Head of Customer Success

📋 Description

• • Pearly is seeking a visionary and results-oriented Head of Customer Success to architect and scale our Customer Success function during a pivotal growth phase. As a fast-growing B2B SaaS and payments company serving over 2,500 offices, we are at a critical juncture where leveraging Customer Success is paramount to driving scalable and sustainable growth. This is a unique, ground-floor opportunity to build a world-class Customer Success operation from its inception.
• • With a robust customer base and strong underlying unit economics, Pearly currently possesses nascent CS operations. This presents a blank canvas for you to design and implement the infrastructure, team structure, and strategic initiatives that will propel Pearly's next phase of expansion. Your mandate is to transform our current operations from a 'gut feel' approach to a data-driven model within the first 12 months. This includes establishing key metrics, developing segmented service models tailored for private practices versus larger groups and DSOs, productizing implementation and support processes, and fostering a culture that drives exceptional retention and measurable expansion revenue.
• • If you are a builder who thrives on creating impactful systems rather than maintaining existing ones, and you desire complete ownership to shape how a high-growth technology company engages with and supports its customers, this role is an ideal fit for your ambitions.
• • **What You Will Own:**
• • **Infrastructure & Operations:** You will be responsible for establishing baseline metrics that are currently non-existent, including Customer Satisfaction (CSAT), time-to-value, customer health scores, and capacity forecasting. You will architect the end-to-end customer journey, meticulously mapping out workflows from the initial Pilot phase through Onboarding to Expansion. This involves aligning tools, reporting mechanisms, and feedback loops to accelerate time-to-value and systematically eliminate friction points.
• • Your continuous effort will focus on identifying and resolving bottlenecks within the customer success system, ensuring it improves quarter after quarter. The ultimate goal is to deliver increasing customer value, more rapidly, and at a scalable level. You will create distinct customer journey maps with differentiated service models specifically designed for various customer segments, such as private practices, group practices, and Dental Support Organizations (DSOs).
• • A key component of your role will be to implement self-service systems, processes, and tools that enhance scalability, elevate the customer experience, and significantly improve retention rates. This proactive approach to operational excellence will be foundational to Pearly's long-term success.
• • **Retention & Growth Enablement:** You will own the Gross Revenue Retention (GRR) target of 95% and the Net Revenue Retention (NRR) target of 125%. The NRR target encompasses enabling sales-led expansion, driving programmatic upsells, and supporting product-led growth initiatives across both our software and payments offerings.
• • You will implement robust processes, systems, and data analytics to surface critical customer insights that contribute to durable, top-tier GRR. This includes understanding the key drivers of customer retention and churn, monitoring customer health, analyzing usage patterns, and identifying expansion opportunities.
• • You will design clear processes and establish accountabilities between the Customer Success and Sales teams to ensure high pilot conversion rates, effective ROI demonstration, and enhanced team productivity. A proactive Customer Success motion will be built to guarantee customer retention and accelerate expansion revenue in close coordination with Sales, with strategies differentiated for DSOs, groups, and private practices.
• • A crucial partnership will be forged with the Product team to establish effective feedback loops. These loops will inform the strategic product roadmap and drive improved adoption and usage of Pearly's comprehensive platform.
• • **Team & Leadership:** You will serve as an engaged and strategic partner to the CEO and the broader leadership team, actively shaping Pearly's culture and embodying our core values. Your leadership will extend to building a high-performing Customer Success team, ensuring clear role differentiation across Implementation, Support, and Customer Success Management (CSM) functions.
• • You will drive the creation of a 'productized' implementation process, defining clear roles and Service Level Agreements (SLAs) between Customer Success and Sales. Furthermore, you will spearhead cross-functional initiatives, collaborating closely with Sales, Product, Engineering, and Operations teams to achieve shared objectives and foster a cohesive go-to-market strategy.
• • This role offers the unique opportunity to build a foundational function within a rapidly scaling company, directly impacting customer loyalty, revenue growth, and overall business success. You will be instrumental in defining the customer experience and ensuring Pearly continues to deliver exceptional value to its growing client base.