Vice President of Sales

Medicare Sales Park Ridge, Illinois Opportunities available throughout U.S.


Position at Clear Spring Health

Group1001 is a consumer-centric, technology-driven family of insurance companies on a mission to deliver outstanding value and operational performance by combining financial strength and stability with deep insurance expertise and a can-do culture. Group1001’s culture emphasizes the importance of collaboration, communication, core business focus, risk management, and striving for outcomes. This goal extends to how we hire and onboard our most valuable assets – our employees.

Location can be Remote or Park Ridge, IL 

Company Overview

Clear Spring Health is part of Group One Thousand One (“Group1001”), a customer-centric insurance group whose mission is to make insurance more useful, intuitive and accessible so that everyone feels empowered to achieve financial security.  Clear Spring Health is dedicated to helping seniors protect their health and well-being by providing Medicare Advantage plans in select counties of Colorado, Illinois, North Carolina, and Virginia, plus Georgia and South Carolina.  In addition, Clear Spring Health sponsors Medicare Prescription Drug plans in 42 states.

Job Summary

The Medicare Advantage marketplace is constantly changing. This Vice President of Sales position will fully understand changing dynamics in distribution while discerning existing best practices to leverage in the growth of our Medicare Advantage health plans. This national sales leader is ultimately responsible for building the necessary strategy and capabilities to execute a successful customer acquisition plan through key growth channels (captive field sales and broker sales, focused at the local market level) across all defined geographies. The individual will work collaboratively across multiple functional areas to align resources and effort around the achievement of the plan. Success for this individual is defined as anticipating and building capabilities within established time lines and achieving plan sales goals through expanding existing partnerships and ideating new tactical distribution opportunities.

This leader will demonstrate superior capabilities in executive leadership, driving strategy development and execution, strong influencing and negotiation skills, business owner mindset and the ability to successfully lead in ambiguous and changing markets. A highly motivated sales leader must have a strong business/industry acumen within Medicare Advantage.

Main Accountabilities

  • Plays a critical role across the Enterprise in establishing national distribution strategies on behalf of the company.
  • Helps to set the vision and strategy for the company’s markets and products.
  • Achieve sales results and sales efficiency (in alignment with the overall business strategy) with input from Executive Leadership.
  • Monitors business performance and external market activity and adjusts strategy accordingly.
  • Reports out quantitatively on a weekly basis of progress to goal.
  • Supports the development and delivery of membership and financial projections and goals for the local sales channel, including field sales and local partner distribution, in partnership with business leaders.
  • Provides results-driven leadership and management to ensure sales/distribution activities and decisions are aligned to the strategy.
  • Creates an environment that leverages analytics, technology, best practices, innovation and talent.
  • Provides leadership oversight of all day-to-day channel sales activities and pertinent operations, such as lead management.
  • Provides clear decision-making on issues affecting the local markets.
  • Supports cross-functional decision-making and teaches ownership mentality to local market sales leaders.
  • Identifies retention strategies and works through the sales leadership team to execute.
  • Oversees capacity planning to appropriately scale needed number of contracted Sales Reps and Brokers in accordance with sales forecasts.
  • Supports the development of company’s sales culture which enables the segment to grow and address the transition happening in the marketplace.
  • Focuses on change management and driving new ways of thinking about our go-to-market approach, where needed.
  • Researches, analyzes and monitors industry activity, demographic trends and consumer insights to capitalize on market opportunities.
  • Builds, motivates and cultivates a high-performance team.
  • Develops direct reports and provides opportunities to stretch skills, ultimately creating clear career paths to success.
  • Fosters a success-oriented, accountable culture in the team that brings intellectual curiosity, questions “business as usual” practices and creates awareness of where a different approach/solution from traditional channel management is required.
  • Monitors the effectiveness of training/development programs for the local sales channel.
  • Will be heavily involved in the creation of “Clear Spring Health University” a full sales curriculum for Sales Reps and Broker sales partners.
  • Drives effective change leadership practices to provide the proper amount of support to our teams while leading them through the evolution of our business strategy.
  • Leverages sales integrity and compliance teams as partners to drive growth in a compliant business manner.


  • Bachelor’s degree required; advanced degree desirable.
  • 10 + years of experience in a sales environment, preferably in Government Programs Health Care Sales.
  • In-depth knowledge and understanding of Medicare Advantage and across the Medicare product spectrum. (MA, SNPs, PDP)
  • Experience in developing and delivery of sales and marketing strategies.
  • Ability to travel 50% to 75% nationally.
  • Preferred – Experience leading and scaling field sales and local partner development channels.
  • Preferred – Experience delivering distribution partner value & service excellence.
  • Preferred – Outstanding track record of business achievement.
  • Excellent written and verbal communication skills.
  • Excellent analytical & problem-solving skills.