — | ||
| Q1 25 | — | — | ||
| Q4 24 | — | — | ||
| Q3 24 | — | — | ||
| Q2 24 | — | — | ||
| Q1 24 | 0.34× | — |
Financial Flow Comparison
Revenue → gross profit → operating profit → net profit for each company.
Revenue Breakdown by Segment
OSG
| Other | $28.7M | 43% |
| Specialty Property Casualty Program | $23.1M | 34% |
| Accident Health | $9.6M | 14% |
| Specialty Automobile | $3.1M | 5% |
| Niche Specialty Risks | $2.4M | 4% |
UPLD
Segment breakdown not available.
