Head of Sales
J
JobgetherInsurtech
Remote-first position open to US-based employees.Full-TimeManager
SalaryUS national base salary range of $178,000–$315,000.
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Job Details
- Experience
- 8–12+ years
- Required Skills
- SalesforceCRM
Requirements
- 8–12+ years of sales leadership experience, including direct ownership of inside sales teams of 30+ people in a B2C or high-volume direct-to-consumer environment.
- Proven track record of owning a sales organization, exceeding revenue targets, and scaling performance through headcount growth and operational improvements.
- Deep experience with final expense, whole life, or related protection products is strongly preferred; backgrounds in B2C insurance, insurtech, or high-velocity consumer sales are also relevant.
- Demonstrated experience designing and managing agent compensation plans, performance management frameworks, and staffing models at scale.
- Strong analytical and operational capabilities, with expertise in forecasting, pipeline management, CRM systems, and sales or telephony platforms such as Salesforce and Regal or equivalent tools.
- Ability to translate performance data into clear priorities, rapid decisions, and measurable operational improvements.
- Exceptional coaching and talent development skills, with a track record of strengthening manager capabilities and building high-performance teams.
- Strong cross-functional collaboration skills, with the ability to use customer insights and data to influence Product, Marketing, Finance, and Operations.
- Comfortable operating in a fast-moving, technology-focused environment with a strong bias toward action, ownership, experimentation, and continuous improvement.
- Builder mindset with the ability to balance immediate sales performance with the development of scalable systems, processes, and organizational capabilities.
Responsibilities
- Lead the overall Sales organization, managing multiple teams and managers while driving consistent performance against business objectives.
- Define and own KPIs across production, activity, efficiency, quality, and revenue, establishing a data-driven culture with clear accountability at every level.
- Recruit, develop, and scale high-performing licensed agents and sales managers, creating career paths and maintaining a strong performance culture.
- Build and continuously improve sales playbooks, scripts, processes, and sales motions tailored to high-volume consumer insurance customers.
- Develop coaching programs covering call reviews, shadowing, certifications, performance management, and improvement plans for agents and managers.
- Partner with Product and Marketing to establish experimentation roadmaps, test new sales motions, and identify opportunities to improve customer and business outcomes.
- Work with Finance and Marketing to develop staffing models that support coverage, ramp capacity, productivity, and growth targets.
- Design and evolve compensation plans that align agent and manager incentives with organizational and revenue objectives.
- Use sales performance data, forecasting, pipeline insights, and customer feedback to identify opportunities for operational improvement and rapid execution.
- Build the organizational structure, operating playbooks, and leadership culture required to support continued growth.
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