We are looking for a CTO who owns the technical direction of everything we build and who is equally comfortable in front of a prospective client. This is a dual-mandate role: internally, you are the final authority on architecture, technology choices, and engineering quality across all client projects; externally, you are the technical face of Windmill in pre-sales conversations, discovery workshops, and executive meetings.
Key Responsibilities
Technical Leadership & Delivery * Own all technical decisions across the project portfolio — architecture, technology stack, integration approach, and build-vs-buy calls — and set the standards teams design and build against. * Review and approve solution architectures and technical proposals before they go to clients or into delivery. * Define and enforce engineering standards: code quality, security, performance, scalability, and documentation, across both AI-generated and hand-written code. * Drive our AI-native delivery model — agentic coding tools (Cursor, Claude Code), LLM integration patterns, evaluation, and review discipline — and keep it evolving as the tooling changes. * Own the technology strategy for regulated domains: security architecture, data protection, and compliance-by-design for banking & finance, healthcare, and compliance clients. * Act as the escalation point for technical risk on live projects; step into troubled engagements and unblock them. * Grow the engineering organization: mentor tech leads and architects, shape hiring bars, and build technical career paths. * Partner with Delivery, Product, and Design leadership to keep estimates, scope, and architecture aligned with commercial reality.
Client-Facing & Business Development * Represent Windmill in meetings with prospective clients — present the company, our capabilities, our delivery model, and our track record to both technical and executive audiences. * Lead technical discovery: understand the client’s business problem, current landscape, and constraints, and translate them into a proposed solution and delivery approach. * Own the technical content of proposals, RFP responses, solution designs, estimates, and statements of work. * Handle technical due diligence and security questionnaires from enterprise procurement and compliance teams. * Build trusted-advisor relationships with client CTOs, CIOs, and product leaders, and support account growth after the deal closes. * Contribute to Windmill’s market positioning — thought leadership, conference talks, case studies, and points of view on AI-enabled product delivery.
Required Experience * 10+ years in software engineering, with 4+ years in a senior technical leadership role (CTO, VP Engineering, Head of Engineering, Principal Architect, or similar). * Proven track record of owning architecture across multiple concurrent projects, ideally in a consultancy, agency, or product delivery services environment. * Hands-on depth in modern full-stack development: React or Angular with TypeScript; Java, Node.js, Python, or Ruby on the back end. * Strong cloud and infrastructure background: AWS, Azure, or GCP; Docker, CI/CD, microservices, and event-driven architectures. * Practical experience with AI/LLM-based systems — integration, evaluation, and productionization — and with AI-assisted engineering workflows. * Experience delivering in regulated environments (fintech, healthtech, or compliance) with the security and data-protection practices these require. * Demonstrated pre-sales or client-facing experience: leading discovery, presenting to executives, and shaping proposals that won business. * Excellent spoken and written English (C1+) — you will present to clients in Europe and the US.
Personal Attributes * Decisive — comfortable making the final call with incomplete information, and owning the outcome. * Commercially minded — you understand that technical choices carry cost, timeline, and margin consequences. * Persuasive communicator — able to explain a complex architecture to a CFO and a business constraint to an engineer. * Pragmatic — you optimize for what ships and holds up in production, not for novelty. * Hands-on enough to earn engineers’ respect, senior enough to stay out of their way.
Nice to Have * Experience scaling a distributed engineering organization across multiple countries. * Track record of building a technical partner ecosystem (cloud, AI, or platform vendors). * Public speaking, published writing, or an established professional network in the product engineering space. * Additional European language. * Prior experience in a company of 100–300 people.
What We Offer * Competitive compensation and benefits package. * Remote-first work with a flexible schedule. * A genuine seat at the leadership table — you shape both how we build and what we sell. * Projects that span cutting-edge AI, UX, fintech, and healthtech domains, with enterprise clients across Europe and the US. * Opportunities for professional growth, training, and certifications. * A team that has been designing and delivering digital products for enterprises for over a decade.
