Senior Director, Customer Operations Strategy, AI & Automation

Engageware

About The Position

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.

Requirements

8+ years of experience in Customer Operations, Customer Success Operations, Marketing Operations, Support Operations, Services Operations, or a closely related function within a SaaS or technology company.
4+ years of experience leading teams, major cross-functional initiatives, or both.
Demonstrated success building or scaling operational systems across multiple customer-facing or go-to-market functions, not just one department.
Strong experience with platforms such as Gainsight, Salesforce, Jira, Glean, ThoughtSpot, Clay, BI/reporting tools, and workflow automation systems.
Proven ability to design and improve complex processes that span data, people, and technology.
Experience identifying and implementing AI and automation use cases in business operations, with sound judgment about risk, controls, and where human review is required.
Strong analytical mindset with the ability to move from messy operating reality to clear structure, measurable metrics, and scalable execution.
Excellent communication and stakeholder management skills, with the ability to influence senior leaders and work effectively across technical and non-technical teams.
Strong project and program management discipline with the ability to prioritize competing demands and keep high-impact initiatives moving.
A hands-on operating style. This role is for a leader who can shape strategy and also get deep into the systems, workflows, and details required to make the strategy real.

Nice To Haves

Experience in fintech, regulated industries, or other complex customer environments is strongly preferred.

Responsibilities

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.
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.
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 customer base.
Own the strategy for the operations tech stack, including systems such as Gainsight, Salesforce, Glean, Jira, ThoughtSpot, Clay, and related workflow and reporting tools.
Ensure customer signals, marketing lifecycle events, operational events, and account data flow cleanly across systems so teams can act from a shared source of truth.
Improve data quality, taxonomy, and workflow hygiene across the tools that power Customer Success, Support, Services, and Marketing Operations.
Lead the design of scalable workflows for customer-impact prioritization, ticket linkage, escalation documentation, account intelligence, campaign-to-customer handoffs, and cross-functional collaboration.
Partner with technical teams on system administration priorities, integrations, permissions, data models, and automation design.
Build and oversee the reporting framework for the customer organization and its marketing lifecycle dependencies, including metrics, dashboards, and recurring operating reviews for leadership.
Establish clear visibility into customer health, support performance, services delivery, escalations, renewals, automation impact, and key lifecycle conversion points.
Develop measurement approaches that quantify the business value of automation and AI, including time saved, touch reduction, faster response, improved consistency, and better customer and revenue outcomes.
Turn operational data into actionable insights for leadership, helping the organization prioritize the right interventions, investments, and process changes.
Support weekly, monthly, quarterly, and ad hoc KPI analysis for senior leadership.
Build a high-performing Operations function that combines strategic thinking, analytical rigor, systems fluency, and practical execution.
Coach and enable others on process discipline, systems thinking, and effective use of AI and automation.
Lead change management for new workflows, tools, reporting structures, and operating standards across the customer organization and its key partnerships with Marketing.
Create strong adoption plans so process and tooling improvements are actually used in the field, not just launched.
Lead by example with a balance of strategic leadership and hands-on problem solving.