Senior Director, Customer Operations Strategy, AI & Automation

Engageware is looking for a hands-on, strategic, and data-driven Senior Director of Operations Strategy, AI & Automation to lead the operating model, systems strategy, and automation roadmap across Customer Success, Support, Services, and Marketing Operations.

You will be responsible for turning great customer and go-to-market work into scalable systems by standardizing how teams operate, improving visibility into performance and risk, and identifying where AI and automation can reduce manual effort, improve consistency, and create better customer and business outcomes.

Reporting directly to the Chief Customer Officer, you will work cross-functionally with Product, Engineering, Revenue Operations, IT, and Marketing leadership to build the processes, tooling, data flows, and operating discipline required to scale a modern, AI-enabled customer organization with strong lifecycle and operating alignment.
Key Responsibilities

Strategic Leadership & Customer Operating Model

- Serve as the senior leader for Customer Operations strategy across Customer Success, Support, Services, and Marketing Operations, setting the vision for how the organization scales with consistency, discipline, and leverage.

- Define and lead the operating model for the customer organization and its key lifecycle touchpoints with Marketing, including core workflows, ownership boundaries, cross-functional handoffs, governance, and management cadences.

- Identify and implement process improvements that reduce friction across the customer lifecycle, from demand generation and handoff through onboarding, adoption, support, escalation, renewal, and services delivery.

- Partner with Customer Success, Support, Services, and Marketing leaders to translate business goals into measurable operating plans, systems requirements, and execution priorities.

- Build an organization that operates with one-team consistency across products, regions, and customer segments rather than relying on local workarounds or individual heroics.

AI & Automation Strategy

- Define and drive the roadmap for applying AI and automation across the customer organization, balancing practical workflow automation with higher-leverage AI use cases.

- Identify where manual work can be eliminated, standardized, accelerated, or improved through automation in areas such as health scoring, QBR preparation, customer insights, case triage, escalation workflows, knowledge access, and service delivery operations.

- Create a framework to evaluate automation opportunities based on impact, feasibility, risk, and change-management cost.

- Partner with Product, Engineering, and IT to implement internal tooling, workflow orchestration, and agent-assisted processes that improve customer outcomes and team efficiency.

- Establish clear guardrails for where automation is appropriate, where AI should assist but not decide, and where human judgment must remain primary.

Customer Success, Support, Services & Marketing Operations

- Own the systems and processes that support account health management, proactive customer motions, renewal readiness, support escalation management, services coordination, and lifecycle marketing handoffs.

- Improve operating discipline across the organization by standardizing playbooks, stage definitions, service motions, escalation paths, campaign and follow-up workflows, and handoff expectations.

- Design workflows that help the organization move from reactive service to proactive, insight-led customer engagement.

- Partner with Support leadership to improve SLA visibility, case flow, triage quality, and escalation readiness.

- Partner with Services leadership to improve project visibility, delivery consistency, capacity planning inputs, and customer handoffs before, during, and after implementation work.

- Partner with Marketing Operations on lifecycle processes, data quality, segmentation inputs, campaign handoff logic, and reporting alignment across the funnel and custome