> Markdown version of [/jobs/ext/4620653-chief-technology-officer-mid-market-orlando](https://www.wearedevelopers.com/jobs/ext/4620653-chief-technology-officer-mid-market-orlando). Every page supports `.md` or `Accept: text/markdown`. Links point to the HTML versions so they work for humans too. Agent guide: [/agents.md](https://www.wearedevelopers.com/agents.md). --- # Chief Technology Officer (Mid-Market) - Orlando - **Company:** Signify Technology - **Location:** Orlando, FL, United States - **Experience:** Experienced - **Contract:** Permanent contract - **Skills:** Java (Programming Language), Artificial Intelligence, Amazon Web Services, Microsoft Azure, C Sharp (Programming Language), C++ (Programming Language), Continuous Integration, DevOps, Github, Python (Programming Language), PostgreSQL, Microsoft SQL Server, Node.Js, Software Engineering, Datadog, Cloud Platform System, ReactJS, Large Language Models, Snowflake, Technical Debt, Containerization, AngularJS, Kubernetes, Cloud Optimization, Terraform, Splunk, New Relic (SaaS), Docker, Jenkins, Databricks - **Published:** November 7, 2026 - **Apply:** https://www.juju.com/job/28_25303_96ab4c284bd5d3ab1ad8ff6ef1e31aaa ## About the Role * 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. ## Description * 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).