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 a strong people leader and a practical technologist - someone who 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, identifying high-impact opportunities to improve workflows and productivity while safeguarding data privacy and security.
- Own the company's reporting data model, serving as steward of a single source of 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 and maintain a tested incident response and disaster recovery plan.
Budget & Vendor Management - Oversee the technology department budget and manage vendor, 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 travel industry a 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
