Director, Scaled Success - SMB

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.

• →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

• 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

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

• 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.