Matt Arsenault, VP of Corporate Development & Strategic Alliances at Jamf

Venture-backed companies are priced at their future state, not their current revenue. When growth stalls and another fundraising round stops making sense, the gap between VC valuation and what a strategic buyer will pay becomes the hardest conversation in any deal process. Matt Arsenault, VP of Corporate Development & Strategic Alliances at Jamf, has run this play across hundreds of targets. His work starts before the deal does, with the founder relationship, the cap table, and a clear-eyed conversation about risk tolerance that most corp dev teams never have.

What You'll Learn

• Why a $25M offer today can beat a $125M VC exit three years out
• How AI is shrinking the moat of wrapper-product startups and changing target screening
• The seven stakeholder groups in any acquisition and why most founders miss them
• How liquidation preferences and cap table structure change the math behind any offer
• Why VC relationships matter as much as founder relationships before a deal starts
• How to structure deals for underwater targets without losing the team
• What entrepreneurs should know about VC terms before taking their first check

If you're working a deal where the founder's VC valuation is the first thing they said and the last thing they'll let go of, DealPilot, powered by M&A Science, gives you the guidance to close the gap without overpaying.

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This episode of M&A Science is presented by DealRoom.

DealRoom just launched the only MCP server built for Buyer-Led M&A™ — so your AI and your deal data finally work together. Connect Claude, ChatGPT, or Copilot directly to DealRoom and let your AI read your pipeline, analyze due diligence documents, and automatically write findings back.

See for yourself: dealroom.net/mcp

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[00:01:14] Introduction and Kison's overview

[00:03:32] Matt Arsenault's background and path into M&A

[00:05:17] How VCs actually value companies: the two major components

[00:06:52] Where VC and strategic buyer valuations diverge, and why

[00:09:29] The current market for VC-backed acquisition targets

[00:10:39] Rule of 40, profitable growth, and what AI is changing

[00:25:01] The liquidation preference math: $25M today vs. $125M later

[00:31:38] Cap table dynamics, voting power, and co-founder alignment

[00:33:10] How to have the valuation conversation with a founder

[00:35:35] How to structure deals when a company is underwater

[00:36:45] Stakeholder management: severance, retention, and employee equity

[00:44:03] Structural tools for bridging valuation gaps

[00:49:21] What entrepreneurs should know before taking their first VC check

[00:51:03] Due diligence war stories: what a code scan revealed

Nathan Rust, Lutz Lehmann, Troy Pospisil, Jeremy Segal, Patrick Mumman, Tej Brahmbhatt, George Helock, and Angie Astle

Eight deal professionals share the M&A moments that never make the CIM. A birthday cake in a management presentation that confirmed a culture fit and influenced a bid. A buyer who died before close, forcing a nine-month restart from scratch. Eight years of customer revenue data on a 1980s IBM that management claimed did not exist. A target quietly heading toward Chapter 11 while diligence was underway. Unexpected events mid-deal are not exceptions. They are the deal. How you read them is what separates experienced practitioners from everyone else.

What You'll Learn:

• How cultural signals in a management presentation can influence a bid decision
• What to do when a buyer dies before close and the sell process has to restart
• How to find data that management says does not exist
• Why late-stage valuation surprises from founders are a signal you could have caught earlier
• How to take a bankrupt target through Chapter 11 and still close the deal
• Why experienced advisors document every surprise the moment a deal closes

If you're running deals and want pattern recognition built from thousands of real M&A situations to back your judgment, DealPilot, powered by M&A Science, gives you the deal guidance and advisor access to know which surprises you push through and which ones mean walk away.

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This episode of M&A Science is presented by DealRoom.

DealRoom just automated Pipeline Management with AI so you can spend less time updating deals, and more time working them. Automatically push deal context from Outlook to DealRoom Pipeline and use AI to keep deal target data and tasks updated, so follow-ups never slip through the cracks. No manual logging. No stale pipeline data.

See for yourself: https://hubs.ly/Q045fXp50

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[00:00] Intro

[04:11] Birthday cake in the management presentation

[07:10] Recruiting bankers from the sell side

[09:04] Culture fit as a bid decision factor

[10:03] When the buyer dies before close

[11:46] Nine-month restart from scratch

[17:04] Management says the data does not exist

[18:39] Finding Susie and the 1980s IBM

[22:25] IP ownership surprise at signing

[24:43] Bootstrap founders and commitment signals

[27:43] When bankers favor PE over strategics

[30:40] 78-year-old seller, a fistfight, and an earn-out

[32:25] The 12-year sales cycle

[35:23] Teaching a CEO to speak like an investor

[43:14] Aviation IPO pulled mid-road show

[45:52] Background check kills the deal a week before close

[50:03] Forever corporation: how Chugach approaches M&A

[54:47] HVAC target heads toward bankruptcy mid-diligence

[55:59] Becoming the secured creditor to save the deal

Brent Baxter, Sam Delestienne, Steve Hoffman, John Strenger, and Matt Melsen

Winning a banker-run auction at 5% under the highest bid. Closing a deal when co-sellers have not spoken in months. Getting through 22 countries of employment complexity with a client who refused to work with EOR providers. Acquiring a Netherlands-based public company and discovering the due diligence documents were in Dutch. These are the problems that no playbook prepares you for. Four corp dev professionals share how they handled them, and what it cost when they got it wrong.

What You'll Learn

• How to win a competitive auction when you're not the highest bidder
• What seller conflict at the closing table looks like (and how to get a deal back on track)
• When an employer of record works in a cross-border carve-out and when it creates permanent establishment risk
• Why management trust in the buyer can outweigh the highest bid number
• What a first European acquisition actually costs in compliance, legal, and cultural surprises

If you're running deals where the numbers are right but the relationship isn't, or you're in a market you haven't operated in before, DealPilot, powered by M&A Science, connects you with advisors who have closed deals in exactly that situation.

____________________

This episode of M&A Science is presented by DealRoom.

DealRoom just launched the only MCP server built for Buyer-Led M&A™ — so your AI and your deal data finally work together. Connect Claude, ChatGPT, or Copilot directly to DealRoom and let your AI read your pipeline, analyze due diligence documents, and automatically write findings back.

See for yourself: dealroom.net/mcp

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[00:00] Intro

[03:12] Partners who came to blows over valuation

[03:37] The closing table walkout

[05:47] Every deal craters on Friday

[07:54] Why managing emotions is the hardest job after LOI

[13:30] A door blows off an Alaska Airlines jet mid-process

[16:00] Winning at $15M under the highest bid

[18:23] Trust and reputation as deal currency

[23:09] The "baby ugly" lesson

[25:06] Preempting banker processes

[32:14] What EOR is and when it works

[33:52] Permanent establishment risk with C-level hires

[34:48] CBA compliance across 22 countries

[40:38] First European cross-border acquisition

[42:38] Dutch documents and data residency surprises

[46:20] Why in-person matters more in Europe

[50:38] The $100M tax exposure that was not real

[55:57] Outro