Director of Sales

About the role

As a Director of Sales at Medallion, you’ll play a pivotal role in scaling our Enterprise business. You will lead a team of high-performing Account Executives who are responsible for driving new business, expanding strategic accounts, and building long-term relationships with the nation’s largest healthcare organizations.

This is a highly visible leadership position ideal for a strategic, metrics-driven sales leader who thrives in fast-paced environments and excels at coaching teams through complex sales cycles. You’ll partner closely with cross-functional leaders across Marketing, Customer Success, Product, and Finance to shape and execute our go-to-market strategy.

This role reports to the Chief Revenue Officer, and base compensation may range from $165,000-$200,000. In addition to base salary, Medallion offers variable compensation, equity, and a comprehensive benefits package. Final compensation will be determined based on a variety of factors including skills, experience, and location.

What you'll do

• Sales Leadership & Execution
• • Lead and scale a team of quota-carrying Enterprise Account Executives, fostering a performance-driven, collaborative, and inclusive culture
  • Build and reinforce best-in-class sales methodology grounded in MEDDPICC and Command of the Message
  • Set strategic account plans and partner with reps on pipeline development, deal execution, and territory optimization
  • Develop and manage sales forecasts, territory plans, and KPIs to ensure predictability and consistent growth
  • Partner with Sales Enablement to onboard, coach, and up-level team performance with ongoing training and development
• Strategy & Cross-Functional Collaboration
• • Partner with executive leadership to define and iterate on the go-to-market strategy for the Enterprise segment
  • Work closely with Revenue Operations to assess pipeline health, improve sales efficiency, and enhance forecasting accuracy
  • Collaborate with Marketing to inform campaign targeting and generate high-quality pipeline
  • Act as a voice of the customer internally, bringing structured feedback to Product and GTM teams to influence roadmap and messaging
  • Engage with high-priority prospects and customers as an executive sponsor and strategic partner
• Process Optimization & Scale
• • Design and implement scalable, repeatable sales processes to support rapid growth
  • Evaluate and refine sales tools and CRM workflows to increase team productivity and visibility
  • Drive rigorous deal reviews and implement mutual action plans to reduce deal slippage and increase conversion
  • Leverage data to experiment, learn, and adapt tactics to win in a competitive and evolving market

Qualifications

• 8+ years of experience in Enterprise B2B SaaS sales, with 4+ years directly managing quota-carrying sales teams
• Demonstrated success navigating complex, multi-threaded sales cycles within enterprise accounts
• Track record of exceeding revenue goals and scaling sales teams in high-growth environments
• Fluency in MEDDPICC, Command of the Message, and modern sales tech stacks (e.g., Salesforce, Gong, etc.)
• Demonstrated ability to build strategic account plans and close enterprise deals
• Deep understanding of SaaS economics and how to drive deal velocity while protecting margin
• Exceptional communication, executive presence, and negotiation skills — confident in engaging at the C-Suite level
• A player-coach mentality with willingness to get in the trenches when needed