Director, Platform and AI Sales

Portage Ventures GP Inc.

United States

Hybrid

USD 125,000 - 143,000

Full time

14 days+

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Job summary

League is a leading Canadian healthcare AI company with a platform that powers consumer, member, and patient experiences for insurers, providers, and retailers in Canada and the US. We are expanding our Go-to-Market team and seek a Director, Platform & AI Sales to lead enterprise sales across priority segments and carry a quota for our AI-powered platform.

You will work with Solution Engineering, Partnerships, and Product Marketing to design impactful partnerships, drive digital health

Qualifications

8+ years of experience selling PaaS or SaaS solutions with digital transformation focus.
Proven experience selling AI-powered solutions.
Experience in digital health or consumer/patient engagement is a strong asset.
Deep knowledge of healthcare industry, especially public healthcare services and health plans.
Track record of quota attainment in enterprise sales environments.
Ability to build trust with C-suite stakeholders in large organizations.
Proficiency with Salesforce and sales acceleration tools.
Experience creating polished client presentations and webinars.

Responsibilities

Expand League's footprint in Canada and build on existing customer relationships.
Own end-to-end sales process for target platform accounts from strategy to closing revenue.
Build pipeline using personal network and align with BD/Marketing for ABM campaigns.
Meet and exceed sales objectives and maintain accurate forecasts.
Negotiate complex software and professional services agreements from initial contact to signature.
Pair healthcare expertise with AI capabilities to uncover business problems and solutions.
Collaborate with executives to craft narratives and tailored materials for meetings.
Help shape and improve sales processes and buyer journeys in new verticals.
Surface product needs and feedback to executives and product leadership.
Ensure smooth account handoffs from sales to customer strategy and delivery.

Skills

Enterprise sales

AI sales

C-suite engagement

Quota attainment

Education

Bachelor's degree in Business or equivalent

Tools

Salesforce

Job description

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.

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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.

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

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.

Here are some additional resources to learn more about League: