Enterprise Account Executive

About Us

We are the leading player in the SaaS analytics and workflow space for dental practices, launched in 2015 to help dentists manage and grow their practices. Our best-in-class tech makes it more fulfilling to be a dental professional and easier to be a patient. Nearly 9,000 dental practices utilize our platform to practice smarter, generating an average top-line production increase of 50% in the first 12 months.

Whether a practice wants a comprehensive 2-year growth plan or simply a more effective Morning Huddle, we take the busy work out of growth. Our platform helps practices find patients, schedule them, follow up, collect payments, file their forms, design their treatment plans, and so much more. If the profile below sounds like you - let’s talk!

We’re looking for a seasoned Enterprise Account Executive to own and expand relationships with large, multi-location Dental Service Organizations (DSOs). This is a high-impact role selling complex, consultative solutions into executive-level buyers.

• Own the full sales cycle for enterprise and multi-location DSOs (typically 11–200+ locations)
• Lead discovery with DSO executives, operations leaders, and marketing leadership to uncover true operational pain points
• Sell a multi-product platform (analytics, engagement, payments, revenue cycle management) using a value-based, outcomes-driven approach
• Navigate long, non-linear sales cycles involving pilots, phased rollouts, and enterprise procurement
• Partner closely with Customer Success, Product, and Partnerships to design scalable solutions and reduce time to value
• Network and build long-term, trusted relationships with DSO leadership
• Maintain accurate pipeline management and forecasting in Salesforce
• Represent DI as a strategic partner within the DSO ecosystem

• Ability to independently run complex DSO deals from first conversation to enterprise-wide rollout
• Consistent closing of six- and seven-figure ARR opportunities
• High forecast accuracy and strong deal discipline
• Ability to push back on prospects when deal structure or fit is misaligned

• 5+ years of closing experience in B2B SaaS
• 2–3+ years selling enterprise or multi-location accounts
• Direct experience selling into DSOs, healthcare groups, or similarly complex multi-site organizations strongly preferred
• Proven ability to sell consultatively to executive, operational, and clinical stakeholders
• Comfort with ambiguity, long sales cycles, and multi-threaded deals
• Strong pipeline management, forecasting, and CRM discipline
• Executive presence and strong communication skills

• Flexible Time Off + 10 paid holidays
• Competitive Medical, Dental & vision offerings, including free medical premiums for employees, with buy up plan options, AND we match your HSA contributions.
• Company sponsored Life, Disability & AD&D
• Mental Health support programs, Cellphone & Gym membership Discounts
• 100% Paid Parental Leave
• 401K Retirement savings plan with company match up to 5.5% + unlimited access to financial advisors.
• Tuition Reimbursement program

All offers of employment are contingent upon successful completion of a background check, which may include verification of education, employment history, and other credentials. By applying, you confirm that all information you have provided is accurate and complete to the best of your knowledge, and you understand that misrepresentation may result in disqualification or termination.