Chief of Staff (Toronto, CAN)
- Compensation
- CA$160K–CA$180K (OTE: CA$200K–CA$250K)
- Work mode
- Hybrid/On-site
- Location
- Toronto, ON, Canada
- Industry
- Financial Technology
Your market value for this role
Compared with 5 live mandates (same function and level).
Base salary only; excludes equity and bonus. Benchmark your own package →
The mandate
We are looking for a Chief of Staff with 4+ years of experience to work as the COO's right hand as the organization becomes an AI-native legal technology company. The company has grown fivefold since its pivot six months ago, and its goal is to become Canada's largest consumer law business. You should be a strategic, highly analytical builder, ideally with an investment banking or consulting background followed by time at a high-growth startup. You'll own growth and revenue initiatives from start to finish, and the role is a clear path to a General Manager seat with full P&L ownership.
Key responsibilities
- Lead strategic, growth-focused projects with the COO from start to finish, such as pricing tests, add-ons and new service lines beyond immigration
- Work with the Head of Sales to design and measure tests, track the right KPIs and find and fix the biggest conversion leaks
- Run the company's operating rhythm: weekly scorecards and KPIs for every function, a goals dashboard every Monday, and an owner and fix for every off-track goal
- Own financial visibility: a monthly P&L for each business unit, financial and headcount models, and board-ready KPI packs
- Size markets, map competitors and pricing, then launch and measure the growth initiatives that come out of it
- Background in investment banking or management consulting (ideally 1-2 years), or strategy and ops experience at a scaling tech company like Clio
- At least one role at a tech company or high-growth startup where you built and ran things yourself (founder experience is a strong plus)
- Strong analytical skills: you can build financial models, run tests and judge statistical significance, and turn messy data into clear recommendations
- You've owned projects from start to finish, have commercial instinct and know which levers move revenue and profitability
- You write clear memos and decks and can be trusted with confidential financial, compensation and people information
What you bring
- Background in investment banking or management consulting (ideally 1-2 years), or strategy and ops experience at a scaling tech company like Clio
- At least one role at a tech company or high-growth startup where you built and ran things yourself (founder experience is a strong plus)
- Strong analytical skills: you can build financial models, run tests and judge statistical significance, and turn messy data into clear recommendations
- You've owned projects from start to finish, have commercial instinct and know which levers move revenue and profitability
- You write clear memos and decks and can be trusted with confidential financial, compensation and people information
Location & engagement details
Toronto, ON, Canada · Hybrid
Base salary: C$160,000 – C$180,000, depending on experience. Bonus: A performance bonus tied to revenue growth and profitability goals, set for each project. Target total pay (OTE) is C$200,000 – C$250,000. Also includes flexible vacation and competitive health, dental and wellness coverage.; Visa sponsorship details: Not open to any visas (e.g. US the organization, Green Card holders); Hybrid work policy: About 3 days in-office in Toronto, ON (new office move underway)
About this mandate
This is a live c-suite search with direct introductions to the hiring team. The role sits in financial technology and is located in Toronto, ON, Canada on a hybrid/on-site basis, with compensation of CA$160K–CA$180K (OTE: CA$200K–CA$250K).
This is a confidential search. Read the brief above, then apply below for this role. The company name is shared once there's a close match and mutual interest.
Most senior mandates are filled this way — privately, before any listing exists. Read how unadvertised executive roles actually get filled.
- This is a confidential search. The company name and full role details are only discussed on a call with one of our recruiters if there is a close match.
- We use your details — your LinkedIn profile URL and email address — to match you against this mandate and any other closely matched roles.
- A verifiable email address, LinkedIn profile and a recent PDF resume are required. Submissions from bots, spammers or unverifiable profiles are removed.
- There is no call booking at this stage. Calls are scheduled only after we identify a close match.
Who can apply
- C-suite, EVP/SVP, VP and Head of function leaders
- Proven scale-up, venture-backed or enterprise leadership experience
- Track record of building and leading teams in the relevant function
Final hiring decisions rest solely with the hiring company. Outcomes depend on role availability and decisions made by the hiring team.
Apply — Chief of Staff (Toronto, CAN)
This application is for this role only. It is reviewed against the brief above, and you will be contacted if there is a close match.
- This is a confidential search. The company name and full role details are only discussed on a call with one of our recruiters if there is a close match.
- We use your details — your LinkedIn profile URL and email address — to match you against this mandate and any other closely matched roles.
- Handled confidentially — your details are never shared without your consent.
- A referral is an introduction, not a guarantee of an interview or an offer.
- Final hiring decisions rest with the hiring company; outcomes depend on role availability and their decisions.