The Skip Podcast
Nikhyl Singhal
The Skip podcast helps tech professionals get ahead in their career. It's hosted by Nikhyl Singhal, a three-time founder, CPO, and product executive at Meta and Google. Nikhyl has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. He now runs Skip Coach, a career service powered by the world's top CPO community, and has coached hundreds of product leaders through career decisions, management challenges, and transitions.
Subscribe for career insights distilled from real coaching conversations. theskip.substack.com
Subscribe for career insights distilled from real coaching conversations. theskip.substack.com
Episodes
Mentioned books
7 snips
Mar 18, 2026 • 58min
The Post-IPO PM Playbook Is Being Rewritten
Anneka, Chief Product Officer at Rubrik who scales product orgs through IPOs and AI shifts, joins the conversation. She discusses retraining PMs into business owners with P&L focus. She explains leading by example for AI adoption, building onboarding guides and triage agents. She covers balancing rapid AI experimentation with customer safety and why engineering may stop being the bottleneck.
92 snips
Mar 4, 2026 • 1h 1min
Three Job Searches, Three AI Roles: What Actually Worked
Janie Lee, VP of Product at Abridge (AI-native healthcare leader). Julia Roberts, former Pinterest product lead now at OpenAI (retention and growth expert). Ben Dreyer, product leader who moved from DoorDash to Netflix (creative tech and promo products). They recount rapid, curiosity-driven searches, building focused shortlists, why prototypes and live problem work matter, and how long-term relationships and VC signals open hidden AI roles.
73 snips
Feb 18, 2026 • 52min
The Promotion Mistakes That Derail PM Careers
They dig into why promotions feel harder now and how hiring and geography shape opportunities. They walk through real situations where assumed bias masks skill or role mismatches. They unpack the Peter Principle, why leadership skills differ from IC skills, and signs your skip might be building a case against you. They lay out five common promotion mistakes and what to do when you’re passed over.
77 snips
Jan 8, 2026 • 1h 26min
The PM Career Framework for AI (Part 3): AI Labs to Founding
The discussion dives into the complex landscape of AI career options, emphasizing that AI labs seek hands-on builders rather than managers. They explore how experiences at Big Tech may not translate to AI labs, and why location dramatically affects job opportunities. The high demands of AI startups are detailed, including the intense culture that can lead to burnout. Founding a company becomes an emotional test, where even failures contribute positively to one's career narrative. Key tradeoffs for potential career moves are unpacked throughout.
73 snips
Dec 11, 2025 • 1h 8min
The PM Career Framework for AI (Part 2): The Large Tech Playbook
The discussion revolves around the 'doors' framework, helping PMs identify paths in their careers. There's a deep dive into the balance between staying at Big Tech for golden handcuffs versus exploring startups. They challenge the misconception that moving to a smaller company is a step down, framing it instead as an opportunity for career growth. APM programs are highlighted as a fast track for early PMs. The hosts also analyze the appeal of the 'quality middle' private companies amid the competitive tech landscape.
111 snips
Nov 11, 2025 • 1h 12min
The PM career framework for AI
The old product management playbook is obsolete in the AI landscape. Discover why big tech isn’t always the best bet, and how to navigate options between AI startups and stable companies. Learn about the necessity of updating your skills and understanding the value of in-person roles. Explore the shifting appeal of senior IC positions and the risks of extreme work pace in AI. Emphasizing a builder versus a factory mindset, they dissect the importance of obsession in defining career paths. Get ready to rethink your PM journey!
102 snips
Sep 4, 2025 • 1h 3min
Why your career playbook expired: The new rules for 2025 job transitions
Career ladders are being redefined as traditional roles vanish and new ones emerge. Senior individual contributor positions are now deemed more valuable than management roles, causing a shift in career strategies. Big Tech salaries can feel like a trap with growing dissatisfaction. The landscape for startups is booming, with more product leaders venturing out on their own. As AI transforms workplaces, professionals must adapt quickly to thrive in the evolving job market and avoid obsolescence.
54 snips
Jul 9, 2025 • 1h 7min
Graduating Into Uncertainty? How to Actually Land Your First Tech Job
Discover the essential early-career playbook that graduates often wish they had. Learn why your first job should be a sprint, not a stroll, and how to identify roles that foster your growth. Internships take precedence over mere degrees, while storytelling plays a crucial role in job hunting. Embrace short-term positions as stepping stones to success, and recognize the importance of aligning values with your workplace. Finally, find out how to network authentically and take calculated risks for a thriving career.
31 snips
May 19, 2025 • 1h 20min
The Mentor's Superpower: Pattern Recognition That Unlocks Careers
Uncover the secret to career success as mentors pinpoint hidden patterns that can either unlock or hinder your progress. Explore the power of diverse mentorship and why cultivating a network is key. Delve into overcoming self-doubt and learn how to navigate organizational chaos during job changes. Discover valuable strategies for time management and assessing career decisions based on opportunity costs. Finally, gain insights into the art of asking the right questions to elevate your mentorship experience!
56 snips
Mar 26, 2025 • 1h 5min
Super Shadows | When Strengths Limit Growth
This discussion dives into the concept of 'Super Shadows'—the hidden challenges that come with strong abilities and how they can stall career growth. The hosts tackle the struggle of feeling stuck in a rapidly changing work environment and emphasize the importance of self-advocacy and seeking feedback. Listeners learn how to adapt their strengths while recognizing the areas needing growth. Practical strategies are shared to help professionals overcome stagnation and unlock their true potential.
