Lead Sales ExecutiveLocation: Boston

Wellist is seeking a results-oriented Lead Sales Executive with expertise scaling startups with early product-market fit. Reporting directly to the CEO, the Lead Sales Executive will be a high-impact leader with a strong focus on direct selling, moving deals through the pipeline, and closing contracts with CHROs and Total Rewards Officers.

This role is ideal for a proven dealmaker who thrives in an entrepreneurial, fast-paced environment. While strategic insights are valued, the primary focus of this role is hands-on deal execution and pipeline management. As the company grows, the Lead Sales Executive will have the flexibility to expand the sales team as needed to scale revenue growth effectively.

Key Responsibilities

Direct Selling and Pipeline Management:

• • Own the sales pipeline from lead generation through deal closure, with a relentless focus on moving opportunities forward.
  • Cultivate and manage relationships with CHROs, Total Rewards Officers, and other key stakeholders to secure high-value contracts.
  • Develop and execute a repeatable sales process that ensures consistent results and rapid revenue growth.
  • Close deals directly, prioritizing speed and efficiency to achieve aggressive revenue targets.
  • Monitor pipeline health and forecast revenue, ensuring the timely progression of opportunities at each stage.

Revenue Growth Leadership:

• • Build and maintain a robust pipeline to 10x Annual Recurring Revenue (ARR) within 24 months.
  • Prioritize high-value accounts and industries with significant potential for growth, including tech, retail, financial services, and healthcare.
  • Leverage insights from client interactions to refine value propositions and optimize the sales approach.

Team Expansion and Enablement:

• • Closely manage the lead generation efforts with sales priorities, ensuring a steady flow of qualified opportunities.
  • Scale the sales team as needed to meet growth targets, recruiting and onboarding additional sales representatives to maximize coverage.
  • Provide hands-on coaching and support to the team, ensuring alignment with the company’s sales methodology and goals.

Collaboration and Execution:

• • Monitor and report on sales performance metrics to track progress, identify bottlenecks, and drive continuous improvement. 
  • Collaborate with product and operations teams to ensure client feedback informs product enhancements and delivery excellence.

Qualifications

• Proven track record of driving revenue growth to $10M+ ARR, ideally in B2B SaaS or enterprise services targeting HR leaders or similar decision-makers.
• Exceptional sales execution skills, with a focus on dealmaking and pipeline acceleration.
• Experience selling to CHROs, Total Rewards Officers, or HR leadership teams.
• Strong relationship-building, negotiation, and closing skills.
• Ability to thrive in a fast-paced, resource constrained, entrepreneurial environment with competing priorities.
• Experience scaling and leading sales teams to achieve ambitious revenue goals.

About Wellist 

Wellist is a mission-driven digital health company leading the way in revolutionizing how employers enhance employee well-being while reducing costs. Our innovative solution delivers the “right resources at the right time,” using a precision resource-matching platform, targeted activation campaigns, and employee-driven data. By simplifying benefits access and amplifying value from existing benefits partners, we help organizations improve employee outcomes and achieve significant cost reductions. 

Wellist’s outstanding contributions have been recognized by organizations including Fast Company (Most Innovative Companies 2024 - Human Resources), MassTLC (Most Innovative Technology of the Year), Rock Health (Top 50 in Digital Health, Diversity, Leadership), American Business Awards (Company of the Year, Silver Stevie) and BostInno (50onFire). 

Why Join Wellist?

Wellist is committed to improving lives by connecting employees and their families with the resources they need most. As the Lead Sales Executive, you’ll have the opportunity to lead critical operations that directly impact the quality and reach of our services. If you’re a hands-on leader who enjoys solving complex problems and managing scrappy, high-performing teams, we’d love to hear from you.

Why work here 

• A meaningful mission - join a team that makes a difference for patients, employees, and families. 
• Outstanding benefits - excellent medical and dental insurance coverage, life & disability  insurance, up to 3 weeks of PTO and a 3% employer 401(k) contribution
• Opportunity to develop your career with a high-growth, high-impact HR tech startup