Chief Technology Officer

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

📋 Description

• Drive the execution of Toptal’s product and engineering teams, placing AI at the forefront of company development.

• Oversee Toptal’s complete technical architecture, implementing an AI-first approach through agentic engineering practices.

• Develop and maintain the AI architecture along with company-wide best practices in AI engineering.

• Lead projects that implement agents into production environments.

• Set the technical vision and translate strategy into production-ready results.

• Manage the technical architecture for all Toptal products.

• Collaborate with the Product team to design infrastructure that exposes core business logic via modular interfaces.

• Take responsibility for resource management and workforce planning, including task scoping, team sizing, headcount planning, and role definitions.

• Recruit high-performing team members and establish role-specific performance standards.

• Set team expectations, develop team members, and evaluate performance against established standards.

• Mentor engineers on agentic best practices and counsel executives on emerging AI capabilities.

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

• Implement agentic engineering across processes such as matching, vetting, onboarding, delivery, and internal operations.

• Manage AI evaluations, regression suites, review cycles, and measurable quality metrics.

• Enhance engineering output through AI-assisted development, review, testing, and operations.

• Oversee the end-to-end architecture, services, data flows, interfaces, and system boundaries.

• Manage throughput, reliability, platform architecture, build-versus-buy decisions, technical debt, secure-by-design principles, responsible AI practices, and engineering/AI costs.

• Establish a regular execution rhythm with the CEO to assess engineering and AI maturity.

• Present strategic plans, resource allocation, and accountability frameworks to the executive team.

• Develop shared AI architecture and evaluations, and implement agentic workflows into production.

• Demonstrate tangible business impact from agents in at least two core workflows within six months.

• Build a sophisticated engineering organization with AI integrated into its architecture and operational model.

⛳️ Requirements

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

• 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.

• Deep, current, hands-on expertise in modern AI engineering, including foundational models, agentic architectures, harness design, retrieval, context engineering, fine-tuning, and evaluation.

• Proven experience in shipping and operating AI systems in production environments.

• Knowledge of building and fine-tuning foundational models from scratch.

• Experience in deploying agentic systems at scale against real business processes, with measurable outcomes in cost, cycle time, quality, or revenue.

• Rigor in model, prompt, and agent evaluation, with evidence-based improvement metrics.

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

• Demonstrated ability to educate on AI and guide an organization towards adopting new technologies.

• Strategy development based on evidence rather than authority.

• Proven experience in resource management and workforce planning, with a quantifiable hiring success record.

• Currently hands-on; capable of coding and identifying flaws in design documents or evaluation harnesses.

• Strong understanding of distributed systems, service architecture, data-intensive applications, and scalable cloud infrastructure.

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

• Experience leading a globally distributed, remote team in a technology or hyper-growth company is essential.

• Exceptional written and verbal communication skills.

• World-class individual contributor capabilities.

• Resumes and communications must be submitted in English.

🏝️ Benefits

• Fully remote work arrangement.

• Global, borderless work environment.

• Support structure that fosters innovation, social interaction, and enjoyment.