Mid Enterprise - Account Executive


Chicago, IL, USA Remote

Full time

Sep 24

This job is no longer accepting applications.

As an Mid Enterprise Account Executive, you are responsible for driving sales of League’s offerings and SaaS application - including Health Savings Accounts, Wellness Accounts, Group benefits and Corporate Wellness offerings across Canada and the U.S. You will target senior decision makers (VP and C-level) at forward-thinking employers to help them build a culture of health. Your mission is to help our clients’ employees live happier, healthier lives everyday.

In this role, you will:

  • Grow and Manage a defined territory of enterprise clients (3000+ employees).
  • Be an evangelist for League products and services and enthusiastically drive new business sales.
  • Understand the competitive landscape and customer needs so you can effectively position the League solution.
  • Bring a level of hustle day-to-day with the ability to work in a fast-paced environment.
  • Leverage League’s sales methodologies and processes to drive efficient sales cycles.
  • Develop meaningful relationships with HR Professionals and executive leaders in companies across your designated market.
  • Effectively manage daily communication activities and revenue metrics.
  • Accurately forecast sales performance on an ongoing basis.
  • Actively participate in continuous learning sessions and sales coaching. 
  • Team player who is able to work in a collaborative environment and help the team to develop fresh sales strategies and proposals.

Desired Outcomes:

  • Successful achievement of ARR targets quarterly
  • Maintain accurate and up-to-date information in CRM including: customer data, pipeline numbers and revenue forecast
  • Repeatable, predictable success to allow for career development and growth 

Required Education / Certificates / Experience:

  • Bachelor’s degree
  • A minimum of 7 years of high-performance enterprise sales experience in a outbound/hunting environment
  • 5 years of selling to enterprise wide HR / HCM, Benefits, Health Technology required
  • The demonstrated ability to take a deal from cold call to close
  • Experience using Salesforce.com or another CRM
  • Leveraged tools and technology to sell strategically and efficiently
  • Experience working in a high growth technology company a plus

You are:

  • Someone who loves to win and hustles to ensure success; who thrives in a fast-paced environment, and doesn't fade under pressure
  • 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
  • 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
  • An advocate with a passion for health, wellness and driving innovation
  • Excellent communication and presentation skills, both verbal and written
  • A creative spirit and innovative mindset 

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.


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The health benefits experience platform for the world's most forward-thinking organizations.