Head of Customer Success

The Role

Pearly is a fast-growing B2B SaaS and payments company serving 2,500+ offices from private practices, groups, and DSOs. We're scaling rapidly and are at a pivotal moment of leveraging Customer Success to drive scalable growth.

This is a rare ground-floor opportunity to architect and scale a Customer Success function. With a strong customer base and underlying unit economics but nascent CS operations, you have a blank canvas to create the infrastructure, team structure, and strategic motion that will power Pearly's next phase of growth.

In 12 months, you'll have moved from "gut feel" to data-driven operations with established metrics, segmented service models for private practices to DSOs, productized implementations and support, world-class retention and measurable enablement of expansion revenue.

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 where none exist: CSAT, time-to-value, customer health, capacity forecasting.

• Architect the customer journey, from Pilot through Onboarding to Expansion, aligning workflows, tools, reporting, and feedback loops with the goal to accelerate time-to-value and eliminate friction.

• Continuously surface and relieve bottlenecks so the system improves quarter after quarter, delivering more customer value, faster, and at scale

• Create segmented customer journey maps with differentiated service models by customer type.

• Implement self-service systems, process, tools to drive scalability, experience, and retention.

Retention & Growth Enablement

• Own GRR target of 95%+ and NRR target of 125%+. NRR includes enablement of sales-led expansion, programmatic upsells, and supporting product-led growth across software and payments.

• Implement process, systems, and data to surface customer insights that drive durable top tier GRR (e.g. why customers stay or leave, customer health, usage, etc)

• Design process and accountabilities between CS and Sales that enable high pilot conversion rates, ROI demonstration, and team productivity.

• Build proactive CS motion to ensure customer retention and accelerate expansion revenue in coordination with Sales (differentiated between DSOs, groups, and private practices)

• Partner with Product to establish feedback loops informing strategic roadmap and improved adoption & usage of Pearly’s platform.

Team & Leadership

• Be an engaged partner to the CEO and leadership team to shape Pearly's culture and model our values.

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

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

• Drive cross-functional initiatives with Sales, Product, Engineering, and Operations

What You Bring

Required

• 7+ years in Customer Success within growth stage B2B SaaS and/or payments

• Built CS function from early/nascent state with direct P&L ownership or GRR/NRR accountability

• Hands-on experience implementing tools, process, and AI to drive scalable, measurable and productive operations

• Demonstrated experience in segmenting process, operations, and customer growth strategy between high-touch motions for larger customers and lower tech-touch motions for smaller customers.

• Described as a thought partner and growth enabler from prior sales and product teammates

• Data & technical fluency with respect to integrations and analytics

• Experience building teams from 5-10+ people

• Partner-led or product-led growth experience

• Based in Atlanta, GA or Santa Barbara, CA.

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