Chief Technology Officer

Job not on LinkedIn

🔥 0 minutes ago

🇨🇦 Canada – Remote

⏰ Full Time

🔴 Lead

👨‍💼 Chief Technology Officer (CTO)

👻 Ghost score 12%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Toptal

WebsiteLinkedInAll Job Openings

1001 - 5000 employees

Founded 2010

💼 Consulting

📣 Marketing

🎯 Recruiter

💰 Seed Round on 2012-06

Consulting • Marketing • Recruitment

Toptal is an exclusive network of the top freelance software developers, designers, marketing experts, finance experts, product managers, and project managers in the world. The company provides businesses with access to highly skilled professionals to tackle their most important projects. Toptal's offerings allow companies to quickly and flexibly hire top talent for various roles, including developers, designers, and finance experts, among others. These professionals are rigorously tested and vetted to ensure high quality and an excellent trial-to-hire success rate of 98%. With a global presence and a focus on embracing advanced skills such as blockchain and AI, Toptal is leading the future of on-demand work. Companies rely on Toptal for high-skilled freelance talent across various sectors, ensuring they can build amazing teams rapidly and efficiently as per their project needs.

📋 Description

• 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