League

• Lead the AI-native engineering transformation for Apps & Solutions • Build and scale a world-class engineering organization • Set the technical vision and engineering standards • Own executive-level customer relationships • Partner at the company-wide level • Drive cross-functional alignment at the leadership level

• Own the technical direction for member-facing applications • Drive architectural reviews and decisions • Maintain hands-on technical credibility • Own end-to-end delivery accountability for your squads • Drive delivery predictability • Build and maintain delivery metrics • Serve as a senior engineering point of contact for strategic enterprise clients • Translate complex technical realities into clear client communication • Lead engineering delivery for consumer health experiences • Partner closely with Product Management and Design • Own performance management with rigor • Lead the hiring process for your squads • Build inclusive, high-trust team culture • Build the practices that make AI-native delivery real

• Lead the AI-native engineering transformation for Apps & Solutions — drive the adoption of micro-sprint methodologies, agentic capacity management, and AI-informed delivery decisions across all engineering pods; set a target of 40%+ AI-informed delivery decisions across the portfolio and build the operating model that makes it real, not aspirational • Build and scale a world-class engineering organization — lead 50+ engineers through multiple Directors and Engineering Managers, manage through leaders of leaders, develop the EM cohort as a performance management discipline, and build the leadership bench that sustains delivery excellence through growth and change • Set the technical vision and engineering standards — define the architecture direction for Apps & Solutions aligned with League's business objectives and product roadmap; champion CI/CD, observability, cloud-native engineering on GCP, and test automation practices that drive measurable quality improvement across all squads • Own executive-level customer relationships — serve as the senior engineering sponsor for League's most strategic enterprise accounts; own escalation management, delivery confidence, and the executive relationships that determine whether clients stay, expand, or churn • Partner at the company-wide level — work alongside the CTO, CPO, and CDO to shape technology strategy, architecture decisions, and go-to-market execution for enterprise customers; own P&L accountability for engineering delivery across the Apps & Solutions portfolio • Drive cross-functional alignment at the leadership level — work closely with the CPO, CTO, and CDO to ensure engineering decisions are tightly coupled to product roadmap commitments and delivery capacity; own the relationship between engineering velocity and commercial feasibility before commitments leave the building.

• Own the technical direction for member-facing applications • Drive architectural reviews and decisions • Maintain hands-on technical credibility • Own end-to-end delivery accountability for your squads • Drive delivery predictability • Build and maintain delivery metrics • Serve as a senior engineering point of contact for strategic enterprise clients • Translate complex technical realities into clear client communication • Lead engineering delivery for consumer health experiences • Partner closely with Product Management and Design • Own performance management with rigor • Lead the hiring process for your squads • Build inclusive, high-trust team culture • Build the practices that make AI-native delivery real • Maintain strong ownership and judgment over AI-generated outputs • Stay ahead of AI tooling evolution

Design and maintain scalable test automation frameworks, integrate automated tests into CI/CD pipelines, and define end-to-end test strategies while ensuring quality throughout the development lifecycle. Mentor peers on testing best practices.

• Design and implement experiments across fine-tuning, distillation, and optimization of small language models (1–10B parameters) • Rapidly prototype and evaluate new approaches to model performance, efficiency, and reasoning quality • Leverage modern tooling and AI-assisted workflows to accelerate iteration cycles • Build applied systems that connect models, data pipelines, and evaluation frameworks • Focus on “wiring together” components across model training, evaluation, and deployment workflows • Collaborate with engineering teams to transition promising experiments into production environments • Contribute to training data design, including curation, labeling strategies, and synthetic data generation • Work with data partners to explore AI-driven insights and improvements to model performance • Define and run experiments to assess model performance across accuracy, reasoning, and safety dimensions • Contribute to building lightweight evaluation frameworks and benchmarking approaches • Actively leverage AI tools (e.g., Copilot, LLM-assisted coding, research copilots) to improve productivity and experimentation speed • Document and share workflows that improve how the team builds and evaluates models • Partner with Product, Platform Engineering, and AI Orchestration teams to integrate models into real-world use cases • Communicate complex technical concepts clearly to cross-functional stakeholders

• Lead the development of end-to-end lifecycle marketing strategies to increase activation, reduce churn, and maximize MAU across customer segments. • Build and lead a high-performing Member Growth Marketing team. Establish clear priorities, coach for performance, and foster a culture of experimentation, agility, and results. • Work hand-in-hand with the Member Behavior team to identify behavioral patterns and translate insights into actionable campaign tactics. Collaborate across product, content, engineering, and commercial teams to align strategy and execution. • Design, launch, and optimize high-velocity A/B and multivariate tests across email, push, in-app, and new engagement channels. Measure what works, scrap what doesn’t, and scale what moves the needle. • Establish robust performance metrics and dashboards to monitor campaign performance, user engagement trends, and MAU growth. Share insights and results regularly with executive and customer-facing teams. • Support Customer Solutions team with referenceable playbooks, one-pagers, and campaign frameworks that demonstrate how marketing tactics contribute to customer goals. • Ensure the tools and data infrastructure are in place to support personalized, timely, and scalable engagement campaigns. Partner with product and engineering teams on data quality and activation workflows.

• Build and lead a new function responsible for delivery infrastructure, governance, and organizational transformation across the entire Delivery organization. • Own the systems, standards, and capabilities that enable League’s delivery teams to operate with consistency, predictability, and quality at scale. • Define, implement, and continuously refine the Standard Delivery Playbook covering the end-to-end delivery lifecycle from discovery through deployment and post-implementation optimization. • Establish scalable intake, planning, estimation, and release governance processes. • Drive consistency in Agile practices, sprint hygiene, dependency management, and release readiness across all delivery teams. • Own onboarding and continuous training programs for all delivery staff including engineers, project managers, product managers, designers, and QA testers. • Own the standard Jira process: define the desired workflow, then configure the tool to match delivery needs. Drive 100% adoption. • Conduct project margin analysis and drive optimization initiatives toward the 25% target. • Own the strategic transformation program to move the delivery organization from current state to target operating model.

• Design and build production-grade AI systems • Make principled architecture choices regarding RAG and fine-tuning • Build comprehensive evaluation and observability frameworks • Create production-quality Python services • Manage the economics of LLM usage • Partner with Product and Data Science teams • Mentor junior engineers on AI craft • Establish standards for performance and data governance

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. Privacy Policy Review our Privacy Policy for information on how League is protecting personal data.