Chief of Staff
Terminal (YC S23)
Date: 8 hours ago
City: Toronto, Ontario
Salary:
CA$100,000
-
CA$130,000
per year
Contract type: Full time
About Terminal
Terminal is Plaid for Telematics in commercial trucking. Companies building the next generation of insurance products, financial services and fleet software for trucking use our Universal API to access GPS data, speeding data and vehicle stats.
We are a fast-growing, venture-backed startup supported by top investors including Y Combinator, Golden Ventures and Wayfinder Ventures. Our exceptionally talented team is based in Toronto, Canada.
For more info, check out our website: https://withterminal.com
Note: This role is only available to Toronto/GTA-based candidates
About The Role
We’re looking for a Chief of Staff to work directly with our CEO to scale the business and drive execution across everything from strategic initiatives to operations, partnerships, GTM and culture.
This is a high-trust, high-impact role that spans strategy and execution. You’ll help us move faster and with more focus—by building the systems that power how we operate day-to-day, while also owning and delivering on initiatives that drive our long-term growth. You’ll get to work across every function in the company and play a key role in shaping how Terminal runs.
We're looking for someone with the ambition of growing into a VP Operations or COO—and who’s excited to do the hard, unglamorous, and foundational work it takes to build a great company.
We liked this description of the COS role, and are plagiarizing it wholesale:
Patrick Aylward, a vice president and CoS at Horizon Blue Cross Blue Shield of New Jersey, breaks the job down into five roles: serving as an air traffic controller for the leader and the senior team; as an integrator connecting work streams that would otherwise remain siloed; as a communicator linking the leadership team and the broader organization; as an honest broker and truth teller when the leader needs a wide-ranging view without turf considerations; and as a confidant without an organizational agenda. Aylward points out that “while a CEO’s other direct reports typically emphasize their own areas, a good CoS can consider the needs of the whole enterprise.”
The most sophisticated chiefs of staff also assist leaders in thinking through and setting policies—and making sure they are implemented. They anticipate problems and are especially sensitive to issues that require diplomacy. They function as extra eyes and ears by pointing out political potholes their leaders may not recognize. Importantly, a CoS acts with the implicit imprimatur of the CEO—something that calls for humility, maturity, and situational sensitivity.
The CoS role is different from an executive assistant (EA). Unlike an EA, a CoS works autonomously and does not manage routine correspondence and scheduling.
Responsibilities
Terminal is Plaid for Telematics in commercial trucking. Companies building the next generation of insurance products, financial services and fleet software for trucking use our Universal API to access GPS data, speeding data and vehicle stats.
We are a fast-growing, venture-backed startup supported by top investors including Y Combinator, Golden Ventures and Wayfinder Ventures. Our exceptionally talented team is based in Toronto, Canada.
For more info, check out our website: https://withterminal.com
Note: This role is only available to Toronto/GTA-based candidates
About The Role
We’re looking for a Chief of Staff to work directly with our CEO to scale the business and drive execution across everything from strategic initiatives to operations, partnerships, GTM and culture.
This is a high-trust, high-impact role that spans strategy and execution. You’ll help us move faster and with more focus—by building the systems that power how we operate day-to-day, while also owning and delivering on initiatives that drive our long-term growth. You’ll get to work across every function in the company and play a key role in shaping how Terminal runs.
We're looking for someone with the ambition of growing into a VP Operations or COO—and who’s excited to do the hard, unglamorous, and foundational work it takes to build a great company.
We liked this description of the COS role, and are plagiarizing it wholesale:
Patrick Aylward, a vice president and CoS at Horizon Blue Cross Blue Shield of New Jersey, breaks the job down into five roles: serving as an air traffic controller for the leader and the senior team; as an integrator connecting work streams that would otherwise remain siloed; as a communicator linking the leadership team and the broader organization; as an honest broker and truth teller when the leader needs a wide-ranging view without turf considerations; and as a confidant without an organizational agenda. Aylward points out that “while a CEO’s other direct reports typically emphasize their own areas, a good CoS can consider the needs of the whole enterprise.”
The most sophisticated chiefs of staff also assist leaders in thinking through and setting policies—and making sure they are implemented. They anticipate problems and are especially sensitive to issues that require diplomacy. They function as extra eyes and ears by pointing out political potholes their leaders may not recognize. Importantly, a CoS acts with the implicit imprimatur of the CEO—something that calls for humility, maturity, and situational sensitivity.
The CoS role is different from an executive assistant (EA). Unlike an EA, a CoS works autonomously and does not manage routine correspondence and scheduling.
Responsibilities
- Operations:
- Be the product owner of our Company Handbook (SOPs, knowledge repo, dashboards).
- Design, implement and manage SOPs to improve our pace of execution across all functions.
- Identify bottlenecks and proactively build new processes or systems to resolve them.
- Lead our internal operating rhythms: OKRs, growth tracking, P&L reviews, and other rituals.
- Own back office processes across finance (invoicing, billing, accounts receivable, strategic finance), HR systems (benefits, onboarding/off-boarding), and vendor coordination.
- Manage tools and software procurement, subscriptions, and budgets.
- Partnerships:
- Own and foster bullet-proof relationships with all of our telematics integration partners.
- Own our pipeline of inbound and outbound partners to support new integration velocity.
- Work with our partners and engineering team to support development of new integrations.
- Work with our partners, customers and engineering to expand the utility of our integrations.
- Go-to-Market:
- Lead new customer implementations and work with founders on building a repeatable playbook for scaling a new function in customer success and account management.
- Work with our GTM team to create artifacts that support our pre-sale and post-sale motions (e.g. case studies, sales collateral, marketing collateral, new website, managing our social media calendar).
- People
- Keep our office humming: supplies, equipment and procuring new office space when needed.
- With the support of our CEO’s executive assistant, plan and execute bi-annual off-sites, team events and cultural rituals (swag, birthdays, anniversaries, celebrations).
- 3+ years of experience in startups, VC, product management and/or consulting
- Entrepreneurial and scrappy, with an extremely strong ”bias to action” mentality
- Atypically versatile. Able to dive into many roles and do them well
- Strong growth mindset paired with the work ethic to develop into a VP Operations or COO
- Excellent communication skills with ability to connect with executive-level stakeholders
- Excellent project management skills—highly organized, detail-oriented and extremely clear
- MBA or degree in a technical discipline (e.g. computer science, engineering)
- Previous entrepreneurial, startup and/or leadership experience
- Previous experience in enterprise SaaS, infrastructure or developer tooling
- 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
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