In my third episode of live coaching sessions, this caller was feeling dissatisfied with their narrow scope of role and lack of cultural fit in their current company.

The caller wanted guidance on what their next role should be, given their personal situation and professional ambition. Their situation captures a difficult choice facing many superstars: seeking a sizable impact rarely found outside of startups, while also craving the compensation only late-stage companies can afford. We discuss the frameworks and strategies required to approach this career choice wisely.

Privacy is paramount for these calls, so we have anonymized the content and received permission from the caller to ensure no personal or sensitive information is disclosed.
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In today's episode, we discuss:

Aligning the stage of company to your specific situation
Compensation expectations
Risk tolerance in making career moves
The risks and benefits of joining big tech
Why top product executives do tour duties at big companies
How to break a big tech tenure into two roles
Why some big tech projects are more data-driven than others
Why experienced managers should consider IC roles

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Where to find Nikhyl:

Where to find The Skip Podcast:

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Don't forget to subscribe to The Skip to hear Nikhyl and other executives teach unique and timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
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Timestamps:
[00:00:00] Introduction and caller context
[00:02:17] Caller’s question
[00:07:40] Nikhyl’s follow-up questions
[00:10:15] Matching the stage of company to the caller’s situation
[00:11:03] Nikhyl’s recommendation
[00:16:56] Should I join a big tech company?
[00:18:03] Nikhyl’s response
[00:22:08] How do big tech product teams operate?
[00:22:55] Nikhyl’s response
[00:25:58] Why managers should consider IC roles at late-stage companies
[00:29:44] Key takeaways from today’s episode
[00:32:27] Key links for this podcast

This is a public episode. If you would like to discuss this with other subscribers or get access to bonus episodes, visit theskip.substack.com

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