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

Product management is often romanticized as the role of a "CEO of the product," where high-level strategy and vision dictate the day. In reality, the role is far more grounded in the gritty details of execution, communication, and resilience. As the emotional center of the team, a Product Manager is responsible not just for the roadmap, but for keeping momentum alive when challenges arise. Maggie Crowley, Vice President of Product at Toast and former Olympic speed skater, argues that the most successful PMs are those who strip away complexity, embrace unglamorous work, and possess the patience to see their decisions play out over years, not just sprint cycles.

Key Takeaways

• Simplify relentlessly: The best PMs can cut through noise to find the single most important task, using tools like the Minto Pyramid Principle to communicate clearly.
• "Carry the water": Success requires doing the work no one else wants to do—from QA testing to sales calls—because the PM is ultimately responsible for the outcome.
• Structure strategy logically: A robust product strategy connects the company mission to specific team priorities through a rigorous accounting of the current landscape and market opportunities.
• Commit to the long game: True product mastery takes years of repetition; staying in a role long enough to see the consequences of your shipments is vital for growth.
• Validate with "Why Now": Whether writing a strategy doc or a one-pager, defining why a problem matters specifically right now is the key to prioritization.

The Three Pillars of Exceptional Product Managers

While technical skills and domain expertise vary across industries, the behavioral traits that distinguish top-tier product managers remain consistent whether at a seed-stage startup or an enterprise giant. Crowley identifies three non-negotiable characteristics found in the most effective leaders.

1. The Ability to Simplify

In any organization, complexity is the default state. Large companies are bogged down by thousands of OKRs and projects, while startups face an overwhelming number of "fires" to put down. The primary job of a PM is not to add to this list, but to identify the singular priority that matters most.

Simplification is also a communication skill. Many PMs fall into the trap of academic writing, using complex sentence structures to sound authoritative. To combat this, Crowley suggests a tactile approach: read your writing out loud. If it sounds convoluted, it is. Furthermore, adopting the Minto Pyramid Principle—stating the conclusion first, followed by supporting arguments—prevents stakeholders from having to hunt for the point.

"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."

2. Following Up on Results

Many product managers consider a feature "done" the moment it is shipped. However, exceptional PMs maintain a feedback loop that extends weeks or months past the launch date. They set reminders to check dashboards and metrics long after the initial excitement has faded.

This habit serves two purposes. First, it demonstrates reliability to leadership; managers do not need to chase down status updates. Second, and more importantly, it builds product intuition. You cannot learn if your hypothesis was correct if you do not analyze the long-term impact of your work.

3. "Carrying the Water"

The phrase "carrying the water" refers to the willingness to do the hard, unglamorous work required to push a product across the finish line. Unlike engineers who are responsible for code, or designers responsible for UX, the PM is responsible for the business outcome. This means that if a gap exists—whether it is in customer support, marketing copy, or manual data entry—it is the PM’s job to fill it.

"If you ever find yourself saying something like, 'that's not my job,' that's probably a thing you should do. It probably isn't your job... but you can spend your life getting frustrated at that or you can just get over it and get the work done."

Writing a Product Strategy That Actually Works

Product strategy is often discussed in abstract terms, leading to confusion about what the actual deliverable looks like. Crowley outlines a tactical framework for writing a strategy document that serves as a logic chain from the company’s highest goals down to specific team actions. This document is not just for stakeholders; it is a tool for the PM to prove to themselves that their bets are sound.

The Strategy Document Template

To create a comprehensive strategy, organize your document into the following sections:

1. The Mission: Restate the company’s purpose and the specific team’s charter.
2. The Landscape: A deep dive into the context. Include a SWOT analysis, competitor movements, and market shifts.
3. Current State Accounting: Be brutally honest about where the product is today. What is working? What is broken? What is the technical debt load? What are customers screaming about?
4. The Opportunity: Based on the landscape and current state, identify where the team can win. This section defines the unique competitive advantage.
5. The Challenges: What must be true for this opportunity to be realized? What are the risks?
6. The Solution & Plan: Finally, outline the specific bets (limited to three) and the operational plan to achieve them.

By writing this out in long-form prose, you force clarity of thought. Even if stakeholders only read the executive summary, the exercise ensures that every decision on the roadmap has a defensible lineage back to the company mission.

Execution and the One-Pager

Once strategy is defined, execution happens through the "one-pager" or product spec. While formats vary, the effectiveness of this document hinges on the opening section. A successful spec must clearly articulate the background, the problem, and crucially, the answer to "Why Now?"

Many valid problems exist, but few require immediate attention. If a PM cannot articulate why a specific problem takes precedence over others right now, the project likely lacks the necessary urgency or value. This document should serve as the "home base" for the team, recording not just the plan, but the decisions made and the rationale behind them as the project evolves.

Career Growth and Longevity in Product

There is a misconception that product management offers a quick path to decision-making power. In reality, gaining the competence to lead effectively takes years of repetition. Crowley notes that it took roughly four to five years of shipping products before she felt truly confident in her role.

The Value of Staying Put

While job-hopping can increase salary, it often stunts skill development. Staying at a company for three to four years allows a PM to see the full lifecycle of their products. They witness the long-term consequences of their architectural decisions and feature bets. This feedback loop is impossible to close if you leave a role every 18 months.

Breaking into the Field

For those looking to enter product management, the "PM" title is the most significant hurdle. Hiring managers prioritize experience because the role requires immense autonomy. The most reliable paths are lateral moves within a current company or joining early-stage startups where roles are fluid. Once that first title is secured, the career trajectory becomes significantly easier to navigate.

Conclusion

Mastering product strategy and growth is less about learning complex frameworks and more about developing professional maturity. It requires the humility to do the "boring" work, the discipline to follow up on results, and the clarity to write simply. As Crowley suggests, the best product managers are not those with the most complex theories, but those who are willing to take ownership of the outcome, regardless of the obstacles in their path.