Telesales Supervisor

Devoted Health • Waltham, MA

1d • $70,000 - $80,000 • Remote

About The Position

A bit about this role: As a Telesales Supervisor at Devoted Health, you will lead and develop a team of licensed telesales agents selling Medicare Advantage policies across multiple states. Your number one priority is being in front of agents: live coaching, call shadowing, role-playing, and providing immediate feedback to drive sales and conversion while maintaining the highest standards of quality and compliance. You will use data-driven coaching to improve performance across enrollment cycles, manage day-to-day operations, and resolve issues to protect the member experience. Your Responsibilities and Impact will include:

Requirements

• At least 2 years of supervisor/manager experience in a high-volume environment.
• At least 4 years of experience in a call center, telesales, or sales environment.
• Valid/current state health insurance license (or the ability to acquire one prior to your start date).
• An innate "gut feel" for CMS marketing rules; you prioritize regulatory adherence as a reflex rather than a checklist.
• Proven ability to manage the transition between the "lock-in" season and high-pressure AEP/OEP cycles, including the ability to scale teams and manage seasonal fatigue.
• Experience delivering direct, timely, and empathetic feedback to address underperformance early while maintaining team morale.
• Strong analytical skills; proficient with Excel/Google Sheets and able to use dashboards/KPIs to drive tangible improvements.

Nice To Haves

• Previous experience in Healthcare and/or Medicare sales is highly preferred.
• Experience building and delivering formal performance management and corrective action plans.
• An "early adopter" mindset; a proactive interest in learning new software rather than viewing digital evolution as a hurdle.
• Experience using CRM/Marketing platforms (e.g., Salesforce) and contact-center tools.
• Basic knowledge of Large Language Models (LLMs) and AI-assisted agent tools—specifically the ability to support adoption, create simple prompts, and train agents on safe, compliant use.

Responsibilities

• Manage a team of 15+ licensed agents, fostering a culture of high performance, accountability, and mission-driven motivation.
• Deliver real-time training to drive resilient sales results, ensuring a strict balance between high conversion and uncompromising compliance.
• Achieve goals related to phone service levels, call quality, outbound contacts, sales, and appointments.
• Effectively manage remote and onsite teams across multiple time zones (Eastern, Mountain, Pacific, and Hawaii).
• Identify training, tech, or process-related needs to improve the member and agent experience.
• Deliver individual performance metrics to agents, ensuring growth across all enrollment cycles.
• Use data-driven insights to foster professional development and maintain peak team output during both peak and off-peak seasons.
• Handle customer escalation calls with empathy and efficiency.

Benefits

• Employer sponsored health, dental and vision plan with low or no premium
• Generous paid time off
• $100 monthly mobile or internet stipend
• Stock options for all employees
• Bonus eligibility for all roles excluding Director and above; Commission eligibility for Sales roles
• Parental leave program
• 401K program

What This Job Offers

• Job Type: Full-time
• Career Level: Manager
• Education Level: No Education Listed
• Number of Employees: 501-1,000 employees