Chief Technology Officer (CTO)

Profile Overview

We're looking for a hands-on CTO to lead our technical strategy and a senior team of 5 engineers plus a solutions engineer. This is a player-coach role: you'll set architectural direction, solve complex technical problems, and support the team's growth-while remaining close enough to the code to earn the team's respect.

You'll be joining a company at an inflection point: maintaining a stable, high-SLA enterprise product while scaling a newer AI/RAG solution. You'll need to balance both.

Why join now? This is a rare opportunity to lead technical strategy at a company with a stable, profitable core and genuine AI-driven growth momentum. It's a second act built on solid foundations. You'll work with a highly experienced, autonomous team that doesn't need hand-holding, in a fully remote culture built around trust and outcomes. As the person shaping both our legacy platform and our emerging AI products, you'll collaborate directly with the CEO and executive peers. Your technical decisions will have real business weight from day one.

Your responsibilities

Technical Leadership

• Define and drive technical architecture for both our mature search platform and evolving RAG solution
• Make critical technical decisions on scaling, infrastructure, and product evolution
• Solve difficult technical problems that the team escalates
• Guide technology choices and evaluate new tools/approaches (especially AI-assisted development)
• Own deployment strategy, operational readiness, and infrastructure reliability across all engineering initiatives.

Team & People

• Lead and mentor a team of 6 experienced engineers (5 developers + 1 solutions engineer)
• Foster a culture of technical excellence, autonomy, and continuous learning
• Conduct code/design reviews and provide thoughtful technical feedback
• Act as a coach rather than commander - this team values collaboration

Business & Operations

• Review and assess technical requirements in enterprise contracts
• Handle security questionnaires and compliance requirements (SOC2, GDPR, etc.)
• Lead our SOC 2 compliance / audits
• Collaborate with CEO, product, sales and marketing leadership on product roadmap
• Balance technical debt, feature development, and operational stability

Hands-On Contribution

• Contribute to architecture and design (you don't need to write code daily, but you should be able to)
• Stay current with AI/ML developments, especially in RAG and LLM applications
• Champion modern development practices (we use AI-assisted tools like Claude Code, Codex)

What You bring to the table

Must-haves:

• 10+ years of software engineering experience, with significant time in technical leadership roles
• Strong hands-on experience with AI-assisted development tooling (e.g., Claude Code, Cursor, Copilot)
• Working knowledge of our stack or ability to quickly ramp: Java/Kotlin, Python, AWS
• Experience with AI/ML systems, particularly RAG architectures, LLMs, and prompt engineering
• Track record leading senior engineering teams (not necessarily large teams, but experienced ones)
• Comfort with