Executive Personal Assistant

 

Who We Are

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

This is one of the most trusted seats in the company: the person who runs daily life for the CEO so he can focus on leading the company. You will own his calendar, inbox, and logistics across his business, personal, and philanthropic world, along with a share of the work for the family office and foundation behind it. The CEO moves fast and communicates in quick messages, often from his phone, and trusts the people around him to turn instruction into finished work. You will be that person: the one who makes sure he never builds his own invite, chases a loose end, or handles routine admin, and that nothing he hands off gets dropped. It is a high trust role with real proximity to how a growing company, and the people who back it actually operate, and the autonomy to build the systems that make the office run. Based in Toronto, in person, with occasional off site errands and meetings.

How you'll contribute

 

• Build automations for your own day to day work: use Claude to turn the repeatable parts of the role into reliable workflows you can set up once and reuse.
• Own the calendar: schedule, reschedule, and set up rooms and video links across MS Teams, Zoom, and Webex, with one clean invite per meeting.
• Triage the inbox: flag what needs a decision, draft first replies to edit and send, and pick up anything you are copied on until it is closed.
• Turn one line requests into finished work: a drafted email, a checklist, or a fully built calendar invite with every detail in place.
• Arrange travel, reservations, business dinners, hosted events, and leadership offsites, including agendas, venues, and catering.
• Handle personal and philanthropic admin: documents for signature, banking and benefits paperwork, donations and tribute gifts, RSVPs, thank you notes, and a clean record of commitments.
• Support the family office and foundation: schedule meetings with financial institutions and advisors, run logistics for recurring calls, and coordinate routine payments and paperwork up to the point of approval.
• Keep one shared tracker of open items, each with an owner and a next date, that the CEO and the office can check at any time.

 

Who you are

 

• You use AI as a core part of how you work, and you build with it rather than just prompt it: you create automations, workflows, and reusable templates with tools such as Claude to streamline recurring tasks, and you know when a task needs a human instead. You can show real examples during the interview process.
• 5+ years supporting a CEO, founder, or high net worth principal, across both the business and personal sides.
• Expert in Microsoft 365: calendaring, delegate access, inbox management, Teams, OneDrive and SharePoint, Word, and Excel, and comfortable setting up Zoom and Webex from Outlook.
• You write short, polished emails both in the CEO's voice and in your own.
• Disciplined about task tracking that others can check without asking, and proactive about closing loops before anyone chases you.
• Comfortable with financial paperwork and e signature tools such as DocuSign and Adobe Acrobat.
• Family office, private household or foundation experience is a strong plus.
• Calm and accurate under fast, changing instructions, warm and professional with senior external contacts and family alike, and comfortable taking direction from more than one person.
• Absolute discretion with personal, financial, and business information.
• Based in Toronto and able to work in office five days a week.

Salary Range: $90,000 to $120,000. This range reflects expected compensation at the time of posting. Final offers may vary based on skills and overall experience.

 

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.