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).

About Our Client:

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.

Job Description:

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.

Key Responsibilities:

• 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.
  
  

Qualifications:

• 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 preferred.
• Insurance industry or life insurance experience is a plus.
• Life insurance licensing will be required. The selected candidate will be supported through the certification process and will have three opportunities to pass the required exam within the first 30 days.
  
  

Additional Details:

• Target start date: Mid-October
• Full-time, direct-hire opportunity
• Hybrid position based in Frederick, MD
• 8% target annual bonus
• The role offers opportunities for professional development and advancement within a growing organization.
  
  

Perks:

• Hybrid work schedule
• Annual bonus opportunity
• Professional development and career growth opportunities
• Supportive, team-oriented environment
• Opportunity to directly influence employee development and team performance
• Full benefits package
  
  

Addison Group is an Equal Opportunity Employer. Addison Group provides equal employment opportunities (EEO) to all employees and applicants for employment without regard to race, color, religion, gender, sexual orientation, national origin, age, disability, genetic information, marital status, amnesty, or status as a covered veteran in accordance with applicable federal, state and local laws. Addison Group complies with applicable state and local laws governing non-discrimination in employment in every location in which the company has facilities. Reasonable accommodation is available for qualified individuals with disabilities, upon request.