Founding Customer Success Manager

Responsibilities

• Own time-to-value from contract signature to production certification.
• Drive enterprise customers from go-live to deriving real value and activating at scale.
• Establish proactive customer cadence through bi-weekly working sessions and written status updates.
• Create and maintain measurable, customer-signed success plans with baselines and targets.
• Maintain adoption and risk registers with named risks, mitigations, and due dates.
• Align stakeholders across product, data, security, and finance.
• Lead quarterly business reviews (QBRs) that validate or evolve expansion theses.
• Co-author the success-plan template, QBR framework, and activation playbook within the first 90 days.
• Feed recurring activation friction back to R&D.
• Drive go-live, production certification, and activation milestones across enterprise accounts.

Requirements

• Experience owning enterprise customer success at a technical product company, such as a data infrastructure or developer-platform company.
• Demonstrated ownership of retention and activation outcomes, including cohort NDR, activation metrics, or 90-day adoption.
• Experience aligning multiple stakeholders within Fortune 500 accounts, including product, data, security, and finance.
• Sufficient understanding of data pipelines to identify issues, understand their impact on insurance data science teams, and explain them to executives.
• Clear, direct executive communication skills.
• High-urgency operating style with the ability to establish cadence, hold customer counterparts accountable, and drive go-live and activation at scale.

Nice to Have

• Experience building or operating a structured success-plan system.
• Domain exposure to telematics, fleet, insurance, or logistics.
• Experience at companies such as Snowflake, Databricks, Twilio, Stripe, or Fivetran.

Success Measures

• Reduce days from contract signature to first production data flowing by 25% in the first 90 days.
• Increase vehicle utilization versus the contract floor month over month.
• Achieve current, measurable success plans signed by the account champion for 100% of accounts.
• Surface, validate, or evolve an expansion thesis at every QBR.
• Ship version-one success-plan, QBR, and activation frameworks within 90 days.
• Reduce time-to-value as the playbook matures.

Compensation and Benefits

• On-target earnings: $135,000–$165,000 CAD.
• Meaningful equity.
• Brand-new MacBook and computer equipment.
• Health and dental benefits with a flexible healthcare spending account.
• Personal spending account for professional development, fitness, and wellness.
• Four weeks of paid time off plus statutory holidays.
• In-person culture with an office in downtown Toronto.
• Travel as needed for customer onboarding and meetings, up to 15–25%, primarily to the United States.