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Head of CSM

Rootly22 days ago
Toronto
C Level

About the role

Who you are

  • 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

What the job involves

  • We are looking for our first dedicated Head of 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
  • 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

About Rootly

Software Development
51-200

AI-powered on-call and incident response.

Beautiful, modern, and Slack-native incident management—from your first alert to retrospective.

Trusted by 100s of leading companies including NVIDIA, Squarespace, Canva, Grammarly, Elastic, Tripadvisor, and Figma.

See why they rate us 5 stars on G2: https://www.g2.com/products/rootly-manage-incidents-on-slack/reviews