We are looking for a Chief of Staff to work closely with our CEO in scaling our business operations and delivering on diverse strategic initiatives to accelerate Terminal’s operational velocity. In particular, we’re looking for someone who has previously scaled a venture-backed startup beyond Series B and now wants to be part of the leadership team at a high-impact, earlier-stage company. Your work will be critical in establishing the operational excellence and repeatability required for Terminal to continue accelerating into its next stage of growth. Our ideal CoS has the ambition and work ethic to grow with the company into a VP Operations and/or COO.

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 CEOs 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 bosses may not recognize (especially if the bosses are new to the company). Importantly, a CoS acts with the implicit imprimatur of the CEO—something that calls for humility, maturity, and situational sensitivity.

The CoS role is decidedly different from that of the leader’s executive assistant (EA). Unlike an EA, a chief of staff works autonomously and does not handle routine correspondence or manage the leader’s day-to-day schedule.

RESPONSIBILITIES

Design, implement, and manage business processes to ensure the CEO and company priorities are being managed, tracked, and achieved.
Work with founders to convert growth objectives and strategic priorities into quarterly OKRs, manage OKR progress, report weekly growth, and support the team in achieving its OKRs.
Manage our hiring pipeline, office operations, planning of team events and off-site events to grow the team, build team cohesion and foster a productive/collaborative environment.
Represent the CEO in internal and external communications as required, nurturing strong relationships with team members, partners, candidates, customers and prospects.
Design and implement zero-to-one playbooks with our CEO to improve the company’s pace of execution across operations, customer success, hiring pipeline, culture and GTM.
Execute strategic initiatives sponsored by the CEO and proactively propose new initiatives that help unblock the company and accelerate our operational velocity and growth rate.
Build GTM artifacts and processes to drive efficiency and repeatability within our GTM motion (e.g. case studies, sales collateral, new website, conference strategy, content strategy).

REQUIREMENTS

Previous high-growth startup experience having scaled to Series B and beyond
6+ years of operational experience in startups, VC, product management and/or consulting
Entrepreneurial and scrappy, with an extremely strong ”bias to action” mentality
Atypically versatile. Thinks and acts like a CEO. Able to dive into many roles and do them well
Strong growth mindset with the work ethic to develop into a VP Operations or COO
Extremely low ego with a default mode of company-first decision making
Excellent communication skills with ability to connect with executive-level stakeholders
Great project management skills — highly organized, process-driven, and detail-oriented
Willingness to challenge. Able to challenge opinions, assumptions, and actions, but also able to support/execute if and when the company disagrees and goes into a different direction
Willingness to both coach and be coached
Previous entrepreneurial, leadership and/or management experience is a plus
Previous experience in enterprise SaaS and/or developer tooling is a plus

Terminal

Chief of Staff

Toronto, ON, CA 🇨🇦full-time$110K - $140K CAD / 0.50% - 1.00% Equity