Remote Director, FP&A

About League

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.

Position Summary:

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.

What you’ll own:

Integrated planning and forecasting

• 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.

Delivery capacity and demand

• 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.

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.
• Embed governance, human review, source transparency, and accountability into every workflow; 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; 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.

What you’ll bring:

• 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. Claude, MCP-connected tools, or Pigment AI experience is a meaningful advantage.
• Strong accounting and financial-control grounding, with the commercial judgment to turn complex analysis into a clear recommendation.

How you work:

Beyond the technical bar, this seat calls for a specific way of operating:

• 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.

What success looks like:

• One credible outlook. Leadership has a driver-based P&L view with earlier visibility into risks, opportunities, and required actions.
• Integrated delivery economics. Finance and Delivery work from a shared capacity-demand model to make staffing, sequencing, revenue, and margin decisions.
• Pigment is the operating platform. Leaders use governed models and self-service workflows instead of offline spreadsheets and manual Finance requests.
• AI produces measurable leverage. Several controlled agentic workflows are in regular use and have materially reduced recurring analysis and reporting effort.
• A stronger FP&A function. Greater commercial understanding, analytical rigor, clear communication, and independent ownership.

CANADA APPLICANTS ONLY: The Canada-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits. This range reflects the minimum and maximum target for base salaries for the position across all Canadian locations. 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. Where in the band you may land is determined by job-related skills/experience. Your recruiter can share more about the specific salary range specific to your skills and experience during the hiring process.

Compensation range for Canada applicants only

$140,000—$165,000 CAD

AI Fluency & Ways of Working

At League, we are an AI-native organization . We expect all employees regardless of role or level to thoughtfully leverage AI to improve the quality, speed, and impact of their work.

What this means in practice:

• Use AI tools as part of your daily workflow to enhance productivity, problem-solving, and decision-making (e.g., drafting, analysis, coding, research, or process automation)
• Apply judgment and accountability when using AI by reviewing outputs for accuracy, bias, and quality before use
• Continuously learn and adapt as new AI tools and capabilities emerge, incorporating them into your ways of working
• 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

How this scales by level:

• Individual Contributors: Use AI to improve personal productivity and quality of output
• Senior ICs / Managers: Integrate AI into team workflows and improve processes
• Leaders: Drive AI adoption at the organizational level and shape how work is done across teams

What we look for:

• 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

Our employees come from different backgrounds, and we celebrate those differences. We are looking for the best candidates for our open roles, but do not expect applicants to meet every qualification in order to be considered. If you are excited about what you could accomplish at League and believe you can add value to our team, we would love to hear from you.

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 View email address on us.fitly.work .

Our Application Process:

Applying to a role you love can be exhausting, and understanding the next steps can feel vague and uncertain. You have done the hard part of submitting your application; let’s do ours by sharing potential next steps

• You should receive a confirmation email after submitting your application.
• A recruiter (not a computer) reviews all applications at League.
• If we see alignment with League’s needs, a recruiter will reach out to learn more about your goals. The recruiter will also share the team-specific interview process depending on the roles you are exploring.
• The final step is an offer, which we hope you will accept!
• Prior to joining us, we conduct reference and background checks. Additional checks could be required for US Candidates, depending on the role you are exploring.

Here are some additional resources to learn more about League:

Work Location:

We have a mix of office-centric roles based in our vibrant Toronto office, and remote-eligible roles based anywhere in Canada or US. Each job posting will indicate where the role will be based. 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. We are committed to fostering a meaningful work environment and connections for all Leaguers regardless of location.

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Use of AI Notice
We are committed to ensuring fairness and transparency throughout our hiring process. League may use Artificial Intelligence (AI) tools to assist in the screening of applicants for this position. Please check out our stance on using AI in recruitment here .

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Jobicy JobID: 151586