Close · Cybersecurity Services

Mezzanine Debt & Capital Stack for Cybersecurity Services Independent Sponsors

Securities and M&A counsel for independent sponsors structuring cybersecurity services transactions, from LOI to close to the capital markets that open up afterward.

EV range $10M to $130M EV EBITDA $2.5M to $22M Audience Independent Sponsor
The deal context

Mezzanine Debt & Capital Stack on cybersecurity services deals is one of those workstreams that looks routine on a checklist and decides outcomes in practice.

The typical cybersecurity services platform sits at $10M to $130M EV with EBITDA in the $2.5M to $22M range. The thesis runs on MSSP or specialty consulting platform. Cleared workforce is the moat. Cleared workforce can also be the deal-killer in CFIUS reviews.

The moves

How Mezzanine Debt & Capital Stack actually gets structured.

  1. Target senior leverage at 3.0x to 3.5x EBITDA, mezzanine at 1.0x to 1.5x on top.

  2. Negotiate an intercreditor agreement that does not throttle the operator.

  3. Structure mezzanine with PIK toggle and warrants priced into the IRR model.

  4. Confirm covenant headroom of at least 20 percent at close.

  5. In cybersecurity services, layer in FSO succession plan in place as part of the Mezzanine Debt & Capital Stack workstream.

The common mistake

Letting the lender pick the intercreditor terms. Those terms decide what the operator can do on day 180.

Jason's take
"The capital stack is a contract, not a spreadsheet. Read every page of every term sheet."
Jason Powell · Mezzanine Debt & Capital Stack
Capital after close

The deal is one thing. The capital that opens up after close is another.

Most independent sponsors solve the closing capital and then run into the post-close capital problem alone. The capital markets relationships that matter at month 18 are part of this practice.

MONTH 18
Senior refi
MONTH 24
Dividend recap
MONTH 36
Growth equity
YEAR 4–5
Strategic exit
TALK TO JASON

An LOI on the desk, a cybersecurity services target, and a Mezzanine Debt & Capital Stack question worth a real conversation.

Twenty minutes of practitioner-grade input from a securities attorney whose first move is to read the deal, not the engagement letter.