Chief Technology Officer

This is a fully remote position, open to applicants in United States.

📋 Description

• Lead the execution of Toptal's product and engineering teams, placing AI at the heart of all developments.

• Oversee Toptal's complete technical architecture, designing it with an AI-first approach utilizing agentic engineering best practices.

• Develop and manage the AI architecture along with company-wide agentic engineering standards.

• Spearhead initiatives that implement agents into production environments.

• Define technical direction and translate technical strategies into effective, production-ready results.

• Engage in design reviews and code assessments.

• Direct the technical direction and architecture for all Toptal products.

• Collaborate with Product teams to design infrastructure that exposes Toptal's core business logic through modular interfaces.

• Manage resources, workforce planning, headcount planning, role definitions, and hiring commitments.

• Lead the engineering team, establishing standards, developing personnel, and evaluating performance against those standards.

• Mentor engineers on agentic best practices while promoting AI adoption across Toptal.

• Oversee AI technology strategy, including model selection and fine-tuning, harness design, orchestration, retrieval, context engineering, tool integration, guardrails, evaluation, and cost management.

• Implement agentic engineering throughout matching, vetting, onboarding, delivery, and internal operations.

• Manage AI evaluations, regression suites, review loops, throughput, reliability, technical debt, secure-by-design architecture, responsible AI, and engineering cost structure.

• Evaluate engineering and AI maturity and present strategic plans to the executive team.

• Establish a shared AI architecture and evaluations while deploying agentic workflows into production.

• Demonstrate business impact from agents in at least two core workflows within a six-month timeframe.

• Develop an advanced engineering organization with AI integrated into its architecture and operational model.

⛳️ Requirements

• A Bachelor’s degree in Computer Science, Engineering, or a related technical field is essential.

• Over 15 years of progressive engineering leadership experience, including substantial time as a CTO or VP of Engineering, or as a direct report to one at a significant scale.

• Extensive, current, hands-on expertise in modern AI engineering, covering foundation models, agentic architectures, harness design, retrieval, context engineering, fine-tuning, and evaluation.

• Proven experience in shipping and operating AI systems in a production environment.

• Knowledge in building and fine-tuning foundation models from scratch.

• Implementation of agentic systems at scale in real business processes, with measurable impacts on cost, cycle time, quality, or revenue.

• Strong rigor in model, prompt, and agent evaluation with documented improvements.

• Proficiency in model routing, hosted versus self-hosted systems, inference capacity, latency and cost management, and provider portability.

• Demonstrated ability to educate on AI and facilitate organizational adoption of new technologies.

• Capability to formulate strategies and defend them using evidence.

• Proven track record in resourcing and workforce planning, with quantifiable hiring success.

• Currently hands-on, capable of reading and writing code as well as analyzing design documents and evaluation harnesses.

• Strong command of distributed systems, service architecture, data-intensive applications, and large-scale cloud infrastructure.

• Experience in scaling and modernizing a large existing codebase without disrupting business operations.

• Proven experience leading a globally distributed remote team in a technology or hyper-growth company.

• Exceptional written and verbal communication abilities.

• Quick decision-making skills with a focus on ownership, quality, urgency, and operating with incomplete information.

• World-class individual contributor skills.

• Ability to attend scheduled virtual team meetings on camera consistently and reliably.

• Capability to work independently with minimal supervision.

• Proficiency in required digital collaboration tools.

• Strong ability to prioritize and self-manage tasks and deadlines.

• Resumes and communications must be submitted in English.

🏝️ Benefits

• Fully remote workforce and position.

• Virtual team support structure that fosters innovation, social interaction, and enjoyment.