Sales Enablement and Training Manager

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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 Sales Enablement and Training Manager is a critical leadership role responsible for driving the performance and professional development of a large, remote telesales organization focused on Medicare. You will lead, mentor, and manage a team of 7+ Insurance Facilitators and instructional designers to deliver high-impact learning solutions across agent types and skill sets. You will ensure our work environment helps employees develop their skills and fosters career advancement.

• Lead and coach the training team to deliver high-impact virtual facilitation for all licensed and non-licensed agents, setting the benchmark for motivation, engagement, and mastery of complex Medicare material in both group and individual remote settings.

• Serve as the primary adult learning subject matter expert and resource allocator for high-priority, cross-functional projects. Ensure all training deliverables are strategically aligned with key organizational initiatives and business objectives.

• Direct the development, modification, and quality assurance of all instructional content, presentations, and workshops. Guarantee that all materials are accurate, engaging, and adhere to measurable learning objectives and strict compliance standards.

• Transform this data into actionable strategic insights to guide future curriculum investment and resource planning.

• Implement a systematic process for cross-functional collaboration with Operations, Quality, and executive stakeholders to proactively identify critical training needs, diagnose organizational performance gaps, and integrate best-in-class training solutions.

• Serve as the departmental liaison, ensuring clear, professional, and consistent communication regarding training performance, strategic challenges, and resource requirements with managers, colleagues, and executive leadership.

• Instill and monitor a positive, productive, and engaging virtual learning environment across the team and all trainees, ensuring group conduct promotes active participation and professional development

Strategic Leadership and Team Management:

• Lead, coach, and develop a team of 7+ Training Specialists, fostering a culture of high performance, continuous improvement, and deep subject matter expertise in Medicare telesales.

• Manage the remote training environment, ensuring consistency, engagement, and effectiveness across all virtual learning platforms and geographically dispersed learners.

• Leading large agent ramps including W2 and 1099.

Instructional Excellence and Program Oversight:

• Oversee the design, development, and delivery of comprehensive insurance facilitation and support programs, specifically tailored to Medicare products, compliance, and telesales techniques.

• Ensure all learning programs meet rigorous CMS and regulatory compliance standards, minimizing risk and maximizing ethical sales practices.

• Ownership of the Non-Licensed Agent Program (NLAP) focusing on compliance, progression, and preparation for health insurance licensing.

• Directly responsible for accelerating speed-to-competency for new Medicare agents, ensuring compliance, quality, and conversion are met during the critical nesting also known as On-the-Job Training (OJT) period.

• Implement and manage an effective Learning Management System (LMS) strategy, tracking learner progress, ensuring accountability, and leveraging data for continuous program enhancement.

Performance and Impact Measurement:

• Establish clear Key Performance Indicators (KPIs) for training success, linking learning outcomes directly to business results (e.g., speed-to-proficiency, time-to-first sale, quality scores, and agent retention).

• Regularly assess the efficacy of all educational techniques and training methodologies, including blended learning, microlearning, and role-specific simulations, to ensure maximum knowledge retention and skill transfer.

Talent Development and Career Pathing:

• Partner with Operations and HR to create clear career development pathways for sales agents and internal staff, utilizing training as a core driver for internal promotion and skill elevation.

• Champion a work environment that proactively identifies and closes skill gaps, fostering continuous professional development and career advancement opportunities for all employees.

• 3-5 years’ experience driving the performance and professional development of a large, remote telesales while managing a large team.

• Experience with Microsoft and Google Suite

• Learning Management System (LMS)

• Active Health Insurance License

• Up to date on Continuing Education Coursework

• Corporate Trainer Certified (Preferred)

• College Degree (Preferred)

Additional Information

• This role is available for individuals who reside in and have their Resident State License in one of the following states: FL, AZ, IN, NC, TN, TX, GA, MA, or UT

• This is a remote position and candidates should be comfortable working in a virtual environment.

• Flexibility in working hours may be required to accommodate participants from different time zones

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.