SaaS Company (Workflow Automation)
Case Study 03
the choice to work
Primary Goals:
“Protect the upside, diversify risk, and make the exit QSBS-smart.”
Profile
- Entity: C-Corp; founder-held common stock
- Size: ~$25M EV; 92% gross margin; NRR 116%; strong mid-market pipeline
- Founder: Late 30s; most net worth tied up in the company
- Inbound offers from strategics and growth equity
Pain Points
- Concentration risk (single asset dominates net worth)
- No estate structure; founder wants to support family and philanthropy
- Concerned about tax planning if a lucrative offer materializes soon
How We Helped
Think
“Protect the upside, diversify risk, and make the exit QSBS-smart.”
Problem
A straight sale risks a large, immediate tax bill and a missed opportunity to shift appreciation outside the estate.
Feature (Working with Compound Advisory)
- QSBS verification: Confirmed founder’s shares were originally issued C-Corp stock in a qualifying industry—preserving Section 1202 eligibility.
- Estate freeze & diversification: Executed a partial sale to an IDGT on a note (founder receives payments; appreciation shifts out of the estate).
- Charitable planning: Established a DAF for pre/post-liquidity giving and brand halo; aligned with future PR.
- Go-to-market: With IndustryPros, we refined pricing tiers, published cohort KPIs, and staged a targeted process with strategics (integrations) and sponsors.
Benefit
- Taxes: QSBS positioning enabled potential exclusion of a large portion of gains (subject to limits); IDGT moved growth outside the estate while founder retained cash flow from the note.
- Value: Positioning increased indicated enterprise value by ~$4M vs. pre-engagement interest.
- Life: Founder diversified, funded giving goals, and kept optionality for a second act.
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