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...

Centerfield is seeking a dynamic and results-driven Medicare Sales Manager to lead and support a high-performing network of independent, licensed insurance agents (1099 contractors) within our Medicare sales organization. In this role, you will oversee sales performance, drive results across the agent network, and ensure exceptional customer experiences while maintaining compliance with Medicare regulations and company standards.

The ideal candidate is an experienced sales leader with strong coaching abilities, operational discipline, and a passion for helping independent agents succeed in a fast-paced, virtual sales environment. Success in this role means driving revenue growth, improving sales performance, maintaining compliance excellence, and fostering a positive, customer-focused culture across the agent network.

This is a remote position; however, Centerfield is currently registered to employ individuals residing only in the following states: Alabama, Arizona, Colorado, Florida, Georgia, Indiana, North Carolina, South Carolina, Tennessee, Texas, and Utah. Candidates must reside in one of these states to be considered for this opportunity.

How You'll Contribute...

• Monitor a network of independent, licensed Medicare insurance sales agents (1099 contractors) operating in a virtual environment

• Develop and execute sales strategies that drive revenue growth and maximize Medicare sales opportunities across the agent network

• Monitor agent production and performance metrics and analyze trends to identify optimization opportunities

• Ensure compliance with CMS regulations, Medicare marketing guidelines, and company sales standards across the independent agent network

• Collaborate cross-functionally with Quality, Compliance, Operations, and Leadership teams to support business initiatives

• Stay informed on Medicare regulations, industry changes, and competitive market trends

• Foster a collaborative, engaged, and customer-centric culture across the agent network

• Promote accountability, operational excellence, and ethical sales practices across the agent network

• Support continuous improvement initiatives that enhance agent performance and customer satisfaction

What We're Looking For...

• Active insurance license and current Medicare certification required

• Strong verbal and written communication skills

• Excellent sales leadership, customer service, and relationship management abilities

• Strong organizational skills with exceptional attention to detail

• Ability to manage multiple priorities and meet deadlines in fast-paced environments

• Team-oriented mindset with strong collaboration and leadership skills

• Strong problem-solving and decision-making abilities

• Ability to take ownership of work and make thoughtful, calculated decisions

• Passion for coaching, mentorship, and agent development

• Comfort operating within an independent contractor (1099) sales model

• Commitment to compliance, ethical sales practices, and operational excellence

• Proven track record exceeding sales and performance goals

Bonus Points...

• Experience leading high-volume Medicare sales teams, including independent contractor (1099) or commission-based sales forces

• Strong understanding of CMS compliance requirements and Medicare regulations

• Experience improving sales processes, coaching strategies, or operational workflows

• Passion for agent development and customer experience excellence

• Experience supporting remote or virtual, distributed sales teams

Life at Centerfield...

• This is a remote position open to applicants who currently reside in one of the following states: California, Florida, Minnesota, New Jersey, New York, Ohio, Oregon, or Washington.

• Competitive salary + generous quarterly bonus

• Unlimited PTO – take a break when you need it!

• Industry-leading medical, dental, and vision plans + generous parental leave

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

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

• Paid charity and volunteer days (local mentor programs, adopt a pet, beach cleanup, etc.)

• Career growth – we enjoy promoting from within!

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AI & Interview Policy

At Centerfield, we use AI tools internally to support efficiency and fairness in our hiring process, including resume screening and administrative tasks.

Candidates are welcome to use AI tools ethically to prepare for interviews, such as practicing responses or researching questions. However, all responses during the interview process should reflect your own knowledge, experience, and judgment.

The use of AI tools to generate responses during live interviews, technical assessments, or written submissions is not permitted unless explicitly stated otherwise.

To learn more, visit us Here.

Interviews will take place after resumes have been screened for the 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.

For more information about our collection, use, and disclosure of your personal information in connection with our evaluating your candidacy, please visit our Privacy Policy at https://www.centerfield.com/privacy-policy/.

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.