Head of Term Life Insurance Sales

About the Role

We are looking for an ambitious Head of Term Life Insurance Sales to help lead our Term Life Insurance Sales Team in a mission to protect the next million families. As our Head of Term Life Sales, you will own the strategy and full operational engine of our largest sales organization, leading multiple managers and sales teams. You will be tasked with expanding our world-class Term sales organization, by recruiting and training the best Agents. You will collaborate with Product stakeholders to test and experiment into new sales motions. You will partner with Finance to develop staffing models and compensation plans. We're looking for a proven, hands-on sales leader who can drive performance today while architecting the organization, playbooks, and culture needed to win tomorrow.

Duties and Responsibilities

• Lead the Term Life Insurance 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
• 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

Qualifications and Skills

• 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 term life insurance or adjacent protection products strongly preferred; candidates with B2C financial services, insurtech, or high-velocity consumer sales backgrounds
• 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