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Vaco is hiring a Chief Information Officer (CIO) in Lombard, IL. Location: Lombard, IL (Chicago Area) | On-Site About the Opportunity A leading transportation and mobility services organization is seeking a visionary and operationally focused Chief Information Officer (CIO) to lead enterprise-wide technology strategy, digital transformation, cybersecurity, and IT operations. Supporting a large-scale network of transportation services across hundreds of locations nationwide, this organization operates in a highly distributed, mission-critical environment where technology plays a central role in safety, service delivery, workforce productivity, and customer experience. Reporting directly to the Chief Executive Officer and serving as a member of the Executive Leadership Team, the CIO will be responsible for shaping the future technology landscape while ensuring operational excellence across all information technology functions. This executive will serve as a trusted business partner, driving innovation, modernization, and enterprise performance through strategic technology investment and disciplined execution. Position Overview The Chief Information Officer is responsible for developing and executing a comprehensive technology and digital strategy that supports business growth, operational efficiency, safety, and customer satisfaction. This leader will oversee all aspects of information technology, including enterprise applications, infrastructure, cybersecurity, data and analytics, field support services, project management, innovation, and vendor management. Success in this role requires a highly collaborative executive who combines strategic vision with hands-on leadership and a strong operational mindset. The ideal candidate will have experience leading technology organizations in complex, geographically dispersed environments where reliability, scalability, and service excellence are essential. Key Responsibilities Technology Strategy & Digital Transformation Define and execute a long-term technology roadmap aligned with business objectives and customer expectations. Lead enterprise-wide digital transformation initiatives that improve operational efficiency, safety, workforce effectiveness, and customer outcomes. Identify emerging technologies and innovation opportunities that create measurable business value. Serve as a strategic advisor to executive leadership on technology trends, risks, investments, and modernization priorities. Foster a culture that embraces innovation, continuous improvement, and digital adoption. IT Operations & Service Excellence Ensure the reliability, availability, and performance of technology systems supporting a large national operating network. Oversee IT service delivery and support functions, ensuring responsive and effective support for a 24/7 operational environment. Establish strong governance, service management disciplines, and performance metrics across the technology organization. Maintain operational continuity through resilient infrastructure, disaster recovery, and business continuity planning. Drive technology standardization and process optimization across multiple business locations. Enterprise Applications & Data Strategy Lead the strategy, optimization, and governance of enterprise technology platforms supporting operations, finance, human resources, scheduling, maintenance, safety, and customer-facing functions. Modernize legacy applications and streamline the overall technology architecture. Expand data analytics and reporting capabilities to support informed business decisions and operational performance. Promote the use of advanced analytics and business intelligence tools across the organization. Establish a strong data governance framework to ensure quality, consistency, accessibility, and security of enterprise data. Cybersecurity & Risk Management Develop and maintain a comprehensive cybersecurity strategy that protects critical systems, data, and operational assets. Strengthen security governance, risk management, and compliance capabilities. Oversee incident response, disaster recovery, and business continuity programs. Ensure technology practices meet applicable regulatory, legal, and industry requirements. Create a culture of security awareness and accountability throughout the organization. Leadership & Talent Development Build and lead a high-performing technology organization focused on collaboration, innovation, and results. Recruit, develop, and retain top technology talent. Partner closely with operational and corporate leaders to align technology solutions with business needs. Lead organizational change efforts that support successful technology adoption and business transformation. Encourage a customer-focused mindset and culture of accountability across the IT function. Financial, Vendor & Portfolio Management Manage technology budgets, capital investments, and resource allocation to maximize business value. Identify opportunities for cost optimization while maintaining high service levels. Oversee strategic technology vendors, contract negotiations, and supplier performance. Manage the enterprise technology project portfolio, ensuring prioritization, governance, and successful delivery. Establish clear ROI measures for technology investments and transformation initiatives. Qualifications Required Experience Executive-level technology leadership experience in a large, distributed, operationally intensive organization. Demonstrated success leading enterprise technology modernization and digital transformation programs. Significant experience managing mission-critical systems within complex, customer-facing operating environments. Proven track record of building high-performing teams and developing strong leadership benches. Strong business acumen with experience managing large budgets, strategic technology investments, and vendor ecosystems. Ability to influence senior stakeholders and lead effectively within a matrixed organizational structure. Preferred Experience Background in transportation, logistics, infrastructure, industrial services, utilities, field services, or similarly complex industries. Experience operating within multinational or globally integrated organizations. Familiarity with public-sector environments, regulatory compliance requirements, or transportation technologies. Experience overseeing cloud transformation, enterprise application modernization, and advanced analytics initiatives. Leadership Profile The successful candidate will demonstrate: Strategic thinking combined with disciplined execution. Strong business partnership and stakeholder management skills. Excellent communication and influencing capabilities. A pragmatic, hands-on leadership style. Strong operational awareness and customer focus. The ability to lead through change and transformation. High integrity, humility, accountability, and commitment to organizational success. By submitting to this position, you are agreeing to be included in our talent pool for future hiring for similarly qualified positions. EEO Notice Vaco by Highspring is an Equal Opportunity Employer and does not discriminate against any employee or applicant for employment because of race (including but not limited to traits historically associated with race such as hair texture and hair style), color, sex (includes pregnancy or related conditions), religion or creed, national origin, citizenship, age, disability, status as a veteran, union membership, ethnicity, gender, gender identity, gender expression, sexual orientation, marital status, political affiliation, or any other protected characteristics as required by federal, state or local law. Vaco by Highspring and its parents, affiliates, and subsidiaries are committed to the full inclusion of all qualified individuals. As part of this commitment, Vaco by Highspring and its parents, affiliates, and subsidiaries will ensure that persons with disabilities are provided reasonable accommodations. If reasonable accommodation is needed to participate in the job application or interview process, to perform essential job functions, and/or to receive other benefits and privileges of employment, please contact HR@vaco.com . Vaco by Highspring also wants all applicants to know their rights that workplace discrimination is illegal. Representation Notice By submitting to this position, you agree that you will be giving Vaco by Highspring the exclusive right to present your as a candidate for the foregoing employment opportunity. You further agree that you have represented information about yourself accurately and have not affirmatively misrepresented your qualifications. You also agree to maintain as confidential, to the fullest extent permitted by law, any information you learn from Vaco by Highspring about the position and you will limit disclosure of information about the position only to the extent necessary to perform any obligations in furtherance of your application. In exchange, Vaco by Highspring agrees to exercise reasonable efforts to represent you through all solicitation, job screening and resume dispersal. For residents of Ontario, Canada: Based on Highspring’s discussions with its Client, Highspring’s understanding is that this position for employment is a current vacancy (either through Highspring as a contractor or with the client directly). Privacy Notice Vaco by Highspring and its parents, affiliates, and subsidiaries (“we,” “our,” or “Vaco by Highspring”) respects your privacy and are committed to providing transparent notice of our policies. California residents may access Vaco by Highspring HR Notice at Collection for California Applicants and Employees here. Virginia residents may access our state specific policies here. Residents of all other states may access our policies here. Canadian residents may access our policies in English here and in French here. Residents of countries governed by GDPR may access our policies here. Additionally, submissions to this position are subject to the use of AI to perform preliminary candidate screenings, focused on ensuring minimum job requirements noted in the position are satisfied. More details about Vaco by Highspring’s use of AI can be found here (https://www.highspring.com/ai-use-notices/). Further assessment of candidates beyond this initial phase will be conducted by recruiters and hiring managers. Vaco by Highspring does not know and cannot opine on if its client’s use of AI products in hiring. Pay Transparency Notice Determining compensation for this role (and others) at Vaco by Highspring depends upon a wide array of factors including but not limited to: the individual’s skill sets, experience and training; licensure and certification requirements; office location and other geographic considerations; other business and organizational needs. With that said, as required by local law, Vaco by Highspring believes that the following salary range referenced above reasonably estimates the base compensation for an individual hired into this position in geographies that require salary range disclosure. The individual may also be eligible for discretionary bonuses.