What are the responsibilities and job description for the Director of Sales position at Career1Source - Executive Recruiting?
Director of Sales
Chicago, IL or Madison, WI
We’re partnering with a rapidly growing, innovative healthcare organization that is redefining how employers deliver care to their workforce. Backed by strong leadership and significant growth momentum, this company is building a modern, scalable model that is gaining real traction in the market.
They’re looking for a Director of Sales to take ownership of a key territory, build meaningful relationships with employers and advisors, and drive new revenue through a highly differentiated offering. This is a high-impact, high-visibility role with uncapped earning potential and real upside.
What You’ll Do
- Own and grow a defined territory—building a strong, predictable pipeline
- Develop relationships with employers, brokers, and benefits consultants
- Lead the full sales cycle from prospecting through close (complex, multi-month deals)
- Act as a trusted advisor to clients, positioning a modern approach to employee healthcare
- Partner cross-functionally with marketing, operations, and leadership to drive results
- Represent the organization in the market through events, networking, and industry engagement
What We’re Looking For
- 3 years of B2B sales experience (healthcare or benefits-related strongly preferred)
- Experience selling into mid-to-large employers (250 employees)
- Proven ability to build relationships with brokers, consultants, and key stakeholders
- Track record of consistently exceeding quota
- Comfortable managing longer, consultative sales cycles
- Entrepreneurial mindset with a strong drive to win
Why This Role
- Uncapped earnings with strong OTE potential
- Opportunity to help scale a high-growth, disruptive healthcare model
- High level of autonomy with meaningful impact on company growth
- Strong leadership team and clear market opportunity
If you (or someone in your network) might be a fit, I’d welcome a quick conversation.
*Candidates must be eligible to work in the US as well as meet the qualifications listed above in order to be considered for the Director of Sales.