Director of Customer Success

Accountabilities: As Director of Customer Success, you will own the post-sale customer experience and develop the strategies, systems, and team capabilities needed to maximize retention and account growth. Your responsibilities will include: Oversee the complete post-sale customer lifecycle across software products and managed services, from onboarding and implementation to ongoing support, retention, and account expansion. Define and execute the Customer Success strategy and operating model, aligning the function with the organization's transition toward a multi-product, platform-driven business. Lead annual and quarterly strategic planning, establishing goals, priorities, and initiatives that support broader business objectives. Take full accountability for Customer Success performance, ensuring the function consistently delivers against its targets. Lead, develop, and retain the Customer Success team by establishing clear responsibilities, priorities, performance expectations, and accountability. Design and evolve the team structure to support organizational growth and increasing customer needs. Manage the Customer Success budget, including staffing, technology, tools, and external vendors, ensuring spending aligns with departmental objectives. Promote a systems-first approach by leveraging automation, AI, and technology to streamline repetitive activities, improve self-service capabilities, and increase team productivity. Establish effective workflows and coordination processes across departments to ensure timely launches, smooth service transitions, and transparent client communication. Lead onboarding and implementation strategies, ensuring effective handoffs from Sales and rapid time-to-value for new customers and products. Oversee customer support operations and knowledge management, ensuring clients receive fast, consistent, and reliable assistance. Collaborate with Sales, Marketing, Design, Digital Marketing, Product, and Engineering teams to align customer needs and deliver a seamless experience throughout the customer lifecycle. Monitor and report on customer retention, account health, and team performance, providing actionable insights to executive leadership. Own Gross Revenue Retention (GRR) and Net Revenue Retention (NRR) through segmented customer coverage models, health scoring, early warning indicators, and proactive retention strategies. Develop and execute recovery plans for at-risk accounts to minimize churn and strengthen long-term customer relationships. Identify opportunities to improve customer experience, operational processes, and account expansion strategies. Requirements : The ideal candidate is a strategic and hands-on Customer Success leader with a proven track record of improving retention, building scalable operations, and developing high-performing teams. You should combine strong commercial judgment with analytical capabilities, technological adaptability, and excellent stakeholder management skills. Key qualifications include: At least 5 years of experience in Customer Success or a related discipline, ideally within a B2B software or SaaS environment. At least 3 years of experience managing teams, including recruiting, developing, coaching, and holding employees accountable to high performance standards. Demonstrated ownership of customer retention targets, with a proven ability to improve retention performance and explain the factors driving results. Strong strategic and operational expertise, with the ability to translate business objectives and identified opportunities into structured plans and repeatable processes. Experience building Customer Success processes and operating models from the ground up and transforming them into scalable systems. Hands-on experience with automation and AI tools to improve customer outcomes, streamline workflows, and increase team efficiency. Strong decision-making skills and the ability to navigate ambiguity, establish clear priorities, and move initiatives forward independently. Excellent data analysis and reporting capabilities, with experience using CRMs and other business systems to support strategic decisions. Strong written and verbal communication skills, including the ability to explain complex issues, align internal stakeholders, and manage challenging customer conversations with confidence and empathy. Ability to work effectively with executive leadership and cross-functional teams. Preferred Qualifications: Experience in the multifamily real estate industry, with knowledge of property operators, industry dynamics, and purchasing processes. Background in real estate or related sectors with transferable industry knowledge. Experience managing Customer Success operations in a hybrid delivery environment combining software products and managed services. Hands-on proficiency with HubSpot, Asana, Claude, or comparable Customer Success and productivity platforms. Experience in marketing technology or digital marketing services, particularly website solutions, SEO, and paid media. Benefits : Fully remote working arrangement within U.S. time zones. Full-time employment. Approximately 20% travel for customer visits and industry conferences. Opportunity to lead and shape the Customer Success function within a growing, technology-driven organization. Direct collaboration with executive revenue leadership. Significant autonomy to establish Customer Success strategies, processes, and operating models. Opportunity to build and develop a high-performing team. Exposure to innovative AI, automation, and self-service technologies. Potential to progress into a broader senior leadership position as the organization scales.