Director of Customer Success
Lead and scale the Customer Success team for Enterprise and Mid-Market segments at a real estate fintech company. Own retention, expansion, and team development while building scalable processes, playbooks, and health scoring frameworks in a high-growth environment.
About the job
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.
Skills
Customer Success, Account Management, B2B SaaS, Health Scoring, Renewal Forecasting, CRM, Kpi Management, Onboarding Frameworks, Qbr, Expansion Playbooks
Similar jobs
Customer Success jobs
Bamboo Health
United States
Leads a behavioral health network engagement team responsible for provider adoption and referral growth across state programs. Requires 5+ years of team leadership, behavioral health and Medicaid expertise, cross-functional execution, strong judgment, and comfort using AI-enabled operating tools.
Hightouch
United States
Leads and scales a team of Technical Architects supporting enterprise customers from onboarding through retention and expansion. Requires 8–10 years in client-facing or technology-focused roles, people-management experience, and deep expertise in enterprise implementations, APIs, databases, and data integration.
Abridge
New York, NY
Own strategic health system partnerships, serving as the primary executive and clinician-facing relationship leader while driving adoption, retention, and expansion. The role requires strong healthcare knowledge, customer-facing experience, technical aptitude, and excellent communication skills.
Braintrust
San Francisco, CALeads and builds Braintrust’s post-sales organization across professional services, technical account management, and enablement. The role combines hands-on customer delivery with team scaling, retention and expansion ownership, operational design, and executive partnership across Sales, Finance, Customer Experience, and Engineering.
Faro Health
United States
Leads complex ecosystem and innovation programs for pharmaceutical customers, bridging business strategy, clinical development, data, and technology. Requires 8+ years in consulting or strategic advisory work, strong life sciences knowledge, executive communication, and experience driving multi-stakeholder transformation programs.