Chief Technology Officer – AI‑First Leadership

About the role

Toptal is seeking a hands‑on Chief Technology Officer to lead its product and engineering teams with an AI‑first mindset. You will own the full technical architecture, drive AI strategy, and ensure rapid, high‑quality delivery across the company.

Key responsibilities

• Define and execute Toptal’s AI technology strategy, including model selection, fine‑tuning, harness design, orchestration, retrieval, context engineering, tool integration, guardrails, evaluation, and cost control.
• Build and scale agentic engineering solutions that power core business processes such as matching, vetting, onboarding, and delivery.
• Own the end‑to‑end technical architecture, from services and data flows to interfaces, ensuring reliability, performance, and responsible AI compliance.
• Lead resourcing and workforce planning: scope roadmaps, size teams, set hiring standards, and recruit A‑players.
• Coach engineers on AI best practices, drive adoption of AI‑assisted development, and measure outcomes through rigorous evaluation and regression testing.

Required profile

• 15+ years of progressive engineering leadership, including CTO or VP of Engineering experience at scale.
• Deep, hands‑on expertise in modern AI engineering: foundation models, agentic architectures, fine‑tuning, and production deployment.
• Proven track record of scaling AI systems with measurable impact on cost, cycle time, quality, or revenue.
• Experience leading globally distributed, remote engineering teams in a high‑growth, multi‑tenant platform environment.
• Strong communication skills and ability to create and sell technical strategy to executive leadership.

Required skills

• Foundation model development and fine‑tuning
• Agentic system design and orchestration
• Retrieval and context engineering
• AI evaluation, regression testing, and guardrails
• Distributed systems and service architecture
• Data‑intensive applications
• Cloud infrastructure and cost‑aware inference scaling