Regional Sales Director, Mid Market

Optimyl Benefits; Denver (CO); Remote; USD 140,000 - 160,000; Full time

Job summary

A leading company in healthcare transformation seeks a Regional Sales Director who will generate growth by forming partnerships with brokers focused on mid-sized employers. The ideal candidate will have a track record in B2B sales, particularly within health insurance, and will play a vital role in expanding the company's broker distribution model.

Benefits

Medical, dental, vision insurance

Short- and long-term disability

401(k) with match

15 vacation days

Supportive collaborative culture

Generous performance-based incentives

Qualifications

• 2+ years of B2B sales or broker distribution experience required.
• Must have life & health license or be able to obtain it promptly.
• Proactive with excellent communication skills.

Responsibilities

• Make 40+ outbound calls daily to targeted brokers.
• Train brokers on Optimyl’s offerings and sales process.
• Travel within the region (20–30%) to deepen relationships.

Skills

Communication

Sales Strategy Execution

Organizational Skills

Education

Active Life & Health license

Job description

2 days ago Be among the first 25 applicants

Note: This is a remote position, however the individual must be located in the Denver metropolitan area.

At Optimyl Benefits, we're transforming the healthcare landscape for 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.

Our mission is ambitious—and we're already making waves. By joining our team, you'll have the opportunity to make a tangible impact while developing your skills alongside a collaborative, tight-knit group of professionals.

Overview

The Regional Sales Director is responsible for generating profitable growth by building strong partnerships within the regional broker community focused on mid-sized employers (51+ enrolled). 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 mid-market space
• Create awareness of Optimyl’s offerings, including plan design, cost-containment strategies, and network flexibility
• Recruit and onboard brokers who specialize in 51+ enrolled groups
• 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 (20–30%) to deepen broker relationships and close key deals

Ideal Profile

• 2+ years of B2B sales or broker distribution experience (health insurance experience strongly preferred)
• Active Life & Health license in your state (or ability to obtain promptly)
• Self-motivated and proactive—able 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

Compensation

• Total Compensation: Salary + Commission + Bonus
• Average Annual Income: $200,000
• First-Year Expected Income: $75,000 – $130,000
• Incentives: All-inclusive sales trips for top performers

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
• 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.

Seniority level

• Seniority level

  Entry level

Employment type

• Employment type

  Full-time

Job function

• Job function

  Sales and Business Development

• Industries

  Insurance

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