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.
Help build how Terminal runs. You'll work directly with our Chief of Staff to solve operational problems, drive cross-functional projects, and build reliable systems across workplace, people, events, and finance. You’ll be the go-to for all things related to our office in King West. You’ll maintain established vendor relationships, coordinate with building management, and ensure our office is stocked across IT, supplies and snacks.
We have two offsites a year for our team, and you’ll work with our team leads and travel vendors to plan and execute each one. You’ll also own hosting customer-centric events, such as dinners, roundtables, and visits. You’ll help make sure our customers are billed correctly and pay on time, while also making sure we pay our bills on time. That means executing accounts payable, vendor onboarding, expense tracking, billing reviews, and collections outreach.
As the team and company scale, you’ll establish standard operating procedures, maintain our Terminal handbook, and use AI and automation to increase efficiency across the business and your focus areas.





2–5 years across business operations, People ops, events management, or a startup generalist role, with explicit examples of workflows you executed through end-to-end implementation rather than pure coordination.
You maintain a high bar for accuracy across task lists, vendor management, calendar logistics, and confidential HR records.
Systems and data fluency: You are skilled in spreadsheets, HR platforms like Rippling, Slack, and document hubs (Notion/Drive), leveraging AI tools thoughtfully to multiply productivity.
Bonus points
~ You've helped build a function or company from scratch, supported People, hiring, finance, or events systems at an early-stage startup, and regularly used AI to automate work your team was doing by hand.

You'll know the heartbeat of Terminal's office, hiring process, and events, and own and improve many of them. Full-time
Travel: Limited but occasional for offsites & conferences as needed

Meaningful equity, plus the benefits below.

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

Phone Screen (30 min)
# On-site culture loop + final (180 min)

If you need an accommodation at any stage — applying, interviewing, or completing an assessment — email View email address on jobs.ashbyhq.com 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.

📌 Operations Specialist (Full Time) (Toronto)
🏢 Terminal
📍 Toronto