Jeremy Segal, Executive Vice President of Corporate Development, Progress (NASDAQ: PRGS)

Buyers who mistake a high LOI bid for a winning strategy are easy prey for sellers who know the growth equity playbook. Jeremy Segal's position: precision at the LOI stage is a stronger differentiator than price.

Jeremy Segal is EVP of Corporate Development at Progress (NASDAQ: PRGS), a publicly traded software company that has nearly doubled revenue through M&A, from under $400 million to nearly $1 billion. He has closed roughly 50 acquisitions across his career at Progress, LogMeIn, and Akamai.

How do you build a cost-optimization model before LOI for lines you know you can execute? How do you win a competitive process against PE without the highest headline number? When a seller restricts access during the announce-to-close window, how do you decide whether to escalate or walk? And how do you handle a workforce that expected an IPO and got an acquisition instead? Jeremy answers each one.

What You'll Learn

Building a pre-LOI cost optimization model on what you can actually execute
How to use existing infrastructure to outbid PE on price
Escalating diligence friction before it kills a deal
Why a no-retrade commitment builds trust with sellers
Structuring retention pools when a target's IPO falls through
What target profile actually fits a disciplined buyer
Why private valuations haven't caught up to public markets

If you're building deal models before LOI and want a framework for translating those assumptions into an operational plan you can actually execute, DealPilot, powered by M&A Science, has Buyer-Led M&A™ frameworks to help you close the gap between what you modeled and what you deliver.

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Episode Chapters

[00:00] Intro

[05:07] Why M&A has to be the growth engine

[07:36] Deal cadence and financial discipline

[09:42] Pipeline strategy and the five-year roadmap

[12:46] How the synergy model works before LOI

[17:15] The no-retrade commitment

[17:48] Chef: beating PE on a competitive deal

[24:56] ShareFile: carve-out from Cloud Software Group

[28:07] What to look for in a carve-out diligence

[33:48] MarkLogic: when the seller restricts access

[38:48] When seller motivation becomes an orange flag

[40:09] What counts as a material change warranting a retrade

[41:12] How public market cycles affect the deal pipeline

[48:09] Advice for a first-time acquirer

[49:46] The craziest thing in M&A

[53:02] Early Warning Signs in Diligence