Founding Customer Engineer

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 scaling, expansion, and retention of existing customers, not only through new logos, making this role the operational core of the company’s growth. We’re hiring our first Customer Engineer to own the post-sign technical lifecycle inside Terminal’s enterprise accounts, end-to-end. You won’t inherit a production-readiness standard or an implementation playbook; rather, you’ll have the opportunity to write them. Working in a dedicated pod with a Strategic Account Manager and a Customer Success Manager, you take each customer from signed contract to production readiness and then to technical scaling across the fleets, and you build the system that every Customer Engineer after you will inherit. You own the technical truth of the account: what is integrated, what is certified, and what it will take to scale. You turn integration ambiguity into a dated, defensible path to go-live, and you own every technical escalation until it is closed. 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 delivered enterprise implementations in a post-sales context, specifically, not something adjacent. WHAT YOU OWN, AND WHAT YOU DON’T You own three things: - The technical path to: technical solutioning, integration design, and the Definition of Done for every go-live, the milestone that the whole pod’s time-to-value depends on. - Enablement and technical scaling: getting each customer’s technical team self-sufficient on the platform, then scaling from the first production fleet to full fleet syncing at contracted quality. - Technical escalation ownership: you own incidents and integration escalations end to end, and you pull in a Sales Engineer when load crosses the threshold. You do not own commercial negotiation or pricing (the Strategic Account Manager), or adoption mechanics and the success plan (the Customer Success Manager). You also do not own bespoke professional services, pure support work, or roadmap commitments made without product-team alignment. 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) Own the technical path to production readiness - Own technical solutioning and integration design for each enterprise account: delivery mode (Streaming / Warehouse Replication / API pull), data environment, and known dependencies, confirmed and documented at kickoff. - Own the Definition of Done for go-live across all four domains: technical readiness criteria, data-quality validation gates, security and compliance sign-off, and customer-side readiness. - Publish the readiness checklist to the customer at kickoff, not at go-live: they know the criteria from day one. Proposed ways to measure success and progress - Time-to-readiness: production readiness milestones met on the milestone calendar set at kickoff. - Data quality: vehicle count matched to source, backfill verified, latency within SLA at readiness. 2) Enablement and technical scaling - Enable the customer’s technical team: dashboard training, a runbook for common issues, and a confirmed escalation path with their technical contact. - Scale from first-production fleet to full fleet syncing; monitor sync health, latency, and API error rates in PostHog, and act on threshold alerts before the customer does. - Own technical escalations end-to-end. Pull in a Sales Engineer when three or more concurrent workstreams are open, or when an incident and an active milestone run at once. Proposed ways to measure success and progress - Coverage: monthly active vehicles scaling toward and past the contract floor. - Reliability: P0/P1 incidents resolved within SLA; recurring issues eliminated, not just closed. 3) Build the founding Customer Engineer playbook - As the first CE, co-author the production-readiness Definition of Done, the kickoff technical playbook, and the common-issues repository alongside the founding technical account manager and COO in your first 90 days. - Add every issue pattern that recurs twice to the repository within two weeks of the second occurrence; feed structural fixes back to engineering. - Build the system that every Customer Engineer hired after you inherits. Proposed ways to measure success and progress - Playbook: v1 production-readiness checklist and kickoff technical playbook shipped within 90 days. - Repeatability: time-to-readiness trends down as the playbook matures. WHAT WE’RE LOOKING FOR This is a senior, high-accountability engineering role at a company that has reached product/market fit and is scaling. We’re not looking for someone who has done something adjacent; we need someone who has done this specifically: - You’ve delivered technical implementations for Fortune 500 customers in a post-sales context, not pre-sales SE work, not support-engineer work. You can point to enterprise go-lives you owned end-to-end. - You understand data engineering fundamentals: APIs, data pipelines, warehouse replication, and what data completeness and latency mean to a customer’s data science team. - You know what it costs when a security or data-governance review blocks a go-live at week four, and you know how to drive it to resolution rather than wait on it. - You communicate technical reality to executives without creating panic, and you translate customer requirements into a scope that engineering can act on. - A high-urgency operator: you own escalations, set the technical drumbeat, and drive to readiness on a dated plan. NICE TO HAVE - Domain exposure to telematics, fleet, insurance, or logistics. A strong data-engineering background is a substitute, not a requirement. - You’ve built or operated a production-readiness or go-live standard and have opinions about what makes one hold up under a Fortune 500 security review. - Experience at companies like Snowflake, Databricks, Twilio, or Stripe - the right peer group. TECH STACK Our tech stack includes the following tools and platforms. We do not expect experience with every tool, but you should be comfortable learning and working in a modern, integrated environment like this. Many of our customers run similar (often nuanced) versions of these same technologies, so adapting and leading highly technical discussions with customers is required. Day to day, that means reading and writing TypeScript against real APIs and data pipelines, designing integrations that stay correct as schemas and volumes grow, and guiding customer engineers toward durable patterns for ingestion, sync, webhooks, and queryable vehicle data. Frontend work exists in our stack, but the core of this role is the data and API layer: contracts, reliability, and long-term maintainable solutions. - Backend - Node.js (TypeScript) - AWS serverless architecture, including: - Lambda, DynamoDB, S3, SQS, EventBridge, and Step Functions - Frontend - Next.js, React, TypeScript deployed on Vercel - Styling with Tailwind and shadcn - Infrastructure as Code: - SST and AWS CDK - CI/CD: - GitHub Actions WHAT SUCCESS LOOKS LIKE In the first 90 days - Complete a full technical audit of your pod’s accounts and fully understand all open implementation items. - Partner with the CTO and COO to ship v1 of the production-readiness Definition of Done and the technical kickoff playbook. - Drive at least one key account to production readiness or a confirmed, dated milestone calendar. In 6–12 months - All assigned accounts at production readiness or on a managed milestone calendar. - Fleet coverage scaling toward and past contract floors, with sync health monitored and defended in PostHog. - Run an expansion technical discovery that surfaces new providers and use cases across the book. - Establish the repeatable CE 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 Success Manager; takes account-level direction from the SAM and technical direction from the Founding Technical Account Manager. COMPENSATION - On-target earnings: $200,000-$260,000 - Meaningful equity, plus the benefits below. - The variable is tied to production readiness milestones met on schedule. 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 (30 min) 2. Virtual System Design interview (60 min) 3. On-site technical design + Technical Customer Presentation (72 hrs prep period + 120 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.