- 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

- 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

- 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

Benefits

- Adaptable medical and dental plans

- 401(k) and RRSP matching programs

- Health, lifestyle, learning and family spending accounts

- Employee stock option program (ESOP)

- Flexible time off
- Generous leaves (including parental and sabbatical)- Enterprise SaaS, platform, or healthcare technology background, with ownership of revenue, gross margin, operating expenses, workforce planning, profitability, and executive reporting

- Strong accounting and financial-control grounding, with the commercial judgment to turn complex analysis into a clear recommendation

- 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

- 10+ years in FP&A;, strategic finance, or corporate finance, including experience leading and developing others

- Advanced financial modeling and hands-on experience with a modern planning platform. Pigment model building, administration, or implementation experience is strongly preferred

- Delivery, implementation,



professional services, or resource-capacity planning experience — specifically the link between supply, demand, utilization, revenue, and margin

- Experience helping scale a Series D or comparable high-growth company

- 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’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

- 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 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 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

- Ability to balance efficiency with quality and sound judgment

- Demonstrated experience using AI tools in a practical, responsible way

- Curiosity and openness to experimenting with new technologies- 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

📌 Director of FP&A (Toronto)
🏢 League
📍 Toronto