Accounting / Finance / Education / Software

Chief of Staff Full-time

At KEV, we help school districts eliminate the school finance blind spot. Our platform gives district finance teams real-time visibility and traceability into every dollar collected at the school level – whether it’s cash, cheque, or digital. From field trips to fundraisers, we help them manage every dollar with confidence. More than 27,000 schools across North America trust KEV to manage over $8 billion annually. By unifying payments, accounting, and reporting, KEV simplifies life for bookkeepers, builds trust with parents, and gives finance leaders the oversight their current systems cannot. It’s how we help schools stay compliant, reduce risk, and focus on what matters most, student success.

Backed by Five Arrows, the PE arm of Rothschild & Co., KEV is investing more than ever to support K-12 in a world of tighter budgets, rising scrutiny, and fast-changing tech. We’re headquartered in Toronto, with offices across North America.

If you’re excited by the idea of building tech that protects schools, empowers finance teams, and improves education through better systems, KEV is the place for you.

This role is for an active vacancy.

About the role

KEV Group is a $100M SaaS and payments company serving schools and districts, on a path to $300M through organic growth and acquisitions. We’re looking for a Chief of Staff to the CEO to make sure the executive team works on the right things and gets them done.

You’ll report to our CEO, Bram Belzberg. You’ll own the company’s rhythm of decisions: executive alignment, OKRs and the leadership operating cadence. Our CFO owns the rhythm of numbers: plan, budget and forecast. Together, you’ll run one operating system.

This is a senior operating role, not an executive assistant or project coordinator role. You’ll have no large team, but you will have the CEO’s mandate to set the leadership agenda, track commitments to closure and escalate when they slip.

What you’ll own

Executive alignment and OKRs

  • Turn the CEO’s priorities into company OKRs, with clear owners, measures and links to our strategic pillars.
  • Track OKRs and cross-functional dependencies; bring status to the monthly business review.
  • Lead the quarterly OKR reset, working with the CFO so that OKRs and the budget are agreed together.

Leadership operating cadence

  • Run the weekly CEO staff meeting: agenda, pre-reads, decisions and the action log.
  • Own the quarterly executive offsite and the annual strategy and three-year planning cycle.
  • Keep one integrated leadership calendar, including the CFO’s financial cycle, the CCO’s GTM–R&D operating reviews and the CHRO’s talent and performance cycles.
  • Close actions on time, and escalate to the CEO when commitments slip.

Board and governance

  • Assemble the quarterly board pack and keep it on schedule. The CFO team owns the financials; Legal owns statutory governance.
  • Track board and executive actions to closure; improve how decisions are made and recorded.

Strategic projects

  • Lead two or three CEO-sponsored initiatives at a time, such as pricing, entering an adjacent market or redesigning the customer journey.
  • Define scope, owners and milestones, then hand finished work to a line leader.

M&A coordination

  • Run the weekly M&A pipeline review with the CEO, Corporate Development, Finance, Legal and R&D.
  • Keep the deal decision log and board approval timeline; coordinate integration handoffs.

CEO communications and leverage

  • Draft CEO communications to the company and the leadership team, with the CHRO.
  • Act as the CEO’s thought partner: prepare decisions, pressure-test plans and protect the CEO’s time.
  • Lead a small Business Operations team, including OKR and cadence support.

What you won’t own

Keeping these boundaries clear lets you lead without becoming a bottleneck.

  • The rhythm of numbers. The budget, forecast, variance reporting and the monthly business review against plan stay with the CFO.
  • Money levers. Budget approvals, headcount releases, pricing floors and contract approvals stay with the CFO.
  • Line teams. You won’t manage functional teams. Projects you lead move to a line owner once they’re up and running.
  • Access to the CEO. Executives keep direct access to Bram. Your job is to make their time with him count, not to screen it.

How success is measured

First 30-90 days: learn the business and the leadership team. Take over the weekly CEO staff meeting and action log. Map the current OKRs and cadence, and propose an integrated 2027 leadership calendar.

First 6 months: run the Q1 OKR reset and one board cycle end to end. Lead at least one CEO-sponsored project to a clear decision.

First 12 months: the leadership team runs on one predictable rhythm. Executives say decisions are faster and clearer.

Who You Are

  • 8–12 years of experience, including at least 3 years in an operating role: Chief of Staff, Strategy & Operations or Business Operations.
  • Experience at a B2B SaaS, fintech or payments company with roughly $50M to $500M in revenue, ideally while it was scaling quickly.
  • A record of designing or running an OKR system and leadership operating cadence across a C-suite.
  • A foundation in strategy consulting, investment banking or corporate development is a strong plus.
  • Exposure to board work and M&A: diligence, deal processes or post-merger integration

Capabilities

  • Influence without authority. You move senior leaders through credibility, preparation and follow-through.
  • Clear thinking and writing. You can turn a messy problem into a two-page decision memo.
  • Commercial and financial fluency. You read a P&L, understand SaaS and payments metrics, and build a simple model.
  • Operating rigor. You set up systems that keep running when you’re not in the room.
  • Discretion and judgment. You handle board, M&A and people matters with care.
  • Low ego, high ownership. You’re comfortable making others successful and handing work off.

Nice to have: experience in education technology or the public sector; bilingual English and French; an MBA or equivalent.

What We Offer

  • Competitive compensation – We believe in rewarding great work with fair, competitive pay.
  • Meaningful benefits– Because your well-being matters; both at work and at home.
  • Retirement Savings Support – We help you plan for your future with company-matched programs, including RRSP matching in Canada and 401(k) contributions in the U.S.
  • Hybrid model – 3 days in the office to collaborate and connect, with flexibility the rest of the week.
  • Flexible PTO – Take the time you need to recharge with close to 4 weeks of vacation and a company-wide holiday closure
  • Office perks – Enjoy a fully stocked snack bar and occasional catered lunches—because we know that great conversations (and ideas) often start around good food.

Why You’ll Love Working at KEV

  • Make a real difference every day – At KEV, your work supports children, parents, and schools across North America. We don’t just build software, we create solutions that simplify lives and strengthen communities. Our mission is rooted in impact, and every team member plays a vital role in shaping the future of K-12 education.
  • The KEV Way – At KEV, you’ll never feel stuck in the status quo. You’ll be part of a team that’s constantly questioning, improving, and innovating—always with one guiding focus: How does this help our schools and the students they serve? It’s a culture that challenges you to do your best work while reminding you why it matters.
  • Grow with us – We’re scaling fast, and so are our people. At KEV, you’ll have real opportunities to learn, develop, and shape your career. Whether advancing in your role or exploring a new path, you’ll be supported every step of the way.
  • Work alongside excellence – You’ll be part of a team with integrity who treat their colleagues with respect. who are accomplished but humble, collaborative but accountable. It’s a place where you can do your best work while feeling supported and inspired by the people around you.
  • Celebrate Community and Culture – At KEV, we connect, recognize, and celebrate our people. Join Club KEV for team-building fun, hear directly from customers in our Voice of Customer Series, stay aligned with Monthly Townhalls, and be inspired by the KEVite Awards, where top contributors are recognized by their peers.

This job description indicates the general nature and level of work expected. It is not designed to cover or contain a comprehensive listing of activities, duties, or responsibilities required by an individual joining the KEV team in this or any other capacity.

KEV Group is pleased to accommodate individual needs in accordance with the Accessibility of Ontarians with Disabilities Act, 2005 (AODA), within our recruitment process. If you require accommodation at any time throughout the recruitment process, please speak with your recruiter.

KEV Group is an equal opportunity employer who agrees not to discriminate against any employee or job applicant because of race, color, religion, national origin, sex, physical or mental disability, or age.

KEV may use AI-enabled tools to support components of our recruitment process. These tools are used to support human decision making. All hiring decisions are made by our People and Culture team in partnership with Hiring Managers.

Visit our website for more information and details about working at KEV.

Job Overview