Scaling a company is difficult. Exiting one successfully is even harder. Doing it multiple times requires a very different mindset.
In this episode of Sales Lead Dog, host Chris sits down with Jeff Fleischer, a senior operating executive, capital advisor, and entrepreneur with more than 25 years of experience scaling and exiting technology and cybersecurity companies.
Jeff has served as CRO, SVP, and CEO across both public and private markets. He has helped build, scale, and sell multiple businesses through hypergrowth, acquisitions, and strategic exits to companies such as McAfee, JPMorgan Chase, Raytheon, BlackRock/Pamplona, and Audax.
Today, Jeff is the Founder of ProScale Partners and is launching Grainview Capital, where he advises founders, private equity firms, family offices, and strategic investors during critical growth and transition stages.
What This Episode Covers
This conversation goes deep into the realities of scaling and exiting companies, including:
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Growth strategy and go-to-market execution
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Leadership alignment during hypergrowth
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Capital formation and investor expectations
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Operating discipline under pressure
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The most common failure points companies hit as they scale
Jeff shares real-world lessons from operating inside fast-moving environments where clarity, speed, and execution determine outcomes.
🔍 What You’ll Learn in This Episode:
– How operators scale companies through hypergrowth
– Why leadership alignment is critical to execution
– What founders misunderstand about scaling and exits
– The role of capital strategy in growth and M&A
– Lessons from cybersecurity, AI, and infrastructure platforms
🎧 About Sales Lead Dog
Sales Lead Dog is a podcast for founders, executives, and revenue leaders focused on leadership, growth, culture, and modern go-to-market strategy.
🔗 Connect & Learn More
Guest Links
🔹 Jeff Fleischer on LinkedIn
🔹 ProScale Partners
Sales Lead Dog & Resources
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