About League Founded in 2014, League is the leading healthcare consumer experience (CX) platform, powered by artificial intelligence (AI), reaching more than 63 million people around the world and delivering the highest level of personalization in the industry. Payers, providers, and consumer health partners build on League’s platform to deliver high-engagement healthcare solutions proven to improve health outcomes. League has raised over $285 million in venture capital funding to date, powering the digital experiences for some of healthcare’s most trusted brands, including Highmark Health, Manulife, Medibank, and Shoppers Drug Mart. Position Summary: League is seeking a strategic, data-driven, and highly collaborative VP, Sales Operations to enable and accelerate revenue growth through world-class go-to-market planning, operational rigor, and performance management. Reporting directly to the Chief Revenue Officer, this leader will own the design, execution, and continuous optimization of League’s sales operating model. The VP, Sales Operations will partner closely with Go-to-Market, Product, Product Marketing, Engineering, Marketing, and Finance teams, to ensure predictable growth, scalable processes, and exceptional execution across the full revenue lifecycle. As a core member of League’s Growth Leadership Team —alongside the Chief Revenue Officer, Chief Business Officer, VP Sales, VP Account Management, VP Solution Engineering, and SVP International—this role will have significant influence on League’s growth strategy and operational excellence as the company scales. This is a high-impact opportunity to shape how League grows and delivers value to customers while improving the health and well-being of millions. What you'll do: Go-To-Market Strategy & Planning Own and evolve League’s end-to-end sales operating model, including territory design, capacity planning, quota setting, and coverage strategy. Partner with GTM leadership to translate growth strategy into executable plans and operational priorities. Forecasting, Pipeline & Performance Management Establish best-in-class forecasting processes, pipeline hygiene standards, and inspection cadences to ensure accuracy and predictability. Deliver clear, actionable insights on performance trends, risks, and opportunities to executive leadership. Sales Process & Enablement Optimization Design, document, and continuously optimize sales processes across the customer lifecycle (new business, expansion, renewals, upsells and cross-sells). Partner with Sales Enablement to ensure teams have the right tools, playbooks, and insights to execute effectively. Data, Analytics & Insights Define and align with strategic company KPIs and CRO’s objectives, dashboards, and reporting across bookings, pipeline, win rates, cycle times, and productivity. Use data to identify inefficiencies, inform decisions, and drive continuous improvement. Systems & Tools Ownership Own CRM strategy (e.g., Salesforce) and sales productivity tools, ensuring strong adoption, data integrity, and scalability. Partner with IT to evaluate, implement, and optimize systems that support growth. Cross-Functional Leadership Act as a connective leader across Sales, Account Management, Finance, Marketing, Product, and Operations to align incentives, processes, and outcomes. Support pricing, packaging, and deal governance in partnership with Finance and Legal. Team Leadership Build, lead, and mentor a high-performing Sales Operations team, fostering a culture of accountability, rigor, and continuous learning. Security-Related Responsibilities Ensure access management is performed in compliance with the employee's role and responsibilities Responsibility and accountability for executing League's policies and procedures within the department/ team Notification of HR, Legal, Compliance & Security of any incidents, breaches or policy violations Compliance with Information Security Policies What you'll bring: Compensation range for USA applicants only $225,000 — $275,000 USD 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. Recognize and Avoid Employment scams. Practice safe job searching. Scammers are getting craftier and leveraging fake job postings to get personal information. Know the warning signs and protect yourself from scammers. Learn more here . 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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