Director of Sales

Job Summary:

As the Director of Sales at Medefy Health you will lead and scale our regional and territory sales teams, driving revenue growth through strategic leadership, sales execution, and operational excellence. You’ll play a pivotal role in shaping Medefy’s go-to-market strategy, mentoring a high-performing sales team, and partnering closely with executive leadership to expand our national footprint.

About our awesome company, Medefy Health...

Medefy Health (www.Medefy.com) is a leading SaaS benefits navigation company, dedicated to simplifying the way employees’ access and utilize their benefits. Our mission is to drive better health and financial outcomes for our users while supporting HR teams and broker partners with seamless, data-driven solutions.

Our company is headquartered in Tulsa, OK. We’re proud to be Oklahoma’s #1 fastest-growing company and rated by Inc. Magazine as the 37th fastest-growing tech company and the 288th fastest-growing company overall in the USA, and our story is still being written!

Healthcare is only getting more complicated, and more expensive, for employers and their employees. This is where Medefy Health comes in. We’re on a mission to eliminate the stress on hard-working families caused by an impossible to navigate healthcare system. All while saving them, and their employers, a significant amount of time and money. We demolish barriers between healthcare and the people who need it, and we need your help to further our mission!

Job Duties & Responsibilities:

• Lead, coach, and grow a team of regional and territory Sales Executives and support staff.
• Set clear KPIs and accountability frameworks to drive predictable performance.
• Use data and analytics to project sales, identify new markets, and inform strategy.
• Develop and execute strategic business plans that expand Medefy’s customer base.
• Drive new business through personal prospecting and relationship building nationwide.
• Collaborate cross-functionally with Marketing, Customer Success, and Product to align goals and optimize outcomes.
• Own the pipeline: ensure CRM accuracy, forecast reliably, and track goal attainment.
• Represent Medefy at key industry events, conferences, and partner engagements.
• Hire, onboard, and develop exceptional sales talent, ensuring a culture of accountability and growth.
• Support operational excellence through budgeting, territory planning, and performance evaluations.
• Performs other duties as assigned.

You must have at least the following:

• Bachelor’s degree in Business, Marketing, or related field—or equivalent experience.
• 2+ years of experience leading a multi-person sales team, including remote management.
• 3–5 years of experience as an individual producer with a record of exceeding goals.
• Proven success growing year-over-year team revenue.
• Experience in benefits technology, brokerage, or healthcare services.
• Strong command of structured, data-driven sales processes.
• Experience with CRM and enablement platforms (e.g., HubSpot, Salesforce, ZoomInfo).
• Exceptional communication, presentation, and influencing skills.
• Strong leadership, coaching, and organizational abilities.

It would be great if you have:

• SaaS or software sales experience.
• Mid-market sales expertise.
• Technically adept and adaptable to evolving tools and systems.
• High level of conscientiousness and integrity.

Supervisory Duties:

• Hires and trains regional and local sales executives and support staff
• Organizes and oversees the schedules, territories, and performance of regional and local sales executives
• Conducts performance evaluations that are timely and constructive
• Handles discipline and termination of employees in accordance with company policy

Travel Requirements Percentage: Up to 75% may be required. Remote work enabled.

Physical and Mental Requirements:

Remote Work Environment:

• This position is performed remotely in a home-office setting.
• The employee must ensure a quiet, private workspace free from distractions and suitable for video conferencing and focused work.
• A reliable high-speed internet connection is required.

Physical Demands:

• Prolonged periods of sitting at a desk and working on a computer (up to 8+ hours per day).
• Frequent use of a computer keyboard, mouse, and screen; ability to type at least 55 WPM.
• Occasional movement within the home office environment (e.g., retrieving office supplies or documents).
• Vision abilities required include close vision for computer use and reading documentation, with or without corrective lenses.

Communication Requirements:

• Must be able to communicate effectively in English using written and verbal channels (email, chat, video conferencing, phone).
• Must be able to read and interpret complex written information such as healthcare documentation, performance reports, and company procedures.
• Must be responsive and present during scheduled working hours and team communications, including virtual meetings and collaboration platforms.

Cognitive and Emotional Demands:

• Ability to manage multiple complex tasks and competing priorities in a high-paced environment.
• Strong critical thinking and decision-making skills with attention to detail.
• Ability to exercise independent judgment and problem-solving under time constraints.
• Must be able to adapt quickly to changing workflows, operational needs, and team dynamics.
• Must maintain a high level of confidentiality and discretion in handling sensitive information.
• Requires emotional resilience, especially when assisting users in distress or resolving escalated member concerns.
• Must be able to maintain composure and a professional demeanor under pressure.

Work Schedule & Attendance:

• Must be punctual, dependable, and maintain performance expectations without direct on-site supervision.

**Job description is not a comprehensive listing of all the activities, duties or responsibilities that are required of the employee. Duties, responsibilities, and activities may change, or new ones may be assigned at any time with or without notice.