Chief Technology Officer

Posted 2 weeks ago

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About the role

  • Chief Technology Officer driving AI-first architecture, agentic engineering, and distributed team execution at Toptal. Owning technical strategy, hiring, platform reliability, and production AI outcomes.

Responsibilities

  • Drive execution for Toptal’s product and engineering teams and put AI at the core of company development
  • Own Toptal’s full technical architecture and build it AI-first using agentic engineering practices
  • Create and own AI architecture and company-wide AI engineering best practices
  • Lead initiatives that put agents into production
  • Set technical direction and turn strategy into production-ready outcomes
  • Own the technical architecture of all Toptal products
  • Collaborate with Product to design infrastructure exposing core business logic through modular interfaces
  • Own resourcing and workforce planning, including scoping work, sizing teams, planning headcount, and defining roles
  • Hire high-performing team members and establish role-specific standards
  • Set team standards, develop people, and assess performance against those standards
  • Coach engineers on agentic best practices and advise executives on new AI capabilities
  • Own AI technology strategy, including model selection, fine-tuning, harness design, orchestration, retrieval, context engineering, tool and MCP integration, guardrails, evaluation, and cost control
  • Deploy agentic engineering across matching, vetting, onboarding, delivery, and internal operations
  • Own AI evaluations, regression suites, review loops, and measurable quality
  • Improve engineering output through AI-assisted development, review, testing, and operations
  • Own end-to-end architecture, services, data flows, interfaces, and system boundaries
  • Own throughput, reliability, platform architecture, build-versus-buy decisions, technical debt, secure-by-design architecture, responsible AI, and engineering/AI costs
  • Establish an execution rhythm with the CEO and assess engineering and AI maturity
  • Present strategy, resourcing plans, and accountability frameworks to the executive team
  • Stand up shared AI architecture and evaluations and put agentic workflows into production
  • Demonstrate business impact from agents in at least two core workflows within six months
  • Build an advanced engineering organization with AI embedded in its architecture and operating model

Requirements

  • Bachelor’s degree in Computer Science, Engineering, or a related technical field is required
  • 15+ years of progressive engineering leadership, including significant time as a CTO or VP of Engineering, or as a direct report to one at meaningful scale
  • Deep, current, hands-on command of modern AI engineering, including foundation models, agentic architectures, harness design, retrieval, context engineering, fine-tuning, and evaluation
  • Experience shipping and operating AI systems in production
  • Knowledge of building and fine-tuning foundation models from the ground up
  • Experience deploying agentic systems at scale against real business processes, with measured outcomes on cost, cycle time, quality, or revenue
  • Rigor about model, prompt, and agent evaluation, with evidence-based improvement measurement
  • Command of model routing, hosted versus self-hosted infrastructure, inference capacity, latency and cost budgets, and provider portability
  • Proven ability to teach AI and move an organization toward adopting new technology
  • Strategy creation based on evidence rather than authority
  • Proven ownership of resourcing and workforce planning, with a quantifiable hiring track record
  • Currently hands-on; able to read and write code and identify flaws in design documents or evaluation harnesses
  • Command of distributed systems, service architecture, data-intensive applications, and cloud infrastructure at scale
  • Experience scaling and modernizing a large existing codebase without stopping the business
  • Experience leading a globally distributed, remote team at a technology or hyper-growth company is required
  • Outstanding written and verbal communication skills
  • World-class individual contributor capability
  • Resumes and communication must be submitted in English

Benefits

  • Fully remote work arrangement
  • Global, borderless work environment
  • Support structure encouraging innovation, social interaction, and fun

Job type

Full Time

Experience level

Lead

Salary

Not specified

Degree requirement

Bachelor's Degree

Tech skills

CloudDistributed Systems

Location requirements

RemoteCanada

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