Role: Outbound Sales Supervisor (Insurance Lead Generation Team)

Company Overview

A growing U.S.-based insurance agency specializing in Medicare and ancillary insurance products. The company is rapidly expanding its outbound lead generation department and building a scalable sales operation to support licensed insurance agents.

Role Overview

We are seeking an experienced Outbound Sales Supervisor to lead and manage a team of high-volume cold callers responsible for generating qualified insurance opportunities.

This role focuses on team management, performance tracking, call coaching, quality assurance, dialer optimization, and daily sales operations. The ideal candidate has proven experience leading outbound calling teams, understands performance metrics, and can motivate agents in a fast-paced sales environment.

The supervisor will initially oversee approximately 15 outbound callers, with the opportunity to support continued growth as the department scales.

Schedule: Full-Time (40+ hours per week)

Working Hours: Aligned with team operating hours
Monday to Friday, 9:00 AM – 8:00 PM EST

Client Timezone: Eastern Standard Time (EST)

Key Responsibilities

Team Leadership & Performance Management

• Supervise daily activity and performance of a team of outbound cold callers
• Monitor attendance, productivity, call volume, and lead generation results
• Ensure agents consistently meet daily and weekly KPI targets
• Provide ongoing coaching, feedback, and motivation to improve performance
• Identify performance gaps and create improvement plans for struggling agents
• Support onboarding and training of new team members as the department expands

Call Quality & Sales Coaching

• Review call recordings and live calls to evaluate agent performance
• Coach agents on:
  • Script delivery
  • Tonality and confidence
  • Objection handling
  • Lead qualification
  • Transfer quality
• Ensure agents follow approved scripts and compliance guidelines
• Share best practices and successful call strategies across the team

Dialer & Lead Management

• Monitor activity within Ready Mode or similar dialer platforms
• Track call outcomes, conversion rates, and agent productivity
• Ensure leads are properly managed and followed up
• Identify opportunities to improve workflows and increase contact rates
• Collaborate with leadership to optimize scripts, processes, and campaigns

Reporting & Operations

• Prepare regular reports on team performance and key metrics including:
  • Calls completed
  • Contacts reached
  • Qualified leads generated
  • Transfers completed
  • Agent performance trends
• Communicate results and improvement opportunities to management
• Help build scalable processes as the team grows from 15+ agents

Requirements

• Minimum 2+ years of experience supervising outbound sales, telemarketing, or call center teams
• Previous experience managing cold callers or appointment setters
• Strong understanding of outbound sales KPIs and performance management
• Experience coaching agents on scripts, objections, and phone techniques
• Excellent English communication and leadership skills
• Comfortable managing remote teams and tracking productivity
• Ability to motivate a team in a high-volume calling environment
• Strong organizational and reporting skills
• Ability to work independently and solve problems proactively

Highly Regarded Skills & Experience

• Previous experience in insurance, Medicare, healthcare, or financial services campaigns
• Experience managing teams of 10+ outbound agents
• Familiarity with Ready Mode or similar power dialer systems
• Experience scaling outbound teams and improving conversion rates
• Knowledge of CRM systems and lead management workflows
• Background in quality assurance or sales training

Scope

• Manage the daily performance of a 15-person outbound calling team
• Improve lead generation volume and quality
• Maintain accountability, structure, and consistent sales activity
• Support training and development of cold callers
• Create repeatable processes as the company scales toward a larger sales operation
• Act as the communication bridge between callers, management, and licensed insurance agents

Independent Contractor Perks
HMO Coverage for eligible locations
Permanent work from home
Immediate hiring
Steady freelance job

Side Note

This is a permanent work-from-home role under an Independent Contractor arrangement. Candidates must have their own computer and reliable internet connection, and are responsible for their own taxes and benefits. Professional hourly fees are established based on your performance in the application process.

Please click the "Apply" button to complete your application, including the assessment questions, technical check, and voice recording. Your hourly pay rate will be established based on your performance in the application process; submissions with all requirements fulfilled will receive priority review.