Head Of Technology Operations Jobs in Florida (NOW HIRING)

Help Shape the Future of Modern Mobility

Role Overview

This role sits at the center of Travelpro’s transformation—from a trusted legacy brand into a design-led, consumer-obsessed modern mobility company.

The Head of Technology & Network Experience leads our technology function across the U.S. and Canada from our Boca Raton, FL headquarters. The role owns the Microsoft ecosystem, the Fortinet network and security stack, VPN and connectivity, JD Edwards EnterpriseOne, and the full software and subscription portfolio, and it implements and secures AI in partnership with the Head of Digital Transformation. In the first 6 to 12 months, success means a stable, well-secured environment, a maturing JD Edwards practice, and clear technology standards across both countries. The role partners closely with Operations, Finance, and Customer Service, manages our MSP partners, and works alongside our Canada-based JDE expert. It is a hands-on leadership role created to support the rapid growth of our U.S. operations

What You’ll Do

• Serve as the hands-on JD Edwards EnterpriseOne expert for the U.S. organization, owning system stability, integrations, reporting, and continuous improvement.
• Own and administer the full Microsoft ecosystem (Microsoft 365, Entra ID, Intune, and Windows endpoints) across all U.S. and Canadian sites.
• Manage the Fortinet network and security stack (FortiGate firewalls and routers, switching, wireless, SD-WAN) and all VPN, remote access, and site-to-site connectivity.
• Implement and secure AI across the business, owning the security, access, and governance posture company-wide, while the Head of Digital Transformation owns AI strategy and tool selection.
• Own the full software and subscription portfolio and hold our MSP partners accountable for service quality, scope, and cost.
• Lead cybersecurity, disaster recovery, and business continuity, and deliver network and technology training to raise everyday technology fluency.
• Plan and optimize the IT budget across both countries, and act as a trusted technology advisor to senior leadership.
• Provide leadership to our Canada-based Technology & Network Experience Lead, a deep JDE expert who reports into this role, building shared bench strength on the platform.

What It Takes

• 8+ years in IT or infrastructure leadership, including multi-site responsibility and direct vendor or MSP management.
• Hands-on JD Edwards EnterpriseOne or SAP experience is required; this role must be, or rapidly become, an expert in the company’s ERP.
• Experience in distribution, manufacturing, or consumer products is preferred.
• Proven success managing MSP partners and outsourced or co-managed IT.
• Practical experience implementing and securing AI tools in a business environment.
• Team leadership, with the ability to lead change and align stakeholders across locations.

Capabilities

• Strategic thinking paired with hands-on execution and a bias for results.
• Strong communication and stakeholder alignment across executive, operational, and frontline audiences.
• Analytical, data-informed decision-making.
• Adaptability in a fast-paced, growth-oriented environment.
• Sound judgment and the discipline to bring order to evolving systems and priorities.

Why this role matters

• Our U.S. operations have grown to roughly three times the size of Canada, and the technology function needs U.S.-based leadership to match.
• Reliable, secure, well-run technology underpins our distribution, DTC, and customer service performance.
• Strong JD Edwards stewardship protects the backbone the entire business runs on.
• Disciplined AI implementation and security let us move quickly on AI without taking on undue risk.

Qualifications

• Bachelor’s degree in Information Technology, Computer Science, Management Information Systems, or a related field; MBA or equivalent a plus.
• Expert-level JD Edwards EnterpriseOne, or a comparable Tier 1 ERP such as SAP (required).
• Hands-on expertise across Microsoft 365, Entra ID, Intune, and Windows endpoint management.
• Strong Fortinet and next-generation firewall, VPN, switching, wireless, and SD-WAN networking across multi-site environments.
• Proficiency with Power BI or a comparable business intelligence platform.
• Solid grounding in cybersecurity frameworks, regulatory compliance, and data privacy.
• Certifications such as Fortinet NSE, Microsoft 365 Certified, or CompTIA Network+/Security+ preferred.

Working Environment

• On-site at the Boca Raton, FL headquarters, with hands-on interaction with IT, network, and server-room equipment.
• Ability to lift up to 25 pounds occasionally (servers, network gear, laptops).
• Flexible hours for after-hours maintenance windows and incident response.
• Occasional travel to the Jackson, GA and Los Angeles distribution operations and the Canadian office.

What We Offer

A Culture Built for Growth:

We believe in collaboration, accountability, innovation, and continuous improvement. We move fast, support one another, and challenge ourselves to keep evolving.

Flexibility & Wellbeing:

Flexible Time Away, company-paid holidays, and hybrid work flexibility.

Comprehensive Benefits:

Medical, Dental, Vision, Health Savings Accounts, and wellness programs.

Invest in Your Future:

401(k) company match.

Community & Connection:

Employee-led engagement initiatives focused on wellbeing, collaboration, and creating a workplace where everyone belongs.

About Travelpro®

Travelpro® was founded by airline pilot Bob Plath, whose firsthand travel experience inspired the invention of the original Rollaboard® suitcase — changing modern travel forever. Today, we are building on that legacy as we evolve into a modern mobility and travel lifestyle brand designed for today’s global traveler. Our products combine aviation-level performance with elevated design, helping ambitious people move confidently through every journey.

Travelpro®

Tested by the Best. Designed for What’s Next.

Travelpro® is an equal opportunity employer committed to building a diverse and inclusive workforce. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other protected characteristic under applicable law.

Travelpro® is a drug-free workplace