Chief Technology Officer

Our client, a market leader in their space, is seeking a highly strategic and hands‑on Chief Technology Officer to lead a significant technology and product transformation.

The business has built a successful and established distribution platform and is now entering its next phase of growth: developing proprietary technology products, owning more of the end-to-end customer experience, and embedding AI capabilities across the organization. The company operates in a complex, highly regulated industry and sees a major opportunity to modernize how consumers engage with essential services. Profitable and well‑established, the organization combines the stability of an existing market leader with the speed, ambition, and operating style of a high‑growth company.

This is not a traditional “people management” CTO role. The company is looking for a builder — someone who is deeply technical, highly product-oriented, and excited to remain close to architecture, systems design, and development. The CTO will play a central role in defining the company’s long‑term technology vision while also personally driving execution across critical systems and platforms. This individual will help shape an AI‑first technology ecosystem, establish scalable infrastructure and data architecture, and guide the organization through a meaningful period of innovation and transformation.

The environment is lean, fast‑moving, and execution-focused. The team already leverages modern AI tooling extensively, and the ideal candidate believes strongly in the ability of small, highly capable teams to create outsized impact through intelligent systems, automation, and strong technical leadership.

• Define and execute the company’s overall technology strategy, including platform direction, architecture, and investment prioritization
• Translate commercial and operational objectives into a scalable technology roadmap
• Personally architect, build, and ship core systems while setting a high technical standard across the organization
• Oversee infrastructure, applications, data architecture, security, vendor relationships, and internal technology operations
• Identify areas where AI and machine learning can create meaningful competitive advantage and operational efficiency
• Design and manage centralized data architecture across multiple systems and data sources
• Ensure strong governance around information security, compliance, and controls, including HIPAA and SOC2 considerations
• Evaluate build‑vs‑buy decisions and manage external technology partners effectively
• Serve as a strategic partner to the executive team and communicate technical priorities clearly to non‑technical stakeholders

• The ideal candidate is a highly technical executive with strong product instincts and a demonstrated history of building and scaling modern technology platforms.
• Active hands‑on engineering experience, with a track record of personally shipping products and systems end‑to‑end
• Deep full‑stack technical expertise across applications, infrastructure, data, and systems architecture
• Practical experience deploying AI/ML technologies, including LLMs and agent‑based systems, into production environments
• Experience operating successfully in regulated industries such as insurance, healthcare, financial services, or similarly complex sectors
• Strong judgment around scaling efficiently through automation, tooling, and strategic leverage rather than excessive headcount growth
• Executive presence and the ability to communicate complex technical concepts clearly to senior leadership and boards
• Expertise designing scalable data systems across fragmented and disparate data environments
• A forward‑thinking mindset with a willingness to challenge legacy approaches and modernize systems thoughtfully

• Founder or founding‑engineer experience
• Prior Insur Tech or adjacent industry experience

The role is based in Miami, FL, with a hybrid schedule of three in‑office days per week (Monday, Tuesday, Thursday).

Base salary range: $250,000–$300,000, plus additional incentive opportunity.