Head of Engineering

Creative Chaos; United States; On-site; USD 180,000 - 240,000; Full time

Job summary

Creative Chaos seeks a Head of Engineering to lead its engineering organization, shaping strategic direction and hands-on technical execution across client engagements.

The role combines high-level architectural governance with practical engineering leadership, mentoring teams, and defining AI-native practices. You will drive staffing plans and own the client relationship while maintaining rigorous technical standards.

Qualifications

• 8+ years building software; 3+ years leading engineers directly.
• Experience running engineering across several simultaneous client engagements.
• You still read code and review it; this is a hands-on leadership role.
• Have hired engineers, and let one go; both matter.
• Comfortable telling a client the design is wrong, early in engagement.
• You are listened to; can hold a room, teach a workshop, and disagree with a client politely.
• AI-native in practice; use coding agents and understand governance and security implications.
• Direct, written communication; most decisions are made in writing for US clients.
• Useful—not required: distributed/offshore leadership and complex integrations.

Responsibilities

• Own the engineers across accounts: hiring, performance, growth, and retention.
• Set the bar for AI standards, architecture review, testing and security posture.
• Manage staffing and assignment decisions across client accounts.
• Own the technical relationship with clients; be the trusted advisor on architecture.
• Lead hiring plans for future AI-native engineers and capabilities.
• Lead client-facing communication, workshops, and training sessions.

Skills

Software leadership

Client-facing leadership

AI-native tooling

Workshop facilitation

Code review

Hiring decisions

Written communication

Stakeholder management

Job description

Job Summary:

Creative Chaos is looking for a Head of Engineering to lead our engineering organization and drive the technical direction, execution, and growth of our technology teams.

This is a senior leadership role for someone who can operate at both the strategic and technical level — shaping engineering practices and architecture while working closely with leadership, product, clients, and engineering teams to deliver high-quality software solutions.

What you own

The engineers. Everyone technical at Creative Chaos reports into you: hiring, the technical screen, performance, growth, and the decision that someone is not working out. Today they are spread across client accounts, and the account sets the priorities. You set the standard.

The bar. What Creative Chaos will and will not put its name on. AI standards, workflows and best practices, architecture review, code review, testing, security posture, infra, tools, and what qualifies as an exceptional working experience with a client. Today this is held informally by whoever is most senior on an account. Your job is to make it a standard, to coach and mentor toward it, and to hold it across every account whether or not you are in the room.

Who is on what. Staffing across accounts, including the bench. You own the assignment decisions and the utilization that follows from them.

The technical relationship with the client. You are the person who tells a client their architecture is wrong, and the person a client's CTO calls when they want a second opinion. Several of our engagements exist precisely because two or three consultants failed there first.

The hiring plan. What kind of engineers we need next week, next month, and over the next year, and how we find them. Our positioning depends on senior, AI-native engineers with excellent communication skills, and they are the hardest people in the market to hire.

The half of this job that is not technical

Roughly half of this role is standing in front of people and being believed.

You will spend a large part of your week explaining: to a client why their architecture will not hold, to an engineer why the work is not ready, to a room of thirty people how to actually work with AI agents instead of talking about them. Our clients are primarily US customers. They buy confidence as much as capability, and you are frequently the most senior technical person they will ever speak to.

You are also the coach. Training, workshops, and code review as teaching rather than as gatekeeping. The standard only holds if people want to meet it.

If you are the strongest engineer in the room but nobody seeks you out, this is not your role. We are weighting this equally with technical depth, and we will screen for it.

What you do not own

Contracts, invoicing, pricing, and the commercial relationship. Those sit with the Head of Engagements. You two will argue about staffing, and that argument is the point: one of you owns the client, one of you owns the quality, standards and work put out by the engineers.

The first 90 days

By day 30:

you know every account, every engineer, and where the real quality risk sits. You have told us at least one thing about our delivery that we did not want to hear.

By day 60:

AI standards are being implemented in engineering. You are running training sessions and workshops, and helping people in their respective areas.

• 8+ years building software; 3+ years leading engineers directly.
• Experience running engineering across several simultaneous client engagements, or running an in-house org and understanding what changes when the work is someone else's business.
• You still read code and review it. This is not a role where you stop being technical.
• You have hired engineers, and you have let one go. Both matter.
• Comfortable being the person who says the design is wrong, to a client, early.
• Someone people listen to. You can hold a room, teach a workshop, and disagree with a client without losing them.
• AI-native in practice, not opinion: you use coding agents daily and you have specific views on where they break. Much of our work now involve inheriting applications a client's own staff built with AI, with no governance, no security review, and one person who understands them.
• Direct, written communication. Our clients are in the US and much of our team is not, so most decisions are made in writing and read hours later.
• Useful, not required: distributed and offshore team leadership; heavy data and integration work against systems that do not want to be integrated (ERP, unstable APIs, no direct database access); experience taking a services business toward owning a product.