Founding Customer Success Manager

ABOUT TERMINAL Terminal builds telematics data infrastructure for the commercial fleet industry. Commercial auto insurers and fleet software companies, including industry leaders like Intact Insurance, Penske, and Progressive, 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. For more on working at Terminal, see our careers page at withterminal.com/careers http://withterminal.com/careers. Note that this role is only open to Toronto/GTA-based candidates. ABOUT THE ROLE 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 to 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 that 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. WHAT YOU'LL DO 1) 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 for our response. 2) 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,s 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. 3) 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 so that every CSM hired after you inherits it. WHAT WE'RE LOOKING FOR - You've 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). - You've 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. - You 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. - You communicate clearly and directly with 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 HAVE - You've 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. WHAT SUCCESS LOOKS LIKE How we'll measure success - Time-to-go-live: Reduce days from contract signature to first production data flowing by 25% in the first 90 days. - Adoption: vehicle utilization vs. contract floor, growing month-over-month across the book of business. - Success-plan coverage: 100% of accounts have a current, measurable success plan signed by the account champion. - Expansion thesis: surfaced, validated or evolved at every QBR. - Playbook: v1 success-plan template, QBR framework, and activation playbook shipped within 90 days. - Repeatability: time-to-value trends down as the playbook matures. In the first 90 days - Take ownership of activation plans for your accounts and establish the cadence with each customer. - Partner with the COO and your team to ship v1 of the success-plan template, the QBR framework, and the activation playbook. - Drive at least one account to a major go-live, production-certification or equivalent milestone. In 6–12 months - Work diligently and consistently to drive activation at scale within the relevant enterprise accounts. - Bring new accounts from contract signature to production certification within target timelines. - Run quarterly business reviews (QBR) that support activation at scale and surface new expansion theses across the book. - Establish the repeatable CSM playbook every future hire inherits. PRACTICAL DETAILS - Location: Toronto-based - Travel: as needed for customer onboarding and meetings (up to 15–25%, vast majority to the US). - Reports to: COO (who leads Terminal's post-sales function). Operates in a dedicated account pod with a Strategic Account Manager and Customer Engineer; takes account-level direction from the SAM. COMPENSATION - On-target earnings: $135,000 - $165,000 - Meaningful equity, plus the benefits below. The variable is tied to time-to-production-certification and the adoption score at the first QBR. The structure is defined before you start — you won’t be negotiating it in your first week. BENEFITS - Strong compensation and equity packages. - Brand new MacBook and computer equipment. - Top-tier health/dental benefits and a 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. THE INTERVIEW PROCESS 1. Intro call with COO (30 min) 2. Skillset assessment interview (60 min) 3. Case study + QBR presentation (72 hrs prep period + 60 min) 4. On-site culture loop + final (180 min) Accessibility and accommodation 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.