Director, Scaled Success - SMB

Dental Intelligence Inc.

2d • Remote

About The Position

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.

Requirements

• 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
• A builder's mindset — comfortable creating process and playbooks where none exist yet
• Ability to travel ~once a quarter for leadership meetings

Nice To Haves

• healthcare, dental, or vertical SaaS experience strongly preferred
• Experience in dental, healthcare, or practice-management software
• Experience building CS AI risk signal framework

Responsibilities

• 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
• 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.
• 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
• 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
• 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

Benefits

• 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!

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed