#80: Becoming an IC again is how products leaders will stay relevant in the AI era | Gokul Rajaram (Investor and Company Helper; ex-Google, ex-Facebook)

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Oct 20, 2025

Gokul Rajaram, an investor and former product leader at Google and Facebook, discusses the evolving landscape for product managers in the AI era. He emphasizes the trend of senior leaders returning to individual contributor roles to maintain relevance. Gokul explores the importance of hands-on experience, effective hiring practices, and modern execution strategies like prototype-first development. He also highlights the significance of understanding customer needs and the value of joining companies with a strong mission and growth trajectory.

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ADVICE

Ship Only With Clear Customer Outcomes

Define clear customer behavior outcomes as the success metric before shipping any feature.
Treat every launch as an experiment with control groups and measurable hypotheses.

ADVICE

Prove Value Inside Customer Cohorts

Structure experiments inside customer accounts to measure pre/post value when you lack broad cohorts.
Prove economic value like cost savings or revenue lift to convince customers to pay and expand.

INSIGHT

Outcome Pricing Depends On Attribution

Outcome-based pricing suits products where the vendor can control the delivered outcome.
Usage or seats remain proxies when full attribution isn't under your control.

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If you’re a product leader wondering whether climbing the ladder is still the best path - or sensing a shift in where the real leverage is in the age of AI - this episode will change how you think about your role.

Gokul Rajaram (DoorDash board member, ex-Square, Google, Facebook) joins Marc and Ben for a powerful conversation about why many senior product leaders are stepping back into IC roles—and why that might be the smartest move you can make in today’s tech landscape. They unpack how the AI-native era has redefined leverage, why hands-on experience is critical to building credibility and staying relevant, and how the best PMs are evolving into multi-skilled builders who blend product, design, analytics, and engineering.

They also explore what great product execution looks like today, how to hire (or become) a truly modern product leader, and what to prioritize if you’re joining a breakout company in a fast-moving space.

Whether you’re a CPO, aspiring founder, or senior PM eyeing your next move, this conversation offers deep clarity on navigating your career in the AI era.

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In this episode, we covered the following topics:

* (01:22) Why many product leaders are returning to IC roles in AI-native companies

* (05:05) What founders get wrong when hiring Heads of Product too early

* (09:16) How product execution is evolving: prototypes over PRDs

* (22:15) Building features vs driving measurable customer outcomes

* (28:48) Why most CPO hires fail and how to promote from within instead

* (34:17) How to evaluate which company to join: mission, trajectory, talent density, founder courage

* (43:09) The importance of joining a company with high talent density and visionary leadership

* (51:47) Should you optimize for company moats early on? Gokul’s contrarian take

* (56:06) The power of low ego, high energy, and grabbing work no one else wants

* (1:03:22) Why gratitude fuels energy and career momentum

* And more!

Links:

* Gokul’s X: https://x.com/gokulr

* Gokul Rajaram: https://www.linkedin.com/in/gokulrajaram1/

* Marc: https://www.linkedin.com/in/marcbaselga/

* Ben: https://www.linkedin.com/in/benerez/

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