Enterprise Account Executive

Toothio is a cutting-edge labor marketplace start-up transforming how dental practices hire and dental professionals find work by providing on-demand, skilled, and dependable dental staff. We connect dental hygienists and assistants with dental practices who need support. Our mission is to create a seamless, efficient experience for both dental practices and professionals alike. Toothio is backed by Craft Ventures, among other strategic investors.

As an Enterprise Account Executive, you’ll play a key role in both net-new sales and partner retention. You’ll be responsible for driving conversations with DSO offices, demonstrating the value of our AI recruiter, Mel, and converting interest into long-term relationships. This role blends strategic sales execution, outbound prospecting, and client success—ideal for someone who thrives in a startup-paced environment and is passionate about disrupting an outdated industry.

• Prospect and cold call DSO offices, building and maintaining a strong pipeline of new business opportunities.
• Present and sell Toothio’s AI Recruiter, Mel, and other staffing solutions to new and partnered offices.
• Develop deep relationships with partners to ensure customer satisfaction, retention, and expansion.
• Partner with internal teams to deliver seamless onboarding and identify upsell/cross-sell opportunities.
• Track and manage sales activity using CRM tools, reporting progress and insights regularly.
• Stay on top of market trends, industry news, and DSO needs to position Toothio competitively.

• 1+ year preferred in tech, SaaS, or healthcare/dental sales—DSO or dental industry experience is a plus.
• Proven ability to manage full sales cycles, from prospecting to close and post-sale relationship management.
• Strong communicator with experience selling to office and regional-level decision-makers.
• Resilient, coachable, driven, and comfortable working in a fast-moving, high-performance environment.
• Highly organized and able to manage multiple priorities under pressure.
• A team player who values collaboration and brings a positive, solutions-oriented mindset to every interaction.

• Fully remote — work from anywhere in the U.S.
• Unlimited PTO for work-life balance
• Comprehensive Benefits and Compensation: $50K Base + 60K Commissions (Uncapped) - Medical, Dental, and Vision
• High-growth, startup culture with a supportive, innovative team
• Opportunity to join a category-defining company making real impact in dental staffing

Join us if you’re ready to sell smarter, support better, and make a difference in an industry ready for change.

To apply, send your resume and a brief note about why you’d be a great fit to Claudia Taylor at

• Associate

• Full-time

• Sales and Business Development

• Hospitals and Health Care