In this conversation, Steve Love, a seasoned CFO with over $1 billion raised from VCs and $2 billion in M&A transaction experience, pulls back the curtain on high-stakes M&A. Love shares his insights from overseeing complex acquisitions like Heap's purchase of a complementary "session replay" company and Heap's eventual sale to ContentSquare. He candidly discusses navigating challenges, aligning stakeholders, prepping for diligence, and making strategic M&A decisions as a CFO. Whether you're a CFO, finance professional or simply M&A-curious, Love's tactics for evaluating targets, modeling forecasts, negotiating terms, and executing integrations provide a rare behind-the-scenes look at what it really takes to architect successful transactions.

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This show is produced by Turpentine: a network of podcasts, newsletters, and more, covering technology, business, and culture — all from the perspective of industry insiders and experts. We’re launching new shows every week, and we’re looking for industry-leading sponsors — if you think that might be you and your company, email us at erik@turpentine.co.

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LINKS:

https://sift.com/

X/SOCIAL:

@sashaorloff (Sasha)

@SteveLoveCFO (Steve)

TIMESTAMPS:

(00:00:00) Intro and preview

(00:01:24) Steve Love's impressive background

(00:02:39) Diving into M&A: When and why to acquire

(00:03:34) Case study: Heap's product acquisition

(00:05:17) Evaluating market players and integration challenges

(00:13:29) Integration and transition best practices

(00:17:43) Sponsor: NetSuite | Attio

(00:20:21) The biggest surprise after acquisition

(00:22:33) The first thing CFOs do after signing

(00:32:29) Sponsor: Beehiiv | Brave

(00:33:02) Negotiating severance packages

(00:37:34) Executing a sell-side transaction

(00:37:55) Handling market checks and bankers

(00:49:52) Differences between private and public company sales

(01:02:13) Biggest misconceptions about a CFO's role

(01:03:03) Wrap