Senior Level Medicare Sales Representative Jobs
Senior level medicare sales representative jobs place experienced professionals in charge of territory strategy, complex enrollment pipelines, and the sales teams or book-of-business outcomes that define results at this stage. Openings concentrate across Insurance, Technology & Software, and Healthcare & Medical Services, with a mix of field-based, hybrid, and remote roles, and employers like CVS Health, Banner Health, and Salem Infotech hiring at this level now.
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See related jobsWelcome to Transitions Benefit Group, your go-to resource for everything benefits related. For more than a decade, we’ve provided people with the resources and guidance needed to make an informed decision about their Medicare, retirement, and health insurance needs
SUMMARY
Leads the implementation of the sales strategy and delivers business growth, profitability, and customer retention in alignment with the business strategy and financial objectives. Responsible for achieving set revenue targets, setting team sales goals, expanding the company's market share in channel or line of business, and managing the sales team to ensure maximum productivity and efficient use of resources. Performs Sales Duties
ESSENTIAL DUTIES AND RESPONSIBILITIES
Develops strategic sales plans to achieve targets.
Leads and motivates the sales team to maximize performance.
Analyzes market trends to identify opportunities and challenges.
Manages client relationships to ensure satisfaction and retention.
Coordinates with marketing to align sales strategies.
Monitors and reports on sales metrics.
Oversees budgeting and financial forecasting for sales.
Complies with agency management system data standards and data integrity (enters complete and accurate information);
Performs all duties in accordance with all company policies and procedures, and all federal, state and local laws, wherein the Company operates.
Performs other duties as assigned.
QUALIFICATIONS
EDUCATION / EXPERIENCE
Bachelor's Degree in business administration or related field or equivalent combination of education and experience
Six (6) or more years industry sales experience
Three (3) or more years sales strategy and market analysis experience
Demonstrated progressive career experience in sales management
Valid Insurance License
SKILLS
Strong understanding of sales strategy techniques, interpreting sales metrics and market data, and customer relationship management
Knowledge of the insurance industry procedures, practices and terminology
Working knowledge of federal, state and local laws as well as industry regulations
Knowledge of supervisory techniques to accomplish instruction, motivation and training of personnel
Skill in maintaining effective working relationships with all customers, employees and the general public
Strong planning, organizational and prioritization skills
Excellent communication and collaboration skills, capable of effectively engaging with diverse teams and stakeholders
Skill in negotiating and problem solving to resolve internal and external conflicts
Proficient in Microsoft Office Suite
Ability to communicate effectively, both orally and in writing, in a constructive manner
Ability to demonstrate organizational leadership qualities and develop and foster trusting relationships
Ability to analyze and accurately interpret budgets, financial reports and statistical data
#LI-REMOTE
#LI-GS1
Welcome to Transitions Benefit Group, your go-to resource for everything benefits related. For more than a decade, we’ve provided people with the resources and guidance needed to make an informed decision about their Medicare, retirement, and health insurance needs
SUMMARY
Leads the implementation of the sales strategy and delivers business growth, profitability, and customer retention in alignment with the business strategy and financial objectives. Responsible for achieving set revenue targets, setting team sales goals, expanding the company's market share in channel or line of business, and managing the sales team to ensure maximum productivity and efficient use of resources. Performs Sales Duties
ESSENTIAL DUTIES AND RESPONSIBILITIES
Develops strategic sales plans to achieve targets.
Leads and motivates the sales team to maximize performance.
Analyzes market trends to identify opportunities and challenges.
Manages client relationships to ensure satisfaction and retention.
Coordinates with marketing to align sales strategies.
Monitors and reports on sales metrics.
Oversees budgeting and financial forecasting for sales.
Complies with agency management system data standards and data integrity (enters complete and accurate information);
Performs all duties in accordance with all company policies and procedures, and all federal, state and local laws, wherein the Company operates.
Performs other duties as assigned.
QUALIFICATIONS
EDUCATION / EXPERIENCE
Bachelor's Degree in business administration or related field or equivalent combination of education and experience
Six (6) or more years industry sales experience
Three (3) or more years sales strategy and market analysis experience
Demonstrated progressive career experience in sales management
Valid Insurance License
SKILLS
Strong understanding of sales strategy techniques, interpreting sales metrics and market data, and customer relationship management
Knowledge of the insurance industry procedures, practices and terminology
Working knowledge of federal, state and local laws as well as industry regulations
Knowledge of supervisory techniques to accomplish instruction, motivation and training of personnel
Skill in maintaining effective working relationships with all customers, employees and the general public
Strong planning, organizational and prioritization skills
Excellent communication and collaboration skills, capable of effectively engaging with diverse teams and stakeholders
Skill in negotiating and problem solving to resolve internal and external conflicts
Proficient in Microsoft Office Suite
Ability to communicate effectively, both orally and in writing, in a constructive manner
Ability to demonstrate organizational leadership qualities and develop and foster trusting relationships
Ability to analyze and accurately interpret budgets, financial reports and statistical data
#LI-REMOTE
#LI-GS1
See All 5 Senior Level Medicare Sales Representative Jobs
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Senior Level Medicare Sales Representative Jobs: Frequently Asked Questions
How do I get a senior level medicare sales representative job?
Employers at this level look for candidates who can demonstrate consistent territory growth, independent management of a complex book of business, and experience guiding junior agents or coordinating cross-functional enrollment campaigns. A current state health insurance license is typically required, and candidates with a history of leading Medicare Advantage or Part D sales through full enrollment cycles tend to have a clear edge over generalist applicants.
Which companies hire senior level medicare sales representatives?
Companies hiring senior level medicare sales representatives right now include CVS Health, Banner Health, and Salem Infotech, based on current listings on Migrate Mate as of November 2026. Hiring at this level is led by regional and national health insurance carriers, Medicare Advantage plan sponsors, and benefits distribution organizations that need experienced producers to anchor high-volume enrollment markets.
Are there remote senior level medicare sales representative jobs?
Yes, though many senior roles carry some field or community engagement component given the relationship-driven nature of Medicare sales. About 60% of senior level medicare sales representative openings are remote or hybrid as of November 2026, reflecting employer flexibility for high performers who can manage territory outcomes independently without requiring on-site supervision.
What makes a medicare sales representative role senior level?
Senior level roles are defined by independent ownership of a territory or account portfolio, responsibility for hitting enrollment targets without close supervision, and often a mentoring or lead function over junior agents. At this stage, employers expect candidates to shape sales strategy, manage complex client relationships, and contribute to plan or product growth beyond simply executing assigned leads.
Which industries hire the most senior level medicare sales representatives?
Senior Level medicare sales representative roles concentrate in Insurance, Technology & Software, and Healthcare & Medical Services, based on current listings on Migrate Mate as of November 2026. These sectors drive hiring at this level because they operate large Medicare-eligible member bases, manage multi-line benefit products, and rely on senior producers to protect retention and lead annual enrollment period performance.