About this role.
League is hiring a senior, quota-carrying Director of Platform & AI Sales to grow enterprise healthcare platform sales in Canada. The role owns the full sales cycle, from account strategy and self-sourced pipeline through complex negotiation, close, and account handoff. Candidates need at least eight years of SaaS or PaaS sales experience, demonstrated AI solution sales, enterprise quota attainment, and strong knowledge of Canadian public healthcare and provincial or territorial health plans. The position partners closely with solution engineering, partnerships, product marketing, and executives to design high-value digital health partnerships. It offers a Canada-only base salary range of CAD 175,000–200,000, plus undisclosed bonus, equity, and benefits.
Role DNA
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Job Complexity
5/5Pace & Pressure
5/5Autonomy Level
5/5Communication Load
5/5Salary analysis
Estimated compensation compared with the broader CA market for similar roles.
Core skills
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Cover letter sample
Dear Hiring Team,
I am excited to apply for the Director, Platform & AI Sales role at League. My enterprise SaaS sales experience, healthcare-market knowledge, and ability to build trusted executive relationships align well with League's mission to improve consumer, member, and patient healthcare experiences.
I bring a consultative approach to developing pipeline, shaping complex platform partnerships, and navigating software and services negotiations through close. I would welcome the opportunity to help expand League's Canadian footprint while using AI responsibly to improve sales execution and customer outcomes.
Thank you for your consideration. I look forward to discussing how I can contribute to League's next phase of growth.
Sample interview questions
I would begin by mapping the account's strategic priorities, digital maturity, procurement structure, and key clinical, operational, and executive stakeholders. I would then use discovery to quantify engagement or care-navigation gaps, build a value narrative tied to measurable outcomes, and create a mutual action plan that aligns technical validation, commercial terms, and executive sponsorship.
I would lead with the business problem rather than the technology, such as improving patient follow-through, member engagement, or operational efficiency. I would connect League's AI capabilities to specific workflows and outcomes, validate feasibility with solution engineering, and ensure claims are responsible, secure, and appropriate for regulated healthcare settings.
I maintain a disciplined account plan with clear qualification criteria, next steps, stakeholder maps, and forecast categories in Salesforce. I review pipeline quality regularly, identify risks early, and use conversion data to focus my time on opportunities with a compelling business case, executive access, and an achievable path to close.
I establish alignment early across legal, procurement, security, technical, and executive stakeholders, including a shared timeline and decision process. When issues arise, I clarify the underlying concern, involve the right internal experts, preserve commercial momentum, and seek practical solutions that protect both the customer relationship and company objectives.
I use AI tools to accelerate account research, meeting preparation, follow-up drafting, and analysis while retaining accountability for final outputs. I verify accuracy, avoid entering sensitive customer information into unapproved tools, and apply human judgment to ensure communications are precise, secure, and relevant.
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
League is a leading Canadian healthcare AI company building the digital health experiences that make it easy for people to access, understand, and act on their health. Our platform powers personalized consumer, member, and patient experiences for some of the world’s leading health insurers, providers, and pharmacy retailers, with a footprint that’s scaling quickly across our core healthcare payor market and our fast-growing provider market in Canada and the US.
As we continue to expand our team in Canada, our Go-to-Market team is growing to power this next phase of growth — and we’re looking for a Director, Platform & AI Sales to help lead the way.
As a Director, Platform & AI Sales, you’ll be a core part of the Go-to-Market team, working across priority segments including public sector payors and providers, private insurers, retail healthcare, and digital health innovators. You’ll lead complex, enterprise-scale business development and sales initiatives, and carry a quota for League’s AI-powered consumer experience platform.
Working closely with other Go-to-Market functions — including Solution Engineering, Partnerships, and Product Marketing — you’ll strategize, scope, and design impactful customer partnerships that power the digital transformation of the consumer, member, or patient experience.
In This Role, You Will:
- Expand League’s footprint in Canada, building on the strength of existing customer relationships.
- Own the end-to-end sales process for target platform accounts — from sales strategy and pipeline development to closing revenue and growing customer relationships.
- Build pipeline using your own network, and partner with the Business Development and Marketing teams on account-based marketing campaigns that convert into closed revenue and quota attainment.
- Meet and exceed sales objectives, and maintain accurate, up-to-date sales forecasts.
- Negotiate complex software and professional services agreements from initial conversation through signature.
- Create demand by pairing healthcare industry expertise with an understanding of C-level priorities — uncovering business problems and matching them to League’s solutions, including our AI capabilities.
- Partner with League executives and Go-to-Market leaders to build compelling narratives and tailored materials for meetings with prospective accounts.
- Help shape and improve sales processes and buyer journeys, especially in new industry verticals.
- Surface product needs and feedback from Powered by League prospects and industry verticals to executive and product leadership.
- Ensure smooth account handoffs from the sales process into customer strategy and delivery.
About You:
- 8+ years of experience selling PaaS or SaaS solutions, with a focus on digital transformation and/or consumer and patient engagement
- Proven experience selling AI-powered solutions
- Experience in a consulting role focused on digital health or consumer experience is a strong asset
- Deep knowledge of the healthcare industry, particularly public healthcare services and provincial/territorial health plans
- A track record of consistent quota attainment in complex, enterprise sales environments
- Ability to build trust and win support from C-suite stakeholders at large organizations
- Proficiency with Salesforce and sales acceleration/enablement tools
- Experience creating polished documentation for client presentations and webinars
- Bachelor’s degree in Business or equivalent experience
CANADA APPLICANTS ONLY: The Canada-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 Canadian 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 Canada applicants only
$175,000—$200,000 CAD
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
Review our Privacy Policy for information on how League is protecting personal data.
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