Head of Customer Success

The Role

Pearly is a fast-growing B2B SaaS and payments company serving 2,500+ dental offices from private practices to DSOs. We're at a pivotal moment: transforming our Customer Success organization (implementation, support, and customer success management) into a scalable growth engine.

Initially, this is a hands-on, player-coach role growing the team and function over time. You'll join a lean team of 3 and roll up your sleeves daily while building the function. We need someone who thrives doing the work, not just delegating it.

You'll architect and scale CS operations to support our rapid-growth model: 1 week setup, 30-day pilots, and high-retention self-serve capabilities. With strong underlying unit economics but nascent operations, you have a blank canvas to build the customer journey, infrastructure, team, and systems that enable us to expand our product offering and scale from 2,500 to 10,000+ offices.

If you're energized by building rather than maintaining, and want complete ownership to shape how a high-growth technology company serves its customers, this is your role.

What You'll Own

Infrastructure & Operations

• Establish baseline metrics: CSAT, time-to-value, customer health, capacity forecasting

• Architect the customer journey (Pilot → Onboarding → Expansion) to support <1 week pilot setup and 30-day conversion cycles

• Build segmented service models by customer type (private practices, groups, DSOs) balancing tech-touch and high-touch approaches

• Implement self-service systems, tools, AI that drive retention and scale without linear headcount growth

• Continuously identify and eliminate bottlenecks to improve velocity and customer value quarter over quarter

Retention & Growth Enablement

• Own GRR target of 95%+ and NRR target of 125%+ (includes office expansion, supporting sales-led growth, programmatic upsells, and product-led growth)

• Surface customer insights that drive retention: why customers stay or leave, health scores, usage patterns

• Design clear accountabilities between CS and Sales that drive high pilot conversion, team productivity, and

• Build proactive CS motion that accelerates expansion revenue (differentiated by customer segment)

• Partner with Product to establish feedback loops that inform roadmap and improve platform adoption

Team & Leadership

• Build CS team with clear role differentiation (Implementation, Support, CSMs) as we scale

• Create "productized" implementation and support with defined roles and SLAs between CS and Sales

• Partner with CEO and leadership team on culture and strategic initiatives

What You Bring

Required

• 7+ years in Customer Success at growth-stage B2B SaaS and/or payments companies

• Built CS from early/nascent state with direct P&L ownership or GRR/NRR accountability (120%+ NRR results)

• Player-coach mentality: Willing to handle escalations, analyze data, and get hands dirty while building the team

• Hands-on experience implementing CS platforms, automation, and AI to drive scalable operations

• Experience segmenting operations between high-touch (DSOs/groups) and tech-touch (private practices) motions

• Described as a thought partner and growth enabler by prior Sales and Product teammates

• Technical fluency with integrations, analytics, and data

• Experience building teams from 3 to 10+ people

• Based in Atlanta, GA or Santa Barbara, CA. Remote ok with periodic travel for exceptional candidates.

Benefits

• Competitive salary, equity, and healthcare benefits

• Meeting-light culture

• Work with an A+ smart and passionate team

• Flexible vacation/time-off policy

• Opportunity to make your mark at an accelerating company with great product-market fit