E9: An Insider's Guide After $2B of M&A with Serial CFO Steve Love of Sift, Dialpad, and Heap

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. 🔥 Apply to join over 400 founders and Execs in the Turpentine Network: https://hmplogxqz0y.typeform.com/to/JCkphVqj RECOMMENDED PODCAST: 📈 ECON 102 W/ NOAH SMITH - Keeping econ entertaining - Noahpinion author Noah Smith and Erik Torenberg break down business news and politics every week. Spotify: https://open.spotify.com/show/3Mos4VE3figVXleHDqfXOH Apple: https://podcasts.apple.com/id1753399812https://podcasts.apple.com/id1753399812 SPONSORS: 📊 Attio is the next generation of CRM. It’s powerful, flexible and easily configures to the unique way your startup runs, whatever your go-to-market motion. The next era deserves a better CRM. Join ElevenLabs, Replicate, Modal and more at https://bit.ly/attioturpentine NETSUITE 📈 NetSuite has 25 years of providing financial software for all your business needs. More than 36,000 businesses have already upgraded to NetSuite by Oracle, gaining visibility and control over their financials, inventory, HR, eCommerce, and more. If you’re looking for an ERP platform head to NetSuite: http://netsuite.com/zen - NetSuite has extended a one-of-a-kind flexible financing program for a few more weeks. BEEHIIV 🐝 Power your newsletter with Beehiiv, the newsletter platform built for growth. Connect with premium brands, scale your audience, and deliver a beautiful UX that stands out in an inbox. Head to https://Beehiiv.com and use code "MOZ" for 20% off your first three months BRAVE 🎯Get first-party targeting with Brave’s private ad platform: cookieless and future proof ad formats for all your business needs. Performance meets privacy. Head to https://brave.com/brave-ads/ and mention “Turpentine” when signing up for a 25% discount on your first campaign. --- 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 [email protected]. --- 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