Director of Customer Success

• Dealpath is hiring a Director of Customer Success to lead and scale a high-performing Customer Success organization responsible for retention, expansion, adoption, and customer satisfaction across a portfolio of enterprise and strategic accounts
• In this role, you’ll manage and develop a team of Customer Success leaders and Customer Success Managers, establish operating rhythms and scalable processes, and partner cross-functionally with Sales, Implementation, and Product to ensure customers realize measurable value from Dealpath.
• You’ll bring a mix of strategic thinking and hands-on execution—building the playbooks, metrics, and team structure required to scale
• Lead, coach, and develop a team of Customer Success Managers and the managers who lead them, including hiring, setting clear goals, running regular 1:1s, and managing performance. Build strong frontline leaders who can grow and coach their own teams to create a high performing organization
• Own performance against key metrics including Gross Revenue Retention (GRR), Net Revenue Retention (NRR), renewals, expansion pipeline, adoption, and customer health
• Drive enterprise renewal strategy and execution; ensure strong account planning, stakeholder mapping, and multi-threading across customer organizations
• Identify risk early and lead executive-level escalation management to protect renewals and customer trust
• Define and operationalize the customer lifecycle: onboarding handoff, adoption milestones, value realization, and ongoing success planning
• Partner with customers to build success plans tied to business outcomes, usage goals, and measurable ROI
• Ensure high-quality enablement and training experiences (virtual and in-person) that drive adoption across complex customer teams
• Build and refine customer health scoring, reporting, and dashboards to create visibility and accountability across the organization
• Standardize processes for renewals, expansion identification, playbook execution, and executive communications
• Improve cross-functional workflows and SLAs across Implementation, Product, and Sales
• Partner with Sales leadership on expansion strategy, process alignment, and smooth account transitions
• Partner with Product and Engineering to surface customer feedback, influence roadmap priorities, and reduce recurring friction points
• Represent the voice of the customer internally and ensure issues are prioritized appropriately

Benefits

• Equity grant
• 401k plan
• Medical, vision, & dental
• Flexible vacation plan
• Health & wellness stipend
• Fully-stocked kitchen
• Commuter reimbursement
• Hybrid work policy

• Operational rigor: ability to build repeatable processes, define success metrics, and drive accountability through data and cadence
• Comfort partnering cross-functionally with Sales, Product, Implementation, and Support to drive outcomes end-to-end
• Strong executive presence and communication skills; ability to lead QBRs, renewal conversations, and escalations with senior stakeholders
• 3+ years of people management experience, including hiring, coaching, and performance management (experience managing managers is a plus)
• 8+ years of experience in Customer Success, Account Management, Consulting, or similar customer-facing roles in B2B SaaS (enterprise experience strongly preferred)
• Proven track record owning retention and growth outcomes (renewals, expansions, GRR/NRR) across complex, multi-stakeholder accounts
• Bachelor’s degree or equivalent practical experience
• Experience in commercial real estate, fintech, or enterprise workflow platforms
• Familiarity with Salesforce (and CS tools like Gainsight/Totango or similar)
• Experience building customer health models, segmentation frameworks, and scalable CS playbooks
• Experience supporting complex onboarding and change management programs