Director of Technology

Trek Travel provides global cycling, hiking, and walking vacationsofa lifetime with the goal of helping more people actively explore and experience the world. We are looking for a Director of Technology to lead our technology team and shape how technology powers the way we design, sell, and deliver world-class bike and hiking trips. The ideal candidate is both astrong peopleleader and a practicaltechnologist-someonewho can inspire a team, build trusted relationships across departments, and implement modern systems and AI tools that fit seamlessly into our business. This is a full-time, exempt position based at our Madison, Wisconsin office, with a hybrid schedule and regular in-office presence expected. This position reports directly to the President of Trek Travel.

POSITION RESPONSIBILITIES INCLUDE, BUT NOT LIMITED TO:

Leadership & Team Development

• Lead, mentor, and develop the technology team, including hiring, goal setting, performance management, and career development across IT, ecommerce, and development staff.
• Provide support, training, and guidance to internal and external technology users, assessing computing needs and system requirements.

Strategy & Roadmap

• Translate company vision into an enterprise systems strategy and multi-year technology roadmap, partnering with department heads and senior leadership to align technology with operational and strategic goals.
• Lead planning and execution of company-wide technology initiatives, including project management, change management, and staff training across departments.

Systems, Infrastructure & AI

• Own the architecture and integrations connecting our booking, ecommerce, ERP, CRM, and financial systems, including performance, reliability, and upgrades of core business systems and the Microsoft Power Platform environment.
• Lead the ecommerce and software development functions, setting technical direction and quality standards for the team.
• Develop and execute Trek Travel's AI strategy and governance standards,identifyinghigh-impact opportunities to improve workflows and productivity while safeguarding data privacy and security.
• Own the company's reporting data model, serving as steward ofa single sourceof truth for business metrics.

Security & Compliance

• Own the information security program, including risk management, endpoint protection, access controls, MFA, patching, and least-privilege reviews.
• Ensure cybersecurity and regulatory compliance across guest booking and payment systems (PCI-DSS, GDPR, state privacy laws), including annual assessments, penetration testing, and remediation.
• Deliver ongoing security awareness training andmaintaina tested incident response and disaster recovery plan.

Budget & Vendor Management

• Oversee the technology department budget and managevendor,consultant, and SaaS relationships across the full lifecycle — from selection and negotiation to renewal and performance review.

WHAT ELSE WE'D LIKE TO SEE FROM YOU:

• Bachelor's degree and 8+ years of progressive technology experience, including 3+ years leading and developing technical teams.
• Deep technical experience across IT management, programming, ERP systems, database administration and security, and web/application development.
• A practical, hands-on technologist with strong technical architecture instincts and a well-rounded background across development, data, security, infrastructure, ecommerce, CRM, and ERP.
• Excellent communication and analytical skills, with a solution-oriented, “how can I help” attitude and strong troubleshooting instincts.
• Values hospitality and customer service, with an interest in the active travelindustrya plus.

TREK TRAVEL OFFERS:

• A fast-paced, casual, motivating, and fun company culture where initiative and pro-activity are highly valued.
• Medical, dental, and vision insurance
• Flexible Spending Accounts (FSA)
• Short- and long-term disability and life insurance
• Paid parental leave
• 401(k) with company match
• Generous PTO, paid holidays, and volunteer time off
• Rewards for sustainable commuting
• Employee and outdoor industry discounts