Medicare Sales Manager (1099 Operations) - Remote

Hi, We're Centerfield!

Supercharged customer acquisition. Centerfield delivers outcome-based digital marketing solutions and personalized omnichannel experiences for the world’s leading brands. Powered by our proprietary Dugout platform, Centerfield acquires customers at scale for leading residential service, insurance, e-commerce, and B2B brands. Centerfield’s digital experiences and digital brands, such as Business.com and BroadbandNow.com, reach more than 150 million in-market shoppers annually. Centerfield is headquartered in Silicon Beach and is proud to be recognized by Built in LA as a Best Place to Work in Los Angeles.

The Opportunity...

Are you interested in being part of a high-growth organization that values you as a teammate and provides hands-on support to help you achieve your team’s sales goals?

A subsidiary of Centerfield, QuoteManage is a national Medicare telesales brokerage firm seeking a Medicare Sales Manager to lead a fully remote team. We specialize in Medicare and senior products, helping consumers across the country find the best plans for their needs. QuoteManage leverages the digital marketing engine of our parent company, Datalot, to drive high-volume inbound calls to our licensed agents.

In this role, you will lead a team of 25+ 1099 Medicare sales agents responsible for converting inbound consumer demand into enrollments across health, prescription drug, vision, and dental plans. You will own your team’s ability to effectively convert a high volume of inbound calls into successful enrollments.

Success in this role is defined by your ability to drive conversion rates, coach agents in real time, and maximize revenue performance—especially during the high-stakes Annual Enrollment Period (AEP). You will ensure agents consistently capitalize on live call opportunities, overcome objections, and deliver a high-quality consumer experience.

QuoteManage operates in a performance-driven, incentive-heavy environment, and you will play a key role in reinforcing a culture built on accountability, competition, and results—supported by AEP-driven commissions, daily spiffs, and ongoing promotional incentives.

At the end of the day, we want every agent to be successful and proud to be part of the QuoteManage team. Come join us!

How You'll Contribute...

• Drive a high-performance sales culture across a fully remote team of 25+ independent agents, balancing accountability with energy and motivation

• Provide real-time coaching on live calls, helping agents overcome objections and close complex Medicare enrollments

• Monitor calls and deliver actionable feedback to improve close rates and maximize inbound lead conversion

• Own team performance metrics, including conversion rate, talk time, and lead utilization

• Manage scheduling and coverage across an 8am–8pm EST window to ensure full utilization of inbound demand

• Lead and engage a 1099 workforce, driving consistency, retention, and output in a contractor-based model

• Ensure adherence to CMS guidelines and Medicare marketing compliance, maintaining high-quality and ethical sales practices

• Partner with Quality, Compliance, and Workforce Management (WFM) teams to optimize performance and lead utilization

• Analyze team performance data to identify trends, coach to gaps, and drive continuous improvement

What You Bring to the Table...

• 2+ years managing Medicare sales teams in a call center or telesales environment

• Experience managing 15–25+ agents with direct accountability for performance metrics

• Deep knowledge of Medicare Advantage, Supplement, and Part D products

• Proven success in a high-volume inbound sales environment

• Experience leading teams through Annual Enrollment Period (AEP)

Bonus Points...

• Experience managing 1099 / independent contractor agents

• Background in brokerages or telesales organizations (e.g., SelectQuote, GoHealth, eHealth, Assurance IQ, etc.)

• Strong familiarity with dialers and CRM systems (Salesforce, Five9, NICE, etc.)

• Demonstrated ability to coach in real time and improve conversion rates

Important Notes...

• Full-time, fully remote position

• Must have reliable high-speed internet

• Must reside in and hold an active Resident License in one of the following states: FL, NC, TN, TX, GA, or UT

Life at Centerfield....

• Competitive total compensation, including commission

• Extensive training programs and learning resources

• Generous PTO and holiday schedule

• Industry-leading medical, dental, and vision plans

• 401(k) company match plan – fully vested on day 1

• Award-winning culture & team spirit (featured in LA Business Journal & Built In LA)

• Career growth – we promote from within!

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To learn more, visit us Here.

Interviews will take place after resumes have been screened for minimum requirements. Please note that this position is not restricted solely to the responsibilities listed above and that the job scope and responsibilities are subject to change.

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Centerfield Media is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, age, religion, sex, national origin, disability, protected veteran status, or any other characteristic protected under federal, state or local law.