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Head of Support

Rootly

Toronto, Ontario, Canada (Office) permanent

Posted: January 2, 2026

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Quick Summary

We are looking for a Head of Support to join our team in Toronto, Ontario, Canada, as the company is expanding its operations in the region.

Job Description

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

At Rootly, we are committed to helping our customers successfully utilize our services throughout their entire journey with us. A large part of that is helping our technical users get support quickly and efficiently; it’s what our customers love about us.

As Head of Support, you’ll lead an incredible team of support engineers who engage with our customers through Slack, email, and calls to ensure they walk away from a Rootly interaction with a smile on their face.

Leaders at Rootly dive into the details. If you enjoy jumping into the queue, working directly with customers, and developing the support leaders of the future, this is the role for you.

You will be responsible for:

• Being a technical expert; no one will know Rootly better than you.

• Deeply understanding the product and providing actionable feedback to Product and Engineering.

• Leading escalations with large customers and jumping into the queue to help your team.

• Building lightweight processes to help speed up responses to our customers.

• Building and scaling a growing team of support engineers around the world.

• Owning support KPIs such as SLAs/SLOs, CSAT, response and resolution time, and overall quality of service.

• Designing scalable global support operations, including coverage models, staffing, and tooling to support Rootly’s growth.

• Acting as a key cross-functional partner to Engineering, Product, and Customer Success to ensure customer insights, bugs, and feature requests flow efficiently across the company.

• Establishing structured escalation frameworks and incident response workflows for high-severity issues.

• Creating training, onboarding, and career development programs to grow support engineers into future leaders.

What You'll Need

• Lead by example; you’ll be out in front with your team.

• 6–8 years of Solutions Engineering, Technical Support, or Software Engineering experience (or a mix!).

• Strong technical literacy across APIs, debugging workflows, logs/monitoring tools, and modern DevOps/SRE environments (experience with tools like Datadog or Sentry is a plus).

• Experience mentoring and growing others into a support engineer role.

• Ability to thrive under pressure, maintain a results-oriented mindset, and collaborate effectively as part of a team.

• A background working in a DevOps environment is ideal.

• Experience operating or supporting incident management, escalation, or on-call processes is a strong advantage.

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.

• Learning and development budget at your discretion to support your growth.

• 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, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status.

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