Description
About the Role
Delavan Holdings is a diversified operating company with businesses spanning automotive retail, hospitality, industrial services, seasonal operations, and professional services. Our technology environment has grown organically alongside the business.
We are hiring our first enterprise Chief Technology Officer (CTO) to provide strategic direction, improve scalability, and use technology as a lever to drive efficiency, growth, and long-term business performance, without disrupting operations.
This role is designed for a business-minded technology leader who understands how to operate in frontline-heavy, non-corporate environments and partner closely with leadership to move the organization forward. This is not a consulting role and not a theory-driven position.
What This Role Is Really About
This role focuses on using technology to drive measurable business outcomes across a diverse portfolio of companies. The CTO will help identify where technology can improve margins, reduce friction, enable growth, and prepare the organization for the future—while ensuring solutions remain practical, usable, and appropriate for the majority of the workforce.
The emphasis is on applying the right technology, in the right places, to deliver real efficiency and scalability.
Key Responsibilities
Enterprise Technology Leadership
- Lead enterprise IT strategy across multiple business units with different operating models
- Partner closely with executive and business leaders to align technology initiatives with business goals
- Establish clear ownership, governance, and accountability across systems and platforms
Business Enablement and Growth
- Use technology to drive operational efficiency, scalability, and profitability
- Identify opportunities where automation, data, and AI can reduce manual work and improve decision-making
- Apply structured project management and continuous improvement approaches (e.g., Six Sigma or similar methodologies) to technology initiatives
- Support capital planning and prioritization for technology investments across the portfolio
Architecture, Systems, and Software Management
- Design and implement a shared services model covering identity, security, data, and integrations
- Establish standards for software lifecycle management, vendor selection, and system ownership
- Improve identity and access management, including role-based access and single sign-on
- Ensure systems are secure, scalable, and aligned with future business needs
Change Management and Adoption
- Lead modernization efforts in frontline, non-technical, and culturally diverse environments
- Drive adoption through practical improvements that reduce friction and make work easier
- Communicate clearly and plainly, focusing on outcomes and usability rather than buzzwords
Team and Vendor Leadership
- Partner with and strengthen existing IT leadership to support enterprise priorities
- Build and scale a right-sized internal IT organization aligned to business needs
- Hold vendors accountable for performance, value, and outcomes
What Success Looks Like
In the first year, success will look like:
- A clear enterprise technology strategy aligned to business objectives
- Better use of existing systems and thoughtful introduction of new tools where gaps exist
- Improved efficiency, scalability, and operational clarity across business units
- Stronger access controls, system ownership, and software governance
- Technology decisions that support growth and prepare the organization for the future
- Leaders confident that IT is helping move the business forward
Requirements
Required Experience
- Senior technology leadership experience (CTO, VP of IT, Head of Technology, or equivalent)
- Experience supporting multi-entity or holding-company environments
- Proven success modernizing immature or fragmented technology environments
- Strong understanding of ERP, HRIS, identity and access management, integrations, and enterprise systems
- Direct ownership of execution and outcomes (not advisory-only roles)
Preferred Experience
- Automotive, manufacturing, hospitality, logistics, services, or similar industries
- Family-owned or private equity-backed organizations
- Seasonal or high-turnover workforces
- Leading change where adoption and usability mattered more than perfection
Work Model
This is an onsite, hands-on executive role based in southern Wisconsin. The role requires regular engagement with operators and business leaders and is not remote.
Benefits and Stability
Delavan Holdings offers a competitive executive benefits package, including medical, dental, and vision insurance; a 401(k) with company match; paid time off and paid holidays; and executive-level compensation aligned with experience and impact. The organization offers long-term stability within a diversified, family-owned enterprise.
Our Operating Culture
This role is well suited for leaders who prefer practical solutions over theory, value clarity and accountability, and are comfortable working across very different business models. Success comes from delivery, follow-through, and respect for frontline teams. We focus on what works and how to make it work better.
Compensation
Competitive executive compensation aligned with experience and impact.
