Eeke de Milliano, Head of Global Product at Stripe, shares her vast experience from roles at Retool and Constellate. She discusses the daunting challenges of executive hiring, pinpointing red flags and key qualities to look for in candidates. Eeke emphasizes the importance of aligning a new leader's vision with company values and offers practical advice for successful hiring. She also explores how introspection and understanding one's strengths can streamline the process, alongside valuable lessons learned from transitions between startups and established companies.
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insights INSIGHT
High Executive Hire Failure Rate
Executive hires fail often due to unclear expectations and mismatched values.
Founders often focus on candidate skills without defining their needs.
volunteer_activism ADVICE
Introspection Before Hiring
Understand your values, team needs, and company's future before hiring.
Introspection helps define the ideal leader for your specific context.
question_answer ANECDOTE
Stripe's Culture Guide
At Stripe, Eeke wrote a guide to the company culture for potential candidates.
The goal was to deter those whose values didn't align with Stripe's.
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Scaling People is a detailed roadmap for company builders to put the right operating systems and structures in place to scale their companies sustainably. The book provides tactical guidance on crafting foundational documents, strategic and financial planning, hiring and team development, and feedback and performance mechanisms. It includes dozens of pages of worksheets, templates, exercises, and example documents to help create scalable operating systems and lightweight processes. Drawing on nearly two decades of experience as a Google and Stripe executive, Claire Hughes Johnson offers actionable insights and a human-centric approach to developing talent and building a sustainable, scalable company.
Pattern Breakers
Why Some Start-Ups Change the Future
Mike Maples Jr.
Peter Ziebelman
Pattern Breakers, written by Mike Maples Jr. and Peter Ziebelman, challenges traditional startup wisdom by revealing the hidden forces that drive extraordinary success. The book is based on extensive research and real-world examples from transformative startups like Twitter, Twitch, and Lyft. It emphasizes the importance of a different mindset and actions to harness developments that others might miss or initially see as crazy. The authors provide practical advice on how to transcend ordinary thinking, capitalize on market opportunities, and build a community of true believers to revolutionize industries.
Eeke de Milliano is the Head of Global Product at Stripe, helping drive innovation and success in the company's product line. Before this role, she was Head of Product at Retool and co-founded Constellate. Eeke previously spent 6 years as Product Lead at Stripe, working with the company during their hyper-growth era.
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In today’s episode, we discuss:
Eeke’s wealth of experience as an executive leader
The challenges companies face when hiring new executives
Common hiring red flags and pitfalls
Practical advice for measuring success
Why learning your strengths is an underrated piece of the process
In Depth 
