Chief of Staff, North America

Zen Educate; Chicago (IL); Hybrid; USD 120,000 - 160,000; Full time

Job summary

Zen Educate seeks a Chief of Staff, North America, to partner with the North America leadership team and scale operations across Growth, Finance, and People. You’ll own the operating cadence, drive cross-functional projects, and turn ambiguity into actionable plans with clear owners and outcomes.

Based in Los Angeles or Chicago (hybrid), you will shape strategy, perform sharp analysis, and dive into frontline processes to accelerate growth while maintaining a strong focus on execution and

Qualifications

• Minimum 5 years of experience in strategy, operations, consulting, or similar roles.
• Proven ability to operate across function boundaries and drive outcomes.
• Demonstrated track record of delivering complex projects in fast-growing environments.

Responsibilities

• Own operating cadence and cross-functional projects with leadership.
• Turn ambiguous problems into clear plans with owners and outcomes.
• Support new market launches and scale commercial rollout.
• Build dashboards and decision-making systems for scaling.
• Partner with senior stakeholders to shape strategy and priorities.

Skills

Strategic planning

Cross-functional leadership

Analytical thinking

Communication skills

Ownership and accountability

Stakeholder management

Ambiguity tolerance

Job description

Reports to: Chris Berry, Managing Director, North America

Location: Los Angeles or Chicago, Hybrid

Compensation: USD $120,000 to $160,000 base, plus equity, depending on experience

We’re up to something big.

Zen’s mission is to fully staff classrooms, so all children can thrive and educators avoid burnout. We do this by combining a product that schools and educators love with a hard-working, education-obsessed team.

Since launching in North America, we’ve been growing 4x year over year. That kind of growth creates hard, complex, urgent problems across the business. We’re now looking for a Chief of Staff, North America to work closely with our leadership team as we scale.

This is a role for someone energized by these challenges. Someone who can move quickly, create clarity from ambiguity, and turn rapid growth into better systems, sharper decisions, and stronger execution. The right person will be able to operate at both altitude and ground level, shaping strategy, doing sharp analysis, and getting deep into frontline processes when that is what the business needs.

Why Zen

There is a staffing crisis in education. Too many teachers are leaving the profession, not enough are coming in, and school leaders are being forced to manage daily staffing gaps with limited budgets and limited visibility.

That’s why Zen exists.

We’re building 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 in education.

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, which matters to us. It reflects 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.

Why this role exists

We’re scaling fast, and 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 do not yet have a clear owner.

It is a broad remit by design. The business needs someone who can move fast across functions, bring structure to ambiguity, and make important work happen.

You’ll report to Chris Berry, Managing Director, North America, who made a similar move from consulting into startup revenue and operations. That means you’ll get close coaching from someone who understands the transition and will push you to grow quickly.

What you’ll do

No two days will be the same. You might be working on things like:

• Partnering with leadership to refine strategy and priorities
• Driving projects across Growth, Operations, Customer Success, Finance, and People
• Supporting new market launches and commercial rollout plans
• Building the operating cadence, dashboards, and decision-making systems we need to scale
• Turning ambiguous problems into clear plans, owners, and outcomes
• Jumping into urgent business problems when there is no obvious owner

The pace will be high. The work will be hands-on. The ownership will be real.

What we’re looking for

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 do not need to have been a Chief of Staff before, but you do need to have shown that you can take on hard problems, create clarity and momentum, and drive real outcomes.

Traits that usually correlate with success in this role:

• 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

No one at Zen is above the work, and that is especially true for the Chief of Staff.

This is not a role for someone who wants a narrow lane. It is a role for someone who wants to be trusted with some of the most important problems in the business and help solve them.

What you might like or dislike

We move quickly. Priorities can change. You’ll often be working with imperfect information, and the business will still need a decision.

We value ownership. 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.

Growth and progression

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. That could be in operations, strategy, commercial, general management, or something else entirely.

But this is not a fixed ladder with a guaranteed next step. The combination of business need and your ability to step into it will determine what comes next.

Compensation And Benefits

• USD $120,000 to $160,000 base, depending on experience, plus equity.
• Equity compensation
• 18 Paid Vacation Days and 10 Paid Company Holidays
• Comprehensive medical, dental, and vision insurance
• 401(k) retirement plan with no match
• Sick leave
• Paid biweekly