Fractional CIO Needed for Systems Integration, Business Intelligence, AI Strategy

Overview We are a growing, privately held group of operating companies in the heavy equipment, equipment dealership, auction, rental, service, parts, and logistics industries. We are seeking an experienced Fractional Chief Information Officer to assess our current technology environment, develop a practical technology roadmap, and help lead the implementation of priority initiatives across multiple business units and locations. We are looking for a business-oriented technology leader who can help us improve: Systems integration Process automation and AI implementation Data and Inventory visibility CRM adoption and accountability Executive dashboards Phone system capabilities Cybersecurity oversight Vendor accountability Standardization across operating companies and locations The ideal consultant will be comfortable moving between strategy and execution. We do not need a report that sits on a shelf with no one to execute it. We need a leader who can identify priorities, simplify decisions, select the right vendors and tools, and help drive implementation. Business problem to solve Our businesses have grown across multiple operating models, systems, vendors, and locations. We need stronger visibility, more consistent processes, and better integration between the systems that support sales, inventory, rentals, service, parts, auctions, logistics, marketing, finance, and leadership reporting. We want to reduce duplicate data entry, improve the quality and timeliness of information, strengthen accountability, and give leadership trusted data for faster decision-making. Initial engagement We expect the initial engagement to include a structured technology and business systems assessment, followed by a prioritized roadmap. Phase 1 deliverables: Assess the current technology environment, including key systems, vendors, integrations, data flows, reporting processes, and operational pain points. Identify urgent risks, quick wins, and longer-term priorities. Develop a practical 12- to 24-month technology roadmap with sequencing, estimated resource needs, decision points, and recommended ownership. Evaluate our current phone system environment and recommend a plan for upgrade, vendor selection, and implementation. Recommend an approach to improve inventory visibility, including equipment locations, attachments, transfers, rental status, and related reporting needs. Develop a business intelligence and dashboard strategy for leadership reporting. Evaluate CRM adoption, data quality, workflow consistency, and sales management visibility. Identify practical AI and automation opportunities that can save time, improve reporting, strengthen customer response, and reduce repetitive manual work. Review cybersecurity posture, vendor coverage, disaster recovery, business continuity, and major risk gaps. Recommend an implementation governance model, including decision rights, project cadence, vendor accountability, and progress reporting. Likely implementation priorities The exact sequence will be finalized after the initial assessment, but current priorities include: Immediate priorities Technology assessment and systems inventory Phone system upgrade and implementation planning Practical AI strategy and initial use cases Inventory visibility improvements Data ownership and reporting standards Near-term priorities Executive dashboard development CRM optimization and adoption Integration between CRM, accounting, inventory, rental, dealership, auction, logistics, and marketing systems Reduction of duplicate data entry and spreadsheet-based reporting Vendor performance management Cybersecurity and continuity improvements Longer-term fractional CIO responsibilities Depending on fit and the assessment results, the selected consultant may continue in an ongoing fractional capacity to: Lead technology roadmap execution Oversee system selection and implementation projects Coordinate internal stakeholders and outside vendors Improve data governance and reporting reliability Develop executive dashboards and KPI visibility Support CRM adoption and process standardization Identify and implement workflow automation Guide responsible AI adoption Strengthen cybersecurity oversight Establish repeatable technology decision-making standards Provide executive-level recommendations on technology investments What this role is not This is not primarily a role for: Routine help desk management Printer, laptop, or desktop troubleshooting Server administration Basic managed IT support A pure software developer A consultant who only produces recommendations without implementation support We need someone who can translate business problems into practical technology solutions and help drive adoption across the organization. Required experience Candidates should have meaningful experience leading business systems improvement in a multi-location or multi-business operating environment. Strong candidates will have experience with several of the following: Fractional CIO, CIO, CTO, VP of Technology, enterprise applications, or technology transformation leadership Systems integration and enterprise architecture ERP, accounting, CRM, inventory, rental, or operational systems Business intelligence tools such as Power BI or Tableau Dashboard development and executive KPI reporting Data governance and reporting standardization Vendor selection, contract management, and implementation oversight AI use-case identification and workflow automation Cybersecurity oversight, disaster recovery, and business continuity Change management and user adoption Privately held, family-owned, founder-led, or entrepreneurial businesses Experience in equipment dealerships, distribution, rental businesses, logistics, construction, agriculture, automotive dealerships, industrial services, or other multi-location operational environments is strongly preferred but not required. Working style The right person will be: Business-oriented Practical and execution-focused Comfortable challenging unclear priorities Able to simplify complex decisions Comfortable working with ownership, executives, department leaders, branch teams, and outside vendors Willing to get into the details without losing strategic perspective Focused on measurable business outcomes rather than technology for technology’s sake Some onsite discovery work and periodic travel to company locations may be required. Please indicate your availability for onsite work in Pennsylvania and Maryland. What success looks like Success should produce measurable improvement in the business, including: Leadership has reliable visibility into key business metrics Reporting becomes faster, more automated, and more trusted Inventory locations and status are easier to understand CRM adoption and sales visibility improve Systems communicate more effectively Duplicate data entry and manual reporting are reduced Technology vendors are held accountable AI and automation create measurable productivity gains Cybersecurity risks are better understood and addressed Ownership spends less time searching for information and more time making decisions Please include the following in your proposal A brief description of two or three similar engagements you have led. An example of a multi-location, multi-business, dealership, distribution, rental, logistics, or operational environment you have supported. Your approach to the first 90 days of an engagement like this. Your experience with ERP, CRM, inventory, rental, accounting, phone, reporting, and business intelligence systems. Your experience implementing AI or workflow automation in a practical business setting. Your approach to vendor selection and vendor accountability. Your preferred engagement model, expected weekly availability, hourly or project rate, and ability to support onsite discovery work. Whether you personally lead the work or delegate significant portions of the engagement to other team members.