Chief Information Officer (Mid-Market) - Orlando

About the role

Signify Technology partners with growing mid-market companies across Central Florida (roughly 200 to 2,000 employees, $50M to $750M in revenue) in sectors including healthcare services, hospitality and travel, distribution and logistics, and defense-adjacent manufacturing. We are building a confidential shortlist of CIO-level leaders for clients whose business has outgrown the IT function that got them here and who now need an executive to own business technology end to end. This posting represents the type of opportunity we are currently engaged on rather than a single named vacancy, and we discuss specific client openings, fit, and timing on a first conversation. All conversations are handled discreetly. Role Location: Orlando, FL metro. Onsite or hybrid (3+ days in office). Local or relocating candidates only.

Responsibilities

• Own the enterprise IT strategy, roadmap, and budget (opex and capex), and present them to the CEO, CFO, and board.
• Lead the IT organization across infrastructure, business applications, service desk, security, and data, typically 15 to 80 people plus managed service partners.
• Own the core business systems: ERP (NetSuite, Microsoft Dynamics 365, Epicor, or SAP), CRM (Salesforce or Dynamics), and HRIS (Workday, UKG, or ADP).
• Lead a major transformation program such as an ERP replacement, cloud migration, or post-acquisition systems integration, on time and on budget.
• Own infrastructure and end-user computing on Microsoft 365, Azure or AWS, Intune, and ServiceNow or Jira Service Management, including multi-site operations.
• Partner with or oversee the security function on NIST CSF, SOC 2, HIPAA, or CMMC, and serve as executive owner of cyber risk and insurance.
• Build the data and reporting foundation (Power BI, Snowflake, or equivalent) so leadership runs the business on trusted numbers.
• Drive practical automation and AI adoption across finance, operations, and customer service with a clear ROI case.
• Own vendor strategy, MSP relationships, contract negotiation, and the decision of when to use external partners and staff augmentation.

Requirements

• 12 or more years in IT, with 5 or more years leading IT leaders (manager of managers).
• Current or recent seat as CIO, VP of IT, or Head of IT at a mid-market company (roughly 200 to 2,000 employees).
• This is a hands-on executive role; candidates whose leadership experience is only inside Fortune 500 or large enterprise environments are unlikely to be a fit.
• Direct ownership of an IT budget and vendor portfolio, not execution against someone else's.
• Has personally led at least one ERP implementation or replacement, or a comparable enterprise-wide systems program.
• Working knowledge of the Microsoft ecosystem (M365, Azure, Entra ID, Intune) and at least one major ERP and CRM.
• Experience taking an organization through a security framework or audit (SOC 2, NIST CSF, HIPAA, or CMMC).
• Experience in a PE-backed, acquisitive, or multi-site environment strongly preferred.
• Industry experience in healthcare, hospitality, distribution, or manufacturing is a plus and weighted by client.
• Able to work onsite or hybrid in the Orlando metro.
• Legally authorized to work in the United States.

Benefits

• Medical, dental, and vision coverage
• 401(k) with employer match
• Paid time off and paid holidays
• Executive ownership of the IT roadmap, budget, and vendor strategy
• A seat at the executive table with direct CEO and board exposure
• A visible transformation mandate rather than a keep-the-lights-on seat

Pay

$195,000 to $260,000 base plus 20 to 30% performance bonus (DOE).

Schedule

Onsite or hybrid (3+ days in office) in the Orlando, FL metro area; local or relocating candidates only.