Head of Platform Engineering 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

This is a rare opportunity to join Rootly as the founding leader of Platform Engineering and to shape the foundation that powers incident response and on call for some of the world’s most forward thinking engineering teams.

As Head of Platform, you will own two critical outcomes for the company:

1. Infrastructure Reliability and Scale, building a rock solid, redundant, scalable, operationally mature, and cost efficient infrastructure platform that supports our next tenfold of growth
2. Developer Experience and Velocity, crafting a world class developer experience that enables product engineers to move extremely fast, with safety and confidence, and that shapes how Rootly builds, tests, deploys, and operates
3. This is not a traditional ops role. This is a high leverage engineering leadership position for someone who combines deep technical skill, systems thinking, taste, and the ability to inspire teams to raise the bar. You will define strategy, hire the team, own the roadmap, and build the platform that makes Rootly engineering world class.

If you thrive where ownership is real, intensity is celebrated, and the platform you build directly determines the company’s trajectory, you will love it here.

What You'll Do

Platform leadership and vision

• Own the vision, strategy, and roadmap for Rootly’s infrastructure and developer platform
• Build and lead a high performing Platform Engineering organization that may include SRE, infrastructure, DevEx, and internal tooling
• Establish a culture where reliability, performance, and developer experience are non negotiables
• Act like an owner, spotting problems early, mobilizing teams, and driving solutions from concept to completion

Infrastructure reliability and scale

• Architect a highly available, redundant, and scalable infrastructure foundation
• Lead capacity planning, cost management, performance tuning, and long term infrastructure scaling
• Drive operational maturity through infrastructure as code, declarative infrastructure, configuration management, and repeatable automation

Developer experience and productivity

• Enable product engineers to move extremely quickly by optimizing local dev environments, ephemeral cloud environments, fast CI and CD, and reliable canaries
• Provide tooling that abstracts infrastructure complexity and removes friction from development
• Ensure every engineer can ship confidently, frequently, and safely

Reliability, observability, and incident response

• Own platform wide SLOs, SLIs, and error budgets and use them to drive prioritization
• Oversee observability tooling, monitoring, alerting, and incident response processes
• Partner with product engineering teams to ensure services meet reliability and performance goals and to improve runbooks and postmortems

Execution, communication, and leadership

• Drive high quality execution with urgency while balancing long term bets with tactical wins
• Raise the bar and inspire engineers to think bigger, move faster, and deliver exceptional results
• Collaborate closely with Product, Engineering, and leadership to align platform investments with company strategy
• Recruit, mentor, and develop top tier platform engineers and create a culture of excellence

What We Are Looking For

We care about impact, ownership, and technical judgement. Degrees and big name logos are not required.

Minimum Qualifications

• 10+ years in platform, infrastructure, SRE, or DevOps roles, with increasing leadership responsibility
• Experience leading platform or SRE teams, including hiring, mentoring, and building culture
• Deep expertise with cloud infrastructure, AWS preferred, distributed systems, scaling, and redundancy
• Proven experience designing or operating high scale production systems and delivering operational maturity
• Strong background in observability, performance tuning, and scaling strategies
• Comfortable writing production grade software to solve infrastructure problems, Ruby or Go is a plus
• Strong architectural judgement and systems thinking that anticipates scaling pain before it becomes real

Preferred Qualifications

• Experience delivering DevEx tooling that materially improved developer velocity
• Experience navigating startup to hypergrowth transitions and scaling infra and teams accordingly
• High standards for taste and craftsmanship in platform engineering
• Exceptional communicator, able to translate complex technical decisions for technical and non technical audiences
• Bias toward action with the judgement to optimize versus ship at the right times

What Success Looks Like

By 6 to 12 months you will have

• Built a small but elite Platform team with clear ownership and high morale
• Dramatically accelerated engineering velocity with faster deploys, shorter tests, and fewer bottlenecks
• Established high availability infrastructure with clear SLOs and stronger reliability across the board
• Delivered developer tooling that makes engineering faster and more enjoyable
• Positioned Rootly to scale tenfold in customers, traffic, and complexity

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.