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Toptal, a global network of top talent with $200+ million in annual revenue and a fully remote workforce, is seeking a Chief Technology Officer to drive execution across product and engineering while establishing AI as the core of the company's technical strategy and architecture.
In this role, you will own Toptal's full technical architecture and rebuild it AI-first, utilizing best practices for agentic engineering. You will create and own the AI architecture and best practices that the rest of the company adopts, including deploying agentic systems at scale against core business processes (matching, vetting, onboarding, delivery, internal operations) with measured outcomes on cost, cycle time, quality, and revenue. You will be responsible for making AI quality measurable through evals, regression suites, and review loops, and for rebuilding how the platform gets built and operated to raise output per engineer through AI-assisted development, review, testing, and operations.
You will own resourcing and workforce planning as a hands-on doer: scoping work, sizing teams, planning headcount, defining roles and bars for every seat. Hiring is your highest-leverage work. You will set standards, develop people against those standards, and know exactly who is meeting them. You will be one of Toptal's foremost experts on AI, coaching engineers on agentic best practices and pushing AI into every function.
You will own the architecture end-to-end, from services and data flows to interfaces and system boundaries. You will own throughput, reliability, the platform layer, build-versus-buy decisions, technical debt, secure-by-design architecture, responsible AI, and the engineering and AI cost structure down to inference and token spend. You will collaborate closely with Product to design infrastructure that exposes Toptal's core business logic through modular interfaces.
This role demands high-energy execution, attention to detail, and urgency. You will be in design reviews and in the code, not adjacent to them. You conceive strategy, form your own view of where engineering and AI should go, build the case, and bring the CEO a strategy to react to, not a request for direction. You are expected to be a world-class individual contributor who will not be here just to tell other people what to do.
In the first week, you will learn Toptal's model and platform architecture and establish a direct working rhythm with the CEO. In the first month, you will assess the engineering function and AI maturity honestly, and bring the executive team a strategy. In the first three months, you will execute your own plan with clear accountability and put one agentic workflow into production with measured results. In the first six months, you will show business impact from agents in production in at least two core workflows. In the first year, you will run an engineering organization recognized as one of the most advanced in the industry.
Qualifications and Requirements:
- Bachelor's degree in Computer Science, Engineering, or a related technical field required; advanced degree strongly preferred
- 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: foundation models, agentic architectures, harness design, retrieval, context engineering, fine-tuning, and evaluation; must have shipped and operated these in production and know how to build and fine-tune foundation models from the ground up
- Agentic systems deployed at scale against real business processes, with measured outcomes on cost, cycle time, quality, or revenue, and a record of retiring what did not work
- Rigor about evaluation: ability to explain precisely how you knew a model, prompt, or agent change was an improvement, with evidence to show
- Command of the economics: model routing, hosted versus self-hosted, inference capacity, latency and cost budgets, and staying portable across providers
- Further ahead on AI than the executives around you, able to teach it, and proven at moving an organization to adopt something it was not asking for
- Ability to create strategy rather than administer it, and win arguments on evidence rather than authority
- Proven ownership of resourcing and workforce planning, with a quantifiable hiring track record and ability to make hard calls when someone is not clearing the bar
- Currently hands-on: read and write code, take apart design documents or eval harnesses and find flaws, command 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 replacing load-bearing systems in flight
- Experience leading a globally distributed, remote team at a technology or hyper-growth company required; experience with a high-volume two-sided marketplace or multi-tenant platform is a significant plus
- Outstanding written and verbal communication skills
- Speed, ownership, and quality: move with urgency, decide without perfect information, treat everything delivered as a reflection of yourself
- Must be a world-class individual contributor to thrive at Toptal
- Fluent in English (resumes and communication must be submitted in English)
