Associate Director, Mid-Market Sales

We are seeking an Associate Director, Mid-Market Sales to lead a high-performing team of 4–8 Account Executives and capture a significant opportunity in the HR/Benefits market. In this role, you will drive revenue by developing talent, scaling best practices, and partnering cross-functionally to optimize go-to-market execution. You will report into the Director of Commercial Sales.  This role is full-time and can be fully remote, however, east coast base and NYC accessible is preferred.   

What you’ll be doing: 

• Lead, coach, and develop a team of full-cycle sales reps focused on selling into HR and Benefits leaders at mid-market enterprises (2,500–10,000 employees).
• Drive performance through structured onboarding, ongoing coaching, and skill development to ensure every rep is equipped to exceed quota.
• Partner with Marketing, Customer Success, and Product teams to build scalable go-to-market strategies and improve sales execution.
• Own team pipeline management, forecasting accuracy, and business reviews with the VP of Sales to ensure predictable revenue outcomes.
• Represent the company at client meetings, industry events, and conferences to expand market presence and strengthen executive relationships. Occasional travel may be required for such events. 
• Contribute strategic insights and innovative approaches to positioning our solutions in a competitive HR/Benefits market.

What success looks like in this role:

• Achieve sales targets as assigned
• Hire, develop and retain talent
• Collaborate cross functionally to drive new pipeline and wins

What we expect from you: 

• Previous track record of success in achieving sales targets
• 2+ years of sales leadership preferred Working knowledge of Google Office Suite (Google Docs, Sheets, Slides, Forms, etc.)
• Strong working knowledge of the benefits space
• Proactive approach to activating new customers
• Experience developing creative solutions to complex problems
• Strong statistical and analytical skills
• The ability to travel up to 10% of the year (if required)

The target base salary range for this position is $146,000 - $182,500 with a OTE range of $292,000 - $365,000 and is part of a competitive total rewards package including stock options and benefits. Individual pay may vary from the target range and is determined by a number of factors including experience, location, internal pay equity, and other relevant business considerations. We review all employee pay and compensation programs annually using Radford Global Compensation Database at minimum to ensure competitive and fair pay. 

Benefits provided by Spring Health:

Note: We have even more benefits than listed here and below, your recruiter will provide more in-depth information as you continue in the interview process. Benefits are subject to individual plan requirements and eligibility criteria.

• Health, Dental, Vision benefits start on your first day at Spring. You and your dependents also receive access to One Medical accounts HSA and FSA plans are also available, with Spring contributing up to $1K for HSAs, depending on your plan type.
• Employer sponsored 401(k) match of up to 2% for retirement planning
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents.
• We offer competitive paid time off policies including vacation, sick leave and company holidays.
• At 6 months tenure with Spring, we offer parental leave of 18 weeks for birthing parents and 16 weeks for non-birthing parents.
• Access to Noom, a weight management program—based in psychology, that’s tailored to your unique needs and goals. 
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses.
• Access to Wellhub,  which connects employees to the best options for fitness, mindfulness, nutrition, and sleep in one subscription
• Access to BrightHorizons, which provides sponsored child care, back-up care, and elder care
• Up to $1,000 Professional Development Reimbursement a year.
• $200 per year donation matching to support your favorite causes.

Not sure if you meet every requirement? Research shows that women and people from historically underrepresented communities often hesitate to apply for roles unless they meet every qualification compared to other similarly-qualified candidates. At Spring Health, we are committed to fostering a workplace where everyone feels valued, empowered, and supported to Thrive. If this role excites you, we encourage you to apply.

Ready to do the most impactful work of your life? Learn more about our values, what it’s like to work here, and how hypergrowth meets impact at Spring Health: Our Values

Our privacy policy: https://springhealth.com/privacy-policy/

Spring Health is proud to be an equal opportunity employer. We do not discriminate in hiring or any employment decision based on race, color, religion, national origin, age, sex, marital status, ancestry, disability, genetic information, veteran status, gender identity or expression, sexual orientation, pregnancy, or other applicable legally protected characteristic. We also consider qualified applicants regardless of criminal histories, consistent with applicable legal requirements. Spring Health is also committed to providing reasonable accommodations for qualified individuals with disabilities and disabled veterans. If you have a disability or special need that requires accommodation, please let us know.