Chief Technology Officer

Own Toptal’s AI technology strategy and the architecture beneath it: model selection and fine-tuning, harness design, orchestration, retrieval, context engineering, tool and MCP integration, guardrails, evaluation, and cost control, exposed as primitives every team composes against.

Deploy agentic engineering at scale against the work that runs this business: matching, vetting, onboarding, delivery, and internal operations. Own the outcomes those agents are accountable for.

Make AI quality measurable. Own the evals, the regression suites, and the review loops, so quality here is proven rather than claimed.

Rebuild how the platform gets built and operated, raising output per engineer through AI-assisted development, review, testing, and operations. Engineers have to want this, not comply with it, and creating that pull is on you.

Decide what a team should look like now that the roles have blurred, where the product manager believes they can design and code, the engineer believes they can do product and design, and the designer believes they can code and do product.

Own resourcing and workforce planning: scope the roadmap into buildable work, plan headcount and sequence, write the specs, and hit time-sensitive hiring commitments.

Own the bar for the team: assess talent honestly, develop people against the bar, and hold it as the organization grows.

Own the architecture end to end, from services and data flows to interfaces and system boundaries, and hold the standards that keep it coherent as it grows.

Own throughput, reliability, and the platform layer beneath them, including the AI-dependent paths where latency, drift, and provider outages are real failure modes. Own build-versus-buy, technical debt, secure-by-design architecture, responsible AI, and the engineering and AI cost structure down to inference and token spend.

Learn Toptal’s model and platform architecture, and meet the leaders you will depend on across Engineering, Product, Industries, and Services.

Establish a direct, working rhythm with the CEO.

Assess the engineering function honestly, and assess AI maturity with it: what is really in production, what is measured, what is duplicated, and what should be shut down.

Assess the team against the bar this role requires, and bring the executive team a strategy no one asked you for.

Be executing your own plan, with a review cadence and clear accountability at every level, and your resourcing plan presented.

Stand up the shared AI architecture and evals, and put one agentic workflow into production with a baseline and a measured result.

Show business impact from agents in production in at least two core workflows, with the evidence behind it.

Have the leadership team you need, with the bar visibly raised, and throughput and reliability moving on the paths that matter most.

Run an engineering organization recognized inside and outside Toptal as one of the most advanced in the industry, with the pull on AI now coming from engineering.

Have AI leverage embedded in the architecture and the operating model, not living in a portfolio of pilots, and the team you built delivering against plan.

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.

As Toptal’s Chief Executive Officer, Taso manages Toptal’s core team of hundreds of team members distributed throughout the world, with a focus on innovation. Since Toptal was founded in 2010, Taso has led it to become the largest high-skilled, on-demand talent network in the world. Taso serves on the board of multiple organizations, advising on talent strategy and innovation for Fortune 100s and nonprofits. Taso has guest lectured at Harvard Business School, Wharton, and Oxford on talent management and entrepreneurship.

We're changing the way the world works. Toptal is not only a place to progress your career and design your own lifestyle, but also a company where you'll learn how to develop innovations that push business and technology forward.