Head of Operations, Service Delivery

Success Matcher Recruitment; Toronto; Hybrid; CAD 250,000 - 320,000; Full time

Job summary

Success Matcher Recruitment in Toronto is seeking a Head of Operations to own end-to-end delivery across five practice areas and coach a growing leadership team. You will shape the operating playbook, define KPIs, and drive AI adoption with senior leaders to scale execution and efficiency.

You will turn forecasts into capacity and hiring plans while managing costs and margins, partnering with finance and CPO/CTO to push measurable AI-enabled improvements.

Qualifications

• 5–12 years in operations leadership.
• Experience leading 20–50+ people including managers.
• Proven record of process redesign with productivity gains.
• Hands-on budgeting, capacity planning, and unit economics.
• Experience driving AI or automation with clear business outcomes.
• Commercial, decisive mindset with readiness to roll up sleeves.
• Authorized to work in Canada; able to work hybrid in Toronto.

Responsibilities

• Own end-to-end delivery across five practice areas.
• Coach Practice Leads and Managing Attorneys with structured cadences.
• Define KPIs, dashboards, and rhythms using internal tools.
• Manage delivery cost, productivity, and contribution margin.
• Collaborate with CPO/CTO on AI adoption roadmap.
• Turn sales forecasts into capacity and hiring plans.
• Shadow case managers to understand process bottlenecks.

Skills

Operations leadership

People management

Process redesign

Budgeting & capacity planning

AI/automation adoption

Commercial mindset

Hybrid work collaboration

Job description

Our client is a profitable, long-established legal services business that has reinvented itself as an AI-native legal tech company. Since the pivot, it has grown 5x in six months, reaches millions of people every month through its platform and online community, and is scaling from ~60 to 100+ people. Its ambition is to become Canada's largest consumer law business, expanding into new practice areas.

What You'll Do

• Own end-to-end delivery: Take full accountability for case throughput, turnaround times, backlog, capacity utilization and service levels across five practice areas.
• Lead the leaders: Coach Practice Leads and Managing Attorneys through structured management cadences, operating reviews and scorecards that drive accountability.
• Build the operating playbook: Define the KPIs, dashboards and rhythms the business runs on, using an internal command-centre dashboard and AI-native case management tools.
• Drive the economics: Own delivery cost, productivity and contribution margin, and partner with Finance on budgets and forecasts.
• Modernize with AI: Work alongside the CPO and CTO to design and execute a roadmap for automation and AI adoption across delivery.
• Plan for growth: Turn sales forecasts into capacity and hiring plans, giving the COO clear, data-driven visibility into what's coming.
• Stay close to the work: Shadow case managers and get hands-on with files when needed to understand where the process really breaks.

Why Join

• Growth with a safety net: Join a company in hypergrowth that's also profitable and built on nearly 50 years of legal expertise. You get scale-up energy without startup fragility.
• Real ownership: This is a Head of role with a blank canvas. You'll write the playbook, not inherit someone else's.
• Direct line to the top: Report to the COO and work closely with the CPO and CTO, alongside colleagues from leading Canadian fintech and legal-tech scale-ups.
• Cutting-edge tools: Lead operations in a business where AI and automation are core to how work gets done, not an afterthought.
• Meaningful impact: Your work directly shapes how quickly and reliably everyday Canadians get legal help.
• Strong rewards: Competitive base plus meaningful variable upside, with OTE up to CA$300K.

What You'll Bring

• 5-12 years in operations leadership, including 3+ years leading high-volume service delivery
• Experience leading 20-50+ people, including managers who run their own teams
• A proven record of process redesign with measurable gains in productivity, quality and cost
• Hands-on ownership of budgets, capacity planning and unit economics
• Experience driving AI or automation adoption with clear business outcomes
• A decisive, commercially minded approach and a willingness to roll up your sleeves
• Authorization to work in Canada and the ability to work hybrid in Toronto