skills/capital/planning-exit-timing-and-strategy/SKILL.md
Evaluates exit alternatives (strategic sale, IPO, secondary, continuation) with market conditions, buyer universe, and return optimization. Use when planning exits, evaluating exit timing, or comparing exit routes.
npx skillsauth add casemark/skills planning-exit-timing-and-strategyInstall this skill globally with one command. Works with Claude Code, Cursor, and Windsurf.
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Evaluates exit alternatives (strategic sale, IPO, secondary, continuation) against current market conditions, buyer/investor appetite, and fund return requirements to recommend optimal exit timing and route.
Assess current return profile — Calculate gross and net MOIC and IRR at current fair market value. Model returns at a range of exit multiples (e.g., 8x–12x EBITDA) and dates (next 6, 12, 18, 24 months). Identify the multiple and timing needed to hit fund return targets (e.g., 2.5x gross MOIC, 20%+ net IRR).
Evaluate each exit route:
Score and rank alternatives — Build a decision matrix weighting: achievable valuation, execution certainty, time to close, tax efficiency [VERIFY applicable tax structures — Section 1202, blocker corp considerations, state-level differences], management alignment, and LP preference.
Develop timing recommendation — Map each exit route against market windows. Identify triggers that would accelerate or delay execution (e.g., "if trailing EBITDA exceeds $50M by Q3, initiate dual-track process"). Flag dependencies such as audited financials, regulatory pre-clearance, or management incentive plan restructuring.
Draft exit roadmap — Sequence preparatory workstreams: vendor due diligence, management presentation, data room build-out, advisor selection (investment bank, legal counsel), and board/LP communication plan.
The deliverable is a structured exit planning memo containing:
tools
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