Head of Sales

New
J
JobgetherInsurtech B2C Sales
Based in United StatesFull-TimeManager
Salary$178,000–$315,000 OTE
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Job Details

Experience
8–12+ years of sales leadership experience
Required Skills
SalesforceCRM

Requirements

  • 8–12+ years of sales leadership experience, including direct ownership of inside sales teams of 30+ people in a B2C, high-volume, or direct-to-consumer environment.
  • Proven success leading sales organizations, exceeding revenue targets, and scaling performance through headcount growth and operational improvement.
  • Strong background in final expense, whole life, insurance, insurtech, protection products, or another high-velocity consumer sales environment.
  • Experience creating and managing agent compensation plans, performance-management frameworks, staffing models, and organizational structures at scale.
  • Strong analytical and operational capabilities, including forecasting, pipeline management, CRM and telephony systems such as Salesforce, Regal, or equivalent platforms.
  • Demonstrated ability to translate performance data and customer insights into practical actions and measurable improvements.
  • Excellent coaching and talent-development skills, with a track record of developing managers and building high-performance cultures.
  • Strong communication and cross-functional collaboration skills, with the ability to influence Product, Marketing, Finance, and Operations stakeholders.
  • Comfortable working in a fast-moving, technology-focused environment characterized by ambiguity, high ownership, experimentation, and a strong bias toward action.
  • Builder's mindset with the ability to balance immediate performance requirements with the design of scalable systems, processes, and organizational capabilities.

Responsibilities

  • Lead multiple sales teams and managers, establishing clear expectations, accountability, and performance standards across the organization.
  • Define and manage KPIs covering production, activity, efficiency, quality, and other indicators of sales performance.
  • Recruit, develop, and retain high-performing licensed agents and managers while creating career paths and a strong performance-oriented culture.
  • Build and continuously refine sales playbooks, scripts, processes, and sales motions designed for high-volume consumer and protection-product customers.
  • Develop structured coaching programs covering call reviews, shadowing, certifications, performance improvement plans, and manager development.
  • Partner with Product and Marketing to establish experimentation roadmaps, test new sales motions, and translate customer insights into growth opportunities.
  • Work with Finance and Marketing on workforce planning, staffing models, ramp capacity, coverage, and productivity targets.
  • Design and optimize compensation structures that align agent and manager incentives with business outcomes.
  • Own forecasting, pipeline management, operational planning, and sales performance reporting, using data to drive rapid decisions and improvements.
  • Serve as a strategic cross-functional partner and help shape the organization, processes, and culture required for sustainable growth.
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$178,000–$315,000 OTE
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