Head of Customer Success

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 are looking for our first dedicated Head of Customer Success. We’ve scaled extremely rapidly and are looking for someone who can help bring in the right processes, at the right time to take us to the next level. You will be expected to get very deep into the details and still lead some accounts; every leader at Rootly is also an operator.

In this role you will own Net Revenue Retention and be accountable for turning Customer Success into a durable growth engine as Rootly scales into the enterprise.

You’ll help scale onboarding, adoption, retention and expansion. You will build and mentor a high performing CSM team, create scalable playbooks and define customer success metrics. You will partner closely with Sales, Product, Engineering and Support to ensure customers gain maximum value and to drive net retention, customer satisfaction and operational excellence.

You will be responsible for:

• Reporting into the VP of Sales, you will own Customer Success & Satisfaction at the highest level.

• Own onboarding, configuration, and adoption programs to deliver consistent customer outcomes at scale.

• Partner with Sales to define strategic engagement plans for named accounts and ensure scalable handoffs across the lifecycle.

• Drive retention and expansion by leading programs that reduce underutilization and surface upsell opportunities.

• Define health signals and use product and usage data to identify at risk accounts and lead cross functional remediation.

• Build, coach, and grow a high performing CSM team.

• Own analysis of churn and lost accounts, surface root causes, and lead initiatives to recover customers or prevent future losses.

• Create repeatable playbooks, automation, and tooling to increase efficiency and consistency of customer success work.

• Serve as the voice of the customer across Product, Engineering, and Marketing, driving product improvements, roadmap priorities, and service innovation based on customer insights

What You'll Need

• 5+ years of prior experience in a customer facing leadership role such as Head of Customer Success or Director of Customer Success, with experience hiring, coaching, and scaling a team.

• Previous experience at a SaaS company supporting technical products or cybersecurity solutions. Familiarity with DevOps, observability, or incident management is ideal.

• Act like an owner, willing to dive in and take the hardest individual problems and support your team through them as we scale.

• Proven ownership of onboarding programs and experience scaling onboarding for enterprise and mid market customers.

• Experience developing enablement materials and delivering webinars and training at scale.

• Comfortable using MySQL, Looker, Tableau, or similar tools, and Salesforce, to gather and analyze data and define health signals.

• Demonstrated ability to prioritize work and manage time across competing initiatives.

• Ability to thrive under pressure, remain results oriented, and lead effectively across teams.

• Track record of defining and reporting key success metrics such as net retention, churn, adoption, and customer satisfaction, and using those metrics to drive improvement.

• Experience creating playbooks, processes, and tooling to scale customer success operations.

• Comfortable influencing product and roadmap decisions with customer insight.

• Strong presentation, written, and verbal communication skills, including presenting to executives and customers.

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.