Remote Telesales Sr. Supervisor – Licensed Insurance Sales bei Keystone Advisors

Who We Are Keystone Advisors partners with leading insurance carriers to deliver best-in-class health coverage across 49 states. We specialize in helping individuals, families, and small businesses navigate ACA plans, Medicare Advantage, Medicare Supplements, and ancillary products like dental, vision, and prescription coverage. We are growing fast and looking for high-performing leaders to help us raise the bar in healthcare sales performance.

The Role: Sales Supervisor – Telesales (Licensed) We are seeking a proven Sales Supervisor with a background in managing licensed telesales agents within a high-velocity call center environment. This is a quota-carrying leadership role where you’ll be expected to drive production, optimize conversion, and scale high-performing sales teams. You’ll oversee daily execution while ensuring every rep is positioned to hit their number and exceed it. This is not a passive management role. We want a closer-turned-leader who thrives on team-based performance, works well under pressure, and can turn KPIs into actionable coaching.

What You’ll Do

• Lead, coach, and manage a team of 10–15 licensed telesales agents focused on ACA, Medicare, or supplemental insurance plans
• Own daily, weekly, and monthly sales targets and ensure reps consistently meet or exceed production goals (e.g., call volume, conversion rate, revenue per lead, talk time, close rate)
• Conduct regular call calibrations, side-by-sides, and performance reviews with sales reps
• Collaborate with sales management to optimize workflows and real-time call strategies
• Monitor pipeline hygiene and ensure proper documentation in CRM and lead systems
• Develop individual performance improvement plans (PIPs) for underperformers
• Build sales campaigns and execute on strategic enrollment season goals (e.g., OEP, AEP, SEP)
• Drive a competitive, energetic team culture that rewards execution and accountability
• Recruit, interview, and onboard new licensed agents with the support of HR and training
• Partner with Training & QA to maintain high compliance and sales quality standards
• Analyze sales trends and funnel metrics to identify areas for optimization
  
  Key Metrics You Will Be Measured By
  • Daily agent dials and talk time
  • Quote-to-application conversion
  • Revenue per lead
  • Call-to-close ratio
  • Agent retention and average tenure
  • Team production vs. forecast
  • QA & compliance scorecards
  • Training-to-ramp time

Qualifications
2+ years in a sales leadership role within a licensed health insurance call center
Active Life & Health License (Group 1) in home state (required)
Demonstrated track record of leading successful sales teams in an inside sales model
Experience managing ACA or Medicare telesales campaigns (preferred)
Strong command of CRM software (e.g., Five9, Salesforce, Radius, or similar)
Intermediate to advanced Excel skills (v-lookups, pivot tables)
Bachelor’s degree in Business, Healthcare, or related field preferred

Who You Are
You have a closer’s mindset—but you know how to build closers, too
Comfortable running sales floor standups, pipeline reviews, and coaching huddles
Thrive in fast-paced, deadline-driven environments
Results-oriented with an analytical, metrics-first management style
Calm under pressure, and a natural motivator who lifts people up
Strong communicator with a bias toward transparency and action
Bilingual (Spanish/English) is a strong plus

What We Offer
Competitive salary + team production bonus
Health Insurance (Medical, Dental, Vision)
Generous PTO and Paid Holidays
Quarterly performance recognition and company events
Strong culture of mentorship, transparency, and upward mobility
Career development opportunities across multiple lines of business