> Markdown version of [/jobs/ext/2058067-head-of-engineering-cto](https://www.wearedevelopers.com/jobs/ext/2058067-head-of-engineering-cto). 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). --- # Head of Engineering / CTO - **Company:** Class Valuation, LLC - **Location:** Chicago, IL, United States - **Experience:** Expert - **Contract:** Permanent contract - **Skills:** Artificial Intelligence, Continuous Integration, Distributed Systems, Software Engineering, Legacy Systems - **Published:** August 14, 2026 - **Apply:** https://www.dice.com/job-detail/1981b1fd-5608-47fd-9578-bccc96431533 ## About the Role Senior engineering leadership experience within trading, big tech, infrastructure, or high-scale startup environments * Strong track record leading large engineering organisations and driving technical strategy * Experience modernising complex or legacy systems at scale * Deep understanding of distributed systems, reliability, scalability, and operational excellence * Strong organisational leadership and engineering process mindset * Experience improving developer productivity, tooling, CI/CD, observability, or platform engineering practices * Familiarity with modern AI-assisted engineering workflows is highly desirable The firm is open-minded on industry background and is particularly interested in leaders who can bring mature engineering practices and external perspective into a high-performance trading environment. ## Description * Define and drive long-term engineering strategy across the trading platform * Improve engineering maturity, development workflows, tooling, and operational processes * Lead initiatives around observability, monitoring, reliability, and production stability * Drive platform scalability and architectural evolution * Introduce modern software engineering standards and best practices * Lead AI-enabled engineering initiatives and workflow automation * Partner closely with trading, research, and infrastructure leadership * Mentor and scale a high-performing engineering organisation ## Related Videos - [The Software Engineer 2030: From Coder To AI Orchestrator? - Patrick Schnell](https://www.wearedevelopers.com/videos/1825-the-software-engineer-2030-from-coder-to-ai-orchestrator-patrick-schnell) - [How to TDD in legacy code](https://www.wearedevelopers.com/videos/309-how-to-tdd-in-legacy-code) - [Best Practices for AI-Assisted Development of Distributed Systems](https://www.wearedevelopers.com/videos/100200-best-practices-for-ai-assisted-development-of-distributed-systems) - [The Avengers Initiative (Practical Ethics for Software Engineers)](https://www.wearedevelopers.com/videos/2070-the-avengers-initiative-practical-ethics-for-software-engineers) - [Modern Data Architectures need Software Engineering](https://www.wearedevelopers.com/videos/1030-modern-data-architectures-need-software-engineering) - [Engineering/Manager Pendulum: Generating compound interest on your career](https://www.wearedevelopers.com/videos/100348-engineering-manager-pendulum-generating-compound-interest-on-your-career) ## Related Articles - [Navigating the AI Shift](https://www.wearedevelopers.com/magazine/629-navigating-the-ai-shift) - [How to Become an AI Engineer](https://www.wearedevelopers.com/magazine/331-how-to-become-an-ai-engineer) - [What is Software Engineering in the Age of AI?](https://www.wearedevelopers.com/magazine/640-what-is-software-engineering-in-the-age-of-ai) - [Best US AI Conferences for CTOs in 2026: Build vs. Buy, Vendor Evaluation, and Peer Intelligence](https://www.wearedevelopers.com/magazine/736-best-us-ai-conferences-for-ctos-in-2026-build-vs-buy-vendor-evaluation-and-peer-intelligence) - [How We Built a Worry-Free System That Runs for 10+ Years – And What We’d Do Again](https://www.wearedevelopers.com/magazine/751-how-we-built-a-worry-free-system-that-runs-for-10-years-and-what-we-d-do-again) - [Is Software Engineering Over-Saturated?](https://www.wearedevelopers.com/magazine/418-is-software-engineering-over-saturated)