Chief Information Officer (Mid-Market) - Orlando

Signify Technology; Orlando (FL); Hybrid; USD 195,000 - 260,000; Full time

Benefits offered by this job

Medical, dental, and vision coverage

401(k) with employer match

Paid time off and paid holidays

Executive ownership of IT roadmap

Job summary

Signify Technology in Orlando, FL seeks an executive CIO/Head of IT to own the enterprise IT strategy, roadmap, and budget, leading 15–80 staff and MSPs. The role combines hands‑on leadership with strategic oversight across ERP, CRM, HRIS, security, and data platforms.

You will drive major transformations, cloud migration, and AI‑enabled automation with clear ROI, reporting to the CEO and board while ensuring compliance with NIST CSF, SOC 2, HIPAA, or CMMC.

Qualifications

• 12+ years in IT with 5+ years leading IT leaders.
• Current or recent CIO, VP of IT, or Head of IT at a mid‑market company.
• Direct ownership of IT budget and vendor portfolio.
• Led ERP implementations or replacements across an enterprise.
• Strong Microsoft ecosystem experience and at least one major ERP/CRM.

Responsibilities

• Own the enterprise IT strategy, roadmap, and budget to report to the CEO, CFO, and board.
• Lead IT across infrastructure, apps, service desk, security and data with 15–80 staff.
• Own core systems: ERP, CRM, HRIS; drive major transformation programs.
• Oversee cloud/infrastructure and end‑user computing; manage MSPs and partners.
• Partner on security frameworks and cyber risk; enable data‑driven leadership.

Skills

IT leadership

Budget management

ERP implementations

Cloud strategy

Security governance

Tools

NetSuite

Dynamics 365

Epicor

Salesforce

Workday/UKG/ADP

Power BI

Azure/AWS

ServiceNow/Jira Service Management

Job description

Job type: Perm

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

Role Location: Orlando, FL metro. Onsite or hybrid (3+ days in office). Local or relocating candidates only.

The company: 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 and 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.

Job 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

• Competitive base salary plus performance bonus
• 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

Due to high application volume, we’ll reach out directly to candidates whose experience most closely matches the requirements of this role.

Accessibility Statement: We make an active choice to be inclusive towards everyone every day. Please let us know if you require any accessibility adjustments through the application or interview process.

Our Commitment to Diversity, Equity, and Inclusion: Signify’s mission is to empower every person, regardless of their background or circumstances, with an equitable chance to achieve the careers they deserve. Building a diverse future, one placement at a time.

Check out our DE&I page here: https://www.signifytechnology.com/diversity-and-inclusion/