Founding Technical Recruiter

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.

This role is only open to Toronto/GTA-based candidates.

About the role

We are hiring a Founding Technical Recruiter to build and own Terminal's technical hiring function from the ground up. This is for a senior recruiter who has already closed exceptional technical talent in competitive markets and now wants a mandate with direct company-level impact: protect talent density while Terminal scales from a small, high-output team into the next version of the company.

Terminal moves more than 2 terabytes of data a day for some of the largest insurance and fleet management companies, with petabyte-scale ahead. We do it with a team most people would guess is five times the size. That is deliberate. Staying small keeps us fast, but it only works if every hire raises the bar. A below-bar hire at this stage does not just add nothing; they slow the people around them and reset what the team thinks good looks like.

You will report to Raghav, our CEO, who spends a significant amount of his time on hiring: sourcing, closing, sitting in loops, and writing the pitch. You will work just as closely with Connor, our CTO, and our technical leads. They own the technical bar. You own whether it holds as we grow.

Data platform engineering is the priority: engineers who can build streaming and storage systems that stay correct as data moves from terabytes to petabytes. You will run the rest of our engineering and data searches alongside it, and build the recruiting system every future hiring partner inherits.

What you'll do

1) Own technical recruiting end-to-end

• Run full-cycle recruiting across engineering, data, and other technical roles, with data platform engineering as the priority.

• Own sourcing, screening, scheduling, references, offer, and close. There is no coordination layer behind you.

• Build and maintain a live map of the Toronto engineers we want, so searches start warm instead of cold.

• Run outbound personally and write the kind of candidate messaging that reflects Terminal's bar.

Proposed ways to measure success and progress:

• Pipeline health: qualified senior technical candidates in an active process against each priority search.

• Sourcing quality: response and conversion rates from target technical profiles, not just raw outbound volume.

• Hiring velocity: time to qualified state and time to accepted offer by role.

2) Protect the technical bar and close senior talent

• Calibrate the bar with CTO and technical leads before searches open, then hold it in debriefs when the team gets excited.

• Build interview loops, scorecards, and debrief practices that ensure five interviewers consistently evaluate the same candidate.

• Close senior and staff engineers who are holding other offers, including compensation conversations that require fluency with early-stage equity.

• Review new hires after 90 days, six months, and twelve months against the bar we set, then feed what you learn back into the loop.

Proposed ways to measure success and progress:

• Bar quality: pass-through and post-hire signal stay consistent as volume increases.

• Close rate: offer acceptance on priority senior technical candidates.

• Interviewer calibration: debriefs lead to clearer decisions and fewer late-stage resets.

3) Build the hiring operating system

• Run hiring as a system. Ashby is live, and the tooling exists; you own the numbers behind it.

• Protect interviewer hours, the scarcest input in hiring. Keep loads inside agreed caps and redistribute panels before anyone is stretched.

• Partner with the CEO and leadership on headcount sequencing, role design, offer calibration, and when a problem should be solved with hiring versus AI/tooling for the existing team.

• Feed the employer brand with the story of Terminal's engineering culture and tell marketing and operations exactly who that story needs to reach.

Proposed ways to measure success and progress:

• Operating cadence: weekly hiring review in place, with clear owners, metrics, and decisions.

• Funnel instrumentation: response rate, pass-through, offer acceptance, time to hire, interviewer hours per hire, and hiring velocity visible by role.

• Repeatability: a technical recruiting playbook that future recruiters can inherit.

What we're looking for

This is a senior, high-accountability role at a company where hiring is the constraint on scaling. We're not looking for someone who has done something adjacent; we need someone who has done this specifically:

• You've recruited in-house at an early-stage startup: 5+ years recruiting, with at least two of them owning a full cycle.

• You've closed senior and staff engineers in a competitive market, against competing offers, in comp conversations that include early stage equity, and can point to the closes.

• You can source technically: two engineers can both say they work with data at scale and mean completely different things. You can read a profile and tell depth from exposure, and hold credible conversations with senior and staff engineers about the systems they've built.

• You run your pipeline the way a strong seller runs a book of business: you know your funnel numbers, and "some good candidates in process" is not a forecast to you.

• A company builder: you have views on how teams get built, you want to be in the room when those calls get made, and your own work reflects the standard you are hiring against.

• Comfort building alone: no coordination team behind you, in an environment that keeps changing.

• Strong writing: most first contact with the people we want is written, and it is the first evidence they have of our bar.

• AI in your own workflow: hands-on across sourcing, screening and scheduling, with the instinct to automate your work before asking for additional resources.

Nice to have

• Experience as the first recruiter at a company, building the function from zero.

• Recruiting for companies with highly technical products and staff.

• An existing network across Toronto's engineering and data communities.

• You have worked somewhere with a high bar quality and talent.

What success looks like

In the first 90 days

• Build a prioritized map of the Toronto engineering and data talent market.

• Take ownership of active technical searches, prioritizing data platform engineering.

• Establish the weekly hiring review and baseline funnel metrics.

• Calibrate the technical bar with the CEO, CTO, and technical leads.

• Ship v1 of the technical recruiting operating system: sourcing map, loop structure, debrief practice, close process, and metric dashboard.

In 6–12 months

• Deliver against the hiring plan while preserving talent density and interviewer capacity.

• Create a repeatable technical recruiting system across sourcing, screening, loop design, debriefs, close, and onboarding feedback.

• Improve predictability across response rate, pass-through, offer acceptance, time to hire, and interviewer hours per hire.

• Build the foundation for the next layer of recruiting support without adding process for its own sake.

Practical details

• Location: Toronto-based.

• Travel: Limited. Occasional campus, community and industry events.

• Reports to: CEO

Compensation

• Base: $115,000-$152,000

• Meaningful equity, plus the benefits below.

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. Sourcing and strategy working session (60 min)

3. Technical bar calibration interview (45 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.