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.

What You’ll Do

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.

Deliver customer value and adoption

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 scalable processes, and metrics

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.

Cross-functional leadership and customer advocacy

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.

What We’re Looking For

Bachelor’s degree or equivalent practical experience.
8+ years of experience in Customer Success, Account Management, Consulting, or similar customer-facing roles in B2B SaaS (enterprise experience strongly preferred).
3+ years of people management experience, including hiring, coaching, and performance management (experience managing managers is a plus).
Proven track record owning retention and growth outcomes (renewals, expansions, GRR/NRR) across complex, multi-stakeholder accounts.
Strong executive presence and communication skills; ability to lead QBRs, renewal conversations, and escalations with senior stakeholders.
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.

Nice to Have

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.

The Perks & Culture:

Medical, dental, and vision insurance.
Health Savings Account (HSA) & Flexible Spending Account (FSA) options.
401(k) retirement plan.
Paid Parental Leave.
Flexible Time Off (FTO) policy.
Commuter benefits program.