Director, FP&A

League Inc.•Toronto, ON

2h•CA$140,000 - CA$165,000•Hybrid

About The Position

League is one of the fastest-growing technology companies in Canada and the leading healthcare experience platform. Getting healthcare is often the easy part — finishing it is where things fall apart: people book the appointment and skip the follow-up, fill the prescription and stop taking it, get the referral and never make the call. That gap costs health plans and health systems money, and it costs people their health. League closes that gap — identifying what each person needs to do next, clearing what’s in their way, and getting it done, for the 70 million+ people whose care already runs through our platform. Health plans and health systems trust us to do this at scale. Organizations like Manulife, SCAN, Geisinger, and Medibank on the payer side, and Baptist and Shoppers Drug Mart on the provider side. This is a player-coach builder role. Reporting to the AVP, FP&A, you will drive the integrated planning and performance management across revenue, expenses, workforce and delivery capacity. Your central mandate is to make Pigment and governed AI workflows the operating infrastructure for decision-making at League: faster, more reliable, and directly accessible.

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.
You get it done. Execution is your dominant gear. You create structure from incomplete information, move with pace, and close things out rather than leaving them open.
You run independently. You take messy, ambiguous problems fully off your leader's plate and operate for long stretches without needing check-ins.
You partner before you push. You build enough trust that stakeholders bring you the real numbers unprompted. You hold a firm point of view and land hard messages without turning them into confrontation.
You decide quickly, within the rules. The role carries a high volume of small calls. You make them at pace and know which ones genuinely need escalation.
You earn speed by getting the fundamentals right. 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 fast. 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.
You're steady through change. Decisions that change and scopes that expand don't knock you off course. You're driven and team-oriented, with no ego play and no need to be the one who was right.
You're comfortable in both modes. Energized by cross-functional relationships and equally heads-down.
Demonstrated experience using AI tools in a practical, responsible way
Curiosity and openness to experimenting with new technologies
Ability to balance efficiency with quality and sound judgment

Nice To Haves

Pigment model building, administration, or implementation experience is strongly preferred.
Claude, MCP-connected tools, or Pigment AI experience is a meaningful advantage.

Responsibilities

Lead rolling forecasting and scenario planning end to end: from assumptions through leadership alignment, and support the annual operating plan.
Co-own the consolidated P&L outlook with the AVP, FP&A, connecting revenue, gross margin, operating expenses, headcount, EBITDA, and the cash implications of decisions.
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.
Partner directly with the Chief Delivery Officer and Delivery Operations to build one forward-looking view of delivery supply and demand.
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.
Drive a recurring cadence that surfaces capacity gaps and margin pressure early and ends in clear staffing, sequencing, scope, or spend decisions.
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.
Embed governance, human review, source transparency, and accountability into every workflow; measure impact through forecast quality, adoption, time saved, and decision velocity.
Serve as a senior Finance partner across Delivery, Go-to-Market, Product, Engineering, People, and G&A; understanding each function's operating reality and bringing a clear financial point of view.
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. This structure is lean by design: AI-augmented workflows are intended to scale output without scaling headcount.