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Side-by-side financial comparison of KINGSWAY FINANCIAL SERVICES INC (KFS) and Upland Software, Inc. (UPLD). Click either name above to swap in a different company.
Upland Software, Inc. is the larger business by last-quarter revenue ($49.3M vs $38.6M, roughly 1.3× KINGSWAY FINANCIAL SERVICES INC). On growth, KINGSWAY FINANCIAL SERVICES INC posted the faster year-over-year revenue change (30.1% vs -27.5%). Over the past eight quarters, KINGSWAY FINANCIAL SERVICES INC's revenue compounded faster (21.4% CAGR vs -16.5%).
Kingsway Financial Services Inc. is a specialty financial holding firm that primarily offers property and casualty insurance products, including personal auto, commercial liability and property coverage. It operates mainly across North American markets, catering to individual consumers, small business owners and niche commercial client segments.
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.
KFS vs UPLD — Head-to-Head
Income Statement — Q4 FY2025 vs Q4 FY2025
| Metric | | |
|---|---|---|
| Revenue | $38.6M | $49.3M |
| Net Profit | $-1.6M | — |
| Gross Margin | — | 76.5% |
| Operating Margin | 0.8% | 14.5% |
| Net Margin | -4.1% | — |
| Revenue YoY | 30.1% | -27.5% |
| Net Profit YoY | -7.8% | — |
| EPS (diluted) | $-0.07 | $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 | $38.6M | $49.3M | ||
| Q3 25 | $37.2M | $50.5M | ||
| Q2 25 | $30.9M | $53.4M | ||
| Q1 25 | $28.3M | $63.7M | ||
| Q4 24 | $29.6M | $68.0M | ||
| Q3 24 | $27.1M | $66.7M | ||
| Q2 24 | $26.4M | $69.3M | ||
| Q1 24 | $26.2M | $70.7M |
| Q4 25 | $-1.6M | — | ||
| Q3 25 | $-2.4M | $-1.1M | ||
| Q2 25 | $-3.2M | $-13.0M | ||
| Q1 25 | $-3.1M | $-25.8M | ||
| Q4 24 | $-1.5M | — | ||
| Q3 24 | $-2.3M | $-1.7M | ||
| Q2 24 | $-2.2M | $-11.4M | ||
| Q1 24 | $-2.3M | $-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 | 0.8% | 14.5% | ||
| Q3 25 | -2.3% | 10.6% | ||
| Q2 25 | -3.6% | -13.2% | ||
| Q1 25 | -2.5% | -1.7% | ||
| Q4 24 | 6.5% | -2.9% | ||
| Q3 24 | -2.5% | -5.0% | ||
| Q2 24 | 0.5% | -7.7% | ||
| Q1 24 | 2.9% | -129.6% |
| Q4 25 | -4.1% | — | ||
| Q3 25 | -6.5% | -2.2% | ||
| Q2 25 | -10.2% | -24.4% | ||
| Q1 25 | -10.9% | -40.6% | ||
| Q4 24 | -5.0% | — | ||
| Q3 24 | -8.5% | -2.6% | ||
| Q2 24 | -8.3% | -16.5% | ||
| Q1 24 | -8.9% | -135.9% |
| Q4 25 | $-0.07 | $0.01 | ||
| Q3 25 | $-0.10 | $-0.09 | ||
| Q2 25 | $-0.13 | $-0.51 | ||
| Q1 25 | $-0.13 | $-0.97 | ||
| Q4 24 | $-0.08 | $-0.30 | ||
| Q3 24 | $-0.10 | $-0.12 | ||
| Q2 24 | $-0.08 | $-0.47 | ||
| Q1 24 | $-0.09 | $-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 | $8.5M | $29.4M |
| Total DebtLower is stronger | $70.7M | $232.4M |
| Stockholders' EquityBook value | $15.2M | $-48.4M |
| Total Assets | $231.5M | $413.2M |
| Debt / EquityLower = less leverage | 4.66× | — |
8-quarter trend — quarters aligned by calendar period.
| Q4 25 | $8.5M | $29.4M | ||
| Q3 25 | $9.5M | $22.8M | ||
| Q2 25 | $12.3M | $41.0M | ||
| Q1 25 | $6.5M | $33.7M | ||
| Q4 24 | $5.7M | $56.4M | ||
| Q3 24 | $6.7M | $59.7M | ||
| Q2 24 | $9.8M | $232.4M | ||
| Q1 24 | $12.3M | $231.6M |
| Q4 25 | $70.7M | $232.4M | ||
| Q3 25 | $70.7M | — | ||
| Q2 25 | $58.3M | — | ||
| Q1 25 | $59.5M | — | ||
| Q4 24 | $57.5M | $290.2M | ||
| Q3 24 | $58.5M | — | ||
| Q2 24 | $47.3M | — | ||
| Q1 24 | $47.1M | — |
| Q4 25 | $15.2M | $-48.4M | ||
| Q3 25 | $16.6M | $-47.3M | ||
| Q2 25 | $17.4M | $-42.4M | ||
| Q1 25 | $5.5M | $-37.8M | ||
| Q4 24 | $8.4M | $-18.3M | ||
| Q3 24 | $9.9M | $907.0K | ||
| Q2 24 | $20.7M | $6.5M | ||
| Q1 24 | $23.6M | $20.1M |
| Q4 25 | $231.5M | $413.2M | ||
| Q3 25 | $235.1M | $409.1M | ||
| Q2 25 | $207.7M | $441.7M | ||
| Q1 25 | $192.1M | $457.0M | ||
| Q4 24 | $186.6M | $529.5M | ||
| Q3 24 | $191.1M | $554.9M | ||
| Q2 24 | $192.3M | $739.9M | ||
| Q1 24 | $198.0M | $754.9M |
| Q4 25 | 4.66× | — | ||
| Q3 25 | 4.25× | — | ||
| Q2 25 | 3.34× | — | ||
| Q1 25 | 10.91× | — | ||
| Q4 24 | 6.84× | — | ||
| Q3 24 | 5.88× | — | ||
| Q2 24 | 2.29× | — | ||
| Q1 24 | 2.00× | — |
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 | $-3.0K | $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 | $-3.0K | $7.3M | ||
| Q3 25 | $1.5M | $6.9M | ||
| Q2 25 | $337.0K | $3.3M | ||
| Q1 25 | $-1.8M | $8.3M | ||
| Q4 24 | $1.1M | $9.3M | ||
| Q3 24 | $368.0K | $4.3M | ||
| Q2 24 | $557.0K | $5.5M | ||
| Q1 24 | $249.0K | $5.1M |
| Q4 25 | — | $7.2M | ||
| Q3 25 | $1.3M | $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 | 3.4% | 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 | 0.5% | 0.4% | ||
| Q2 25 | — | 1.2% | ||
| Q1 25 | — | 0.7% | ||
| Q4 24 | — | 0.5% | ||
| Q3 24 | 0.0% | 0.2% | ||
| Q2 24 | — | 0.4% | ||
| Q1 24 | — | 0.3% |
Financial Flow Comparison
Revenue → gross profit → operating profit → net profit for each company.
Revenue Breakdown by Segment
KFS
| Other | $14.8M | 38% |
| Roundhouse Electric Equipment Co Inc | $9.7M | 25% |
| MLC Plumbing LLC | $5.7M | 15% |
| Systems Products International Incspi | $3.8M | 10% |
| Advanced Plumbing And Drain | $2.9M | 8% |
| Southside Plumbing | $1.7M | 4% |
UPLD
Segment breakdown not available.
