Inside Sales Representative - Medicare

As an Inside Sales Representative, you’ll take on a fast‑paced inside sales role where real conversations drive real impact. You’ll help individuals navigate important Medicare and Individual insurance decisions, building trust quickly and guiding them toward the coverage that fits their needs. Every interaction is an opportunity to showcase your communication skills, grow your confidence, and fuel your success.

In this role, you’ll lead meaningful sales conversations, deliver an exceptional client experience from start to finish, and actively grow and retain your book of business. You’ll partner with top carriers, stay on top of product and market changes, and contribute to initiatives that elevate the overall client journey and keep Risk Strategies ahead of the industry curve.

If you’re driven, people‑focused, and excited to build a foundation in insurance sales, this role gives you the chance to learn, succeed, and grow your career from day one.

Your Impact

• Place outbound calls to customers interested in ancillary and health insurance products referred by Cornerstone’s licensed industry brokers for both the under and over 65 market.
• Respond to inbound calls from customers with service inquiries or requests for enrollment assistance.
• Cross-selling and retention management of existing book of business.
• Support and adapt to new campaigns and corporate initiatives as directed.
• Present, sell and support all new and existing policies.
• Educate customers on all aspects of insurance plans including qualification of plans, subsidiaries, etc.
• Provide objective information pertaining to coverage, annual notice of change, pharmacy/network coverage and drug formularies.
• Ensure proactive customer service and sales techniques with the highest degree of courtesy and telephone etiquette.
• Place outbound calls to Medicare beneficiaries, confirming and verifying plan enrollment.

Successful Candidate Will Have

• Education: High School diploma or equivalent.
• Experience: Proven sales record essential with a minimum of 1 year direct insurance sales experience.
• Strong customer service skills; experience using internet, Microsoft Office products and databases; exceptional verbal and written communication skills, ability to express assurance, confidence & empathy; ability to understand complex programs, including legislative updates, and possess ability to clearly and concisely explain and articulate these programs to consumers; ability to understand multiple products and multiple levels of benefits within each product; ability to handle repetitive tasks while remaining focused and productive; able to work a flexible schedule and adapt easily to change.
• Specialized knowledge, licenses, designations, etc.: Must have active and current Life and Health insurance licenses. Must possess a solid understanding of the current legislative environment (i.e., ACA). AHIP Certification and FFM Certification desired.

Risk Strategies is the 9th largest privately held U.S. brokerage firm offering comprehensive risk management advice, insurance and reinsurance placement for property & casualty, employee benefits, private client services, as well as consulting services and financial & wealth solutions. With more than 30 specialty practices, Risk Strategies serves commercial companies, nonprofits, public entities, and individuals, and has access to all major insurance markets. Risk Strategies is an Accession Risk Management Group company, with over 200 offices and more than 5,000 employees across the U.S. and Canada.

Our industry recognition includes being named a Great Place to Work, Best Places to Work in Insurance, and on the Inc. 5000 list as one of America’s Fastest Growing Private Companies. We are committed to being good stewards for our company, culture, and communities by having a strong focus on Environmental, Social, and Governance issues.