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:

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.

What you'll be doing:

• 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.

What we're looking for:

• 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.

US APPLICANTS ONLY: The US-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 US 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 USA applicants only

$170,000—$200,000 USD

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 recruitinginfo@league.com.

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:

• 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

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.

Privacy Policy

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