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About the Role
As the first Customer Success Manager, you will own the activation motion within Terminal's enterprise accounts, writing the playbook as you go. You will work in a dedicated pod with a Strategic Account Manager and a Customer Engineer to drive customers from contract signing to go-live and activation at scale. This is a senior, high-accountability role focused on customer retention and expansion, serving as the operational core of the company's growth.
Responsibilities
- Own the time-to-value from contract signature to production certification.
- Drive customer accounts from go-live to deriving real value and activation at scale.
- Set the proactive cadence with customers through bi-weekly working sessions and timely status updates.
- Draft and maintain structured success plans with measurable Notion schemas.
- Maintain an adoption and risk register with named risks and mitigations.
- Own stakeholder alignment across customer product, data, security, and finance teams.
- Lead Quarterly Business Reviews (QBRs) to surface, validate, and advance expansion theses.
- Co-author the success plan template, QBR framework, and activation playbook.
- Provide feedback to R&D on recurring friction points to improve the activation process.
- Build a repeatable CSM playbook for future hires.
Requirements
- Experience owning enterprise customer success at a technical product company (data infrastructure, developer platforms, or similar).
- Proven ability to manage multi-stakeholder alignment within Fortune 500 accounts.
- Understanding of data pipelines sufficient to identify issues and convey their impact to executives.
- Clear and direct communication skills with executives.
- High-urgency operational mindset with the ability to hold customer counterparts accountable.
- Experience building or operating within a structured success-plan system.
- Domain exposure to telematics, fleet, insurance, or logistics is a plus.
- Experience at companies like Snowflake, Databricks, Twilio, Stripe, or Fivetran is a plus.
Skills
- Customer Success Management
- Enterprise Account Management
- Technical Product Management
- Data Infrastructure
- Developer Platforms
- Stakeholder Management
- Risk Management
- QBR Leadership
- Playbook Development
- Communication
- Urgency
- Accountability
Location
- Toronto, Ontario, Canada
Work Type
- On-site
- Full-time
Experience Level
- Senior
Salary/Compensations
- On-target earnings: $135,000 - $165,000
Benefits
- Strong compensation and equity packages.
- Brand new MacBook and computer equipment.
- Top-tier health/dental benefits.
- Flexible healthcare spending account.
- Personal spending account for professional development, fitness and wellness.
- Four weeks paid time off + statutory holidays.
- In-person culture with an office located in downtown Toronto.
About the Company
- Terminal builds telematics data infrastructure for the commercial fleet industry.
- Commercial auto insurers and fleet software companies depend on our platform to access GPS, speeding, and vehicle data from 350+ telematics providers.
- Recently raised Series A led by Battery Ventures.
- Backed by Y Combinator, Golden Ventures, Penske Transportation Solutions, and Intact Private Capital.
- Team works together in person in Toronto, combining early-stage speed with late-stage maturity.
- Processes many terabytes of vehicle data every day.
Equal Opportunity
- Terminal is committed to an accessible hiring process. If you need an accommodation at any stage — applying, interviewing, or completing an assessment — email careers@withterminal.com and we will work with you to meet your needs.
- Accommodations are available under the Accessibility for Ontarians with Disabilities Act (AODA) and the Ontario Human Rights Code, and requesting one will never affect how your application is considered.