Position Summary:

This is a build-your-craft role at the front of League's enterprise motion. You will work alongside two to three Account Directors, prospecting into their assigned book of business as the first point of contact between League and healthcare executives owning digital, member experience, AI initiatives, and innovation across North America.

Your core responsibility is conducting deep account research to map League's value proposition to real organizational challenges, then deploying agentic outreach sequences across email, LinkedIn, and direct calls to create discovery meetings and pipelines.

League is an AI-first company and this role is built that way. You will have the tools to research and sequence at a depth that used to take a team, and the support to keep improving how you use them. Your central mandate is to run League's go-to-market system with rigor, and to make it better from the inside.

What You'll Own

Account research and point of view

• Research accounts in your Account Directors' book at the level of their actual business: quality performance, digital and AI roadmaps, recent leadership changes, earnings commentary, public filings and app store reviews.
• Map League's value proposition to account-specific challenges to build points of view that drive early engagement.
• Bring League executives and subject matter experts into accounts where a peer-level conversation opens a door that a rep cannot.

Outreach and pipeline creation

• Build and deploy agentic outreach sequences on League's technology stack, across email, LinkedIn and direct calls.
• Generate discovery meetings and pipeline while providing Account Directors with high-context research for first calls.
• Support marketing events, campaigns and initiatives where League's prospects are a good fit, and follow up on the interest they generate.

The system itself

• Execute the go-to-market system with discipline while refining underlying AI workflows, skills, and agents, and share what works with the rest of the team.
• Partner with the Marketing team to analyze and iterate on market messaging.
• Keep Salesforce accurate and current, because pipeline decisions above you are made from what you record.
• Learn the enterprise sales motion end to end, from first touch through opportunity progression.

Security-related responsibilities: 

• • Ensure access management is performed in compliance with your role and responsibilities.
  • Execute League's policies and procedures within your team and engagements.
  • Notify HR, Legal, Compliance & Security of any incidents, breaches, or policy violations.
  • Comply with Information Security Policies.

What You'll Bring

• Two+  years of outbound sales experience into large enterprises (ideally healthcare). We are hiring for trajectory, not tenure.
• A genuine, organic interest in building a sales development career.
• Track record of reaching and engaging executive-level buyers.
• Fluency with Claude or other AI-native tools, and evidence you fold them into your day-to-day rather than treating them as an add-on.
• Strong written communication.
• Real curiosity about healthcare and how it is changing. You do not need to know the US healthcare system on day one; you do need to be the kind of person who goes and learns it.
• Experience with long, committee-driven enterprise sales cycles.
• Experience working alongside senior sellers on account strategy.

Helpful, not required

• Exposure to payers, health systems, benefits administrators or consumer health organizations.
• Familiarity with Star Ratings, HEDIS, care gaps, benefits navigation and digital front door.
• Experience with Salesforce, sales engagement platforms, Artisan or LinkedIn Sales Navigator.
• Experience building your own AI workflows, skills or agents.

How You Work

Beyond the functional bar, this seat calls for a specific way of operating:

• You listen as well as you talk. You are comfortable picking up the phone and going outbound, and equally able to sit back, hear what is actually being said, and take it in. Neither mode is a stretch for you.
• You keep up. You process new information fast: new market, new structure, new process; and you can hold pace with a team that moves quickly..
• You run the play. You buy into the system that has been built for you and execute it with discipline. You surface your ideas rather than quietly launching your own version of the stack.
• You grind, then you think. You genuinely enjoy the daily rhythm of the work. Within it, you connect dots and find creative angles that the process alone would not produce.
• You do the thing every day. You are consistent and process-oriented. Results here come from showing up the same way every morning.
• You are discerning with your time. You will be pulled by several Account Directors at once. You know what to say yes to, what to sequence, and what to push back on.
• You ask the hard question. You are supportive and easy to work with, and you still challenge assumptions. This team is optimistic by nature and benefits from someone willing to press constructively.
• You are self-directed. When something is unfamiliar, you go read, listen and dig until you can hold your own on it. You share your ideas and learnings with others on the team.
• You want to win. You lead yourself, you compete, and you bring the energy to keep up with the people around you.

What Success Looks Like

• Meetings that hold. You consistently create discovery meetings with the right executives, and your Account Directors walk in with context they did not have to build themselves.
• Pipeline that progresses. Opportunities you source advance past first meeting because you stayed in the account and helped shape qualification.
• The system gets sharper. Your AI workflows and sequences improve measurably over your first two quarters, and other people on the team adopt what you built.
• You know the market. Within months you can hold a credible conversation about US payer and health system dynamics with someone who does it for a living.
• You are trusted with more. You have the fundamentals of the enterprise sales motion under you and a clear path toward owning accounts.