Director of Enterprise Sales

At The Difference Card, we’re making healthcare benefits work better—for employers and their employees. Since 2001, we’ve helped organizations build smarter, more cost-effective health plans, delivering an average net savings of more than 18% for our clients. Our innovative solutions combine flexible plan design, healthcare reimbursement, risk management, and wellness strategies to help employers get more from their benefits. We’re continuing to expand our offerings through HealthCorum and our provider quality scoring products, creating additional opportunities to deliver innovative, cost-effective healthcare solutions to the market. With a national presence and a people-first approach, we partner with employers and brokers to make benefits simpler, smarter, and more valuable. The Opportunity The Director of Enterprise Sales is a senior leader responsible for driving new business growth within the national large-group employer market (1000+ employees). Reporting directly to the Chief Revenue Officer (CRO), this role focuses on selling The Difference Card’s Third-Party Administration (TPA) services, including HRA, FSA, HSA, and COBRA, as well as our provider quality scoring (PLUM) products. You’ll leverage referrals from Sales Consultants and Marketing while independently sourcing and closing enterprise opportunities. The ideal candidate brings a proven track record of enterprise sales success, strong industry relationships, and the ability to navigate complex sales cycles and build trusted partnerships with senior decision-makers. This role is remote with a preference for candidates located in the Central U.S. region. What You’ll Do Drive Enterprise Sales Growth: Own full sales cycle for large employer groups from prospecting and discovery through negotiation and closing. Build and Convert Pipeline: Independently source national enterprise opportunities while developing and converting referrals and leads from Sales Consultants and Marketing. Team Leadership & Development: Lead, coach, and develop a team of Business Development Specialist, providing strategic direction, ongoing mentorship, and performance management to drive pipeline growth, achieve sales objectives, and foster a high-performing, results-driven team. Sell Strategic Solutions: Position TPA services and PLUM products through consultative selling, aligning solutions with employer needs, benefit strategies, and cost management goals. Develop Key Relationships: Build trusted partnerships with national brokers, consultants, C-suite executives, and benefit decision makers. Lead Complex Sales Opportunities: Navigate lengthy sales cycles, multiple stakeholders, competitive evaluations, and contract negotiations. Own Sales Performance: Manage pipeline activity, maintain accurate forecasts in Salesforce, and consistently deliver against revenue targets. Partner & Influence: Collaborate across Sales, Marketing, and Client Success while sharing market insights to support enterprise growth strategies. What We’re Looking For Bachelor’s degree of equivalent combination of education and relevant experience. 10+ years of sales experience in insurance, healthcare, employee benefits, or a related industry, with demonstrated enterprise sales success. Proven ability to independently source, develop, and close complex deals with large employees (1,000+ employees). Experience selling insurance, TPA services, healthcare solutions, or healthcare point solutions into the enterprise market. Strong understanding of employee benefits, employer sponsored health plans, and healthcare cost management. Established relationships with national brokers, consultants, or enterprise decision-makers preferred. Exceptional communication, presentation, negotiation, and relationship-building skills; Salesforce experience preferred. Willingness to travel nationally as business needs require What Success Looks Like You consistently generate and close enterprise opportunities, building a strong pipeline through independent prospecting and internal partnerships. You deliver measurable revenue growth, meeting or exceeding sales targets. You build trusted relationships with national brokers, consultants, and enterprise decision-makers. You position our solutions strategically, demonstrating clear value to large employers. You help expand our national presence through industry expertise, market insights, and strong sales execution. Why Join The Difference Card? This is an opportunity to join a growing organization at a pivotal stage of expansion and play a meaningful role in shaping our enterprise sales strategy. As our first dedicated enterprise sales leader focused on the large-group employer market, you'll have the autonomy to build relationships, influence go-to-market strategy and drive significant revenue growth. Reporting directly to the Chief Revenue Officer, you'll have a seat at the table with executive leadership and the ability to make an immediate impact on the business. You'll represent a differentiated portfolio of solutions that help employers control healthcare costs, improve employee experiences, and make more informed benefits decisions. If you're energized by building something, winning complex enterprise deals, and being rewarded for your success, this role offers significant earnings potential through a highly competitive compensation package and uncapped incentive opportunity. Compensation: Competitive base salary plus uncapped commission potential ($250k - $350k) What You’ll Gain: Direct visibility and partnership with executive leadership. Opportunity to build and shape a high-growth enterprise sales channel. Comprehensive benefits package, including medical, dental, vision, and retirement offerings. The chance to make a measurable impact on company growth and long-term success. Equal Opportunity Employer EB Employee Solutions, LLC is an Equal Opportunity Employer. We do not discriminate based on actual or perceived race, creed, color, religion, alienage or national origin, ancestry, citizenship status, age, disability or handicap, sex, marital status, veteran status, sexual orientation, genetic information, arrest record, or any other characteristic protected by applicable federal, state, or local laws. We are committed to equal opportunity throughout recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities, and all other aspects of employment. #J-18808-Ljbffr