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Kirk Lipsey

Partner, Corporate Department - Insurance M&A at Paul Hastings LLP

New York, NY, USA

KL
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Why they matter

Leads live-deal insurance M&A counsel at Paul Hastings, currently on SiriusPoint's $250M ArmadaCare sale and Crestline's $17B Rithm Capital deal — a direct line into active insurance/MGA transaction flow.

Background

Kirk Lipsey is a Partner in the Corporate Department at Paul Hastings LLP in New York, where he co-leads the firm's Insurance M&A practice. He joined Paul Hastings in October 2023 from Sidley Austin (alongside M&A partner Chad Vance and insurance-regulatory partner Sanjiv Tata from Mayer Brown), bringing two decades of experience advising insurers, reinsurers, private equity firms, and asset managers on M&A, joint ventures, and block reinsurance deals. He holds a J.D. cum laude from Harvard Law School and an LL.B. with honors from the University of Glasgow.

Notable deals

  • 2025
    Led the Paul Hastings team advising SiriusPoint Ltd. on its $250M sale of ArmadaCare (ArmadaCorp Capital) to Ambac Financial Group
  • 2025
    Co-led (M&A) Paul Hastings' representation of Crestline Investors on its sale of its $17B alternative investment manager to Rithm Capital
  • 2020
    Named 'Financial Services Dealmaker of the Year' at The Deal Awards Middle Market for insurance M&A work
  • 2023
    Moved his insurance M&A practice from Sidley Austin to Paul Hastings as part of a three-partner lateral hire

Call-prep brief

Background

  • Partner, Corporate Department (Insurance M&A), Paul Hastings LLP, New York
  • Moved from Sidley Austin in Oct 2023 as part of a 3-partner insurance team lift-out (with Chad Vance, Sanjiv Tata)
  • Harvard Law (JD cum laude); Univ. of Glasgow (LLB); ~20+ years in insurance/financial-services M&A

Current focus

  • Actively running M&A workstreams on insurance and MGA transactions: SiriusPoint's $250M ArmadaCare sale to Ambac (2025) and Crestline's $17B sale to Rithm Capital (2025, insurance-adjacent alternative asset manager)
  • Practice spans stock/asset sales, block reinsurance, JVs, and public merger transactions for U.S. and cross-border insurers

What he cares about

  • Client roster skews large institutional insurers/reinsurers (Prudential, MetLife, Allstate, SiriusPoint) and PE/asset-manager buyers of insurance distribution platforms (MGAs)
  • Track record and awards (2020 Dealmaker of the Year) suggest he's motivated by high-profile, market-moving transactions, not routine work

Sensitivities

  • Active client conflicts are likely given his current SiriusPoint/Ambac and Crestline/Rithm engagements — screen for conflicts before discussing competing MGA or insurance-services targets
  • As outside counsel, he may be constrained in what he can share about live deal terms or market color tied to current mandates

Questions to ask

  1. What's driving the recent wave of MGA carve-outs and specialty distribution sales (e.g., ArmadaCare-style deals) — is this a durable trend or opportunistic?
  2. Among the insurance brokerage/MGA sponsors he's seeing shop assets, which are genuinely for sale vs. testing the market?
  3. What deal structures (earnouts, long-term capacity/reinsurance ties) are buyers using to bridge valuation gaps on MGA platforms right now?

Outreach draft

Subject
Quick call on insurance MGA deal trends?
Hi Kirk, I've been following Paul Hastings' recent insurance M&A work — the SiriusPoint/ArmadaCare sale to Ambac and the Crestline/Rithm Capital deal both caught our attention as signals of where MGA and specialty distribution valuations are heading. We're a private equity team actively evaluating opportunities in the insurance brokerage and MGA space, and would value 20-30 minutes of your perspective on current deal structures, buyer appetite, and where you see the next wave of activity. Happy to work around your schedule and keep it high-level and conflict-free. Would you be open to a short call in the next couple of weeks? Best, [Placeholder Name]

Linked companies

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