Lead Sales Executive

Wellist - Boston, MA

Full-time - Senior

Boston, MA

Publishing Industries

About the position

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.

Responsibilities

• 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.
• 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.
• 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.
• 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.

Requirements

• 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.

Benefits

• Excellent medical and dental insurance coverage
• Life & disability insurance
• Up to 3 weeks of PTO
• 3% employer 401(k) contribution