VP, Sales (East)

*HealthJoy is a Remote-first company, but the person in this position must reside in the Eastern portion of the US. Come for the mission. Stay for the experience. Let’s keep things simple: we are an unbelievably talented, hard-working, and compassionate team driving towards a mission that impacts every single one of us - even you! Healthcare benefits are complex, underutilized and a mystery for most users. We’re removing that complexity. Now more than ever, employers are adding value to their employees’ benefits like telemedicine and mental health services. HealthJoy’s industry-changing tech platform consolidates those benefits into a simplified benefits experience, saving users time and money. With over $100M in fundraising to date, and the successful closing of our recent Series D, HealthJoy has garnered workplace awards for Inc. 's Fastest Growing Startups and Built In Chicago’s Best Places to Work while growing globally to nearly 400 team members. We’re continuing down the path of high growth and high impact, and this role is a key member of the Sales Team making that happen. Your impact. The Vice President, Sales in our Eastern region will lead the team in driving strategic vision and revenue growth. The role involves building and managing a high-performing sales team, collaborating with cross-functional teams, and developing sales strategies aligned with market demands and customer needs. This role requires a balance of strategic leadership and hands-on execution in a “player/coach” capacity, allowing you to engage directly in key deals while guiding the team. Responsible for achieving team-based revenue growth targets in your region Partner with sales leaders to develop strategy and go to market initiatives that maximize revenue in your region Provide training and feedback to direct reports to improve their sales acumen, including presentation skills, deal cycle management and negotiation Work to saturate the the client portfolio with current broker relationships Develop new broker relationships to expand our distribution footprint Assist in the delivery of product demonstrations & delivery of customer pitches and company overviews Select, hire, counsel/coach, motivate, and develop new and current sales team members Supervise and manage a sales team to meet monthly goals: activity, pipeline, forecast opportunities, and revenue targets Provide accurate reporting on sales activity and forecasting to senior sales management and executive team Sound development of internal and external relationships resulting in excellent work outcomes Exhibit strong tenacity and a proactive mindset, consistently pursuing broker and employer meetings and taking decisive action to drive results. Possess strong sales discovery skills, adept at uncovering employer and broker needs, pain points, and priorities through strategic questioning and active listening. Demonstrate executive presence with exceptional presentation, communication and writing skills tailored for engaging with C-suite executives. Comfortably engages in social settings, showcasing adaptability to meet new people and actively participate in diverse interactions. Willingness to step out of your comfort zones and engage with brokers, TPAs, partners, employers, and prospects. Develop their market by creating and fostering new broker relationships and identifying new broker partnerships. Articulate the HealthJoy cost-containment value proposition, demonstrating how our platform impacts employer business outcomes and enhances the healthcare experience for members. Work in partnership within Sales, Marketing, Customer Success, Product and Sales Enablement; therefore cross-company engagement and orchestration is essential. Demonstrate a deep understanding of the HealthJoy product offerings and effectively communicate how our solutions can deliver cost-saving benefits to brokers and their clients. Foster productive collaboration across various organizational levels and departments, ensuring positive and effective working relationships. Use Salesforce for deal tracking, forecasting and performance management of the team Able to learn the complexities of the healthcare, benefits and navigation industries, and can articulate and run demos using our technology. Your experience. Demonstrated sales leadership experience and accountability for team growth targets; Minimum of 5-7+ years experience in a leadership role, managing senior sales professionals in a field environment Minimum of 10 years of related field sales experience selling directly into benefits brokers/consultants, or through an adjacent channel-heavy motion into benefits agencies (PEO, voluntary benefits, ancillary carriers, TPAs, pharmacy benefits, benefits-adjacent fintech) Proven track record leading layered sales organizations focused on Mid-Market / Enterprise deals ($50K–$500K+ ARR) Familiarity with channel-based sales approach and understanding of what makes reseller sales successful Owned a revenue target with accurate forecasting and disciplined pipeline management Strong analytical approach; you use data to run your team, not just your own deals Experience building or scaling sales processes in a growth-stage environment Ability to travel 50% of time Total Rewards Job Level: 90 This role includes a base salary and commissions. Please email at [email protected] to request the over all compensation. HealthJoy maintains a comprehensive strategy to determine rewarding and competitive packages for individual compensation for new hires, internal promotions and internal job changes. This strategy is based on several factors unique to each individual, including: 1) the skills, experience and qualifications of the individual; 2) the responsibilities and demands of the role; 3) analysis of external market data; and 4) company budget and financial performance. In addition to cash compensation, HealthJoy offers a rich “Total Rewards” package that includes: Medical, Dental and vision insurance packages HSA contribution match Stock options for eligible roles 401k match Paid parental leave Company sponsored Short Term and Long Term Disability coverage Flexible PTO Commitment to Equal Pay At HealthJoy, we are committed to creating a diverse and inclusive workplace where everyone has the opportunity to succeed and thrive. We believe that everyone should be paid based on their qualifications, experience, and the work that they do, and not on their gender, race, or any other personal characteristic. Our compensation practices are essential to fostering a diverse and inclusive culture where we value the contributions of all our employees. We conduct thorough annual reviews of employee pay and our pay practices to ensure we reward the right behaviors and are providing equal pay for equal work. Additionally, we assess the external market and internal equity across like roles. As part of our regular review of pay practices, HealthJoy examines employee pay for potential disparities between persons of different genders, races and ethnicities that are not explainable by objective factors such as performance, experience level, credentials, or location, and are committed to correcting any issues and reviewing practices from unintended outcomes. Commitment to Equal Opportunity HealthJoy is committed to creating a diverse environment and is proud to be an equal opportunity employer. All qualified applicants receive consideration for employment without regard to race, color, religion, gender, gender identity or expression, sexual orientation, national origin, genetics, disability, age, or any other basis forbidden under federal, state, or local law. Don’t meet every single requirement? We know the confidence gap and imposter syndrome can get in the way of meeting spectacular candidates, so please don’t hesitate to apply — we’d love to hear from you. HealthJoy is dedicated to building a diverse, inclusive, and authentic workplace, so if you’re excited about this role and HealthJoy, we encourage you to apply. You may be just the right candidate for this or other roles.