Skip to content

VP of Customer Success

Leads customer success strategy to drive NRR, retention, and expansion ARR for a dental AI SaaS platform. Builds and mentors CS teams while collaborating with Sales, Product, and Marketing to improve client outcomes and reduce churn.

Los Angeles, CASan Francisco, CASalt Lake City, UT+1 moreCustomer SuccessRemote

About the role

Key Responsibilities

Customer Success Strategy

Develop and execute a comprehensive revenue-oriented CS strategy, ensuring all clients realize the full value of Pearl’s products; Own NRR, GRR, and expansion ARR as primary business metrics aligned with Pearl’s growth targets.

Achieve measurable reductions in gross churn and increases in expansion ARR by designing scalable programs using automation, learning management systems, and AI driven tools.

Team Leadership and Development

Build, mentor, and inspire a high-performing customer success team, overseeing onboarding, retention, and account management sub-teams with a strong client-first mindset.

Define clear KPIs, goals, and success metrics; foster collaboration across Customer Success, Sales, Marketing, and Product.

Client Onboarding and Adoption

Partner with implementation and technical support teams to deliver seamless onboarding, ensuring customers achieve measurable ROI quickly after activation.

Create tailored adoption strategies with defined time-to-value targets for different customer segments.

Partnership Management

Scale the Customer Success function through technology, automation, and strategic resourcing; build trusted relationships with KOL and key clients.

Serve as the escalation point for major client issues, ensuring timely resolution and satisfaction.

Cross-Functional Collaboration

Partner closely with Sales, Marketing, and Product to ensure customers realize Pearl's value proposition across their full lifecycle.

Align tools, data, and best practices between SMB and Enterprise Customer Success teams, sharing insights to improve the overall customer journey.

Feedback and Continuous Improvement

Own GRR, NRR, ARR, and time-to-value by segment as primary success metrics; collect and analyze client feedback and usage data to continuously improve retention and expansion outcomes.

Deliver measurable improvement in NPS, retention, and referral rates through systematic feedback loops—including NPS surveys, focus groups, and post launch reviews; collaborate with Product and Engineering to translate client insights into product improvements that drive adoption and retention.

Partner Success & Customer Advocacy

Support channel and technology partners with training, enablement, and resources; represent Pearl in partner meetings to ensure joint success.

Champion the customer's voice across the company, ensuring feedback informs roadmap, service delivery, and ongoing learning and enablement.

Marketing, Promotion & International Expansion

Partner with Marketing to develop retention and expansion campaigns; represent Pearl at key industry events, trade shows, and conferences.

Own Pearl's international CS outcomes—executing tailored regional strategies that protect and grow international ARR.

What You'll Need to Succeed

  • Proven leadership experience in Customer Success within SaaS technology, with a demonstrated track record of owning and growing NRR; dental or medical background is a plus, but not a requirement.
  • Strong track record managing enterprise and SMB accounts with measurable revenue impact and deep understanding of recurring revenue models and customer lifecycle metrics.
  • Exceptional leadership, communication, and stakeholder management skills with a strategic mindset and hands-on execution ability.
  • Passion for technology and innovation in dental care; willingness to travel and operate across multiple time zones.

What We Offer

  • Competitive compensation and benefits
  • Flexible uncapped PTO
  • Professional development opportunities
  • Remote-first work environment

Skills

SaaSCustomer SuccessNrrGrrArrNpsCRMAutomation ToolsKpi ManagementCross-Functional Collaboration

VP of Customer Success

Lead and scale a multi-sub-function CX organization (Support, Success, Expansions) at a high-velocity SMB SaaS company. Own NRR and expansion ARR as board-level KPIs while driving AI-native tooling, proactive retention motions, and cross-functional strategy.

Brooklyn, NYCustomer SuccessOn-site8+ YOENrrCsp

VP of Customer Success & Adoption

Lead and build the customer success function end-to-end, owning onboarding, adoption, retention, and expansion for enterprise accounts. Drive NRR/GRR and build scalable CS playbooks, tooling, and team.

360k – 380kSanta Clara, CACustomer SuccessOn-site12+ YOEQBRsVitally

Head of Onboarding (Director or VP level, depending on experience)

Lead and scale customer onboarding for a SaaS Resident Experience Platform. Build scalable implementation programs, reduce time-to-value, and drive activation rates while managing a team and collaborating cross-functionally.

United StatesCustomer SuccessRemote5+ YOEAutomationKPI Tracking

VP of Customer Engagement

Leads Customer Engagement organization owning full customer lifecycle from pre-sales to expansion. Drives usage, retention, and enterprise adoption through multi-disciplinary teams of strategists, engineers, and support. Requires 10+ years in GTM/Customer Success with technical fluency.

280k – 300kSan Francisco, CACustomer SuccessHybrid10+ YOENrrSales Alignment

VP, Customer Success

Leads Customer Success organization for high-growth B2B SaaS, owning end-to-end customer lifecycle, scaling team and processes for fast implementation, value realization, and adoption. Requires 10+ years CS experience including 4+ years managing teams in early-stage companies.

225k – 275kNew York, NYCustomer SuccessOn-site10+ YOESlackAmplitude