Vice President, Mid-Market Sales
Color
How You’ll Contribute:
- Lead and develop a high-performing team of Mid-Market Sales Directors responsible for territories across the U.S.
- Drive consistent quota attainment and pipeline health through strong forecasting discipline, performance management, and data-driven insights. Roll up your sleeves to work key deals alongside your team when needed, balancing strategy with hands-on execution.
- Coach, inspire, and elevate your team — ensuring each IC develops mastery across the full sales cycle, from prospecting to close, while maintaining a focus on long-term customer relationships.
- Own the hiring, onboarding, and ongoing development of top sales talent, fostering a culture of accountability, excellence, and growth.
- Partner cross-functionally with Marketing, Consultant Relations, Health Plan and Ecosystem Partnerships to optimize territory coverage, lead quality, and deal velocity as well as to test new go-to-market approaches, messaging, and channel strategies in real time.
- Collaborate with leadership to refine segmentation, territory design, and compensation models that scale with growth.
- Track and analyze performance metrics to identify trends, coach improvements, and forecast accurately.
- Champion the voice of the customer, sharing feedback and market intelligence to influence product and GTM strategy.
- Lead by example in operational rigor, clear communication, and commitment to outcomes, setting a high bar for professionalism and follow-through.
- Represent the company externally at key industry events, conferences, and client meetings as a fluent ambassador for our products.
Our Ideal Candidate Will Have:
- 10+ years of experience in B2B sales, including at least 3+ years in a successful people management role leading enterprise or mid-market account executives.
- Proven track record of leading teams to consistently achieve or exceed multi-million-dollar quotas.
- Demonstrated ability to build and scale sales processes, forecasting rigor, and coaching frameworks in a growth environment.
- Strong understanding of complex, consultative sales cycles and selling into HR, Benefits, or Healthcare decision-makers at mid-market employers.
- Exceptional ability to motivate, coach, and hold teams accountable while creating an environment of trust, learning, and performance.
- Strong analytical, operational, and communication skills; adept at translating data into strategy and strategy into action.
- History of success working cross-functionally and influencing without authority across Marketing, Product, and Partnerships.
- Experience managing national or multi-territory coverage models.
- Comfort with ambiguity and a bias for action, you’re energized by solving problems and creating structure in fast-moving environments.
- Hands-on leadership style that blends strategic vision with tactical execution.
- Willingness to travel frequently across the U.S. to support team and client engagements.
- Bachelor’s degree required; advanced degree a plus.
Nice to Have:
- Deep familiarity with selling into employer health benefits, condition management, or healthcare technology markets.
- Experience leading teams through rapid growth, organizational change, or GTM transformation.
- Demonstrated ability to mentor future sales leaders.
- Experience building systems, processes, and metrics from the ground up in a high-growth or startup environment.
What We Offer:
- 💰 Competitive salary
- ✨ Comprehensive medical, dental, vision, life, and disability benefits
- 📈 401k match 📝 Monthly phone and wifi stipend for employees, annual ergonomic stipend
- 🏝 Generous vacation policy, paid holidays and company-wide recharge days
- 🍼 Equal paid parental leave for birthing and non-birthing parents
- Free cancer screening and prevention resources for employees and their adult dependents