Senior Mid-Market Sales Executive

Jobgether

3d • Remote

About The Position

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Senior Mid-Market Sales Executive in the United States.
This role offers a dynamic opportunity to drive growth in the mid-market segment by selling innovative digital solutions that support employee well-being. You will be responsible for cultivating strategic relationships with HR leaders, benefits managers, and executive stakeholders, while guiding complex sales cycles from prospecting to closing. The position requires a consultative, solution-oriented approach to align offerings with organizational needs, backed by strong market insight and competitive awareness. You will collaborate closely with cross-functional teams, contributing to sales strategy, pipeline development, and market expansion initiatives. With up to 25% travel, this role combines autonomy, strategic influence, and hands-on execution in a high-impact environment. Successful candidates will thrive in a fast-paced, results-driven, and mission-oriented culture.

Requirements

• 5+ years of experience in B2B healthcare or digital health sales with a proven track record of selling PEPM-based solutions to employer groups.
• 3+ years of mid-market sales experience with quota-carrying responsibilities.
• Strong understanding of employee benefits programs, self-funded healthcare, and related strategies.
• Exceptional communication, negotiation, and relationship-building skills with executive stakeholders.
• Ability to analyze data, market trends, and sales metrics to inform strategy and optimize outcomes.
• Results-driven, adaptable, and capable of revising strategies in response to evolving market dynamics.
• Experience leveraging digital tools and CRM systems to manage pipelines and sales processes effectively.

Responsibilities

• Develop and execute a robust sales strategy targeting mid-market employer groups to expand digital health solution adoption.
• Build and maintain trusted relationships with key decision-makers, including HR leaders, benefits managers, and executives.
• Utilize a consultative sales approach to assess client needs, present tailored solutions, and demonstrate the value of offerings.
• Conduct market research to identify trends, opportunities, and competitive dynamics within the digital health and wellness space.
• Build, manage, and advance a sales pipeline, ensuring timely follow-up and accurate forecasting.
• Collaborate cross-functionally with marketing, product, customer success, and revenue operations to align strategies and deliver exceptional client experiences.
• Represent the organization at industry events and networking opportunities to enhance brand presence and thought leadership.
• Travel up to 25% to meet clients and attend key industry events.

Benefits

• Competitive on-target earnings of $275,000, with a 50/50 base-to-incentive split.
• Eligibility for equity participation, comprehensive healthcare benefits, 401(k), and flexible time off.
• Remote work flexibility within designated U.S. territories.
• Opportunity to make a meaningful impact in the digital health and well-being sector.
• Professional development and growth opportunities within a mission-driven organization.

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed