The Skip Podcast
The Skip podcast helps tech professionals advance their careers. Hosted by Nikhyl Singhal, a three-time founder and former product executive at Meta and Google, the show shares insights from his experience scaling products like Facebook and Google Photos. He now runs Skip Coach, a career service, and has coached hundreds of product leaders. Subscribe for career advice distilled from real coaching conversations.
Episodes
To Invent Waymo, They Had to Reinvent PM
In this episode, Saswat Panigrahi, Waymo's CPO, joins me for the third conversation in the "Inside PM" series. Saswat joined Waymo in 2016, back when it was still Google's self-driving car project and the entire product team was fewer than five people, and has spent all ten years since on the same product. In this episode, we discuss how his product org had to invent its own way of measuring good
Lessons From Three Product Leaders Living in the Future
This is the next episode in a series on what product management becomes when the AI hype meets real constraints. I sat down with three CPOs living about a year ahead of the rest of us: Sharmeen Chapp, Midjourney's first-ever product hire; Jiaona Zhang (JZ), CPO at Laurel; and Henrik Berggren, who runs product and design at Mutiny. Their teams are tiny on purpose, yet these are companies with years
Inside PM at Stripe: What Comes After "Become a Builder"?
Kevin Yien is the Head of Product for Merchant Experiences at Stripe. Before that he led Product at Mutiny and Square. In this episode, Kevin and I discuss how to keep AI from becoming theater, why a PM shipping to production can be a red flag, and why AI is pulling product management back to its fundamentals of strategy, opinion, and judgment. –Key topics:• Why "PM is dead" is the wrong frame, an
Builder-Executives Are Getting Paid Like Pro Athletes
Product pay is detaching from the old bands the way it did for AI researchers. In the past few weeks I've seen three offers go out to product executives at $10 million a year, and while almost nobody gets that number, it pulls the whole field up. The builder-executive who can build with modern tools and operate at scale now commands two to three times what the same profile did a year ago. In this
How Meta Is Reinventing Product Management
Meta is one of the biggest dinosaurs in the park, yet in a matter of months it rebuilt PM top to bottom, and almost none of it was bought. My guest is Jagjit Chawla, a VP of Product at Meta who’s running a growing share of the Facebook app: Feed, Reels, and more recently Search. I worked alongside Jagjit for nearly ten years across Google, Credit Karma, and Meta, and almost nothing is as I remembe
5 Career Questions Your Old Playbook Can’t Answer
In today's episode, we work through five questions from leaders in the Skip community who are doing well by any measure: a director whose career keeps ending in short stints despite strong performance, a manager whose top performer turned adversarial, an exec fielding multiple outsized offers, a PM who does her best work with a great manager, and a first-time manager whose first report is more exp
10 Job-Search Rules That Just Broke
In this episode, I sit down with three senior product leaders who just came through the senior job search in this market: Dana Ingraham from Harvey, Briana Ings from Atlassian, and Pei-Chin Wang, who’s founding her own company. While the search itself continues to be exhausting, I was surprised to learn that everything else has changed: the playbook is completely out of date, in at least ten diffe
The product skill you must now master: Reinvention
If you're in a career transition right now and wondering whether you did something wrong, you didn't. Every question coming into Nikhyl.AI keeps circling the same idea: do I really have to reinvent? In today’s episode, Carly and I dive into four questions, from people in very different scenarios: A senior PM who feels her career’s gone backwards, an IC5 at a FAANG anchored by immigration constrain
What PM Hiring Managers Actually Screen For
Most interview advice tends to come from the candidate’s perspective - how to prep, share your experiences, and follow up. This conversation pulls back the curtain on the other side of the table. I spoke with hiring leaders from Netflix, Rippling, and EvenUp to learn how three great, yet operationally-different companies evaluate candidates. Surprisingly, all three leaders agreed on one core truth
How to Navigate Org Drama
Work getting political isn't new, but surviving it without derailing your career has never been more challenging. As organizations flatten and restructures accelerate, the instincts that used to work — push back, demand clarity, make noise — often backfire. In this episode, we answer five questions from people caught in reorgs, managing-up dynamics, and situations where the "obvious" move turns ou
The Post-IPO PM Playbook Is Being Rewritten
Most of the conversation about rebuilding product management comes from two ends of the spectrum: AI-first startups with 30 people and no real installed base, or big tech with thousands of PMs and decades of process. This episode is about the third category: companies that went public in the last few years, have real customers and revenue to protect, and are now trying to move like startups again.
Three Job Searches, Three AI Roles: What Actually Worked
Most job search advice comes from people still in the thick of it—anxious, second-guessing, pattern-matching off too little data. This episode is different. We sat down with three product leaders who recently landed roles at Netflix, OpenAI, and Abridge, and did a full postmortem. What they shared upends a lot of conventional wisdom: the spray-and-pray pipeline doesn't work, your AI credentials ma
The Promotion Mistakes That Derail PM Careers
It's promo season, and I've gotten roughly 1000 questions through nikhyl.ai—the pattern is unmistakable: people aren't just asking how to get promoted, they're asking whether the system is broken and whether they should quit over it. In this episode, we dissect five real questions from PMs who've been passed over. What becomes clear is the mistakes aren't in execution—they're in how people think a
The PM Career Framework for AI (Part 3): AI Labs to Founding
The "join a hot company" narrative gets even more complicated once you enter the AI-native part of the market. In Part 3 of our PM Career Framework for AI series, we close out with the doors everyone's obsessing over: AI labs, hot AI startups, ex-growth companies, and founding.We unpack what these companies actually look for (spoiler: it's not "AI experience"), why hands-on builders win over manag
The PM Career Framework for AI (Part 2): The Large Tech Playbook
The “join a hot company” career narrative is getting a lot of PMs into trouble. In Part 2 of our PM Career Framework for AI series, we get practical: how to pick the door that fits you — and spot when a prestigious logo is quietly costing you career momentum. We break down nearly 600 listener questions, then map the first set of doors, from Big Tech and public enterprise to the “quality middle” of
The PM career framework for AI
The old PM career playbook doesn’t work in the AI era. In this episode of The Skip, we lay out a new career framework for product managers, and it’s a lot more “choose your door” than “climb the ladder.” If you’re wondering whether to stay in big tech, jump to an AI startup, double down as a builder, or rethink your whole path, this one’s for you. We talk about why your hard-won product intuition
Why your career playbook expired: The new rules for 2025 job transitions
Career ladders aren't just changing—they're being demolished and rebuilt in real-time. In this emergency "weather report," Carly and I decode four career dilemmas that have completely flipped in the last six months. We explain why directors are taking IC roles (and thriving), why your Big Tech salary might be a golden trap, when to finally leave that stalled growth company, and why founding is sud
Graduating Into Uncertainty? How to Actually Land Your First Tech Job
In this episode, I’m joined by my co-host Carly Malatskey to share the early-career playbook most people wish they had at 21. Whether you're fresh out of college, navigating your first job, or advising someone who is — this episode is for you.–Key topics• Why your first job should feel like a sprint, not a stroll• How to tell if your job is setting you up — or holding you back• The truth about int
The Mentor's Superpower: Pattern Recognition That Unlocks Careers
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. Through 6 listener questions, we break down how mentors spot patterns others miss, and how you can use that insight to unlock your next move. Whether you're leading a team, switching paths, or just feeling off, this episode is packed with tactical advice for unlocking yo
Super Shadows | When Strengths Limit Growth
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned entrepreneur and host of She Leads. We tackle a listener’s career dilemma: feeling stuck and unsure how to adapt to shifting expectations. Using a structured approach, we break down when to make a change, how to advocate for yourself, and how to evolve without losing what makes you successful. Whether you’
Should you Stay or Go? A 5-factor framework for career-defining decisions
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We tackle a listener’s question about whether to stay in their current job or take a new one. Using a 5-factor framework, we break down how to evaluate career decisions based on compensation, skills, lifestyle, long-term success, and work environment. Whether you’re
The Insider's Guide to Tech Compensation, Negotiation, and Career Growth
In this episode, I’m joined by my co-host Carly Malatskey, a former software engineer turned investor and podcast host of She Leads. We dive into a listener's question about multiple tech job offers, and compare three compensation packages. We break down tactics for negotiating comp while exploring how to pick a role that aligns with your superpower. Whether you're actively job hunting or looking
The Widening Tech Career Divide: Big vs Small Tech
In this episode, I’m joined by Carly Malatskey, an engineer-turned-investor and podcast host of She Leads. We dive into one of the most important career questions in tech today: Should you work in big tech or small tech, or found your own company? With the rise of AI and new economic conditions, these choices have never been more different. We break down how industry dynamics have changed, the tra
Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)
I'm joined by product leader turned founder Shreyas Doshi to discuss the founder's journey and when starting a company might be the right move for you. We challenge common startup wisdom and explore why traditional career advice often misses the mark for aspiring founders.Key topics:Which PMs are secretly great founder materialRed flags: when founding isn't for youThe right time to start your comp
Live from Lenny's Summit | Career advice highlights
Welcome to a special episode featuring key moments from my presentation at the very first Lenny and Friends Summit in San Francisco. In this talk, I've distilled the most valuable career insights I've gained from coaching product managers and creating PM content over the past 12 months. In this highlight reel of career advice, I discuss:Rethinking retirementThe career-defining question every leade
Mastering your 30 second resume
A great career story can accelerate growth, yet most struggle to craft one. Even top performers fall short, telling stories that are overly detailed, abstract, jargon-filled, or poorly structured – all of which can lose a listener's interest.The first 30 seconds are crucial; you need to hook your audience quickly. Think of the beginning of your story as a movie trailer: highlight the most engaging
Founder Mode, done right | Shreyas Doshi (ex-Stripe, Twitter, Google, Yahoo)
In this episode, I’m joined by product and leadership expert Shreyas Doshi to dissect Founder Mode, why it’s appealing, and how to activate it. We dive deep into Paul Graham's recent essay which struck a chord in the tech community and resonated strongly with many founders and leaders.We also discuss:Why founder mode is a mindset, not a titleWhether founder mode is good or badBalancing detail and
4 secrets of career-boosting companies
Not all successful companies can supercharge your career. And not all companies that struggle are bad for your career. How can you tell if your company, or one that you are consider, will supercharge your career? In this episode, we'll explore four key characteristics of career-accelerating companies: speed, market position, quality of talent, and development culture. Whether you're job hunting or
Navigating careers while expecting
In this short and sharp "peacast" episode of The Skip, I share insights from a conversation with a pregnant Product Executive facing a career dilemma. She was convinced she needed to leave her current company, but while searching for a job, she got pregnant. And now she's been offered a new role at her company due to a reorganization. We discuss her options: accept the role, take a less senior rol
Stage of company: a career unlock
Many product managers focus on brand names or job titles, overlooking a crucial factor: company growth stage.This episode reveals how a company's phase - from startup to market leader - shapes your work and career path. We explore the four key growth stages, how product management evolves, and how to align your strengths with the right stage.Featuring insights from seasoned product leaders, learn
The art of building your personal brand
Personal branding is a crucial yet often misunderstood aspect of career development. Many professionals mistake personal brand for self-promotion or social media showmanship.This episode debunks these myths and reveals the true power of strategic personal branding. Featuring insights from two tech executives, Annie Pearl of Microsoft and Iska Saric of Meta, we pull back the curtain on how industry
Battling job search anxiety
Navigating job transitions in today's competitive tech landscape is difficult. Many people get stuck between roles, and an extended job search can dent your confidence. You might doubt your past achievements, question your current skills, and worry about what's next.In today’s episode, we tackle job hunting in today’s tough market. I share insights from a real coaching session with a design leader
Avoiding burnout for high achievers
Around 10-20% of my coaching calls tackle burnout. Despite being a deeply personal experience, burnout frequently affects high achievers, who often don't have the time to develop effective coping strategies.In today's episode, we dissect several paraphrased conversations, drawing from years of career coaching experience, offering insights and practical advice to help you manage burnout, set health
Crafting a compelling career story
After a three-month hiatus, The Skip returns with exciting news: April marked my departure from Meta, and I'm now fully focused on The Skip.Though leaving was a difficult choice, the decision highlighted something important: effectively telling your career story matters more than ever in today’s job market. Companies are concerned that some people may have been spectators to growth rather than con
Shedding perceptions: Moving from lone wolf to team player
In my fourth live coaching session, this caller felt like they had earned an unfair reputation as someone who struggles with collaboration in the workplace. The caller wanted guidance on transforming past perceptions into a new reality.The caller reveals both their superpower and its shadow. They are an opinionated product manager, blessed with exceptional taste and intuition. However, these trait
Is my next job at a startup or big tech?
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
Coaching grit, patience & tenure
This is my second episode experimenting with live coaching sessions. The format is my attempt to scale insights on common queries and themes I’m often asked about by listeners.This caller was looking for guidance after finding that a role they joined 4 months ago was not what they expected. Their situation exemplifies the kind of hard problems that leaders have to solve, and we speak about the tra
Are you short changing your career by not managing people?
Welcome back to The Skip; this episode is a little bit special as I’m experimenting with a new format: live coaching sessions. This idea came from the realization that the coaching queries I receive from listeners often have common themes.My hope is that recording and sharing a coaching call like this demonstrates how the frameworks are applied in real conversations and possibly helps others with
Greatest hits on career advice with Peter Yang (Roblox, ex-Reddit)
Much of the career advice out there is for aspiring PMs. But what about those who have one foot on the ladder and are looking to climb the next rung? This episode is about advancing mid to late-stage product management careers. I'm joined by Peter Yang, Product Lead at Roblox, and product newsletter writer, to discuss how established PMs can avoid getting stuck. From pursuing growth over promotion
How to find a great Mentor
This episode is about mentorship. Mentorship is a powerful personal development tool that naturally attracts ambitious people. However, it can be a complicated tool to maximize. Mentorship comes in many forms, with varying degrees of accessibility, quality, and suitability for a given individual. In this episode, I answer questions on 3 topics surrounding the complications of mentorship: how to na
5 rules that will unlock your Product Management career
Today’s episode breaks down my 5 rules for optimizing the most important product in your professional life: your career. These rules synthesize some of the key takeaways from all of my other content about product management and career growth. I break down why each rule matters, and outline some associated mistakes and misconceptions that you should avoid. Whether you’re at a career juncture or are
Shadows of Superpowers (Part 2)
Today’s episode is the second part, and deeper analysis, on “the shadows of your superpowers”. These are a type of development areas that are associated with your greatest strengths. I use example personas to detail 5 common shadows I’ve noticed across my career and coaching. For each, I breakdown why the shadow is elusive, common reactions to receiving feedback around it, and actionable advice fo
Shadows of your Superpowers (Part 1)
Today’s episode breaks down the shadows of your superpowers. These are a type of development area that is associated with your greatest strengths, and these apply to people inside and outside of tech. Shadows are one of the most elusive areas of self-development and, therefore, one of the most limiting to your potential. You may very well be unaware of yours. While shadows are surrounded by compli
Six Superpowers for Product Managers
In this episode of The Skip podcast, Nikhyl Singhal presents an enlightening discourse aimed at aiding tech industry professionals in their career growth. Through a new 30-minute coaching format, Nikhyl explores the transitions between managerial and individual contributor roles, emphasizing the significance of tackling six ambiguities in product management: product, growth, domain, market, organi
How much money do product managers make?
In this episode of The Skip Podcast, host Nikhyl Singhal explains how he helps product managers negotiate compensation. An industry veteran in the tech sector, Nikhyl has worked with 50+ leading executives and dozens of companies to ensure they establish optimal pay packages. He unpacks the concept of equity in both public and private companies and offers a method for comparing job offers based o
Exploring Head of Product career choices: From founding a startup to growth phases
Get ready for an engaging episode of the Skip podcast, where host Nikhyl Singhal dives into the evolving world of startups, head of product roles, and the fascinating field of product management. Discover how the head of product role has transformed in response to growth and hypergrowth dynamics, gain insights into the current market shifts and challenges, and explore the diverse career paths avai
Revisiting career frameworks: How Big Tech, management and IC roles have changed
Join host Nikhyl Singhal in this fascinating episode of ‘The Skip’ Podcast, as he explores the unique characteristics and opportunities of big tech companies in the current economic climate. Nikhyl discusses the challenges and advantages of working in big tech, defined by companies like Microsoft, Apple, Google, Meta, and Amazon. Learn about the changing landscape of the industry and how professio
Should I join (or leave) an ex-hypergrowth company?
In this episode of 'The Skip' podcast, host Nikhyl Singhal discusses the challenges and implications of ex-growth companies in the current market landscape. He delves into the consequences of overvaluation, the impact on employees and company culture, and the emergence of a new crop of prudent, conservative growth companies. Nikhyl provides valuable insights for those considering joining or stayin
The Quest for Success: A Career Story in the Age of A.I. With Markie Wagner
On this episode, The Skip Podcast host Nikhyl Singhal interviews Markie Wagner, an AI expert and founder of Delphi Labs. Markie and Nikhyl discuss the transformative impact of artificial intelligence and its potential to reshape workflows. Markie shares her early experiences with computers and how her passion for building things and writing code led to her impact on the world through STEM educatio
Balancing Work and Life: Insights from Nikhyl and the Skip CPO group
In this podcast episode, Nikhyl is joined once again by Anneka Gupta, Annie Pearl, Briana Ings, and Shirley Lin. The group explores the topics of how to recognize and recover from burnout, as well as to achieve a healthy work-life balance. They discuss the personal nature of burnout and how it's not simply a matter of comparing the two columns of “work” and “life.” The group suggests that if you'r
How to avoid getting stuck in your career with Shreyas Doshi
#5: Welcome back to the Skip podcast! In this episode, Nikhyl invites Shreyas Doshi to discuss the ever-evolving role that Product managers have in today's business world, finding yourself “stuck” in the ‘middle-stage’ of your career and how making high-quality career decisions is more important than ever. Using more than a decade of experience, Shreyas also describes vastly different experiences
Explaining Equity and Executive Compensation with Goodwin Procter
#4: Equity, stock options, and other compensation; a complex topic that has essentially limitless negotiable options. We are going to be walking through the basics to lay a foundation and then we will break down the most common mistakes that people make in this area. If you need to know more about offer letters, vesting stocks, and managing exits this episode is for you!Connect with The SkipThe Sk
Discussing career transitions with Heads of Products from Calendly, ClickUp, Divvy Homes, and Rubrik
Career transitions are filled with dozens of questions and pitfalls. Join Nikhyl Singhal and four product leaders from the Skip CPO group to discuss the challenges associated with big career decisions. Briana Ings (ClickUp), Anneka Gupta (Rubrik), Shirley Lin (Divvy Homes), and Annie Pearl (Calendly) bring dozens of years of leadership experience to the conversation, as they discuss when to leave
Career FAQ with Nikhyl Singhal
Tech moves fast and is ever evolving. But career worries remain constant and can weigh heavily. In this second Skip podcast, Nikhyl Singhal highlights what he calls “career frequently asked questions”: common concerns people share with him, and how you might approach these concerns to reach the best results for your own professional life. Building a career framework is important, but assessing the
Crafting a career framework with Nikhyl Singhal
You’re wondering if you should stay in your current role, or maybe you’re stressed about accepting a new one. Well, you’re not alone. In his decade of career coaching, Nikhyl Singhal has often listened to executives wrestle with these dilemmas. And in this first Skip Podcast, he poses five specific questions that he believes can help you create your best path forward and shape your career framewor
The Skip podcast trailer
The Skip Podcast helps tech professionals get ahead in their career. It’s hosted by Nikhyl Singhal, a successful founder, head of product, and executive. He has helped scale four of the most successful tech products ever: Facebook, Credit Karma, Google Photos, and Google Hangouts. And he coaches more than 100 executives, managers, and rising stars in navigating important career decisions, managem
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