Chief of Staff

Job Description

About the Role

We're looking for a Chief of Staff to operate as a true right hand to leadership — someone who blends operational rigor with strategic judgment, and who can be trusted to make decisions on our behalf without needing every call escalated. This is not a support role. It's a high-leverage, high-trust position for someone who wants to run toward ambiguity, own outcomes end-to-end, and be evaluated on results rather than hours logged.

This Chief of Staff will work remotely with frequent travel to our Vancouver office to work closely with our Co-Founders and leaders.

This role blends two archetypes we've defined internally:

• The Operator — runs the company's operating rhythm (i.e. leadership meetings, prepares investor materials, and facilitates cross-team follow-through). The person who makes sure decisions actually get executed and holds department heads to date. Judged on whether the company runs on time.
• The Strategist — takes on ambiguous, cross-functional problems and owns them end to end (a new state launch, a vendor evaluation, a pricing/promo overhaul, a build-vs-buy call). Does the analysis we'd otherwise have to do ourselves. Judged on the quality of decisions and the projects delivered.

This role leans heavier toward the Operator side , with the Strategist skill set applied to discrete, high-stakes special projects.

What You'll Do

Operating rhythm (Operator)

• Run the company's operating cadence (i.e. leadership stand ups)
• Own reporting on high-visibility work stream — building reliable dashboards and narrative updates so leadership can see progress, risks, and trade-offs clearly ahead of each cycle.
• Define and track KPIs for operational health and surface them in regular business reviews.
• Hold department heads accountable to dates and drive cross-departmental alignment — ensuring things that get decided actually get done .
• Stay in close, regular communication with department heads for status updates, surfacing risks before they become problems.
• Provide coaching and advice to keep the leadership team aligned, organized, and functioning cohesively.
• Drive internal communications efforts across the organization.
• Run growth diagnostics — regular health checks across the business to spot blockers, inefficiencies, and structural gaps before they slow the company down.

Special projects (Strategist)

• Own high-visibility, ambiguous, cross-functional projects end-to-end — e.g., influencer events, a new market/state launch, vendor evaluations, pricing/promo overhauls, or build-vs-buy decisions.
• Own the execution mechanics of organizational change — sequencing communications, aligning stakeholders, and managing resistance — during restructures, leadership transitions, and major process overhauls

Executive partnership

• Make decisions and handle certain calls directly on behalf of the Co-Founders, acting with delegated authority and judgment that aligns with company vision.
• Represent leadership in select external or cross-functional meetings.
• Serve as a trusted thought partner when leadership is working through difficult or ambiguous decisions — a sounding board, not just an executor.

Who You Are

• 7–10 years of experience in a similar role (e.g., Chief of Staff, Head of Business Operations, senior BizOps, or equivalent).
• You reason from first principles, not precedent — you don't need a playbook to figure out what to do.
• You operate with real urgency and have a bias toward action over process.
• You've worked in a startup environment and are comfortable with speed, ambiguity, and shifting priorities.
• Background in consulting, biz ops, program management, strategy, or corp dev — or founder experience.
• Experienced scaling business operations across startup, retail, or highly regulated environments.
• You build trust quickly and can be handed authority without needing constant oversight.
• You're a builder and operator at heart — you want to eventually run something, not stay in a business-operations-style role indefinitely.

You're at your best when you're:

• Making high-stakes decisions where the future depends on it and not everyone agrees.
• Simplifying the complex — whether that's ideas, systems, or communication.
• Leading a team from an idea through to completion.
• Reinventing outdated or stale systems, products, or processes.
• Operating in uncharted territory that calls for simplicity, courage, and a fresh approach.