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Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Director of Technology - **Company:** TREK INC - **Location:** Madison, WI, United States - **Experience:** Expert - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Software System Penetration Testing, Business Systems, Software as a Service, Computer Programming, Payment Systems, Information Security Management, IT Management, PCI Data Security Standards, Software Engineering, Software Requirements Analysis, Software Troubleshooting - **Published:** August 23, 2026 - **Apply:** https://www.careerjet.com/jobad/us3477d8bc3e4d2590df77b5c5db9caa15 ## About the Role * 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. ## Description 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. ## Related Videos - [APIs and Architecture for scaling omnichannel payments](https://www.wearedevelopers.com/videos/90-apis-and-architecture-for-scaling-omnichannel-payments) - [Your Manager Doesn’t Come with a User Manual (But You Can Totally Write One)](https://www.wearedevelopers.com/videos/1495-your-manager-doesn-t-come-with-a-user-manual-but-you-can-totally-write-one) - [Migrating half a million users to a new payment service provider](https://www.wearedevelopers.com/videos/730-migrating-half-a-million-users-to-a-new-payment-service-provider) - [The user in the eye of the Cargo1492 storm](https://www.wearedevelopers.com/videos/96-the-user-in-the-eye-of-the-cargo1492-storm) - [Engineering/Manager Pendulum: Generating compound interest on your career](https://www.wearedevelopers.com/videos/100348-engineering-manager-pendulum-generating-compound-interest-on-your-career) - [Successful talent development in tech: A joint journey of executives and talents](https://www.wearedevelopers.com/videos/1497-successful-talent-development-in-tech-a-joint-journey-of-executives-and-talents) ## Related Articles - [Highest Paying Tech Companies for Developers](https://www.wearedevelopers.com/magazine/220-highest-paying-tech-companies-for-developers) - [Résumé-Driven Development: How IT trends affect the job market for software developers](https://www.wearedevelopers.com/magazine/59-resume-driven-development-how-it-trends-affect-the-job-market-for-software-developers) - [Dev Digest 120 - Apple and peers](https://www.wearedevelopers.com/magazine/455-dev-digest-120-apple-and-peers) - [Navigating the AI Shift](https://www.wearedevelopers.com/magazine/629-navigating-the-ai-shift) - [The Best X (Twitter) Accounts for Developers](https://www.wearedevelopers.com/magazine/294-the-best-x-twitter-accounts-for-developers) - [How We Built a Worry-Free System That Runs for 10+ Years – And What We’d Do Again](https://www.wearedevelopers.com/magazine/751-how-we-built-a-worry-free-system-that-runs-for-10-years-and-what-we-d-do-again)