Hiring: Director, Platform Sales Company: League Location: Chicago, IL Job Posted Time: 2026-09-03 10:43:45 Employment Type: Full-time / Remote Target Skills & Keywords : AI, Digital Transformation, GCP, PaaS, Salesforce, Workday About the job Experience: •10+ years of experience in sales and sales management, with a history of successful quota attainment in a complex enterprise sales environment. Required Skills: •As a Sales Director at League, you're joining at a tipping-point moment in our growth. We've established product-market fit, and we're accelerating pipeline conversion. This is a chance to be part of an incredible growth story and drive impact in helping people live healthier, happier lives. •In This Role You Will •Own the end-to-end sales process for target enterprise Platform strategic accounts. •Generate new pipeline by capitalizing on your network, while collaborating with Marketing and the Business Development teams to execute Account-Based Marketing initiatives. •Negotiate complex partnership agreements through to completion. •Successfully achieve budgeted sales objectives and maintain an accurate, thorough sales forecast. •Ensure and monitor successful handoffs of accounts from the sales process into delivery. •Build the story and the system Qualifications: •Knowledge of the U.S. healthcare industry — payers (health plans, HCM, brokers), providers, and/or pharmacy retailers. •Demonstrated capacity to win the support of key C-suite stakeholders in large corporates. •Proficiency with Salesforce and sales acceleration tools; experience developing polished documentation for client presentations and webinars. •Bachelor's degree in Business or equivalent experience. •You're sharp and quick to learn. You understand how prospects make decisions and can explain how our solution solves their problems simply and clearly, keeping pace with League's rate of innovation. •You have real drive. You have a high motor and a reason for doing this work that goes beyond money or recognition — the kind of purpose that outlasts a string of tough days and "no"s. •You're a culture fit, not a lone wolf. You're collaborative and team-oriented rather than someone who prefers to work independently. This is a team sale: you win over the broader organization, teach others, and show up as a positive teammate. •You're ambitious with substance. Your ambition is grounded in a genuine sense of purpose, not surface-level motivators — it's what keeps you going when the deal gets hard. •You're structured, not freelance. You thrive inside a replicable, rules-based sales process rather than working around it. The U.S. healthcare market rewards sellers who bring structure and control — buyers are wary of "market breakers." •You communicate directly. You favor clear, straightforward communication, while still building genuine relationships along the way. Compensation: •$177,800 - $217,300 / year •Flexible work environment (work from home / hybrid options) •The US-specific compensation range below for this full-time position is exclusive of bonus, equity and benefits Interested candidates, please apply directly through the job posting on company's career page or try via AI auto apply on this platform. Don't miss this opportunity to join a forward-thinking team!