Head of Sales in New York at Jobgether

This position is listed on behalf of a partner company, who manages all applications and next steps. Our partner is looking for a Head of Sales based in United States.

This is a senior sales leadership opportunity focused on scaling a high-performing, high-volume B2C sales organization. You will own the strategy, operating model, and performance engine across multiple sales teams and management layers. The role combines hands-on leadership with long-term organizational design, from hiring and coaching to compensation and staffing strategy. You will use data, customer insights, and experimentation to continuously improve sales performance and efficiency. Close collaboration with Product, Marketing, and Finance will help shape new sales motions and growth opportunities. This is an ideal environment for a decisive, analytical leader who enjoys building teams, systems, and playbooks in a technology-driven business.

• 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.

• 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.

• Remote position available across the United States.
• Target compensation range of $178,000–$315,000 OTE, with actual compensation determined by location, experience, skills, education, and other job-related factors.
• Additional compensation may include applicable bonus and equity opportunities.
• Comprehensive benefits package designed to support employees and their families.
• Opportunity to lead and scale a major sales organization with significant organizational and commercial impact.
• Collaborative, technology-forward environment with opportunities to work closely with Product, Marketing, Finance, and Operations.
• Inclusive workplace committed to diversity, belonging, and authentic representation.
• Opportunity to help expand access to life insurance and make protection more accessible to families across the United States.