Telesales Sr. Supervisor â Licensed Insurance Sales
Telesales Sr. Supervisor â Licensed Insurance Sales
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Job Description
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 youll be expected to drive production optimize conversion and scale high-performing sales teams. Youll 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 Youll Do
- Lead coach and manage a team of 1015 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)
Bachelors degree in Business Healthcare or related field preferred
Who You Are
You have a closers mindsetbut 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
Required Experience:
Manager
Employment Type
Full-Time
