Welcome to Product Market Fit, a podcast all about startups & growth
Jan. 18, 2023

EP9: Pivoting to success; w/ Sara Mauskopf, founder & CEO, Winnie — Product Market Fit podcast

EP9: Pivoting to success; w/ Sara Mauskopf, founder & CEO, Winnie — Product Market Fit podcast

If you follow Tech Twitter then you probably already know who Sara is. Before starting Winnie, Sara was Director of product at Postmates. She was an early employee at Twitter, and also worked at YouTube and Google.

In today’s conversation, Sara shares how her company initially struggled to find product market fit and her journey pivoting the product to success. We also dive into the nature of multi-sided marketplaces; launching new product lines, and how to choose a co-founder.

Sara has got really insightful and down-to-earth advice that I think you’ll find valuable.


  • (0:00) Introduction 
  • (1:50) What is Winnie?
  • (2:18) How did your background lead you to start the company?
  • (3:52) What did the initial product look like?
  • (7:22) How did Winnie iterate to find PMF?
  • (12:20) Gathering customer feedback with NPS
  • (14:26) What are the dynamics of two-sided marketplaces?
  • (17:15) Solving the chicken and egg problem
  • (19:16) Figuring out PMF for each constituent of the marketplace
  • (20:21) Expanding the product offering; the “sophomore act”
  • (23:31) How do you ensure you don’t make assumptions about your customers?
  • (25:57) How big is Winnie today?
  • (28:06) What growth channels have worked for you?
  • (30:38) How to choose a co-founder
  • (33:22) Advice for working with family
  • (35:18) Hiring part-time employees
  • (36:41) Managing a remote team;
  • (38:58) Lessons from working at Google, Twitter & Postmates
  • (40:39) Lightning round (+ The future of Twitter)
  • (45:50) Final thoughts

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Sponsor: This podcast is brought to you by grwth.co. Grwth offers fractional CMOs, paired with best-in-class digital marketing execution to support early-stage startup success. With a focus on seed and series A companies, Grwth has helped a number of SaaS, digital health, and e-commerce startups build their go-to-market function and scale up. To learn more and book a free consultation, go to grwth.co.

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