Head of Sales

About This Role

Heading the Sales department at a leading life insurance technology company, this role owns the strategy and full operational engine of the sales organization. The Head of Sales leads multiple managers and sales teams, expands the organization by recruiting and training agents, and collaborates with Product and Finance stakeholders. This position suits a proven, hands-on sales leader who can drive performance while architecting the organization, playbooks, and culture for future success.

Responsibilities

• Lead the Sales organization, responsible for managing multiple teams and driving performance
• Define and own KPIs across production, activity, efficiency, and quality; foster a data-driven performance culture with clear accountability at every level
• Lead, develop, and scale a high-performing team of licensed agents and managers — hiring top talent, building career paths, and maintaining a culture of performance
• Build and continuously improve sales playbooks, scripts, and sales motions tailored to the Final Expense customer
• Develop coaching programs across call reviews, shadowing, certifications, and performance improvement plans for both managers and agents
• Partner with Product and Marketing teams to develop shared test and experimentation roadmaps
• Set and manage staffing plans in partnership with Finance and Marketing, ensuring coverage, ramp capacity, and productivity targets are met
• Design and evolve compensation plans that align agent and manager incentives with business outcomes

Requirements

• 8–12+ years of sales leadership experience, with direct ownership of inside sales teams of 30+ in a B2C or high-volume direct-to-consumer environment
• Proven track record of owning a sales organization — exceeding revenue targets and scaling a business through headcount growth and operational improvement
• Deep expertise in final expense, whole life, or adjacent protection products strongly preferred; candidates with B2C insurance, insurtech, or high-velocity consumer sales backgrounds will be considered
• Experience designing and managing agent compensation plans, performance management frameworks, and staffing models at scale
• Strong analytical operator fluent in forecasting, pipeline management, and modern CRM and telephony systems (Salesforce, Regal, or equivalent); able to translate data into rapid action
• Excellent coach and developer of talent — track record of building manager capability and creating high-performance team cultures
• Natural cross-functional partner; skilled at using data and customer insight to influence Product, Marketing, and Operations
• Thrives in a fast-moving, tech-forward environment with a strong bias for action, high ownership, and a builder's mindset

Benefits