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 managers, how location and pace become make-or-break constraints, and how to think about risk and chaos ...
Jan 08, 2026•1 hr 26 min
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 elite private companies and recent IPOs. Key topics • The “doors” framework: building a personal st...
Dec 11, 2025•1 hr 8 min
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 is quietly becoming obsolete, why some ex-VPs are happily taking senior IC roles, and how to prepare...
Nov 11, 2025•1 hr 12 min
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 suddenly on everyone's radar. If you're making any career move in 2025, your old playbook will hurt mor...
Sep 04, 2025•1 hr 3 min
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 internships (they matter more than your degree) • How to stand out when applying — and why “spray ...
Jul 09, 2025•1 hr 7 min
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 your career. – Key topics 6 common patterns holding leaders back How mentors can spot them, and what ...
May 19, 2025•1 hr 20 min
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’re navigating subtle shifts or considering a big move, this episode helps you own your superpower—a...
Mar 26, 2025•1 hr 5 min
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 considering a career move now or just want a structured way to assess future opportunities, this ep...
Feb 27, 2025•50 min•Ep. 35
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 to understand tech compensation better, this episode offers practical insights for making informed ...
Jan 30, 2025•56 min•Ep. 34
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 tradeoffs associated with each path, and some exercises for determining the best fit for you. - Key to...
Jan 10, 2025•58 min•Ep. 33
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 material Red flags: when founding isn't for you The right time to start your company Key skills that set you up for success Thriving in ambiguity Debunking the "venture scale or...
Nov 18, 2024•1 hr 6 min•Ep. 32
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 retirement The career-defining question every leader should ask Power years versus foundational years Leveraging career stories Finding peak roles Un...
Nov 01, 2024•22 min•Ep. 31
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 aspects rather than chronologically detailing every event. This episode focuses on crafting a capt...
Sep 20, 2024•54 min•Ep. 30
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 title Whether founder mode is good or bad Balancing detail and delegation The importance of product sense and good judgment Mastering founder mode as a product...
Sep 10, 2024•1 hr 16 min•Ep. 29
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 evaluating your current role, these insights will help you identify environments that truly foster ...
Aug 29, 2024•21 min•Ep. 28
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 role post-maternity leave, or seek opportunities elsewhere. – We also discuss: Maximizing career potent...
Aug 21, 2024•12 min•Ep. 27
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 to identify your ideal company stage and navigate transitions. This episode is your guide to makin...
Jul 30, 2024•44 min•Ep. 26
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 leaders craft and wield their personal brands to open doors, land dream roles, and shape their leg...
Jul 10, 2024•38 min•Ep. 25
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 who's struggling after being out of work for a few months. The episode is packed with concrete too...
Jun 20, 2024•52 min•Ep. 24
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 healthy boundaries, and cultivate a resilient mindset. – In today's episode, we discuss: Why burnout is a...
May 28, 2024•33 min•Ep. 23
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 contributors. Or worse yet, compelling successes at work are ignored or misunderstood due to an articu...
May 14, 2024•41 min•Ep. 22
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 traits also lead them to resist compromise. We confront the caller’s shadow, and explore frameworks and ...
Feb 11, 2024•34 min•Ep. 21
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 t...
Jan 21, 2024•33 min•Ep. 20
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 traits and strategies required to approach these problems wisely. Privacy is paramount for these calls...
Jan 07, 2024•34 min•Ep. 19
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 similar situations. Naturally, privacy is paramount, so we’ve anonymized the content and received p...
Dec 11, 2023•37 min•Ep. 18
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 to knowing when to change companies, we discuss a wide range of strategies to help you continue bui...
Oct 01, 2023•51 min•Ep. 17
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 navigate the resources available, how to be coachable, and tips and tricks I’ve learned as a mentor an...
Sep 10, 2023•51 min•Ep. 16
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 firmly positioned in a role, these rules come with actionable tactics you can implement tomorrow. U...
Aug 13, 2023•28 min•Ep. 15
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 for addressing the development area. Whether these shadows remind you of yourself or of others - in a ...
Jul 30, 2023•39 min•Ep. 14
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 complicated personal and workplace dynamics, understanding them is likely one of your best opportunities t...
Jul 16, 2023•31 min•Ep. 13
