Director Of Technology Jobs

About The Position

Requirements

• 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.

Nice To Haves

• Values hospitality and customer service, with an interest in the active travel industry a plus.

Responsibilities

• 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.
• 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.
• 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.
• 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.

Benefits

• 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