Director, Scaled Success - SMB

What you'll do:

We're seeking a Director of Scaled Success to lead our SMB Customer Success motion and own the health of our largest, highest-velocity customer segment. This leader will be accountable for driving Gross Revenue Retention (GRR) of 85%+ across our SMB book of business by building and running a scaled engagement model that blends proactive adoption programs with a rigorous, data-driven retention and win-back engine.

This is a hands-on leadership role: you'll set strategy, build repeatable playbooks, and manage a team of four — two Scaled Adoption Specialists focused on driving product adoption at scale, and two Retention Specialists focused on saving at-risk accounts and winning back customers who have already churned. You'll be the operational owner of SMB retention outcomes and a key partner to Sales, Product, Support, and Ops in shaping how Dental Intelligence delights and protects its customer base.

Outcomes you’ll own:​​

• Retention & Revenue Outcomes
• • Own SMB gross revenue retention (GRR) performance against an 85%+ target, with full visibility into churn drivers, save rates, and win-back conversion
  • Build and maintain a health-scoring and risk-signal framework to flag accounts before they reach a cancellation request
  • Partner with Finance/Ops to forecast churn risk and retained revenue on a monthly and quarterly cadence
  • Own the end-to-end cancellation workflow — from early warning signals through save attempts, final disposition, and post-churn win-back outreach
• Scaled Adoption
• • Direct the Scaled Adoption Specialists in designing and executing both 1-to-many and 1:1 engagement programs that drive feature adoption and reduce churn risk across the SMB base
  • Define adoption milestones tied to retention outcomes and ensure the team is proactively closing adoption gaps before they become risk signals
  • Work closely with a scaled success content team and CS Ops to continuously test and refine outreach cadences, content, and triggers to improve adoption program ROI at scale.
  • Clearly and effectively report on the results of these scaled adoption efforts so impact can be seen by the business as a whole.
• Retention & Win-Back
• • Direct Retention Specialists (2) in managing the incoming cancellation pipeline — triaging requests, running save conversations, and negotiating outcomes that protect revenue while addressing the customer's underlying concern
  • Build a structured win-back motion for customers who have already been booked for churn, including segmentation, outreach cadence, and reactivation offers
  • Establish clear playbooks, talk tracks, and escalation paths so save and win-back outcomes are consistent and coachable, not dependent on individual heroics
• Team Leadership
• • Coach, and develop a team of 4 (2 Scaled Adoption Specialists, 2 Retention Specialists), setting clear goals, KPIs, and career paths for each function
  • Run weekly pipeline/risk reviews and monthly performance reviews against retention and adoption targets
  • Foster a culture of ownership, urgency, and customer empathy balanced with commercial discipline
• Cross-Functional Partnership
• • Serve as the voice of the SMB customer in Product and Engineering roadmap discussions, surfacing adoption and retention insights that should influence the roadmap
  • Partner with Sales and Onboarding to ensure smooth handoffs into the scaled SMB post onboarding experience, ensuring new customers are set up for long-term retention from day one
  • Work with Marketing/Lifecycle teams to align scaled communications and campaigns with retention priorities
  • Report retention performance, risk trends, and program outcomes to CS leadership and cross-functional stakeholders

What Success Looks Like:

• Drive SMB GRR consistently at or above 85%
• A predictable, forecastable churn pipeline with early-warning coverage across the vast majority of the book
• Measurable lift in product adoption metrics tied directly to scaled adoption efforts
• A win-back program that recovers a meaningful percentage of previously churned revenue
• A high-performing, well-coached team with clear development paths and strong internal engagement

What You'll Need to Get the Job Done:

• 3+ years in Customer Success, Retention, or Revenue-focused roles, with 2+ years directly managing a scaled success team
• Proven track record owning and improving GRR/NRR or retention metrics for a high-volume SMB customer segment
• Experience building and scaling 1-to-many customer engagement programs (adoption campaigns, digital-led CS motions, automation/lifecycle tooling)
• Direct experience running or overseeing a cancellation/save process, including negotiation and objection handling at scale
• Strong analytical skills — comfortable owning health scores, churn forecasting, and reporting on retention/adoption KPIs
• Experience with CS platforms (Gainsight, ChurnZero, Vitally, or similar), CRM tools (Salesforce/HubSpot), and Tableau, BI, or similar reporting tools
• Excellent cross-functional collaboration skills; able to influence Product, Sales, and Marketing without direct authority
• SaaS experience required; healthcare, dental, or vertical SaaS experience strongly preferred
• A builder's mindset — comfortable creating process and playbooks where none exist yet
• Ability to travel ~once a quarter for leadership meetings

What will make us REALLY love you:

• Experience in dental, healthcare, or practice-management software
• Experience building CS AI risk signal framework

What you'll love about us:

• Flexible Paid Time Off + 10 company-wide paid holidays
• Competitive Medical, Dental & vision offerings, with buy up plan options, AND we match your HSA contributions.
• Fully Paid Parental Leave
• 401K Retirement savings plan with company match up to 5.5% of your earnings+ unlimited access to personal financial advisors.
• Learning & Development Reimbursement program
• Company paid Life, Disability & AD&D
• Mental Health support programs, Cellphone & Gym membership Discounts, Corporate Sundance Passes, and more!

Please Note: 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.