Chief Technology Officer - US-Based

Toptal

32d • Remote

About The Position

As Chief Technology Officer, you will drive execution for the product and engineering teams and put AI at the core of everything the company builds. You will own Toptal’s full technical architecture and you will build it AI-first—utilizing best practices for agentic engineering. AI is not a workstream inside the engineer team—its core to it.
You will create and own the AI architecture and best practices the rest of the company utilizes. You will also own the initiatives that put agents into production. You should know how to build and fine-tune foundation models from the ground up, how to engineer best-in-class harnesses, and how to create best practices for agentic engineering that engineering teams adopt to 10x their productivity—without sacrificing quality. Your mindset will be that of a builder and an architect, someone who solves problems in the system itself. No problem will be too large or too small for you to solve yourself. You will set the technical direction and hold the cadenced meetings that turns technical strategy into working, production-ready outcomes. You will be in the design reviews and in the code, not adjacent to them. You will move fast, and you will ensure our engineering team is never the reason an initiative slows down.
You are the technical owner of all Toptal’s products. You will collaborate closely with Product to design infrastructure that exposes Toptal’s core business logic through modular interfaces the rest of the business build on. Alongside a group of hands-on executives, your engineering discipline directly shapes Toptal’s growth, profitability, and operational excellence.
You will own resourcing and workforce planning as a doer: scoping the work, sizing the teams, planning headcount against it, defining the role and the bar for every seat. None of that is beneath the role, and we are not interested in someone who thinks these tasks can be done properly by handing it off to HR. Hiring is the highest-leverage work you do, and we want someone who is visibly excited about hiring A-players—with a sense of urgency.
Then, you lead the team. You will set the standards, develop people against those standards, and know exactly who is meeting those standards.
You will be one of Toptal’s foremost experts on AI, and you will stay ahead of a field that never stops moving. You will coach engineers on agentic best practices, show the executive team what is newly possible with the new AI tooling, and push AI into every function at Toptal.
This role runs on high-energy execution and attention to detail. You will bring urgency to every part of it and measure yourself on outcomes. We are not looking for someone to oversee this work. We are looking for someone to drive it and get into the detiwls.
This is a remote position. Resumes and communication must be submitted in English.

Requirements

• Bachelor’s degree in Computer Science, Engineering, or a related technical field.
• 15+ years of progressive engineering leadership experience, 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.
• Experience shipping and operating AI systems in production, including 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, and a record of retiring ineffective solutions.
• Rigor about evaluation, with the ability to precisely explain how model, prompt, or agent changes were improvements, supported by evidence.
• Command of the economics of AI, including model routing, hosted versus self-hosted options, inference capacity, latency and cost budgets, and provider portability.
• Ability to stay ahead of AI trends, teach AI concepts, and drive organizational adoption of new AI technologies.
• Ability to create strategy rather than administer it, and win arguments with evidence.
• Proven ownership of resourcing and workforce planning, with quantifiable hiring track record and experience making difficult decisions about underperforming employees.
• Currently hands-on with coding, design document analysis, and evaluation harness assessment.
• Command of distributed systems, service architecture, data-intensive applications, and cloud infrastructure at scale.
• Experience scaling and modernizing large existing codebases without disrupting business operations, including replacing critical systems in flight.
• Experience leading a globally distributed, remote team at a technology or hyper-growth company.
• Outstanding written and verbal communication skills.
• Demonstrated speed, ownership, and quality in work delivery.
• Ability to be a world-class individual contributor.
• Regularly and reliably attend scheduled virtual team meetings on camera.
• Work independently with minimal supervision.
• Use all required digital collaboration tools.
• Prioritize and self-manage workflows and deadlines.

Nice To Haves

• An advanced degree is strongly preferred.
• A high-volume, two-sided marketplace or multi-tenant platform experience is a significant plus.

Responsibilities

• Conceive the strategy for engineering and AI, build the case, and present a strategy to the CEO.
• Own Toptal’s AI technology strategy and architecture, including model selection, fine-tuning, harness design, orchestration, retrieval, context engineering, tool and MCP integration, guardrails, evaluation, and cost control.
• Deploy agentic engineering at scale for business processes like matching, vetting, onboarding, delivery, and internal operations, and own the outcomes.
• Make AI quality measurable through ownership of evaluations, regression suites, and review loops.
• Rebuild the platform's development and operation processes using AI-assisted development, review, testing, and operations to increase engineer output.
• Define team structures considering blurred roles in the age of AI.
• Own resourcing and workforce planning, including scoping the roadmap, planning headcount, writing specs, and meeting hiring commitments.
• Set and maintain the bar for team talent, assessing and developing individuals.
• Own the end-to-end architecture, including services, data flows, interfaces, and system boundaries, and uphold standards for coherence.
• Own throughput, reliability, and the platform layer, including AI-dependent paths with potential failure modes like latency and drift.
• Manage build-versus-buy decisions, technical debt, secure-by-design architecture, responsible AI, and engineering/AI cost structure.
• Learn Toptal’s model and platform architecture and meet key leaders within the first week.
• Establish a direct working rhythm with the CEO within the first week.
• Assess the engineering function and AI maturity, identifying production systems, measurements, duplications, and areas for shutdown within the first month.
• Assess the team against the required bar and present a strategy to the executive team within the first month.
• Execute the established plan with clear accountability and a presented resourcing plan within the first three months.
• Stand up the shared AI architecture and evaluations, and deploy one agentic workflow into production with measured results within the first three months.
• Demonstrate business impact from agents in production in at least two core workflows within the first six months.
• Build the necessary leadership team, raise the bar for talent, and improve throughput and reliability within the first six months.
• Run an engineering organization recognized as advanced in the industry, with AI pull originating from engineering, within the first year.
• Embed AI leverage into the architecture and operating model, moving beyond pilots, with the team delivering against plan within the first year.

Benefits

• Global network of top talent
• Largest fully remote workforce
• Support structure that encourages innovation, social interaction, and fun
• Fast-paced environment
• Opportunity to break the mold

What This Job Offers

• Job Type: Full-time
• Career Level: Executive