Director of Customer Success, Enterprise

Lead the Future of Dentistry. Overjet is the world-leader in dental AI. Already, thousands of dental providers and insurers rely on our platform to deliver the best possible care. Now, we’re looking for talented people to fulfill our mission: improve oral health for all. Overjet is where builders become leaders. Everyone here loves to make new things: new products, new partnerships, new content, and a new category of AI technology. And as Overjet grows ridiculously fast, so will you. Simply put, there’s no better place to accelerate your career. Come join us! The Role As Director of Customer Success, Enterprise at Overjet, you will lead Customer Success for some of our largest, most strategic, and most complex customers, with a primary focus on Dental Support Organizations (DSOs). You will lead and develop a team of Customer Success Managers while also serving as a senior strategic partner to key enterprise customers. This is a hands-on, player-coach leadership role responsible for driving retention, adoption, expansion, and long-term customer value across complex, multi-location organizations. You will bring greater structure and consistency to Overjet’s enterprise Customer Success motion by building scalable playbooks, strengthening executive relationships, and using customer and business data to proactively identify risk and growth opportunities. Responsibilities • Drive Retention & Expansion: Own net revenue retention, churn reduction, product adoption, and expansion across Overjet’s strategic enterprise and DSO customers. • Lead & Develop the Team: Recruit, coach, and manage a high-performing Customer Success team with clear goals, accountability, and performance expectations. • Build the Enterprise CS Playbook: Develop scalable customer success strategies, engagement models, health frameworks, and risk mitigation plans for the enterprise segment. • Own the Customer Journey: Ensure strong execution across onboarding, adoption, renewal, and expansion, with proactive management of customer health, risk, and growth opportunities. • Build Strategic Customer Relationships: Develop trusted relationships with executive, clinical, and operational stakeholders and ensure customers realize measurable value from Overjet. • Partner Cross-Functionally: Work closely with Sales, Product, Marketing, and other teams to improve the customer experience, surface customer insights, and influence business priorities. • Drive Visibility & Accountability: Maintain accurate forecasts and reporting on retention, renewals, customer health, and expansion, and lead quarterly complaint trend reviews to support medical device regulatory compliance. Qualifications • 7+ years of experience in Customer Success, Account Management, Strategic Accounts, or a related customer-facing function in B2B SaaS. • 3+ years of experience leading and developing Customer Success or Account Management teams. • Proven experience managing complex enterprise or strategic customers with multiple stakeholders and executive-level relationships. • Demonstrated success driving retention, renewals, adoption, and expansion across a meaningful customer portfolio. • Strong executive presence, commercial judgment, and ability to navigate complex customer conversations and escalations. • Experience building or improving Customer Success processes, playbooks, metrics, and operating rhythms in a scaling organization. • Strong analytical skills and ability to use customer and business data to identify risk, diagnose problems, and drive action. • Experience using AI, automation, and customer success tools to improve team efficiency, customer insights, and decision-making. • Experience with DSOs, multi-location healthcare organizations, dental technology, or vertical SaaS is strongly preferred. Why Overjet? • Competitive Compensation and Equity • Hybrid workplace that provides flexibility, vibrant in-person workspaces, and the ability to build strong connections across all of Overjet - regardless of location • 401k plans with a matching program • Medical, Dental and Vision coverage: 99% employee premium covered, 75% dependent premium covered • Life and AD+D Insurance • 8 weeks Paid Parental Leave • Optional HSA with Employer contribution • Flexible Time Off and company paid holidays • Annual Learning and Development Stipend Our Hybrid Workplace We have a unique hybrid workplace at Overjet — which combines the teamwork of meeting in person, with the flexibility of working from anywhere. Many of our positions are based in San Mateo, New York City, Boston, and Salt Lake City. The Jetters who live in these “geo-hubs” come to the office on Tuesdays and Wednesdays, while having the option to work from home the rest of the week. Our People Team is happy to answer any questions about what hybrid work means for your specific role! Overjet's Values • Excellence: Aim Higher • Velocity: Quickly Deliver Results • Ownership: Go the Extra Mile • Win-win: Care Deeply Company Recognition • Included on Best Places to Work by BuiltIn lists in 2026 https://www.linkedin.com/posts/overjet_were-incredibly-proud-to-share-that-overjet-activity-7414346196640718848-cFGG?rcm=ACoAAChRVxsB6jrIO04hl4zDCmIVA0qDSepyiRA&utm_medium=member_desktop&utm_source=share: #3 overall in the US, #1 in NYC, #1 in San Francisco, and #2 in Boston • #4 on FastCompanys's Most Innovative Companies list in Healthcare for 2026 https://www.fastcompany.com/91497221/healthcare-most-innovative-companies-2026 • Named one of the TIME Best Inventions of 2024 https://www.overjet.com/blog/overjet-named-to-time-best-inventions-of-2024 • Recognized in Newsweek’s Most Loved Workplaces in America 2024 https://www.newsweek.com/top-20-most-loved-workplaces-america-2024-1960025 • Won the Dental Health category at the Digital Health Awards 2024 https://www.digitalhealthhub.org/awards/2024/2024-winnersand 2024 Best Places to Work by Built In https://www.overjet.com/blog/overjet-is-one-of-built-in-s-best-startups-to-work-for-in-2024 • Recognized as one of the Top Startups of 2023 by LinkedIn https://www.overjet.com/blog/overjet-named-to-linkedin-s-2023-top-startups-list-in-united-states • Included on the definitive 2022 Forbes AI 50 https://www.prnewswire.com/news-releases/overjet-named-to-forbes-ai-50-list-of-most-promising-ai-companies-shaping-the-future-301544947.html EEOC Overjet is an equal opportunity employer. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. We believe diversity enriches our team so we hire people with a wide range of identities, backgrounds, and experiences. Even if you don't meet 100% of the qualifications for this job, we strongly encourage you to apply! If you are a Colorado resident: Please contact us by emailing recruiting@overjet.ai to receive compensation and benefits information for this role. Please include the job title in the subject line of the email.