Director of Technology

Trek Travel provides global cycling, hiking, and walking vacations of a 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 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. 

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. 

• →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. 

• 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. 

• 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 

At Trek Travel, we think outside the box, continuously improve, encourage feedback, and give it all we got, all the time, no exceptions. If you have what it takes to join our team and the desire to help shape Trek Travel's future, we wish you the best of luck and look forward to your application!