Our client is a leading provider of education technology solutions that help K–12 schools create safer, more effective digital learning environments. Through its suite of cloud-based solutions, they help school districts manage technology, protect students, gain actionable insights, and support student success.

As they continue to innovate and scale, we are seeking a strategic, execution-oriented leader to drive high-impact initiatives across the organization.

Position Overview

Our client is seeking a Director of Strategic Programs to lead enterprise-wide initiatives focused on AI automation, customer retention, operational efficiency, and business transformation.

This highly visible role will work closely with executive leadership and cross-functional teams to identify opportunities for improvement, develop scalable solutions, and translate strategic priorities into measurable business outcomes.

The ideal candidate combines strong business acumen with hands-on experience, improving customer lifecycle performance, and leading complex operational initiatives. This individual must be equally comfortable developing strategic recommendations and driving their execution.

Success in this role will be measured by tangible improvements in operational productivity, customer retention, organizational scalability, and overall business performance.

Key Responsibilities

Business Transformation

• Assist in executing an enterprise AI automation roadmap aligned with company priorities and measurable business outcomes.
• Identify high-volume, repetitive, or inefficient workflows across customer support, customer success, operations, and other business functions.
• Partner with technology and business stakeholders to integrate automation into existing systems and processes.
• Evaluate emerging AI technologies and determine their practical applications, financial benefits, and organizational impact.
• Establish appropriate governance, performance measurement, and adoption frameworks for AI-enabled initiatives.
• Drive measurable improvements in productivity, process efficiency, service quality, and organizational scalability.

Customer Retention & Revenue Optimization

• Lead strategic initiatives designed to improve customer retention, reduce churn, and increase customer lifetime value.
• Partner with Customer Success, Sales, Product, Finance, and Operations to identify customer health indicators and emerging retention risks.
• Develop data-driven frameworks to identify at-risk accounts, understand root causes of churn, and implement proactive retention strategies.
• Design and operationalize cross-functional retention playbooks, escalation processes, and customer lifecycle improvements.
• Analyze customer experience and operational data to identify systemic issues impacting satisfaction, renewals, and revenue.
• Establish and monitor retention performance metrics, including gross revenue retention, net revenue retention, churn, and customer health.

Strategic Program Leadership

• Lead complex, cross-functional programs that support company growth, operational effectiveness, and strategic priorities.
• Collaborate with executive leadership to evaluate, prioritize, and sequence strategic initiatives based on business impact, resource requirements, and organizational readiness.
• Translate high-level business objectives into actionable implementation plans with clear milestones, ownership, and success metrics.
• Coordinate initiatives across Product, Engineering, Customer Success, Sales, Finance, and Business Operations.
• Identify execution risks, remove organizational barriers, and maintain accountability for program delivery.
• Serve as a strategic advisor to leadership on opportunities to improve business processes, organizational effectiveness, and technology adoption.

Business Operations & Performance Management

• Develop operating frameworks, reporting structures, and performance dashboards that provide visibility into strategic initiatives.
• Establish consistent program governance, executive reporting, and cross-functional operating cadences.
• Define measurable KPIs and ROI frameworks for strategic investments and automation initiatives.
• Identify opportunities to reduce operating costs, improve resource utilization, and scale business operations without proportional headcount growth.
• Drive continuous improvement through process standardization, operational analytics, and technology enablement.
• Present findings, recommendations, and program results to executive leadership.

Required Qualifications

• Bachelor's degree in Business, Technology, Engineering, Information Systems, or a related field.
• 7+ years of progressive experience in strategic programs, business operations, digital transformation, management consulting, or related leadership roles.
• Demonstrated success leading complex, cross-functional initiatives with measurable business outcomes.
• Practical experience implementing AI automation, workflow optimization, or intelligent business process solutions.
• Strong understanding of SaaS business models, customer retention strategies, and recurring revenue metrics.
• Experience partnering with senior executives and influencing stakeholders across multiple functional areas.
• Strong analytical and financial acumen, including the ability to build business cases, define KPIs, and evaluate ROI.
• Experience using operational data, dashboards, and business intelligence to drive decision-making.
• Excellent communication, organizational leadership, and change management skills.
• Ability to operate effectively in a fast-paced environment while balancing strategic thinking with hands-on execution.

Preferred Qualifications

• Experience in B2B SaaS, education technology, or enterprise software organizations.
• Familiarity with AI tools to create efficiencies for this role and the rest of the organization
• Experience with tools and ecosystems such as Salesforce, HubSpot, Gainsight, Zendesk, Power BI, or similar enterprise platforms.
• Experience developing customer health scoring models, churn prediction frameworks, and proactive retention programs.
• Background in management consulting, strategic transformation, revenue operations, or enterprise program management.
• Experience driving organizational adoption of emerging technologies.

What Success Looks Like

First 90 Days

• Build strong relationships with executive leadership and key functional stakeholders.
• Assess existing business processes, automation capabilities, and customer retention performance.
• Identify and prioritize high-impact opportunities for operational improvement.
• Establish baseline KPIs, program governance, and an initial strategic roadmap.
• Launch initial initiatives demonstrating measurable value.

First 6 Months

• Deploy priority AI automation initiatives that reduce manual effort and improve operational efficiency.
• Implement enhanced customer health monitoring and retention playbooks.
• Establish consistent executive reporting and performance visibility.
• Demonstrate measurable progress against agreed business objectives.

First 12 Months

• Deliver quantifiable improvements in customer retention and operational productivity.
• Scale successful automation solutions across multiple business functions.
• Establish repeatable frameworks for identifying, prioritizing, and executing strategic initiatives.
• Create a sustainable operating model that supports continued growth and organizational efficiency.

Ideal Candidate Profile

The successful candidate is a strategic operator and change agent who thrives at the intersection of business strategy, technology, and execution.

This individual is naturally curious about emerging technologies, commercially minded, and passionate about eliminating inefficiencies. They understand how to turn AI innovation into practical business value and how operational improvements can directly influence customer experience and revenue retention.

Above all, this person is a builder and executor—not simply a strategist or project coordinator. They take ownership of outcomes, navigate organizational complexity, and consistently deliver measurable results.