Director of Technology, AI & Digital Transformation

Director of Technology, AI & Digital Transformation Technology Leadership | AI Integration | Automation Engineering | Digital Strategy | Cybersecurity | Business Systems Architecture Red Wing, MN | Full-Time | Multi-Location Leadership Role Build the Future of Technology at One of Minnesota's Largest Marine & Powersports Groups River Valley Companies is seeking an innovative, forward-thinking technology leader to drive our next phase of growth through technology, AI adoption, automation, systems integration, and digital transformation. This is not a traditional IT Director position. We are searching for a unique professional who can think like a strategist, build like an engineer, and lead like an executive. The ideal candidate understands that technology is no longer just about keeping systems running—it is about creating competitive advantages, improving operational efficiency, enhancing customer experiences, leveraging artificial intelligence, and helping businesses scale. With approximately 140 employees across seven locations throughout Minnesota, River Valley Companies is actively investing in technology, AI, automation, cloud infrastructure, cybersecurity, and business process optimization. This leader will help define how technology impacts every department across our marine, powersports, service, sales, finance, marketing, and operations teams. If you're excited about AI, automation, emerging technologies, business systems, data, cloud infrastructure, and solving complex business challenges, we want to talk to you. What You'll Lead AI Strategy & Business Transformation Develop and execute the company's AI roadmap and digital transformation strategy Identify practical applications for Artificial Intelligence across sales, marketing, service, operations, HR, finance, and customer experience Evaluate, implement, and optimize AI-powered tools, agents, copilots, and automation platforms Lead company-wide AI adoption initiatives and employee training programs Create governance, security, and compliance frameworks surrounding AI usage Stay ahead of emerging technologies and identify opportunities that create measurable business value Automation Engineering & Process Optimization Design and implement workflow automation solutions that eliminate manual processes Develop scalable systems that improve efficiency, reporting accuracy, and employee productivity Integrate software platforms to streamline operations across departments Identify bottlenecks and engineer solutions that reduce friction and improve customer experience Build business intelligence, reporting, and analytics capabilities that support leadership decision-making Technology Strategy & Innovation Develop and execute the company's long-term technology roadmap Align technology investments with strategic business objectives Partner directly with ownership and executive leadership on growth initiatives Evaluate emerging technologies and determine practical business applications Lead digital transformation projects from concept through implementation Infrastructure, Cloud & Cybersecurity Leadership Oversee Microsoft 365, Azure, cloud infrastructure, networking, endpoints, and enterprise software systems Ensure high availability, reliability, scalability, and security across all locations Lead cybersecurity planning, risk mitigation, disaster recovery, and business continuity initiatives Maintain technology standards, policies, governance, and compliance practices Monitor evolving cybersecurity threats and implement proactive protection strategies Systems Architecture & Integration Improve connectivity between business systems and dealership software platforms Design scalable technology ecosystems that support future growth Evaluate APIs, integrations, data flows, and enterprise architecture opportunities Create technology standards that improve efficiency and reduce redundancy Support data management, reporting, and business intelligence initiatives Team Member Support & Technology Adoption Serve as the senior technology resource for the organization Lead technology onboarding, training, and adoption efforts Help employees leverage technology to improve performance and efficiency Foster a culture of innovation, curiosity, and continuous improvement Support multiple locations while maintaining exceptional service standards What We're Looking For Required Experience Experience leading technology initiatives, digital transformation projects, or enterprise technology environments Strong understanding of Artificial Intelligence, Automation, Business Systems, Cloud Infrastructure, and Cybersecurity Experience implementing workflow automation, business process improvements, or systems integration projects Ability to translate business challenges into scalable technology solutions Strong project management and change management capabilities Exceptional communication and executive-level presentation skills Ability to balance strategic leadership with hands-on execution Highly Desired Skills AI Integration & Adoption, Generative AI Platforms, Microsoft Copilot Skills/Certification, Directory Service Integrations, AI Governance, Prompt Engineering, Workflow Automation, Power Automate, Power BI, Microsoft Azure, Microsoft 365 Administration/Certification, Business Systems Integration, API Integrations, Data Analytics, Business Intelligence, Cybersecurity, Cloud Computing, Enterprise Architecture, Digital Transformation, Process Improvement, Change Management, Systems Engineering, IT Leadership Preferred Backgrounds We recognize that exceptional candidates may come from a variety of backgrounds, including: Director of Technology IT Director Head of Technology Director of Digital Transformation AI Integration Consultant Automation Engineer Solutions Architect Systems Engineer Enterprise Architect Business Systems Manager Technology Consultant Cloud Infrastructure Leader Operations Technology Leader Why This Opportunity Is Different This is a rare opportunity to build and influence the future technology strategy of a growing organization. You'll have the ability to: Lead AI adoption across the business Build automation that impacts real-world operations Shape technology strategy at the executive level Work directly with ownership and senior leadership Influence business decisions through data and technology Help modernize and scale a multi-location organization Enjoy the products and lifestyle our customers are passionate about Compensation & Benefits Competitive compensation based on experience Medical & Dental Insurance Health Savings Account (HSA) Traditional & Roth 401(k) with employer match Paid Time Off & Paid Holidays Life Insurance Employee Assistance Program (EAP) Additional voluntary insurance options Company-provided apparel Employee discounts on boats, powersports vehicles, parts, accessories, and apparel Access to demo units including pontoons, fishing boats, ATVs, side-by-sides, snowmobiles, personal watercraft, and Slingshots About River Valley Companies River Valley Companies is one of the Midwest's premier marine and powersports dealership groups, serving customers through multiple locations across Minnesota. We represent many of the industry's most respected brands while delivering exceptional customer experiences through our sales, service, parts, and customer support teams. As we continue to grow, technology, automation, AI, and innovation will play a critical role in our future success. If you're passionate about building systems, solving problems, leveraging AI, and driving business transformation, we'd love to hear from you.