Chief Information Officer

Build the Technology Behind City Wide’s Next Billion

City Wide Facility Solutions is seeking a Chief Information Officer (CIO) to serve as the senior technology executive responsible for leading, optimizing, and scaling the information systems and technology infrastructure that will drive City Wide's next phase of growth. Reporting directly to the Chief Financial Officer, the CIO will provide operational and strategic leadership across enterprise systems, data and analytics, cybersecurity, and operational excellence. This is a newly elevated C-suite role and a critical hire for a company on a clear path from $1B to $2B in systemwide sales by 2030. This position is onsite, located in Kansas City (relocation assistance is available).

What You’ll Do

The CIO will own City Wide's information systems roadmap and lead a team that includes a Data Engineer, IT Project Manager, and MS Dynamics 365 AI Developer. Core responsibilities include:

• Develop and execute a forward-looking information systems roadmap aligned to City Wide's growth trajectory across 115+ franchise territories
• Lead and optimize City Wide's core technology stack: Microsoft Dynamics 365 CRM, Business Central ERP, Power BI, Solver, and field operations platforms
• Evaluate and guide the adoption of AI, predictive analytics, and automation to enhance franchise performance and independent contractor management
• Build and advance data and analytics capabilities enabling real-time, insight-driven decisions across the franchise system
• Lead enterprise cybersecurity strategy and data governance across a distributed national network of 100+ locations
• Establish and maintain data privacy, compliance, and regulatory frameworks for a multi-state, multi-province franchise operation
• Partner with the CFO to manage the technology budget and demonstrate clear ROI on technology investments
• Serve as a key advisor to the executive team on emerging technology trends and competitive differentiation opportunities
• Represent technology strategy to franchisees, the Franchise Advisory Council, and key executive stakeholders

Requirements

Who We’re Looking For

• Bachelor’s degree in Computer Science, Information Technology, Engineering, Business, or a related field.
• 10+ years of progressive technology leadership experience, with a minimum of 5 years in a senior technology executive role (CIO, VP of Technology, or VP of Information Systems)
• Demonstrated success leading technology strategy in a multi-unit, franchise, or distributed B2B operations environment strongly preferred
• Proven experience with CRM platforms including Microsoft Dynamics 365 and HubSpot, as well as ERP systems such as Business Central, or comparable enterprise platforms at scale
• Deep expertise in business intelligence platforms (Power BI, Solver, or equivalent), data architecture, and analytics-driven decision support
• Working knowledge of Agile and Scrum project delivery methodologies with the ability to provide executive oversight of concurrent technology projects
• Familiarity with modern data platform architecture including Microsoft Fabric, Lakehouse environments, and ETL/ELT pipeline design
• Strong background in cybersecurity strategy, data governance, and compliance frameworks for multi-state, distributed organizations
• Track record of leading enterprise-wide digital transformation and technology modernization initiatives with measurable outcomes
• Experience managing technology budgets and demonstrating ROI on technology investments to senior financial leadership
• Exceptional communication and executive presence with the ability to translate complex technology strategy into clear business impact for non-technical stakeholders
• Strong leadership and team development skills; proven ability to build and retain high-performing technology teams
• Ability to pass background check (including credit check), drug screen, and reference checks for an Executive-level position

Preferred Skills and Qualifications

• Master's degree in Computer Science, Information Technology, or a related field
• Relevant certifications such as ITIL, PMP, AWS, Microsoft Azure, and/or CISSP
• Experience supporting franchise system growth from 100 to 200+ units, including technology infrastructure design for new territory onboarding
• Experience leading IT governance frameworks (COBIT, ITIL) across distributed, multi-location organizations
• Experience leading ERP system implementations or migrations at the enterprise level, including planning, change management, and post-go-live optimization
• Demonstrated experience implementing AI, machine learning, or advanced analytics in a franchise or multi-unit services environment
• Knowledge of independent contractor management platforms, mobile workforce tools, or field service management software
• Experience with private equity-backed or high-growth franchise organizations preparing for a significant capital event
• Familiarity with Vena financial reporting and planning software, particularly in support of franchise-level budgeting, forecasting, and CFO-driven financial oversight

Benefits

What City Wide Offers You

• Competitive base salary, bonus, and equity.
• Relocation assistance provided for this national search.
• 3 Weeks PTO in Year 1.
• Medical, Dental & Vision coverage.
• 401(k) Match.
• Paid Life & Disability.
• Paid Community Service Time.
• Direct influence with the CFO, the Board, private equity partners, and City Wide's Franchise Advisory Council.

This position is open and actively sourced. City Wide Facility Solutions is an Equal Opportunity Employer. All qualified applicants will receive consideration for employment without regard to race, color, religion, sex, national origin, disability, or protected veteran status.