Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, TripAdvisor)
Maggie Crowley (guest), Lenny Rachitsky (host)
In this episode of Lenny's Podcast, featuring Maggie Crowley and Lenny Rachitsky, Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, TripAdvisor) explores maggie Crowley: Gritty PM habits that actually drive product impact Maggie Crowley, VP of Product at Toast and former Olympic speed skater, shares what really separates great product managers from the rest, beyond the usual buzzwords like strategy and communication.
Maggie Crowley: Gritty PM habits that actually drive product impact
Maggie Crowley, VP of Product at Toast and former Olympic speed skater, shares what really separates great product managers from the rest, beyond the usual buzzwords like strategy and communication.
She highlights three core behaviors: simplifying and focusing on the one thing that matters, rigorously following up on results, and “carrying the water” by doing unglamorous work others avoid.
Maggie also breaks down how to write practical product strategy and one-pagers, critiques over-reliance on being “data-driven” and on product content frameworks, and talks candidly about career growth, failure, and breaking into PM.
Throughout, she emphasizes that PM work is messy, often unsexy, and takes years of reps—but can be deeply fun and rewarding if you focus on impact over frameworks and titles.
Key Takeaways
Great PMs ruthlessly simplify and stick with the most important thing.
Across company stages, the best PMs can cut through noise, choose the single most important problem, say no to everything else, and then stay on it long enough to ship and see results—rather than constantly re-litigating priorities.
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Following up on results is a simple, rare, high-leverage habit.
Most PMs define metrics; very few circle back weeks and months later with, “Here’s what happened. ...
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“When in doubt, it’s your job” — carry the water.
Great PMs willingly do the boring, ambiguous work—QA, support, sales calls, copywriting, implementation, project management—because they own outcomes, not artifacts. ...
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Real product strategy is a written logic chain from mission to roadmap.
Maggie’s approach: document company and team mission, market and competitive landscape, current business/product state, tech constraints, opportunities, challenges, and then propose a small set of bets and a plan. ...
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Over-celebrating being “data-driven” can mask weak product thinking.
Teams that fetishize dashboards often underinvest in qualitative research and judgment, trying to manage everything by metrics. ...
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It takes years of shipping (and failing) to become truly good at PM.
Maggie and Lenny both needed ~4–5 years and many shipped products (including clear failures like a disastrous multi-year rewrite) before they felt competent. ...
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Frameworks and online product content are tools, not checklists.
Because content must be simplified and interesting, it often loses nuance. ...
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Notable Quotes
“If you ever find yourself saying, 'That's not my job,' that's probably a thing you should do.”
— Maggie Crowley
“You do a strategy, but it's 5% of the work. The person with a good strategy who ships less will lose to the PM who ships more and creates impact.”
— Maggie Crowley
“You’re often the emotional center of the team. It’s your job to keep people motivated, excited, and bought in—and to keep that optimism going.”
— Maggie Crowley
“People who are really excited about being ‘data-driven’—to me, that is oftentimes a red flag for their product thinking.”
— Maggie Crowley
“You’re not a good PM if you haven’t shipped something that’s really shitty.”
— Maggie Crowley
Questions Answered in This Episode
How can I tell, in my current role, whether I’m actually simplifying and focusing—or just telling myself I am while juggling too many priorities?
Maggie Crowley, VP of Product at Toast and former Olympic speed skater, shares what really separates great product managers from the rest, beyond the usual buzzwords like strategy and communication.
Get the full analysis with uListen AI
What concrete steps can I take over the next 6–12 months to build a reputation with my leadership as someone who ‘never drops the ball’?
She highlights three core behaviors: simplifying and focusing on the one thing that matters, rigorously following up on results, and “carrying the water” by doing unglamorous work others avoid.
Get the full analysis with uListen AI
Where in my product work have I over-rotated on quantitative metrics and under-invested in understanding the human, qualitative ‘why’ behind the numbers?
Maggie also breaks down how to write practical product strategy and one-pagers, critiques over-reliance on being “data-driven” and on product content frameworks, and talks candidly about career growth, failure, and breaking into PM.
Get the full analysis with uListen AI
How could I adapt Maggie’s strategy-document template to my team’s size and culture without overwhelming stakeholders with a 20-page narrative?
Throughout, she emphasizes that PM work is messy, often unsexy, and takes years of reps—but can be deeply fun and rewarding if you focus on impact over frameworks and titles.
Get the full analysis with uListen AI
If I’m early in my PM career and hungry for promotion, how do I balance staying long enough to see outcomes with moving roles to gain new experiences?
Get the full analysis with uListen AI
Transcript Preview
If you ever find yourself saying something like, "That's not my job," that's probably a thing you should do. And it- you know what? It probably isn't your job and it probably is someone else's job, and you can spend your life getting frustrated with that or you can just get over it and get the work done. And people who are willing to just get the work done will move faster, their products will be more successful, and they probably aren't carrying around all that anger and crappy emotion. Because as a PM, for better or for worse, and maybe this is not how we all want it to be, but you're oftentimes the emotional center of the team and it's your job to keep people motivated, keep people excited, keep them bought into the project, and you just have to, like, keep that optimism going and it's hard work. And part of it can be just like, "You know what? Let me take that on. I'll do this thing, I'll hop on this sales call, I'll implement this with the customer." You just have to do whatever it takes.
(instrumental music) Today, my guest is Maggie Crowley. Maggie is currently vice president of Product at Toast. Prior to this, she was VP and head of Product at CharlieHealth, senior director of Product at Drift, director of Product at BevSpot, product manager at TripAdvisor. She's also got an MBA from Harvard Business School. She was also an Olympic speed skater, which is insane and incredibly cool. And in our conversation, we discuss the three most common threads across the best product managers that she's worked with, hired, and managed; how to very tactically write out a product strategy to share with your team and manager; why being data-driven is a red flag for product thinking; why product content you find online can be dangerous; her best advice for how to break into product management; also, the impact writing online has had on her career; and so much more. Maggie is amazing. I'm excited for you to learn from her like I did. With that, I bring you Maggie Crowley after a short word from our sponsors. This episode is brought to you by ProductRoadmap.ai and Ignition. ProductRoadmap.ai is the first AI roadmapping suite. It helps ensure roadmaps drive revenue by instantly aligning product with your sales and marketing teams to capture upsell opportunities. Built by early leaders from Rippling and Craft, it automatically identifies feature gaps from your CRM data and your customer conversations, adds them to shareable roadmaps easily prioritized by revenue impact, and then seamlessly closes the loop with sales reps via targeted notifications when feature gaps are closed. As part of Ignition's broader go-to-market operating system, ProductRoadmap.ai can also help create better handoffs and collaboration with product marketing teams by giving both teams the tools to research, plan, orchestrate, and measure the process of building products and going to market. Packed with integrations, AI automation, and communication tools, it's truly a one-stop shop for product and marketing to bring things from concept to launch. To sign up, go to ProductRoadmap.ai and use promo code Lenny to get 75% off your first year. This episode is brought to you by Composer, the AI-powered trading platform now with retirement accounts. Algorithmic trading has historically been reserved for the hedge fund elite. Now, with Composer, you can automate your trading with a library of over 1,000 strategies that are easy to understand and tweak using an AI assistant and visual editor. Composer is the first ever algorithmic trading platform where you don't need any coding experience. It includes a full range of trading indicators for you to get creative, and a Discord community of 2,500 traders to discuss your ideas with. Composer also has a powerful back tester to see the historical performance of your strategies, and you can then invest with a single click. Once you invest, Composer will automatically trade for you based on the logic of your strategy. With one billion dollars in trading volume and over one million trades executed, Composer already has many big time investors using the platform regularly. Head to composer.trade and use the code Lenny for an extra week of free trial on your Composer membership. That's composer.trade. Maggie, thank you so much for being here. Welcome to the podcast.
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