Senior Director, AI-First Enterprise Technology

Cypress HCM; Fort Myers (FL); On-site; USD 140,000 - 210,000; Full time

Job summary

Cypress HCM seeks a Senior Director of Enterprise Technology Solutions to lead strategy and execution across ERP, HRIS, and related platforms. You will drive automation, data integrity, and scalable processes while partnering with Finance, HR, Legal, and other functions.

The role blends strategic oversight with hands-on leadership, mentoring teams, and managing vendors to deliver value and regulatory compliance in a fast-paced environment.

Qualifications

• Bachelor's or Master's degree in Information Technology, Computer Science, or a related discipline; equivalent professional experience will also be considered.
• 12+ years of experience leading ERP, finance systems, or enterprise application implementations, optimizations, and rollouts.
• 7+ years of people-management experience.
• Demonstrated success managing large-scale enterprise technology environments in partnership with senior functional leaders.
• Experience with AI and machine learning capabilities in enterprise workflows.

Responsibilities

• Develop and execute the enterprise applications strategy across ERP, HRIS, and supporting business platforms.
• Translate business objectives into clear and actionable technology priorities.
• Oversee solution architecture, platform design, implementation, business readiness, and value realization.
• Lead execution as a hands-on player-coach while mentoring internal team members and external partners.
• Partner with Finance to automate procure-to-pay, order-to-cash, financial close, expense management, and compliance reporting.
• Partner with HR to improve recruiting, onboarding, offboarding, payroll, benefits administration, and workforce analytics.
• Ensure platform stability, security, scalability, and regulatory compliance across systems.

Skills

Strategic leadership

Executive presence

Stakeholder alignment

Education

Bachelor's or Master's in IT/CS or related

12+ years ERP/enterprise apps experience

7+ years people-management

Experience with AI/ML in workflows

Tools

ERP platforms (SAP/Oracle)

HRIS systems

Data governance tools

Job description

Cypress HCM seeks a Senior Director of Enterprise Technology Solutions to lead strategy and execution across ERP, HRIS, and related platforms. You will drive automation, data integrity, and scalable processes while partnering with Finance, HR, Legal, and other functions.

The role blends strategic oversight with hands-on leadership, mentoring teams, and managing vendors to deliver value and regulatory compliance in a fast-paced environment.