Episode 22
From a $60 Softball Fee to Scaling LinkedIn EMEA $35M→$75M — Now She Bets on Herself | Kristin Issac
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She scaled LinkedIn's EMEA customer success operation from 35 million to 75 million in ARR. She built ESPN Digital's EMEA business from zero to 15 million in revenue. She worked inside LinkedIn, ESPN, Disney, Udemy, and the BBC. And then, after 20 years of building other people's visions, Kristin Nichols Isaac chose to plunge. In January 2025, Kristin co-founded Strudel AI — a Madison-based AI startup that is closing one of the most expensive gaps in B2B SaaS: the gap between customer support and engineering. Strudel's platform delivers root cause analysis with 95 percent accuracy on the first pass, resolves technical issues 65 percent faster, and reduces engineering time by 20 percent — all at a fraction of what traditional LLM-based approaches cost. They've closed an $800K pre-seed raise and need $200K to close the round. In this episode, Kristin and Brandi go deep on: → The origin story behind the grit — a single mom, three girls, and a $60 softball fee that felt like a mountain at age eight → How a personality test at 19 told her she was a CEO — and how long it took to act on it → The real fundraising experience for women in tech — including an all-male cap table and the pattern-matching problem → The research behind why boards need at least one-third women before the performance benefits show up → The unconscious bias self-check technique she still uses today: "Would I think this if they were a white man?" → Strudel's current raise status, design partner targets, and what the seed round milestones look like → Why she wants to launch her own fund for female-led businesses after Strudel exits → What it means to build a relationship with money — from a frugal millionaire grandfather who wouldn't take his wife to dinner, to landing in Paris with no job and no place to live This is a conversation about what it looks like when 20 years of corporate-scale experience becomes rocket fuel for your own vision. Connect with Kristin: → Email: kristin@strudel.io → LinkedIn: Kristin Nichols Isaac → Weekly newsletter on LinkedIn (founding a company, go-to-market, and growth) → Learn more: strudel.io
Show Notes
Chapters: 0:00 Introduction & Why You Should Keep Listening 2:15 Defining Prosperity: Same Core Values, Evolving Layers 4:10 The $60 Softball Fee: Grit Born From a Single Mom's Household 11:27 The Plunge Signal: From BBC Startup to Betting on Herself 13:31 A Personality Test at 19 Said "You're a CEO" 18:30 Strudel AI: The Investigation Layer Closing the Gap 22:03 The Capital Gap: What Women Founders Actually Face in the Room 26:36 Research, Pattern Matching & Why One-Third Changes Everything 28:27 The Unconscious Bias Self-Check Every Leader Needs 30:00 Inside the Raise: $800K Committed, $200K to Close 31:52 The Future Strudel Fund: Investing in Women Post-Exit 36:51 Money Lessons From a Great Depression-Era Millionaire Grandfather 41:12 Paris, No Job, No Apartment — and Pure Grit 42:20 How to Find Kristin + Invest in Strudel
About the Guest
Kristin Nichols Isaac is the CEO and Co-Founder of Strudel AI, a Madison-based AI startup building the investigation layer for technical support in B2B SaaS. With 20 years of go-to-market leadership across LinkedIn, ESPN, Disney, Udemy, and the BBC, Kristin has a proven record of scaling businesses at global scale — including growing LinkedIn's EMEA customer success from $35M to $75M in ARR and building ESPN Digital's EMEA business from zero to $15M in revenue. She co-founded Strudel AI in January 2025 alongside CTO Shai Rubin, Ph.D. The platform delivers 95 percent accuracy on root cause analysis, 65 percent faster issue resolution, and 20 percent reduction in engineering time — at a fraction of the cost of LLM-based alternatives. Strudel won the 2025 Pressure Chamber pitch competition and is currently closing a $1M pre-seed round. Find Kristin at kristin@strudel.io or on LinkedIn as Kristin Nichols Isaac.
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