Principal, Value Realization

As a Principal, Value Realization, you will own the moment of truth in League's customer relationships: turning the ROI commitments made during the sale into measured, defensible proof of impact. You will drive the end-to-end post-sales value lifecycle — picking up pre-sales business cases at contract go-live, building the measurement frameworks that track delivery against committed KPIs, and producing the executive-ready ROI narratives that anchor renewals and unlock expansion.

This role sits at the intersection of business value and business development. You will work in lockstep with Account Management, Customer Delivery, Solution Engineering, and Product — translating platform outcomes into customer-validated ROI evidence that closes the loop on what was promised, defends renewals, and creates the commercial foundation for expansion.

• →Own the post-sales Value Realization workstream across League's full customer portfolio — picking up pre-sales business cases at contract go-live and driving measurement of committed outcomes through the full contract term
• →Translate pre-sales value commitments (business cases, ROI models) into post-sales measurement frameworks, defining the KPIs, leading indicators, and lagging indicators that track League's impact.
• →Lead regular value review sessions with customer executive stakeholders, co-presenting performance data with the account manager and narrating the business outcomes League has enabled.
• →Partner with account teams to identify value gaps, at-risk accounts, and expansion signals based on value attainment data.
• →Build and maintain a library of value stories, benchmarks, and proof points that can be leveraged across the sales cycle and customer lifecycle.
• →Develop scalable frameworks, templates, and playbooks that enable the broader post-sales organization to run value realization programs consistently.
• →Collaborate with Product and Solution Engineering to feed customer outcome data back into the product roadmap and solution design process.
• →Stay current on industry trends in digital health, payor, provider, benefits administration, and member engagement to contextualize League's value within the broader market.
• →Present findings and recommendations to senior internal and external stakeholders, influencing strategic decisions with data-backed insights.
• →Security-related responsibilities: 
  • →Ensure access management is performed in compliance with your role and responsibilities.
  • →Execute League's policies and procedures within your team and engagements.
  • →Notify HR, Legal, Compliance & Security of any incidents, breaches, or policy violations.
  • →Comply with Information Security Policies.

• 6+ years of experience in management consulting, customer strategy, business value consulting, or strategic account management — ideally in healthcare, health-tech, or enterprise SaaS.
• Demonstrated ability to operationalize pre-sales ROI commitments into post-sales measurement frameworks, including ROI models, KPI dashboards, and value tracking programs for complex enterprise customers.
• Strong analytical skills; comfortable working with customer data, utilization metrics, and engagement analytics to construct compelling value narratives.
• Exceptional executive communication and storytelling skills — you can distill complex data into clear, persuasive narratives for C-suite audiences.
• Experience working with large, matrixed organizations (Fortune 500 or equivalent) and navigating multiple stakeholder groups.
• Proven ability to work cross-functionally with Product, Engineering, Sales, and Customer Success teams to deliver on customer outcomes.
• Experience in digital health, employee benefits, consumer engagement, or health insurance (major payors, pharmacy retailers, or health providers) strongly preferred.
• Startup and/or growth-stage technology experience is a plus.
• Comfortable owning high-stakes engagements end-to-end, taking pre-sales commitments at contract execution and making them trackable and defensible. 

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.