SlipstreamJobs tracks this role from the company's public career site. Apply directly on the employer's site.
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 positioning AI as core to the company's technical strategy and operations.
In this role, you will own Toptal's full technical architecture and rebuild it with an AI-first mindset. You will create and own the AI architecture, best practices, and initiatives that put agentic systems into production at scale. Your responsibilities span three interconnected domains:
**AI and Agentic Engineering:** Own the complete AI technology strategy—model selection, fine-tuning, harness design, orchestration, retrieval, context engineering, tool integration, guardrails, and evaluation. Deploy agentic engineering against core business workflows (matching, vetting, onboarding, delivery, internal operations) with measured outcomes. Make AI quality measurable through evals and regression suites. Rebuild how the platform is built and operated, raising output per engineer through AI-assisted development, review, testing, and operations.
**Team, Resourcing, and Accountability:** Own resourcing and workforce planning end-to-end—scope the roadmap, plan headcount, write role specs, and execute time-sensitive hiring. Define and hold the bar for the team as the organization grows. Assess talent honestly and develop people against standards. You will be visibly excited about hiring A-players with a sense of urgency; hiring is your highest-leverage work.
**Platform and Execution:** Own the architecture end-to-end (services, data flows, interfaces, system boundaries) and hold standards as it scales. Own throughput, reliability, and the platform layer beneath them, including AI-dependent paths where latency, drift, and provider outages are real failure modes. Own build-versus-buy decisions, technical debt, secure-by-design architecture, responsible AI, and cost structure down to inference and token spend.
You will be in design reviews and in the code, not adjacent to them. You will set technical direction, hold cadenced meetings that turn strategy into production-ready outcomes, and move fast to ensure engineering is never the reason an initiative slows down. You will collaborate closely with Product to design infrastructure that exposes core business logic through modular interfaces. Alongside hands-on executives, your engineering discipline directly shapes Toptal's growth, profitability, and operational excellence.
This role runs on high-energy execution and attention to detail. You will bring urgency to every part and measure yourself on outcomes. You are expected to 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.
First week: Learn Toptal's model and platform architecture; meet key leaders across Engineering, Product, Industries, and Services; establish a direct working rhythm with the CEO.
First month: Assess the engineering function and AI maturity honestly; bring the executive team a strategy no one asked for.
First three months: Execute your own plan with clear accountability; present resourcing plan; stand up shared AI architecture and evals; put one agentic workflow into production with baseline and measured result.
First six months: Show business impact from agents in production in at least two core workflows with evidence; have the leadership team you need with visibly raised bar; throughput and reliability moving on paths that matter most.
First year: Run an engineering organization recognized as one of the most advanced in the industry; have AI leverage embedded in architecture and operating model, not in pilots; team delivering against plan.
**Requirements:**
- Bachelor's degree in Computer Science, Engineering, or related technical field (advanced degree strongly preferred)
- 15+ years of progressive engineering leadership, including significant time as CTO or VP of Engineering, or as 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, evaluation. Must have shipped and operated these in production; must 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; record of retiring what did not work
- Rigor about evaluation: can explain precisely how you knew a model, prompt, or agent change was an improvement; can show the evidence
- Command of the economics: model routing, hosted versus self-hosted, inference capacity, latency and cost budgets, staying portable across providers
- Further ahead on AI than executives around you; able to teach it; proven at moving an organization to adopt something it was not asking for
- Create strategy rather than administer it; win arguments on evidence rather than authority; view on what a team should look like in the age of AI
- Proven ownership of resourcing and workforce planning; quantifiable hiring track record; made hard calls when someone was 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, cloud infrastructure at scale
- Experience scaling and modernizing large existing codebase without stopping the business; replaced load-bearing systems in flight, not only built greenfield
- Experience leading globally distributed, remote team at technology or hyper-growth company (required). High-volume two-sided marketplace or multi-tenant platform is a significant plus
- Outstanding written and verbal communication skills
- Speed, ownership, quality: move with urgency, decide without perfect information, treat everything delivered as reflection of yourself
- Must be world-class individual contributor to thrive at Toptal; will not be here just to tell others what to do
