Chief Technology Officer (Mid-Market) - Orlando

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

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 simulation and training technology, hospitality and travel tech, healthcare services, and logistics. We are building a confidential shortlist of CTO-level leaders for clients who are scaling their product and engineering organizations and need a hands-on technology executive to own the platform. 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.

Responsibilities

• Own the technology vision, product-engineering roadmap, and R&D budget, and present them to the CEO and board.
• Lead and scale an engineering organization of roughly 25 to 150 people across engineering, architecture, DevOps, QA, and data.
• Modernize a platform that has outgrown its first architecture: move from monolith toward services, retire technical debt, and improve release velocity.
• Own cloud strategy and cost on AWS or Azure, including FinOps discipline and infrastructure as code (Terraform).
• Set engineering standards: CI/CD (GitHub Actions, Azure DevOps, or Jenkins), containerization (Docker, Kubernetes), observability (Datadog, New Relic, or Splunk), and secure SDLC.
• Lead the company's practical AI adoption, from embedding LLM features in the product to AI-assisted engineering, with measurable business outcomes.
• Build the data platform strategy (Snowflake, Databricks, or equivalent) in partnership with product and analytics.
• Own build vs. buy decisions, vendor selection, and contract negotiation, including when and how to use external partners and staff augmentation.
• For clients serving government or defense-adjacent customers, own the technology side of compliance (CMMC, NIST 800-171, FedRAMP awareness).

Requirements

• 12 or more years in software engineering, with 5 or more years leading engineering leaders (manager of managers).
• Current or recent seat as CTO, VP Engineering, or Head of Engineering 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 engineering budget and headcount plan, not execution against someone else's.
• Hands-on credibility across a modern stack: one or more of Java, .NET/C#, Python, Node.js, or C++; React or Angular; AWS or Azure; Kubernetes; PostgreSQL or SQL Server.
• Track record of a platform modernization or re-architecture delivered with measurable results.
• Experience in a PE-backed, founder-led, or high-growth environment strongly preferred.
• Industry experience in simulation, hospitality/travel, healthcare, or logistics is a plus and weighted by client.
• Some clients require eligibility for a U.S. security clearance.
• 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; equity or LTIP with some clients
• Medical, dental, and vision coverage
• 401(k) with employer match
• Paid time off and paid holidays
• Executive ownership of the technology roadmap and budget
• A seat at the executive table with direct CEO and board exposure
• The chance to build rather than maintain

Pay

$210,000 to $275,000 base plus 20 to