Job Description

At Optimyl Benefits, we're transforming the healthcare landscape for small and mid-sized employers by delivering accessible, high-quality, and easy-to-use self-funded and level-funded health plans. Built by industry experts, Optimyl offers innovative solutions that empower brokers to help businesses provide competitive benefits packages that truly improve the lives of their employees and families.

Overview

The Regional Sales Representative is responsible for generating profitable growth by building strong partnerships within the Upper Midwest in the 2-50 employee range. This role reports to the Regional Vice President of Sales and is central to our broker-first distribution model.

Responsibilities

• Make 40+ outbound calls daily to targeted brokers in the market space
• Create awareness of Optimyl’s offerings, including plan design, cost-containment strategies, and network flexibility
• Train brokers on Optimyl’s positioning, quoting tools, and sales process
• Provide ongoing, white-glove support through quoting, underwriting, and implementation
• Collaborate with brokers to develop effective selling strategies for their employer clients
• Communicate updates on product offerings, rate changes, and network configurations
• Build strong working relationships with Account Management for seamless implementation
• Track group-level data and activities in the CRM for accurate forecasting and reporting
• Meet daily activity metrics and provide market feedback to the RVP
• Travel within the region (15-20%) to deepen broker relationships and close key deals

Compensation

• Total Compensation: Salary + Commission + Bonus
• First-Year Expected Income: $70,000 - $85,000
• Target Annual Compensation: $125,000 - $250,000
• Incentives: All-inclusive sales trips for top performers

Ideal Profile

• 2+ years of B2B sales or broker distribution experience
• Active Life & Health license in your state or ability to obtain once onboarded
• Self-motivated, proactive, and ability to operate independently with strong follow-through
• Excellent verbal and written communication skills, with confidence in phone and in-person selling
• Highly organized with the ability to manage multiple priorities and shifting timelines
• Track record of executing sales strategies and influencing client decision-making

Core Competencies

• Holds self and others to high performance standards
• Thinks critically and takes decisive action based on market insights
• Builds trust and rapport with brokers, teammates, and internal partners
• Communicates clearly and confidently in writing, on the phone, and in meetings

Why Work at Optimyl?

• Competitive Pay & Benefits: Medical, dental, vision, life insurance, short- and long-term disability, 401(k) with match
• Career Growth: Ongoing training and opportunity to grow with a scaling company
• Supportive Culture: Open, collaborative, and entrepreneurial team environment
• Generous Time Off: 15 vacation days, 8 sick days, and 11 paid holidays annually
• Annual Sales Retreat: Trip to Florida to recharge and collaborate with company employees in other regions.
• Make a Difference: Help reshape how healthcare is delivered to the employers who need it most.

Optimyl Benefits is an equal opportunity employer. We celebrate diversity and are committed to creating an inclusive environment for all employees.

Industry

Insurance

Employment Type

Full-Time; On-Site

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