Executive Vice President of Digital Transformation & Technology

You'll start with the Predictive Index (PI) assessment (takes
Location: Hybrid remote, with onsite collaboration in Onalaska, WI (up to twice per quarter)

Total Cash Compensation (Base + Quarterly Bonus): $200,000-$300,000

Benefits Include:

• Comprehensive health benefits starting the first of the month following hire
• 401(k) with company match
• Quarterly incentive opportunities
• Generous paid time off and paid holidays
• Executive-level autonomy and impact

Your Purpose

Dynamic is entering a pivotal stage of growth. We've organically grown beyond $100 million in revenue and are intentionally investing in people, systems, and technology to cement our position as a national leader. As we expand our national footprint, modernize our enterprise systems, accelerate the use of data and artificial intelligence, and continue to scale our operations, technology must evolve from a support function into a strategic business capability.

We've built a solid technology foundation, yet significant opportunities remain to further mature infrastructure, enterprise applications, cybersecurity, data capabilities, and digital business processes. The next Executive Vice President of Digital Transformation & Technology will lead that evolution by ensuring the company's technology environment remains secure, reliable, and scalable while transforming how the business operates through technology, data, and AI.
Reporting directly to the President and serving as a key member of the Executive Leadership Team, this executive will help shape how Dynamic operates over the next decade. They will translate business strategy into technology execution, and serve as a trusted partner across Operations, Finance, Sales, Customer Experience, Shared Services, and the Executive Leadership Team to improve customer experience, increase operational efficiency, strengthen decision-making, reduce organizational complexity, and create sustainable competitive advantage.

Success will be measured not by the technology implemented, but by the business outcomes technology enables.

Dynamic believes technology should elevate people, not simply replace work. As the company embraces automation and artificial intelligence, we are equally committed to investing in our team members by helping them develop new skills, adapt to changing ways of working, and thrive alongside emerging technologies. The EVP will play a critical role in leading this transformation responsibly, ensuring technology strengthens business performance and enables long-term growth, while valuing and strengthening the people who make it possible.

This is an opportunity to shape how Dynamic operates over the next decade. By strengthening the technology foundation while accelerating enterprise transformation, the EVP will help create a business that is faster, smarter, simpler, and better positioned for sustained growth.

What You'll Do

• Serve as the enterprise leader responsible for aligning technology, data, artificial intelligence, and digital capabilities with Dynamic's strategic priorities. Act as the bridge between executive vision and organizational execution by translating business objectives into technology roadmaps, governance, investment decisions, and measurable business results.
• Shape investment decisions, enterprise priorities, organizational capabilities, and the technology strategy that supports Dynamic's next decade of growth.
• Define and execute a technology roadmap including enterprise technology operations, cybersecurity, infrastructure, business applications, ERP modernization, enterprise data strategy, analytics, artificial intelligence, and technology governance.
• Lead and develop a high-performing technology organization that combines internal talent, contractors, and strategic partners by cultivating future leaders, establishing clear accountability, fostering an execution-oriented culture, and continually elevating the organization's technology maturity.
• Build the organizational capabilities needed to responsibly leverage data and artificial intelligence as sustainable competitive advantages. Partner with leaders, an AI steering committee, and external technology partners to prioritize high-value opportunities, improve readiness, establish governance, oversee responsible AI adoption, and grow successful pilots into scalable business capabilities.
• Serve as the executive sponsor for Dynamic's technology ecosystem, cultivating strategic relationships with ERP providers, cybersecurity partners, cloud and infrastructure vendors, AI partners, and other strategic technology suppliers to ensure the company has access to best-in-class capabilities and expertise.
• Partner with executive leaders across Operations, Finance, Sales, Customer Experience, and Shared Services to redesign business processes and deliver technology solutions that improve productivity, customer experience, compliance, safety, and scalability.
• Champion clean, trusted, actionable data and self-service business intelligence so teams can make stronger decisions with less manual effort.
• Shape a strong portfolio and project management discipline to ensure the right work is prioritized, resourced, delivered, adopted, and measured.
• Balance operational excellence with enterprise transformation by ensuring a secure, reliable, and scalable technology foundation while modernizing enterprise systems and shaping technology into a competitive business advantage.

What You Bring (Briefcase)

• Bachelor's degree in Information Technology, Computer Science, Software Development, Network Administration, Business, or a related field; additional relevant experience will be considered in lieu of formal education.
• 15 years of progressive technology leadership experience, including experience leading IT, enterprise applications, ERP, software development, infrastructure, integrations, or automation functions.
• Experience leading leaders and building strong, accountable technology teams.
• Proven success developing and executing short and long-term technology roadmaps aligned to business strategy.
• Experience overseeing complex technology projects, enterprise systems, integrations, ERP environments, vendor relationships, budgets, and cross-functional business initiatives.
• Strong understanding of project management methodologies and technology delivery models, such as Agile, Scrum, Kanban, Waterfall, or hybrid approaches.
• Experience with cybersecurity, IT controls, audits, system governance, and change management.
• Preferred: Experience with ERP implementation or modernization, ISO 27001 or similar security frameworks, automation, AI-enabled business solutions, data strategy, business intelligence, cloud platforms, or enterprise architecture.

Skills & Abilities (Head)

• Strong business acumen with the ability to connect technology decisions to operational, financial, customer, and growth outcomes.
• Strategic perspective and ability to influence enterprise priorities and drive organizational change
• Ability to simplify complex systems, processes, and technical concepts
• Skilled at building scalable systems, governance structures, metrics, and processes that reduce dependency on tribal knowledge.
• Strong technical breadth across enterprise applications, ERP, integrations, infrastructure, cybersecurity, data, automation, and modern technology platforms.
• Ability to assess what should be built internally, what should be outsourced, and where vendor partnerships can accelerate business value.
• Strong people leadership, coaching, teaching, and talent development skills.
• Ability to lead disciplined technology execution while staying flexible enough to support innovation and rapid business growth.
• Strong communication skills with the ability to influence executives, business leaders, technical teams, vendors, and external partners.

♥ Who You Are (Heart)

You're first and foremost a strategic, future-focused business executive who happens to lead technology. You see technology as a business accelerator - a vehicle for improving performance, not a back-office function. You know how to build trust, create clarity, and lead teams through complexity.

You bring the right balance of vision and execution. You can zoom out to shape the future of enterprise systems, AI, cybersecurity, and data, then zoom in far enough to ensure priorities are clear, projects are moving, teams are aligned, and the work makes a positive business impact.

You're energized by scale, innovation, and continuous improvement. You instinctively simplify, remove complexity, and prioritize the most impactful work. You lead with humility, accountability, and curiosity, and you're excited to help Dynamic build the technology foundation needed for our next stage of growth.