VP Sales

Chicago, IL
Sales – Sales
We’re looking for a Vice President (VP) of Sales to join our growing US Sales organization and meet our ambitious goals for 2019 and beyond.  

The ideal candidate is passionate about health and wellness, HR technology, and has a history of excellence in their pursuits both personally and professionally. They inspire those around them by leading by example, driving a performance-focused culture supported by repeatable and efficient processes that deliver results.

In this role, you will lead a team of 6+ account executives and a Director with a team of account executives- drive net new business, and be a part of League’s leadership team. Further, you will be a part of a company that is changing the way employers deliver true health and wellness to their employees.


    • Managing day to day activities and ongoing metrics for the sales team in your geography
    • Recruit, hire and develop a team of high performing sales reps
    • Active involvement in selling all deals in the early stages and large and complex deals as the team ramps
    • Forecasting and analyzing sales performance metrics
    • Taking personal accountability for revenue targets
    • Working with Sales Enablement to deliver coaching and ongoing sales training initiatives
    • Acquiring and maintaining a working knowledge of League, and the group benefits industry as a whole
    • Driving team success and going above and beyond to mentor highly motivated reps toward future growth roles in at League


    • 15+ years of experience in selling, within an HR/HCM SaaS environment
    • 4+ managing high performance teams
    • History of exceeding personal and team sales quotas  
    • Process minded and detail orientedPrior experience developing go-to-market strategy during a rapid growth period
    • Energetic, positive, and inspirational; knows how to get the best from others
    • Cool under pressure, entrepreneurial, and an effective mentor
    • Experienced collaborator who partners effectively with Finance and Operations


    • An advocate with a passion for health, wellness and driving innovation
    • Someone who loves to win and hustles to ensure success; who thrives in a fast-paced environment, and doesn't fade under pressure
    • A team player who understands that sales is a team sport and, in order to build something special, we need to make each other better
    • A person of high integrity; who gets things done while also doing it the right way with a customer-first attitude
    • A life-long learner who prioritizes learning and development and wants to get better everyday
    • A strategic thinker and problem-solver who can overcome challenges, on-the-fly, in a thoughtful and meaningful way
We believe that diverse teams perform better, and that fostering an inclusive work environment is a key part of growing a successful team. We welcome people of diverse backgrounds, experiences, and perspectives. We are an equal opportunity employer, and we are committed to working with applicants requesting accommodation at any stage of the hiring process.