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Tiptree vs Skyward Specialty Insurance Group: TIPT and SKWD compared
Tiptree is the larger company: $540M of revenue in its latest quarter (Q3 2025) against $455M for Skyward Specialty Insurance Group (Q3 2026). Skyward Specialty Insurance Group is growing faster (+19% against +9% a year earlier). Skyward Specialty Insurance Group is more profitable, with an operating margin of 14.0% against -2.4%.
Where the money goes: TIPT and SKWD
Tiptree (TIPT) · Q3 2025
Tiptree, Q3 2025: revenue $540M (+9% year over year), operating margin -2.4%, net earnings $15.6M, operating cash flow $135M. The chart follows the revenue to costs, profit and cash.
Skyward Specialty Insurance Group (SKWD) · Q3 2026
Skyward Specialty Insurance Group, Q3 2026: revenue $455M (+19% year over year), operating margin 14.0%, net earnings $49.8M, operating cash flow $205M. The chart follows the revenue to costs, profit and cash.
| Tiptree (TIPT) | Skyward Specialty Insurance Group (SKWD) | |
|---|---|---|
| Latest quarter | Q3 2025 | Q3 2026 |
| Revenue | $540M | $455M |
| Revenue growth, Y/Y | +9% | +19% |
| Operating margin | -2.4% | 14.0% |
| Net earnings | $15.6M | $49.8M |
| Net margin | 2.9% | 10.9% |
| Operating cash flow | $135M | $205M |
| Free cash flow | $133M | — |
| Market value | $662M | $2.8B |
| P/E | 1.6× | 14.4× |
| Analysts’ mean target | — | $70.73 |
Questions
Which is bigger, Tiptree or Skyward Specialty Insurance Group?
Tiptree is the larger company: $540M of revenue in its latest quarter (Q3 2025) against $455M for Skyward Specialty Insurance Group (Q3 2026).
Is Tiptree or Skyward Specialty Insurance Group growing faster?
Skyward Specialty Insurance Group is growing faster (+19% against +9% a year earlier).
Which is more profitable, Tiptree or Skyward Specialty Insurance Group?
Skyward Specialty Insurance Group is more profitable, with an operating margin of 14.0% against -2.4%.
More: Tiptree earnings · how Tiptree makes money · Skyward Specialty Insurance Group earnings · how Skyward Specialty Insurance Group makes money
From the companies' latest 10-Q, 10-K or earnings release (10-Q filed Oct 31, 2025; 10-Q filed Nov 6, 2026). Fiscal quarters can end on different dates. Not investment advice.