Enterprise Account Executive

Enterprise Account Executive at HealthBook+ About HealthBook+ HealthBook+ is entering its next growth chapter with a focus on expanding our employee health and wellness solutions. Our platform leverages AI to guide individuals to their next best health action—helping people and families proactively manage their health. We care deeply about our mission: improving the lives of our clients and the people they serve. Our culture is simple: • We are kind, empathetic, and scrappy • We collaborate, but we also know how to GSD • We operate with high autonomy and trust • We help each other level up every day • We focus on the problem, not the person • We value open, direct communication—no surprises The Role We’re looking for an Enterprise Account Executive to drive growth by bringing new employers and healthcare organizations onto the platform. You’ll own the full sales cycle and represent HealthBook+ in all aspects of customer acquisition. This is a high-impact, remote role with direct visibility into leadership. What You’ll Do • Own the full sales cycle from prospecting through close • Drive new business across employers, health systems, and healthcare partners • Build and manage a strong, organized pipeline • Sell into VP and C-suite stakeholders • Develop and execute strategic sales plans to hit revenue targets • Partner with leadership to shape go-to-market strategy • Deliver compelling presentations, demos, and proposals • Maintain accurate forecasting and pipeline visibility • Stay on top of market trends, competitors, and customer needs • Support marketing and partner initiatives (events, campaigns, etc.) • Continuously improve sales processes and partner engagement What You’ll Bring • Experience selling into healthcare is required (health systems, employers, payers, or benefits space) • Strong understanding of employee health, wellness, or population health • Familiarity with health systems and Medicare Advantage is a plus • Proven ability to: • Sell to executive stakeholders • Navigate complex sales cycles • Consistently hit quota • Highly organized and able to prioritize effectively • Comfortable operating in a fast-changing startup environment • Coachable, optimistic, and resilient Who You Are • Strategic thinker who can partner with leadership on long-term growth • Empathetic and genuinely enjoys helping others succeed • Knows when to be scrappy and when to be thorough • Comfortable with ambiguity and solving hard problems • Strong communicator across internal teams and external stakeholders • Confident in saying “no” and explaining the “why” • Motivated by building something meaningful that improves people’s health Requirements • Bachelor’s degree • 3–5+ years of enterprise sales experience • Direct experience in healthcare or employee benefits (required) • Startup experience strongly preferred • Ability to travel up to 50% Compensation & Benefits We offer competitive compensation including: • Base salary + commission • Comprehensive health benefits • Flexible, remote-first work environment • A team that genuinely enjoys working together We’re open to creative compensation packages for the right candidate.