Director of Customer Success

What You'll Do

• Own GRR, NRR, product adoption, and customer health across Enterprise and Mid-Market segments, setting strategy and being accountable for target outcomes.
• Lead, coach, and grow a team of CSMs; establish clear performance expectations, operating cadences, and a culture of customer obsession.
• Build and iterate on onboarding, QBR, and expansion playbooks that scale across hundreds of accounts without sacrificing quality of relationships.
• Serve as the point of escalation for high-value or at-risk accounts, and strategize with senior leadership on effective solutions.
• Partner cross-functionally with Sales, Product, and Support to ensure tight handoffs, strong feedback loops, and a unified customer experience.
• Establish health scoring frameworks and data-driven processes for identifying both churn risks and expansion opportunities early.
• Deliver regular reporting on segment health, renewal forecasting, and team performance to executive leadership.

Required Skills

• 8+ years in Customer Success, Account Management, or post-sale in B2B SaaS, with at least 4 of those years leading and scaling CS teams.
• Demonstrated track record of owning healthy retention and expansion metrics (NRR, GRR, churn) and building the operational infrastructure to manage them: health scoring, forecasting, tiering models.
• Establish and manage key performance indicators (KPIs) to monitor the effectiveness of customer success efforts and make data-driven adjustments.
• Proven ability to design and implement scalable CS processes from the ground up: onboarding frameworks, segmentation strategies, renewal playbooks in a high-growth environment.
• Strong people leader with experience hiring, developing, and retaining CSMs; set a high bar, coach actively, and build teams that outlast your direct involvement.
• Ability to effectively communicate with and present to VP-level customer personas, deliver board-level retention updates, and participate in cross-functional product reviews.
• Data-driven approach to managing a book of business using health scores, product usage signals, and CRM data.

Nice to Have

• Background in real estate, title, mortgage, or adjacent proptech/fintech.
• Familiarity with CS platforms for health scoring and lifecycle automation.
• Exposure to compliance-sensitive or transaction-based SaaS products where trust and security are part of the customer value prop.
• Prior experience scaling a CS org through a Series A → C/D growth phase.
• Comfort with AI tooling applied to CS workflows.