Senior Director, Digital Technology Solutions

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

The Senior Director of Enterprise Technology Solutions will lead the strategy, delivery, and continuous improvement of the organization's corporate technology platforms. This leader will bring an automation and AI-first mindset while serving as the primary technology partner to Finance, Human Resources, Legal, Supply Chain, Procurement, and other business functions.

This high-impact position combines strategic leadership with hands-on execution. The Senior Director will build a connected, efficient back-office technology ecosystem that reduces operational overhead, strengthens data integrity, and enables faster decision-making.

Key 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
• Work with operational leaders to integrate systems, streamline processes, and improve access to meaningful business data
• Champion automation, platform integration, and continuous process improvement across the organization
• Own the full lifecycle of enterprise platforms, including architecture, configuration, integrations, upgrades, support, and vendor management
• Ensure platform stability, security, scalability, and compliance with applicable regulatory requirements
• Oversee integrations between HR, Finance, service management, and other enterprise systems
• Lead data quality and governance initiatives that support accurate analytics and reporting
• Build, mentor, and retain a high-performing team of internal employees and external partners
• Manage technology vendors and system integrators, ensuring performance, accountability, and measurable value
• Establish consistent delivery, change management, release management, and adoption practices
• Serve as a trusted technology advisor to senior business and operational leaders

Education And Experience

• 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
• Strong executive presence, strategic thinking, and results-oriented leadership
• Hands-on leadership style with the ability to align stakeholders and drive initiatives forward
• Experience incorporating AI and machine learning capabilities into enterprise workflows, including automation, predictive analytics, natural language processing, and embedded SaaS tools
• Familiarity with enterprise data platforms and data governance frameworks
• Experience with leading ERP, HRIS, service-management, automation, or enterprise workflow platforms
• Experience operating within regulated environments and supporting compliance requirements such as GAAP, SOX, GDPR, or HIPAA