Lenny's Podcast: Product | Career | Growth

Mastering product strategy and growing as a PM | Maggie Crowley (Toast, Drift, Tripadvisor)

November 5, 2023

AI Summary

5 min read

Maggie Crowley, VP of Product at Toast with experience at Drift, Tripadvisor, and elsewhere, outlines traits that distinguish top product managers, a tactical process for product strategy, and unglamorous realities of the role. Drawing from hiring, managing, and her own path—including an Olympic speed skating background—she emphasizes shipping repeatedly to build intuition amid messiness.

Traits of standout product managers

Across startups and large companies, Crowley identifies three consistent behaviors in the best PMs she has worked with: simplifying to focus on one priority and sticking to it despite distractions; following up on feature outcomes by tracking metrics and sharing results (via calendar reminders); and "carrying the water"—handling boring tasks like customer support, sales calls, QA, or implementation that others avoid. These enable faster shipping and impact, as opposed to glamorous skills like vision or communication, which are table stakes. Psychologically, carrying the water sustains team optimism, as PMs often serve as the emotional center; resisting it breeds frustration and slows progress. Following up builds manager trust (they know "you've got this") and personal learning through reps, which takes years—often four or five—to yield confidence.

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What you'll learn

1 `* (00:57) **Guest Intro & 3 Traits of Top PMs**`
2 `* (04:50) **Simplifying: Prioritize, Cut, & Ship**`
3 `* (21:39) **Follow Up on Results & Build Expertise**`
4 `* (27:42) **Carry the Water: Do Unglamorous Work**`
5 `* (31:42) **Breaking Into PM**`
6 `* (34:36) **Product Strategy Doc Template**`
7 `* (49:52) **One-Pager for Features**`

+ Full timestamped outline available in the app

Show Notes

Maggie Crowley is VP of product at Toast and previously vice president and head of product at Charlie Health, senior director of product management at Drift, and a PM at TripAdvisor. She’s also the host of Build, a podcast dedicated to product and product management. In today’s conversation, Maggie shares:

• The value of building a broad-based PM skill set

• Three qualities of the best product managers

• A step-by-step guide for crafting a product strategy

• How to break into PM

• Why great writing is often just simplifying your writing

• Why being too data-driven is a red flag

• The impact of content creation on Maggie’s career

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Find the full transcript at: https://www.lennyspodcast.com/mastering-product-strategy-and-growing-as-a-pm-maggie-crowley-toast-drift-tripadvisor/

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Where to find Maggie Crowley:

• X: https://twitter.com/maggiecrowley

• LinkedIn: https://www.linkedin.com/in/maggie-crowley-42a97112/

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Where to find Lenny:

• Newsletter: https://www.lennysnewsletter.com

• X: https://twitter.com/lennysan

• LinkedIn: https://www.linkedin.com/in/lennyrachitsky/

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