Head of Customer Success

Pearly • Atlanta, GA

21h

About The Position

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.

Requirements

• 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.

Responsibilities

• 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.
• 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.
• 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

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

What This Job Offers

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