Chief of Staff - Permanent - 19557

Toronto, ON
Hybrid
Posted Oct 23, 2026
1 position

$160,000–$180,000 / year

Opens LinkedIn

Employment type: Full-time
Experience level: Mid-level · 4+ years
Posting language: English
Working hours: 40 hours per week
Office presence: 3 days per week
Seniority: Director
Application method: Direct apply is available

Job summary

Partner with the COO to lead strategic growth and revenue initiatives, including pricing tests, new services, sales conversion improvements, and market launches. Manage the company’s operating rhythm and financial visibility through KPI scorecards, business-unit P&Ls, financial and headcount models, and board-ready reporting.

Job details

Chief of Staff - Permanent - 19557 About the Opportunity Our client, a fast-growing consumer legal services company becoming an AI-native legal technology business, is looking for a Chief of Staff with 4+ years of experience to work as the COO’s right hand. The company has grown fivefold since its pivot six months ago, and its goal is to become Canada’s largest consumer law business. You will 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. Duties include but are not limited to: 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 About You The successful candidate will have the following: 4+ years of experience, ideally including 1-2 years in investment banking or management consulting, or strategy and operations experience at a scaling tech company 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 A track record of owning projects from start to finish, with commercial instinct and a clear sense of which levers move revenue and profitability Clear writing for memos and decks, and the discretion to be trusted with confidential financial, compensation and people information About the Job Permanent, full-time position Base salary: $160,000 to $180,000 Hybrid: about 3 days per week in office in Toronto, ON How to Apply Please apply by clicking the “Apply Now” button below and follow the instructions to submit your résumé. You can also apply by submitting your résumé directly to amcdougall@lrostaffing.com. If you are already registered with us, please contact your Senior Recruiter. Please quote job 19557. LRO Staffing values fairness, confidentiality, and human judgment in every stage of our hiring process. We do not use automated or AI-driven screening tools to assess applications. Each submission is reviewed by an experienced recruiter to ensure a thoughtful and equitable evaluation of every candidate. Thank you for your interest in this role. One of our Recruiters will be in touch with you if your profile meets the requirements for the role and the expectations of our clients. Please note that all candidates must be permitted to work in Canada to be considered for this opportunity.

What you’ll do

Requirements

Candidates need 4+ years of experience, ideally including investment banking, management consulting, or strategy and operations at a scaling technology company, plus experience building and running initiatives at a tech company or high-growth startup. They should have strong analytical and financial modeling skills, commercial judgment, end-to-end project ownership, clear writing, and discretion with confidential information.