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 Are7–10 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.
