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About the Role

The Business Development Representative is the first point of contact between League and executives at large North American payers and health systems, prospecting into an assigned book of business. This role focuses on account research, identifying where League's value proposition aligns with organizational challenges, and deploying outreach sequences to create discovery meetings and early-stage pipeline. The role involves using League's technology stack for research and outreach across email, LinkedIn, and direct calls, and supporting marketing events and initiatives.

Responsibilities

Research accounts at the level of their actual business, including quality performance, digital and AI roadmaps, recent leadership changes, earnings commentary, public filings, and app store reviews.
Map League’s value proposition to the specific challenges facing each account to build a compelling point of view for initial conversations.
Build and deploy agentic outreach sequences using League’s technology stack via email, LinkedIn, and direct calls.
Create discovery meetings and early-stage pipeline, providing context for Account Directors' first calls.
Assist in advancing and co-developing qualification post-first meeting until the account is ready for senior Growth resources.
Support marketing events, campaigns, and initiatives, following up on generated interest.
Refine AI workflows, skills, and agents used in outreach and share effective strategies with the team.
Facilitate peer-level conversations by bringing League executives and subject matter experts into accounts.
Provide feedback to Marketing on the effectiveness of messaging.
Maintain accurate and up-to-date Salesforce records for pipeline decisions.
Learn the end-to-end enterprise sales motion, from initial contact to opportunity progression.
Comply with Information Security Policies.
Ensure access management aligns with role and responsibilities.
Take responsibility and accountability for executing League's policies and procedures within the department/team.
Notify HR, Legal, Compliance & Security of any incidents, breaches, or policy violations.

Requirements

Two to four years of outbound sales experience into large enterprises, ideally in healthcare.
Proven track record of reaching and engaging executive-level buyers.
Experience with Claude or other AI-native tools.
Strong written communication skills.
Experience with long, committee-driven enterprise sales cycles.
Experience working alongside senior sellers on account strategy.
Interest in healthcare and its transformation.
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.
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 violation.

Skills

AI tools
Salesforce
Sales engagement platforms
Artisan
LinkedIn Sales Navigator
AI workflows
AI skills
AI agents

Location

Remote-eligible (Canada or US)
Toronto, ON

Work Type

Full-time
Hybrid

Experience Level

Mid-level

Salary/Compensations

$55,000—$65,000 CAD

About the Company

League is one of Canada's fastest-growing technology companies and the leading healthcare experience platform.
League closes the gap in healthcare by identifying needs, removing obstacles, and ensuring completion of care steps for over 70 million people.
Trusted by major health plans and health systems like Manulife, SCAN, Geisinger, Medibank, Baptist, and Shoppers Drug Mart.
An AI-first company that leverages AI to improve the quality, speed, and impact of work.

Equal Opportunity

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.