---
title: 'Chief of Staff, North America at Zen Educate'
canonical: 'https://feeny.ai/job/chief-of-staff-north-america-zen-educate-chicago-2m78x1jsnh4p'
type: 'job'
last_seen: '2026-09-11'
---

# Chief of Staff, North America at Zen Educate

- **Company:** Zen Educate
- **Location:** Chicago, IL
- **Employment:** full-time
- **Work type:** hybrid
- **Posted:** 2026-05-29
- **Last confirmed live:** 2026-09-11
- **Apply:** https://jobs.lever.co/zeneducate/55aca30f-86f5-4a7b-9bd4-7ca0b0989565

## Job description

Chief of Staff, North America Reports to: Chris Berry, Managing Director, North AmericaLocation: Los Angeles or Chicago, HybridCompensation: 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 yet 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 Interested? Let’s go. If this sounds like the right level of exciting, apply or reach out. And 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.

## About Zen Educate

## Company Overview
- **One-liner**: Zen Educate is a digital platform that connects schools directly with qualified educators, replacing traditional staffing agencies to save money and improve classroom stability.
- **Entity Type**: Private (Series B)
- **Headquarters**: London, United Kingdom
- **Founded**: 2017
- **Founders**: Not publicly available

## Core Business
- Primary industry: Education technology / education staffing
- Target customers: Schools (B2B) and educators (B2C); serves K-12 schools, academies, and trusts in the UK, US, and Canada
- Mission/purpose: "To reinvest in education through innovative technology" – the company aims to redirect funds from agency fees back into classrooms and provide stable, inspiring learning environments.

## Products & Services
- **Zen Educate Platform**: A digital marketplace that matches schools with supply/substitute teachers, teaching assistants, special education staff, early years educators, and other school support staff. The platform handles compliance checks, payroll, and scheduling. Educators sign up online, set preferences, and get matched to daily, long-term, or permanent roles. Schools benefit from faster fill rates (97% of short-term requests) and lower fees (roughly half of traditional agency fees).

## Market Standing
- **Valuation**: Not disclosed
- **Key Metric**: Total funding – Series B led by Round2 Capital (amount undisclosed); over £50 million redirected into classrooms in the UK; $15 million saved in the US since 2022 launch.
- **Notable Investors/Partners**: Round2 Capital; government-approved education staffing supplier; accredited social enterprise and certified B Corp.
- **Growth Signals**: 1,000,000+ hours of classroom instruction delivered; 5,000+ educators empowered weekly; 13,000+ educators on platform; 2,000+ schools actively booking monthly; headcount of 1,196 employees (+52.6% YoY, +740 people); launched in the US in 2022 and expanding rapidly in cities like Minneapolis, Phoenix, Los Angeles; also operating in Canada; acquisitions of Opus Education, Aquinas Education, and AK Education.

## Competitive Advantages
- Technology-driven marketplace that bypasses costly traditional agencies, cutting fees by roughly 50% – saving schools money while allowing educators to earn more.
- Certified B Corp and accredited social enterprise, reinforcing a commitment to social impact over profit.
- High fill rate (97% for short-term requests) and integrated compliance/payroll, reducing administrative burden on schools.
- UK government-approved supplier, adding credibility in the public education sector.

## Strategic Focus
- Continued geographic expansion across the UK, US, and Canada.
- Deepening platform capabilities to attract more schools and educators, with a focus on stability and quality of placements.
- Reinvesting savings into classrooms and educator support to drive systemic change in education staffing.

## Why Work Here
- **Culture**: Mission-driven, ambitious, and collaborative team that "genuinely enjoys working together." Emphasis on ownership, transparency, and impact.
- **Work policy**: Mix of remote, hybrid, and office-based roles depending on location and function (e.g., Account Coordinator roles are remote in Canada; Sales roles are hybrid in Vancouver). Offices across the UK and US.
- **Perks**: Mac laptop, stock options for all employees, yearly pay reviews, comprehensive health insurance (Vitality in UK; Medical/Dental/Vision with 75% coverage in US), life insurance, 401k (US), Cycle to Work scheme (UK), generous vacation, twice-yearly Ship-It Day, clear career frameworks with training and mentoring.
- **Engineering/development**: Dedicated learning time, career progression frameworks, and structured onboarding.

## Sources
1. [zeneducate.com/about](https://www.zeneducate.com/about)
2. [jobs.lever.co/zeneducate](https://jobs.lever.co/zeneducate)
3. [zeneducate.com/careers](https://www.zeneducate.com/careers)
4. [uk.linkedin.com/company/zen-educate](https://uk.linkedin.com/company/zen-educate)
5. [zeneducate.com/us/careers](https://www.zeneducate.com/us/careers)

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