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.
About League
Founded in 2014, and with a total funding currently at $220 million; League is a platform technology company powering next-generation healthcare consumer experiences. Payers, providers, consumer health partners and employers build on League’s platform to deliver high-engagement, personalized healthcare experiences consumers love. Millions of people use solutions powered by League to access, navigate and pay for care.
Position Summary:
The Solution Engineering team is a critical part of League’s growth organization, focused on applying League’s platform capabilities to power new digital consumer experiences in healthcare.
Through collaborating with League’s market development, strategic sales, customer, partner, product & implementation teams, Solution Engineering partners with the world’s leading healthcare organizations to design new digital business models, products, and experiences. League’s growth organization supports organizations across the Payer, Provider, Life Sciences, and Consumer Health markets (i.e., Pharmacy Retail).
As Principal, Solution Engineering, you serve as the technical and subject matter expert within League's Solutions Engineering team. You are responsible for demonstrating a deep mastery of the League platform, as well as specifically showcasing how we architect, integrate, and deploy LLM-powered agent teams to solve complex customer and user challenges in healthcare. Your expertise will be key in articulating how AI-powered solutions deliver a highly personalized and efficient digital health experience for consumers.
In this role:
- As Principal, Solution Engineering, you are a leader on the pre-sales team at League, partnering with Strategic Account Directors to showcase League’s platform capabilities, understand prospective customers’ business & digital requirements, visualize League’s platform capabilities, and collaborate with customers to align their needs with League’s market-leading capabilities and solutions.
- Design Digital Consumer Experiences - you will partner with prospective customers, and their business, product, digital & IT teams to design ‘what’s possible’ in redefining the role of digital experiences and AI in delivering healthcare and benefits for millions of consumers
- Align Platform Capabilities to Business Value - you will demonstrate a deep knowledge and understanding of League’s platform, technology, and AI capabilities with the ability to architect solutions and articulate how those solutions connect to the key business drivers for our prospective customers (e.g., business growth, service automation, experience transformation, high engagement care delivery, population health, etc.).
- Visualize Best-in-Class Health Experiences - bring to life League’s platform capabilities through live demos, presentations, mock-ups, and demonstrations by partnering with League’s product, design, and engineering teams. You will be able to effectively demonstrate how our AI-powered features and agent teams enhance the consumer’s health experience to deliver measurable outcomes.
- Partner for Success - you will work cross-functionally at League with our customer, implementation, product and engineering teams to turn strategy, solutions and requirements into concrete action plans to build, launch, & scale our customers’ new digital health experiences. You will also leverage your AI expertise to influence and evolve League’s go-to-market strategy.
- Growth Team Alignment - you will work with Strategic Account Directors on RFP/RFIs, partner contracts, and technical evaluations
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Security-Related Responsibilities
- Compliance with Information Security Policies
- 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
What We're Looking For:
- 7-10+ years Solutions Engineering / Pre-Sales experience
- 10-15+ years total professional experience
- Experience in leading solution architecture and software demonstrations for AI-native and/or AI enabled/integrated, healthcare IT, digital health and/or patient engagement solutions
- Direct experience with AI/ML solutions in a technical and/or pre-sales capacity.
- Direct experience in partnering with cross functional teams (Product Marketing, Delivery) to effectively bring new innovations to market across the go-to-market lifecycle (inclusive of early market testing and feedback, pricing & packaging, beta customers, etc).
- A strong understanding of AI’s place in the broader healthcare technology ecosystem, including how it integrates with healthcare data sources in a secure and real-world environment.
- Platform-as-a-Service or Software-as-a-Service experience
- Excellent storytelling and communication skills, including presenting complex solutions, concepts & ideas to executive, technical and/or non-technical audiences
- Bachelor's Degree equivalent
Nice-to-Have
- Healthcare industry experience in sales, business development and/or strategy consulting
- Master's Degree equivalent
- Product Management, Engineering, or Solution Architecture experience
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:
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 NoticeWe 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. 
