Chief of Staff, North America

Chief of Staff, North America

Reports to:

Chris Berry, Managing Director, North America

Location:

Vancouver, Canada, Hybrid

Compensation: CAD $120,000 to $180,000 base, plus equity, depending on experience

Zen’s mission is to fully staff classrooms so all children can thrive and educators avoid burnout. We combine a product that schools love with a team that is hard‑working and education‑obsessed. Since launching in North America, we’ve been growing 4× year over year, creating complex problems across the business. We are looking for a Chief of Staff, North America to work closely with our leadership team as we scale.

There is a staffing crisis in education. Teachers are leaving, fewer are coming in, and school leaders must manage daily staffing gaps with limited budgets and visibility. Zen builds a better way for schools to find, vet, and manage temporary educators. Our platform gives school leaders more control, more transparency, and better access to great educators, while helping reduce wasted spend.

Zen is now a 500+ person team operating across the UK, US, and Canada. We’re venture‑backed, well funded, and building toward a national rollout across North America. We’re also a certified B Corporation, reflecting the company we are trying to build: one that grows quickly, performs exceptionally, and stays deeply accountable to schools, educators, children, and the communities we serve. We’re trying to do really well by doing good.

As we scale fast, the work is outrunning the org chart. You’ll work directly with the North American leadership team, owning the operating cadence, driving key cross‑functional projects, and jumping on problems that have no clear owner. You’ll report to Chris Berry, who made a similar move from consulting into startup revenue and operations, and will receive close coaching to grow quickly.

• Partner with leadership to refine strategy and priorities
• Drive projects across Growth, Operations, Customer Success, Finance, and People
• Support new market launches and commercial rollout plans
• Build the operating cadence, dashboards, and decision‑making systems needed to scale
• Turn ambiguous problems into clear plans, owners, and outcomes
• Jump into urgent business problems when there is no obvious owner

The pace will be high, the work will be hands‑on, and ownership will be real.

We’re looking for someone with a demonstrated record of exceptional performance. This is likely a fit for someone with 5 to 10 years of experience, including time in consulting, investing, high‑growth startups, strategy, operations, revenue, marketplaces, or another demanding generalist environment. We care less about the exact path you have taken than your slope, judgment, and evidence that you have operated well in demanding environments.

You need to have shown that you can take on hard problems, create clarity and momentum, and drive real outcomes, even if you have not held the title of Chief of Staff before.

• Relentless drive to deliver outcomes
• Endless curiosity
• Strong analytical judgment
• Clear, logical, compelling communication
• High ownership
• Low ego
• Comfort with ambiguity
• Ability to influence senior stakeholders
• Excitement to move between strategy and hands‑on execution
• Genuine care for the mission, not just the title

We move quickly. Priorities can change, and you’ll often work with imperfect information while the business still needs decisions. You’ll be expected to notice what is broken, figure out what matters, bring people with you, and get things done. For the right person, this will be fast, fun, and career‑accelerating. For the wrong person, it will feel too ambiguous, too broad, and too intense.

Choose your own adventure, then earn it. You’ll work across the organization and be well positioned to move into a senior role over time—operations, strategy, commercial, general management, or something else entirely. This is not a fixed ladder, but the combination of business need and your ability to step into it will determine what comes next.

CAD $120,000 to $180,000 base, depending on experience, plus equity. We reward people who take on more and deliver more.

If this sounds like the right level of exciting, apply or reach out. If you’re not sure you tick every box, but this sounds like the kind of work you’re built for, reach out anyway. Let’s build something that actually matters.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.