Insurance Brokerage Deals: Equity Rollover Done Right
When the deal is insurance brokerage and the question is Equity Rollover, the structure decisions in the first 30 days outlast the next five years. This is where Jason Powell works.
An independent sponsor closing insurance brokerage transactions in the $10M to $150M EV range has a defined set of moves at the Equity Rollover stage. Most of them are not in a generic M&A textbook.
The typical insurance brokerage platform sits at $10M to $150M EV with EBITDA in the $3M to $25M range. The thesis runs on regional retail agency roll-ups. Producer non-competes are unenforceable in too many states to ignore. Plan retention, not litigation.
How Equity Rollover actually gets structured.
Anchor on 15 to 25 percent rollover for a clean alignment story.
Treat rollover as tax-deferred under Section 351 or 721 where the structure allows.
Document tag-along and drag-along rights at the rollover level, not just at the LP level.
Cap exit veto rights for rolled equity to avoid future deadlock.
In insurance brokerage, layer in E&O tail insurance priced and bound as part of the Equity Rollover workstream.
Rolling at the wrong entity level, triggering an immediate tax event on what was supposed to be deferred.
"Rollover is the cheapest alignment tool on the table. Use it; do not abuse it."Jason Powell · Equity Rollover
The deal is one thing. The capital that opens up after close is another.
After close, the call list for refinancing, recapitalization, and growth equity gets short and known. Jason carries that list.
Related deal pages.
LOI Negotiation for Insurance Brokerage
The 4 to 8 page agreement that frames the deal economics, exclusivity, and diligence period.
Independent Sponsor Economics for Insurance Brokerage
The package of deal-by-deal carry, management fees, and transaction fees that compensates the independent spo…
Management Fee Structuring for Insurance Brokerage
The annual fee paid by the deal entity to the independent sponsor for ongoing oversight, board service, and p…
Earnout Structures for Insurance Brokerage
Deferred purchase price contingent on post-close performance, used to bridge buyer-seller valuation gaps.
Equity Rollover for Healthcare Services
roll-up of physician practices and ancillary service lines
Equity Rollover for Home Services
regional roll-ups of HVAC, plumbing, and electrical operators
Bring the insurance brokerage deal. Get Equity Rollover done right.
Direct counsel from a securities and M&A attorney with billions in structured transactions, the independent-sponsor-native playbook, and the capital markets network that opens up post-close.