The Art of the Follow-Up: How Chris Hladczuk Closed $25M

In Season 4, Episode 7 of Turning Pro, Ben Sharf sits down with Chris Hladczuk, founder and CEO of Hanover Park, to talk all things AI, sales psychology, and what it means to be relentless.

Before founding Hanover Park, an AI-native fund admin startup now managing over $1.5B in assets, Chris cut his teeth at Goldman Sachs and scaled Meow to $1.5B in assets as CRO. But this episode is less about resume lines and more about what happens in the trenches — from founder-led hiring and cold outreach to the insane energy it takes to close a $25M deal on your 26th follow-up.

Chris also gets into AI’s role in services businesses, the death of SaaS as we know it, and why he won’t ping his team on Saturdays — no matter how intense the week’s been.

Listen now on Apple, Spotify, or YouTube.

10 Key Takeaways from Chris Hladczuk’s Episode

1. SaaS is Dead. Data is the Moat.
   Forget 100 SaaS lookalikes. The real edge today? Owning unique, high-value datasets. Just like Rippling built on employee data, Hanover Park is doubling down on fund accounting data as its foundation.
   
   
2. You Only Need 26 Follow-Ups.
   Chris closed a $25M deal after 26 touches. His tactic? Make every follow-up different — switch platforms, provide value, share insights, and never be annoying. It’s founder-led sales, not spam.
   
   
3. Founder-Led Sales Is a Superpower.
   Chris doesn’t follow a playbook. He out-hustles. He calls prospects directly, flies cross-country for meetings, and pitches without fluff. The edge? You’re not a sales rep — you’re the founder.
   
   
4. Startups Aren’t Built on Demos. They’re Built on Trust.
   His three-part pitch: 1) Why you should trust me, 2) Why this is 10x better, and 3) Why switching won’t suck. He’ll migrate clients himself and even waive fees. That’s how you de-risk the sale.
   
   
5. You Don’t Need Everyone. You Need the Right Ones.
   Chris filters fast. 9 to 9 office culture? It’s not for everyone. He hires like a sniper, not a net — selling hard up front, then disqualifying quickly if there’s no match.
   
   
6. Build Once, Sell Forever.
   By owning the system of record, Hanover Park can layer on AI tools, portfolio analyzers, inbox parsing, financial automation, all from one centralized data asset. Think Salesforce, but for funds.
   
   
7. Content > Cold Calls.
   Chris uses LinkedIn and Twitter not to sell but to story-tell. The hook? Personal anecdotes founders relate to — like the VC wiring $10M to the wrong account. No pitch. Just resonance.
   
   
8. Work Like a Maniac, But Take Saturdays Off.
   His team works 60-hour weeks, eats Chipotle together at 5pm, and builds AI tools that automate the wildest fund workflows. But Saturdays? Non-negotiable rest days to reset for the long haul.
   
   
9. Culture Isn’t Ping Pong Tables. It’s Obsession.
   This isn’t a "hang out" company. It’s Navy SEAL mode. Engineers tackle insane problems. Fund admins get full autonomy. Everyone’s rowing in sync toward an audacious vision.
   
   
10. This Is the Greatest Tech Shift of Our Lifetime.
    AI will 100x productivity across every vertical. The future? Neural-linked prompts, zero-latency workflows, and founders building billion-dollar companies with 7-person engineering teams.
    
    

Chris’s story is a lesson in high-leverage execution and founder obsession. Whether he’s stalking collapsed email threads or building AI agents for fund managers, he’s proof that relentless still works. In a world full of noise, he plays the long game and plays to win.

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