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Chief Technology Officer

3 weeks, 4 days ago
Europe, Canada
Full-time
Executive
CTO (Chief Technology Officer)
Software Development
Microservices System Design
Apply Now
Toptal

Toptal

Toptal is a curated talent marketplace connecting freelance software developers, designers, finance experts, product managers, and project managers with businesses globally. With a focus on top 3% talent in software engineering, design, and finance, To...

Construction & Engineering
5K-10K
Founded 2010
$4M raised
View All Jobs 26

Description

  • Set Toptal’s AI, engineering, and technical architecture strategy.
  • Design shared AI primitives covering model selection, fine-tuning, orchestration, retrieval, evaluation, guardrails, and cost control.
  • Deploy and measure agentic workflows across matching, vetting, onboarding, delivery, and internal operations.
  • Own end-to-end platform architecture, reliability, throughput, security, responsible AI, technical debt, and infrastructure costs.
  • Establish AI-assisted development, testing, review, and operational practices across engineering.
  • Lead workforce planning, team design, headcount sequencing, hiring, and talent assessment.
  • Set engineering standards, develop leaders and employees, and maintain accountability as the organization grows.
  • Partner with Product to expose core business logic through modular, scalable interfaces.
  • Maintain hands-on involvement in design reviews, code, evaluation harnesses, and production execution.
  • Build a globally distributed engineering leadership team and deliver measurable business outcomes from AI adoption.

Requirements

  • Bachelor’s degree in Computer Science, Engineering, or a related technical field; advanced degree strongly preferred.
  • 15+ years of progressive engineering leadership experience, including significant CTO or VP Engineering experience or equivalent scale.
  • Hands-on production experience with foundation models, agentic architectures, harnesses, retrieval, context engineering, fine-tuning, and evaluation.
  • Track record deploying agentic systems against real business processes with measured cost, cycle-time, quality, or revenue outcomes.
  • Expertise in model evaluation, regression testing, model routing, inference capacity, latency, cost budgets, and provider portability.
  • Experience owning engineering strategy, workforce planning, quantified hiring outcomes, and performance standards.
  • Current ability to read and write code and expertise in distributed systems, service architecture, data-intensive applications, and cloud infrastructure at scale.
  • Experience modernizing large existing codebases and replacing critical systems without disrupting business operations.
  • Experience leading globally distributed remote teams in a technology or hyper-growth company; marketplace or multi-tenant platform experience preferred.
  • Outstanding written and verbal communication, urgency, ownership, sound judgment, and world-class individual-contributor capability.

Benefits

  • Fully remote position with team members distributed globally.
  • Opportunity to shape AI architecture and agentic engineering across a large remote technology organization.
  • Direct collaboration with the CEO and executive leadership.
  • Ability to influence core products, platform strategy, growth, profitability, and operational excellence.

Interested in this position?

Apply directly on the company website

Apply Now

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