League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. That gap costs health plans and health systems money, and it costs people their health. Health plans and health systems trust us to do this at scale.

Reporting to the AVP, FP&A;, you will drive the integrated planning and performance management across revenue, expenses, workforce and delivery capacity. Integrated planning and forecasting Lead rolling forecasting and scenario planning end to end: from assumptions through leadership alignment, and support the annual operating plan. Build driver-based models that link commercial activity, customer delivery, workforce capacity, and profitability; making risks and trade-offs explicit.

Run monthly and quarterly performance reviews and produce clear executive and Board narratives that drive actions for leaders. Establish capacity by role, skill, location, and time horizon, with visibility into utilization, committed work, bottlenecks, and hiring or contractor requirements. Translate contracted implementations, in-flight work, scope changes, and weighted pipeline into demand, then connect it to revenue timing, cost to serve, and gross margin.

Pigment and agentic AI as planning infrastructure Own the FP&A; functional roadmap for Pigment (architecture, integrations, controls, and adoption) with Finance Systems, Data, IT, and business stakeholders. Build role-based dashboards and AI-powered workflows (Pigment's Analyst, Modeler, and Custom Agents, plus Claude via MCP) enabling leaders to self-serve on variance analysis, forecasting, scenario modeling, anomaly detection, and hiring or vendor decisions. measure impact through forecast quality, adoption, time saved, and decision velocity. Business partnership and function building Serve as a senior Finance partner across Delivery, Go-to-Market, Product, Engineering, People, and G&A; Own revenue and expense partnership: 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 as the team grows. 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. ~ Pigment model building, administration, or implementation experience is strongly preferred. ~ 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. Beyond the technical bar, this seat calls for a specific way of operating: You are rules-anchored and control-minded: You don't experiment with the fundamentals: controls, data security, and financial judgment are never where you move rapid. Your appetite for risk shows up only where the fundamentals have already made it safe.

You don't cut corners under pressure, and you preserve financial judgment, data security, and accountability while driving AI adoption. Leadership has a driver-based P&L; view with earlier visibility into risks, opportunities, and required actions. Finance and Delivery work from a shared capacity-demand model to make staffing, sequencing, revenue, and margin decisions.

Leaders use governed models and self-service workflows instead of offline spreadsheets and manual Finance requests. Several controlled agentic workflows are in regular use and have materially reduced recurring analysis and reporting effort. Greater commercial understanding, analytical rigor, clear communication, and independent ownership.

The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits.



The salary range is intentional to account for the performance and career progressions a Leaguer will experience in the role throughout their time at League.

Compensation range for Canada applicants only $140,000 - $165,000 CAD We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work. drafting, analysis, coding, research, or process automation) Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use Identify opportunities to improve how work gets done from personal productivity to team-level workflows by leveraging AI effectively Operate with strong data responsibility and security awareness, especially when working with sensitive or regulated information Individual Contributors: Use AI to improve personal productivity and quality of output Senior ICs / Managers: Ability to balance efficiency with quality and sound judgment 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. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position.

Privacy Policy

Review our Privacy Policy for information on how League is protecting personal data. We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Regardless of the role’s posted location, all Toronto-area Leaguers (living within 65 km of our downtown HQ) collaborate in-office Monday through Thursday.

Depending on your distance to the office, you’ll enjoy 10 or 20 Flexible Remote Days each quarter for focus and deep-work time. Learn about our platform, leadership team and partners Highmark Health, Google Cloud, League: new digital front door to seamless care Former Providence President and Workday EVP of Corporate Strategy join League Board of Directors League raises $95 million USD in Series C to build world’s leading healthcare CX platform Forbes x League: The Platformization Of Healthcare Is Here Fast Company x League: If we want better innovations in healthtech, we need more competition #

📌 Director FP&A - Telecommute (Toronto)
🏢 League
📍 Toronto