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, 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 at minimum to ensure competitive and fair pay.

Don’t meet every requirement? Studies have shown that women, communities of color and historically underrepresented talent are less likely to apply to jobs unless they meet every single qualification. At Spring Health we are dedicated to building a diverse, inclusive and authentic workplace, so if you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we strongly encourage you to apply. You may be just the right candidate for this or other roles!

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

Hypergrowth meets impact

What to expect working here:

• You will be held accountable to an exceptionally high bar and impact
• This may be the fastest work environment you will ever experience in terms of growth, decision-making, and time to impact
• You will be empowered to set your own boundaries and asked to adapt them in critical moments when the company needs you
• You will create processes & products that have never existed before
• You will have very direct conversations and receive continuous feedback to push you to become the most thriving team member and performer you can be
• Change is a constant here: your role, team, responsibilities, and success metrics will shift as the company grows

And…

• You get to be surrounded by some of the brightest minds in the field  
• You get to learn and grow at an extremely accelerated pace
• You will experience transparency, integrity, &  humility from leadership 
• You will be empowered to constantly challenge the status quo
• You get the space to experiment & innovate
• You get to make a transformational impact for the company, mental health, and for real human lives — and you will see that impact quickly
• You will become more resourceful and resilient
• You get to be part of a winning team that opens doors in the future

Benefits provided by Spring Health:

Your Total Health:

• Health, Dental, Vision benefits start on your first day at Spring Health. You and your dependents also receive an individual One Medical account which is valued at $199/year per user. HSA and FSA plans available
• A yearly allotment of no cost visits to the Spring Health network of therapists, coaches, and medication management providers for you and your dependents
• 10 allocated sick days per year
• Flexible paid time off in addition to 12 paid holidays throughout the year
• Access to Gympass, an on-demand virtual benefit that provides wellbeing coaching, and budget management.
• Spring Renewal: When you hit your four-year Springaversary, you’ll be awarded a four week, fully paid, sabbatical leave to renew and recharge. 

You And Your family:

• 4-4.5 months of fully paid parental leave
• Spring Health provides team members and their families with sponsored access to Bright Horizons® child care, back-up care, and elder care.
• Access to fertility care support through Carrot, in addition to $4,000 reimbursement for related fertility expenses

Supporting you financially through:

• Our People team benchmarks all salaries using the Radford Global Compensation Database for technology and life sciences industries. Radford benchmarks salaries with 3,589 global firms, 6.5 million employees, and 98 countries across the globe. We do this to ensure all of our team members are paid equally and competitively.
• On top of competitive and benchmarked salary, Spring Health offers incentive pay (based on role), and equity that begins vesting as we celebrate your first year with the company!
• Employer sponsored 401(k) match of up to 2% after 90 days of employment

Creating a culture you can thrive in:

• Flexible work arrangements: 66% of Spring Health team members work fully remote while 33% work in a hybrid model from our New York City offices
• Focus Fridays: no meetings, no distractions, just time for you to get work done.
• Focus Weeks: In Spring 2023, we held our first ever Focus Week, we canceled all non-essential meetings, minimized distractions, and you, our team members, to dive into the key work that gets chopped up or deprioritized during the regular day-to-day. We saw a 36% jump in the average energized score after those five days of flow state work and are finalizing a plan for quarterly Focus Weeks for team members.
• Up to $1,000 Professional Development Reimbursement per calendar year.
• $200 per year donation matching to support your favorite causes

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

Don’t meet every requirement? Studies have shown that women, communities of color and historically underrepresented talent are less likely to apply to jobs unless they meet every single qualification. At Spring Health we are dedicated to building a diverse, inclusive and authentic workplace

To ensure intentional and equitable hiring practices, we use a balanced candidate slate in our interviews. This approach guarantees that our pool of qualified candidates includes individuals who are underrepresented in our organization at all levels. This is a key performance indicator (KPI) for our recruiting and hiring teams, reported quarterly to maintain accountability.