Head of Product Management at Rootly in Toronto, Ontario, CA

About Rootly

At Rootly, we are on a mission to be the go-to way companies respond when things go wrong, helping every organization be more reliable. We do this by building an industry-leading incident management platform that allows companies around the world consistently and quickly resolve incidents. We are not simply transforming an industry, we are carving an entirely new +$B segment ourselves and need incredible talent to achieve this ambitious goal together.

Customers love Rootly. Some of the fastest growing companies around the world such as NVIDIA, Figma, Canva, Tripadvisor, Squarespace and more rely on Rootly to power their critical incident management process. They obsess over our delightful enterprise-ready platform and unique partnership model. See why our customers have reviewed us 5 stars on G2.

Investors love Rootly. We are backed by some of the most respected funds in the world from Y Combinator to operators like the CTO of Dropbox and GitHub. We'd be happy to disclose our entire funding and profitability picture live during the interview. As a culture we relentlessly put transparency first. We conduct monthly financial reviews as a team so everyone has a pulse on the health of the business and publish what we are building in our weekly changelog.

About the Role

We're looking for a Head of Product who can translate vision into execution-ready priorities. If you want real ownership over what a category-defining product becomes, this is the role.

You'll own the product strategy and the outcomes, and you'll be accountable for both the product and the people building it. You'll take competing signals from customers, sales, engineering, and leadership and turn them into a sequenced plan with clear rationale that the entire company can rally behind. And when the answer is "not now" or "not ever," you'll be the one who makes that call and makes it stick.

What You'll Do

• Own the product strategy and build a prioritization framework grounded in where Rootly needs to be competitively in 12+ months, creating a shared language for saying no that founders and GTM can trust even when it costs a deal.
• Work as a true partner with engineering, GTM and leadership: one team with shared accountability, as opposed to a handoff across a fence
• Build and lead the PM function: Lead and elevate Rootly’s team of strong product managers, and scale the team to support the product strategy
• Raise the bar on product rigour: instil an outcomes-driven product culture where the team measures adoption and impact after every launch and feeds those learnings back into what we build next
• Think beyond the next quarter: develop the competitive positioning and product thesis that helps Rootly achieve its aggressive long-term growth goals
• Be the single point of accountability for what we build and what we don't: say no with clear reasoning that drives trust across the entire business

What You'll Need

• 8+ years of product management experience with increasing leadership scope in B2B SaaS, including experience building and leading a PM team
• You've set product strategy at a growth-stage company: owned the "what" and the "why," not just executed a plan handed to you
• You’re craft-obsessed with strong product instincts. You stay close to the product and move fluidly between long-term strategy and the details, with informed, nuanced opinions on whether a specific product is good or bad and whether it’s current shape is likely to drive the right outcomes.
• You have strong enough conviction to push back on a technical founder and the communication skills to make them trust your judgment more because you did
• You've built prioritization systems that actually stuck and operating rhythms that product teams have internalized
• You're energized by ambiguity: you take a messy landscape of competing priorities and create clarity from it
• Experience with developer-facing products (incident management, DevOps, observability, or adjacent) is a strong plus. What matters more is your ability to ramp fast and think like an owner

Why Rootly?

We're not just another startup. We're building something category-defining and want teammates who crave ownership, love solving hard problems, and thrive in a high-bar, high-impact environment.

Here's what you can expect when you join Rootly:

• Competitive compensation and early equity in a fast-growing, venture-backed company.
• Comprehensive medical, dental, and vision coverage.
• 3 weeks of vacation, plus unlimited sick and mental health days, and a company-wide end-of-year shutdown to recharge.
• $500 stipend for home office setup.
• Unlimited token usage and access to AI tools
• A fast-moving, high-impact environment where your leadership and ideas directly shape the future of the company.

If this sounds like the kind of challenge and opportunity you're looking for, apply now and let's build something great together.

Rootly is an equal opportunity employer. We aim to create an environment where every team member at Rootly feels like they belong so they can have a greater impact on our business and customers. We do not discriminate on the basis of race, religion, colour, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.