Founding Customer Success Manager

Terminal•Toronto, ON

9d•CA$135,000 - CA$165,000•Onsite

About The Position

Terminal builds telematics data infrastructure for the commercial fleet industry. Commercial auto insurers and fleet software companies, including industry leaders like Intact Insurance, depend on our platform to access GPS, speeding, and vehicle data from 330+ telematics providers. We recently raised our Series A led by Battery Ventures and are backed by Y Combinator, Golden Ventures, Penske Transportation Solutions, and Intact Private Capital. Our team works together in person in Toronto, combining early-stage speed with late-stage maturity while processing many terabytes of vehicle data every day. Post-sales at Terminal is NOT a support function - it is our primary growth engine. Our model compounds through the retention and expansion of existing customers, not through new logos, which makes this role the operational core of the company's growth. We're hiring our first Customer Success Manager to own the activation motion inside Terminal's enterprise accounts. You won't inherit an end to end playbook, rather, you'll have the opportunity write it. Working in a dedicated pod with a Strategic Account Manager and a Customer Engineer, you drive each customer from signed contract to go-live and then to activation at scale, and you build the system every CSM after you will inherit. You bring the urgency and drumbeat that move large, complex organizations forward - running the cadence, helping customer counterparts reach milestones, and turning operational friction into momentum. You take account-level direction from the SAM and report to the COO. This is a senior, high-accountability role: we're hiring someone who has done this specifically, not something adjacent. What you own, and what you don't. You own three things: Time-to-value: the days from contract signature to production certification, the single most important leading indicator of whether a customer expands or churns. Activation: getting each customer to the point of deriving real value, while developing the repeatable motion behind it. The success plan and QBR narrative: the structured system that keeps each account on track and surfaces expansion. You do not own commercial negotiation, pricing, or technical implementation. Those belong to the Strategic Account Manager and the Customer Engineer. The pod model exists so each role can go deep rather than broad. Role clarity is a feature, not a limitation: if you find yourself doing someone else's job, your job is to name it, not absorb it.

Requirements

Owned enterprise customer success at a technical product company: data infrastructure, developer platforms, or similar, not a horizontal SaaS tool, and can point to the retention and activation outcomes you owned (cohort NDR, Activation metrics, 90-day adoption).
Managed multi-stakeholder alignment inside Fortune 500 accounts: product, data, security, finance and you know what it costs when security blocks a go-live at week seven.
Understand data pipelines well enough to know when something is broken, why it matters to an insurance data science team, and how to convey that to an executive without creating panic. You don't need to build them.
Communicate clearly and directly for executives; QBR narratives that lead with feature adoption don't get past you.
A high-urgency operator: you set the drumbeat, hold customer counterparts accountable, and drive to go-live and activation at scale.

Nice To Haves

Built or operated inside a structured success-plan system and have opinions about what makes one work. You know the difference between a measurable KPI and a narrative goal.
Domain exposure to telematics, fleet, insurance, or logistics.
Experience at companies like Snowflake, Databricks, Twilio, Stripe, or Fivetran — the right peer group.

Responsibilities

Drive time-to-value and activation
Own the days from contract signature to production certification — your single most important metric and the leading indicator of expansion vs. churn.
Drive each account from go-live to deriving real value, then to activation at scale (vehicle utilization vs. contract floor).
Set the proactive cadence: bi-weekly working sessions and written status updates within 24 hours of every call. No customer waits on us to respond.
Own the success plan, quarterly business review (QBR), and risk
Draft a structured success plan at kickoff a measurable Notion schema with baselines and targets, signed by the customer (not a narrative doc) — and maintain it at every account review.
Keep an adoption and risk register: named risks with mitigations and due dates. Own stakeholder alignment across various customer stakeholders including product, data, security, and finance - not just the champion.
Lead the QBR in the customer's language: surface, validate, and either advance or evolve the expansion thesis every quarter. A QBR that produces only a status update has failed.
Build the founding CSM playbook
As the first CSM, co-author the success-plan template, QBR framework, and activation playbook alongside the COO and team in your first 90 days.
Feed recurring friction back to R&D so activation gets easier over time.
Build the system every CSM hired after you inherits.