Sales Supervisor

Job Title: D2C Sales Supervisor

Industry: Insurance

Location (city, state): Frederick, MD

Assignment Type: Direct Hire

Pay: $90,000 – $105,000 / year + 8% target bonus

Work Schedule: Monday–Friday, 8:30 AM–5:00 PM;
Hybrid schedule with work-from-home flexibility on Mondays and Fridays

Benefits: This position is eligible for medical, dental, vision, and 401(k).

Addison Group’s client is a well-established insurance organization with a nationwide customer base and a strong focus on delivering a positive customer experience. Their direct-to-consumer sales team is fast-paced, collaborative, and highly focused on performance, coaching, and professional development.

Addison Group is partnering with our client to hire a D2C Sales Supervisor to support a growing direct-to-consumer sales team. This person will provide hands-on leadership to a team of Inside Sales Agents, helping employees stay on track with sales, quality, productivity, and customer service goals.

The ideal candidate is a people-focused leader who enjoys being actively involved with their team. This is not a role for someone who wants to manage from a distance. The Supervisor will spend significant time working alongside the team, understanding individual strengths and challenges, providing coaching, and helping employees build confidence and improve performance.

• Lead and support a team of approximately 6–10 Inside Sales Agents in a fast-paced call center environment.
• Monitor sales activity, productivity, quality, attendance, and other key performance indicators.
• Conduct regular one-on-one meetings and provide consistent, actionable coaching.
• Listen to customer calls and use observations to identify opportunities for individual development.
• Serve as a first point of contact for agent questions, challenges, and customer escalations.
• Build strong working relationships with both newer and experienced team members.
• Identify performance trends and work with employees to create practical plans for improvement.
• Help maintain a positive, accountable, and collaborative team environment.
• Support sales contests, incentive programs, training initiatives, and other activities designed to increase engagement and productivity.
• Partner with management and internal teams to improve workflows, processes, lead management, and overall sales effectiveness.
• Assist with interviewing, onboarding, training, and ongoing development of new team members.
• Track team performance and provide updates on progress toward sales and productivity goals.
• Ensure team members follow required licensing and appointment guidelines.
• Assist with performance reviews, documentation, career development, and other employee-related processes.
• Help identify system or workflow issues and collaborate with internal partners to resolve them.
• Prepare and maintain reports related to sales activity, productivity, quality, staffing, and performance.

• 5–10+ years of leadership experience, ideally managing a team of 6 or more employees.
• Experience leading teams in a sales, call center, customer service, or similarly metrics-driven environment.
• Strong communication and interpersonal skills with the ability to connect with a variety of personalities.
• Demonstrated ability to coach employees by identifying individual strengths, weaknesses, and development opportunities.
• Comfortable using performance data and metrics to guide coaching conversations.
• Highly engaged leadership style with the ability to work alongside a team and lead by example.
• Strong organizational skills and ability to prioritize in a fast-paced environment.
• Empathetic, approachable, and confident communicator.
• Proficiency with Microsoft Office, including Word and Excel.
• Bachelor’s degree…