Head of Sales, Voluntary Benefits

The Jacobson Group
Florida, FL

Job Description:
An employee benefits provider is seeking a Head of Sales, Voluntary Benefits. The Head of Sales, Voluntary Benefits is responsible for developing and executing innovative strategies to drive revenue growth and expand market presence. This dynamic leader will build a scalable sales team and organizational structure from the ground up, while fostering strong client relationships to support a high-performing voluntary benefits business. They will design results-oriented sales processes and establish a robust pipeline of opportunities that deliver predictable and repeatable outcomes. This hands-on leader will travel regularly to assess the sales and account management teams, participate in ride-alongs, and engage directly with top clients. This is a retained search.

Responsibilities:
  • Develop and implement a comprehensive sales strategy and tools to drive profitable growth and increase market share. Execute standardized sales methodologies with accountability measures, manage the productive and sustainable sales pipeline to ensure a consistent flow of qualified leads, and improve sales cycle and close rates.

  • Utilize data-driven insights to optimize sales processes, forecast trends and monitor performance to build a predictable, defensible sales organization that clearly demonstrates ROI. Leverage CRM data and other tools to establish clear and measurable metrics to drive consistent progress and pinpoint areas for improvement.

  • Lead client-facing opportunities that are pivotal to generating new business, maintaining and growing existing client relationships, and achieving sales targets. Engage directly with clients and work alongside the sales team to understand client needs, develop tailored solutions, and close critical deals.

  • Attract, develop, and inspire a high-performing team of sales professionals and account managers.


Requirements:

  • 10+ years of sales experience with 5+ years of sales leadership

  • Experience in supplemental benefits; property and casualty insurance experience (preferred)

  • Proven track record of building effective sales strategies and high-performing teams that demonstrate the behaviors and actions necessary for scalable and repeatable growth

  • Experience establishing scalable sales processes, performance metrics and accountability systems that drive consistent results

  • Expertise in managing pipelines, identifying targets, generating leads, prospecting, qualifying leads, prioritizing outreach and actions, and forecasting sales and closing ratios

  • Proficiency in CRM software utilization to analyze data and drive sales strategies

  • Bachelor’s degree (preferred)

Posted 2025-10-27

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