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. Nikhyl 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, management challenges, and personal crossroads to maximize their happiness and professional life.
Subscribe to this podcast to hear from him and other executives as they teach unique career lessons.
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The Insider's Guide to Tech Compensation, Negotiation, and Career Growth
Episode 34
Thursday, January 30, 2025 • Duration 55:57
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 career decisions.
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community
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Timestamps
(00:00) Tactic for negotiating comp
(01:54) Unpacking the mailbag format
(03:09) Three job offers: which one should I take?
(06:02) Understanding bonus structures
(09:32) Why equity still matters today
(17:38) Breaking the equity exit trap
(25:29) Equity versus your market rate
(30:37) Don't chase comp early on
(34:12) Aligning the role to your superpower
(37:47) Negotiating comp: Start with what matters most
(47:30) When to discuss salary
(51:49) Problems with averaged comp
The Widening Tech Career Divide: Big vs Small Tech
Episode 33
Friday, January 10, 2025 • Duration 57:31
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.
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Key topics:
How AI is reshaping the tech job market
The (under-appreciated) differences between big tech and small tech
How PM and engineering roles have changed
How to assess your potential as a founder
What your worries reveal about your ideal work environment
Ready to start a startup? | Shreyas Doshi (Former PM leader at Stripe, Twitter, Google)
Episode 32
Monday, November 18, 2024 • Duration 01:06:01
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.
Live from Lenny's Summit | Career advice highlights
Episode 31
Friday, November 1, 2024 • Duration 22:15
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
Understanding the shadow of your superpower
The relationship between personal brand and reputation
Breaking down burnout
Building your support network through Skip Community
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 captivating 30-second introduction to your career story that engages listeners and enhances your professional profile. We've taken a unique approach by inviting Skip community members to submit their career stories for a live workshop. You'll hear real examples of me coaching engineering and product leaders, demonstrating the transformation from initial attempts to polished and punchy narratives.
We also discuss:
Common storytelling mistakes that everybody makes
Techniques for weaving a theme into your story
Effective strategies that will hook listeners
Adapting your story for various audiences and situations
Balancing between brevity and showcasing your unique value
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.
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 career growth.
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.
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We also discuss:
Maximizing career potential without sacrificing family
Reframing career decisions in the context of long-term growth
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 making strategic career moves in product management by leveraging the often-overlooked power of company growth stages.
We also discuss:
The 4 stages of company growth: drunken walk, product market fit, hypergrowth, and established market leader
How PM roles evolve across stages
Matching your skills to each stage
Intentionally choosing your company stage
The value of diverse stage experience for successful PMs
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 legacies.
The episode provides actionable strategies to build an authentic and compelling brand that catapults your career forward.
We also discuss:
The critical distinction between reputation and brand
Why you don’t need to become an influencer
The power of ‘peak roles’ in accelerating your career
Tailoring your brand story to specific audiences
Strategies for expanding your professional network
Discover shows related to The Skip Podcast, based on actual content similarities. Explore podcasts with similar topics, themes, and formats, backed by real data.
Don't forget to subscribe to The Skip to hear me coach you through 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) Teaser: Big tech vs small tech: Should you do both?
(00:35) Intro
(03:15) Why this discussion matters
(05:06) The biggest change in tech during 2024
(08:20) Why everyone should consider being a founder
(10:14) How to assess your potential as a founder
(14:44) How PM & engineering changed in 2024
(23:06) The all-important differences between big and small tech
(28:55) Assessing your fit for big vs small tech
(36:18) The challenges and benefits of working at both scales
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community
Timestamps
(00:00) Teaser: Why average PMs can make great founders
(01:17) Introduction
(02:34) The essential first step before founding
(06:21) Successful founder traits
(10:48) Managing at scale vs managing uncertainty
(18:25) Thriving in ambiguity
(21:29) Red flags: when founding isn't for you
(23:34) The surprising link between average PMs and founding success
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community
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Timestamps:
(00:00) How to help the Skip community
(01:37) Lenny’s Summit
(04:10) Breaking your career into levels
(07:33) Crafting a compelling career story
(10:26) All elite PMs find “peak roles”
(12:15) “The reputation you build today is the brand you’ll have tomorrow”
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter. You can also email me at nikhyl@skip.community
Timestamps
(00:00) Teaser: Unpacking founder mode
(02:47) What Shreyas has been up to
(04:04) Shreyas’ take on founder mode
(08:59) Why judgment and product sense is critical
(13:04) Balancing detail and delegation
(20:57) The key question for founders about ownership
(23:01) Not every company needs a CPO or Head of Product
(28:07) When product people should prioritize detail
(31:32) What everyone gets wrong about Steve Jobs
(34:22) Shreyas’ observation about John and Patrick Collison
(38:17) Nikhyl’s observation about Mark Zuckerberg
(40:05) Founder vs manager mode
(43:40) Should leaders avoid manager mode?
(48:17) Chase impact, not optics
(57:00) The 3 types of product leaders
(60:46) Aligning your environment, opinion, and superpower
(63:10) Shreyas’ non-consensus view on building product
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: nikhyl@skip.community
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, Twitter or email me at: nikhyl@skip.community
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Timestamps
(00:07) Applying my career framework to the caller’s case
(02:13) Caller context
(02:52) Why one option is a “no-brainer”
(03:58) The value of wartime leadership experience
(07:43) Why you won’t regret choosing family > career
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
Timestamps
(00:00) Intentionally choosing your company stage (episode teaser)
(01:25) The importance of company stage
(02:47) 3 common questions from PMs
(05:383) The link between PM and company stages
(07:48) The 4 company stages
(13:45) What’s unique about early-stage PMs
(15:24) How PM evolves when there’s customer traction
(18:00) Product management at a hypergrowth company
(21:50) One example of what changes between the first three stages
(24:49) PM at an established leader
(30:04) How to know which stage is right for you
(37:03) Spotting when it’s time for something new
(38:36) Choose your stage of company wisely
(41:38) Why top product people have multi-stage experience
Don't forget to subscribe to The Skip to hear me coach you through timely career lessons. If you’re interested in joining me on a future call, send me a note on LinkedIn, Threads, or Twitter.
