In this episode, host Sera Tajima interviews Jodi Alperstein, a seasoned product leader who has served as SVP of Product and GM at Digital Ocean, VP of Product and GM at Twilio Segment, and VP of Product at Hired. Jodi shares her extensive journey from early product management roles at E-Trade to leading global teams at public companies. With over two decades of experience across financial services, SaaS, and technology companies, Jodi's career spans from early-stage startups to public companies where she's led global teams of up to 350 people and managed businesses generating up to $650 million in revenue.

Connect for more good energy:

➕ Conscious Tech: https://seratajima.substack.com

➕ LinkedIn: ⁠https://www.linkedin.com/in/seratajima⁠

➕ Advising: https://www.seratajima.com/advising

Chapters

[00:00:00] Jodi's Journey to the C-Suite

[00:04:17] Day in the Life of a VP of Product: Metrics, Teams & Deep Work

[00:06:49] Product Leadership Challenges: Balancing Empathy with Accountability

[00:09:14] Hiring Strategy: Culture Add vs Culture Fit in Product Teams

[00:13:43] Managing Mis-Hires: Evaluation, Alternatives & Respectful Transitions

[00:17:59] Design & Product Structure: Organizational Evolution as Startups Scale

[00:20:38] Scaling After Product-Market Fit: Growth Engines & Intentional Hiring

[00:27:45] Hyperscaling Signals: When Demand Outpaces Supply & Unit Economics

[00:30:37] Top Reasons Startups Fail: Runway Management & Team Composition

[00:39:05] Product Leadership & Finance: Understanding Unit Economics

[00:43:34] Design Evolution: AI Impact & System Thinking in Modern Design

[00:47:57] AI Tools & Ethics: Balancing Innovation with Intellectual Property

[00:51:50] Company Culture: Creating Signature Experiences & Motivation Theory

[00:57:32] Building Effective Growth Teams: Process Over Perfection

[01:00:03] Career Pathways: From Designer to Product Leader

[01:05:16] Lightning Round: Leadership Books, Success & AI

Where to find Jodi:

https://www.linkedin.com/in/jodialperstein/

BONUS - Moojibaba’s Story