Head of Sales (B2B) (Remote)

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.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.
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; 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
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

Excellent sales leadership, customer service, and relationship management abilities
Ability to manage multiple priorities and meet deadlines in fast-paced environments
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
This is a remote position open to applicants who currently reside in one of the following states: Competitive salary + generous quarterly bonus
Industry-leading medical, dental, and vision plans + generous parental leave
Paid charity and volunteer days (local mentor programs, adopt a pet, beach cleanup, etc.)
LI-Remote
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