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About the Role

This is a player-coach builder role reporting to the AVP, FP&A. You will drive integrated planning and performance management across revenue, expenses, workforce, and delivery capacity, making Pigment and governed AI workflows the operating infrastructure for decision-making at League.

Responsibilities

• Drive integrated planning and forecasting, including rolling forecasting and scenario planning.
• Co-own the consolidated P&L outlook, connecting revenue, gross margin, operating expenses, headcount, EBITDA, and cash implications.
• Build driver-based models linking commercial activity, customer delivery, workforce capacity, and profitability.
• Run monthly and quarterly performance reviews and produce executive and Board narratives.
• Partner with the Chief Delivery Officer and Delivery Operations to build a forward-looking view of delivery supply and demand.
• Establish capacity by role, skill, location, and time horizon, with visibility into utilization, bottlenecks, and hiring requirements.
• Translate contracted implementations, in-flight work, scope changes, and weighted pipeline into demand, connecting it to revenue timing, cost to serve, and gross margin.
• Drive a recurring cadence to surface capacity gaps and margin pressure early, leading to clear staffing, sequencing, scope, or spend decisions.
• Own the FP&A functional roadmap for Pigment, including architecture, integrations, controls, and adoption.
• Build role-based dashboards and AI-powered workflows enabling self-service on variance analysis, forecasting, scenario modeling, anomaly detection, and hiring or vendor decisions.
• Embed governance, human review, source transparency, and accountability into every workflow.
• Serve as a senior Finance partner across Delivery, Go-to-Market, Product, Engineering, People, and G&A.
• Own revenue and expense partnership, including headcount, backfills, organizational changes, vendor commitments, and investment cases.
• Build the FP&A function and set the standard for models, forecasts, executive materials, and communication.

Requirements

• 10+ years in FP&A, strategic finance, or corporate finance, including experience leading and developing others.
• Experience helping scale a Series D or comparable high-growth company.
• Enterprise SaaS, platform, or healthcare technology background, with ownership of revenue, gross margin, operating expenses, workforce planning, profitability, and executive reporting.
• Delivery, implementation, professional services, or resource-capacity planning experience, specifically the link between supply, demand, utilization, revenue, and margin.
• Advanced financial modeling and hands-on experience with a modern planning platform.
• Demonstrated deployment of AI, automation, or agentic workflows in Finance or business operations.
• Strong accounting and financial-control grounding, with the commercial judgment to turn complex analysis into a clear recommendation.
• Execution is your dominant gear; create structure from incomplete information, move with pace, and close things out.
• Operate independently, taking messy, ambiguous problems off your leader's plate.
• Partner effectively with stakeholders to build trust and gain access to accurate information.
• Make decisions quickly and appropriately, knowing when to escalate.
• Anchor on fundamentals like controls, data security, and financial judgment.
• Remain steady through change, with a driven and team-oriented approach.
• Comfortable with cross-functional relationships and heads-down work.

Skills

• Pigment model building, administration, or implementation experience is strongly preferred.
• Claude, MCP-connected tools, or Pigment AI experience is a meaningful advantage.
• AI Fluency: Thoughtfully leverage AI to improve work quality, speed, and impact.
• Apply judgment and accountability when using AI.
• Continuously learn and adapt to new AI tools and capabilities.
• Identify opportunities to improve work processes using AI.
• Operate with strong data responsibility and security awareness.

Location

• Canada
• US

Work Type

• Full-time
• Office-centric (Toronto)
• Remote-eligible (Canada or US)
• Hybrid (Toronto-area employees collaborate in-office Monday-Thursday, with 10 or 20 Flexible Remote Days each quarter)

Experience Level

• Senior

Salary/Compensations

• $140,000—$165,000 CAD

About the Company

• League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform.
• We close the gap in healthcare by identifying what each person needs to do next, clearing what’s in their way, and getting it done.
• Health plans and health systems trust us to do this at scale for over 70 million people.
• We are an AI-native organization.
• We celebrate differences and are looking for the best candidates, not expecting applicants to meet every qualification.

Equal Opportunity

• We are committed to equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or Veteran status.
• If you are an individual in need of assistance at any time during our recruitment process, please contact us at recruitinginfo@league.com.