Maggie Crowley
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.
Career Skills
Breaking into product management often requires securing the title first, as hiring managers heavily screen for prior PM experience.
"If you can get someone to stamp you with the product manager role, take it. Because... it's what we screen on... once you get that first job, it all gets easier."
Communication Skills
High-quality presentations are built from a logical outline and clear headlines before any visual design begins.
"I start with an outline on paper and then I draw little boxes for the slides and I write out the headline of the slides. And then once I have a tight outline... then I sketch out how I want the slides..."
Effective writing should mirror natural conversation and be stripped of unnecessary complexity.
"When you write something, read it out loud, literally just read the thing you wrote out loud and half the time you'll realize it's way too complicated... Just say that thing. The thing that you said t..."
Structure documents to deliver the most important information immediately rather than building up to a conclusion.
"The Minto principle is something that I would recommend everyone do, which is put the headline, the full conclusion first and then you're supporting argument second."
Inviting early, harsh feedback from cross-functional partners builds buy-in and improves the final product.
"The first person I go to is typically speaking my engineering counterpart and I say, shred this, go through it, rip it apart, vomit comments on it, tear this down how it gets better."
Engineering Skills
A comprehensive product strategy must account for the technical constraints and maintenance needs identified by engineering.
"Where are your technical hurdles? What are the big pieces of tech debt? What are your engineering and technical teams always harping on that they want to invest in?"
Hiring & Teams Skills
The PM serves as the team's 'emotional center,' responsible for maintaining morale and alignment.
"As a PM, for better or for worse... 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."
Leadership Skills
Failed projects often stem from skipping discovery and underestimating the complexity of technical rewrites.
"I remember... we decided we needed to do a rewrite, red flag number one... It didn't take six months, it took two and a half years... We skipped discovery. We didn't really write a one-pager, we just..."
PMs must act as the 'gap fillers' for the team, taking on any task necessary to ensure the product's success.
"You can't be a good PM if you're not willing to do the hard boring unglamorous work of customer support, sales, marketing, writing, copy, project management, you have to do that stuff."
Product Management Skills
A robust strategy document connects high-level mission to tactical execution through a clear, documented logic chain.
"You should be able to walk all the way from your company's mission down to the individual priority on your team and see the logic chain and why you got there."
Great prioritization requires the discipline to stick with a single focus until completion despite competing fires.
"The best PMs not only can find the one thing to work on, but they can stay with that one thing long enough to actually finish it."
The hardest part of prioritization is the emotional and professional courage required to say no to good ideas.
"Getting to the one thing you should do is extremely difficult and being able and having the gumption to say no to all those other things is really hard, because there's probably at any given time, 10..."
Closing the loop on metrics after a launch is a rare but high-value activity that demonstrates accountability to leadership.
"The really, really good PMs remember to follow up... if a PM comes back to me and says, 'Hey, remember we did that thing, here's what happened.' I can't tell you how rare that is."
Strategy requires a deep, documented understanding of the market landscape and competitor positioning.
"In that section I put in what's going on with our business? What's happening with our products? What's our point of view on the market? Who are our competitors? A SWOT analysis, key risks that we migh..."
A successful PRD centers the team on the 'why' and the specific urgency of the problem before discussing solutions.
"The most important section in my opinion in the document is the first part, which is like what is the background and context? What is the problem, why does it matter and why does it matter now?"
Over-reliance on dashboards can mask a lack of understanding of the human users and their motivations.
"People who are really excited about being data-driven, to me that is oftentimes a red flag for their product thinking... they're over-emphasizing quantitative data at the expense of qualitative data a..."