Chief Technology Officer - US-Based
Toptal · USA
About this role
## Chief Technology Officer (US-Based) ### About Toptal Toptal is a global network of top talent in business, design, and technology—enabling companies to scale teams on-demand. With **$200M+ in annual revenue** and team members worldwide, Toptal is the world’s largest **fully remote** workforce. The company moves fast, encourages innovation, and builds with a strong support structure for virtual teams. --- ### Role Overview As **Chief Technology Officer**, you will: - **Drive execution** for Product and Engineering - Put **AI at the core** of everything Toptal builds (AI is not a side workstream—it’s central to engineering) - Own **Toptal’s full technical architecture** and build an **AI-first** platform using best practices for **agentic engineering** - Create and own the **AI architecture, best practices, and agent workflows** used across the company - Lead with a **builder/architect mindset**—solving problems directly, including the hard ones This is a **remote** role. **Resumes and communication must be submitted in English.** --- ### Responsibilities #### AI & Agentic Engineering - Own Toptal’s **AI technology strategy** and architecture: model selection & fine-tuning, harness design, orchestration, retrieval, context engineering, tool/MCP integration, guardrails, evaluation, and **cost control** - Deploy **agentic engineering at scale** across business-critical workflows (matching, vetting, onboarding, delivery, internal operations) - Make **AI quality measurable**: own evals, regression suites, and review loops - Rebuild how the platform is built and operated to raise **output per engineer** via AI-assisted development, review, testing, and operations #### Team, Resourcing, & Accountability - Own resourcing and workforce planning: scope the roadmap, plan headcount sequencing, write specs, and hit time-sensitive hiring commitments - Set and uphold the **bar for talent**; develop people against standards and hold accountability as the org grows - Lead hiring with urgency—excited about bringing in **A-players** #### Platform & Execution - Own architecture end-to-end: services, data flows, system boundaries, and standards for long-term coherence - Own throughput, reliability, and platform layers—especially AI-dependent failure modes (latency, drift, provider outages) - Own build-vs-buy decisions, technical debt strategy, **secure-by-design**, responsible AI, and engineering/AI cost structure (including inference/token spend) --- ### Expected Timeline (High Level) - **First week:** Learn Toptal’s model/platform architecture; establish a working rhythm with the CEO - **First month:** Assess engineering function and AI maturity; evaluate team against the bar; deliver an evidence-based strategy - **First 3 months:** Execute your plan with review cadence and accountability; stand up shared AI architecture + evals; ship one agentic workflow with measured results - **First 6 months:** Demonstrate business impact from agents in at least two core workflows with evidence; raise leadership bar; improve throughput/reliability - **First year:** Build an engineering organization recognized for advanced AI leverage; embed AI into the operating model (not pilots) --- ### Qualifications - **Bachelor’s degree** in CS/Engineering or related field (advanced degree strongly preferred) - **15+ years** progressive engineering leadership, including significant CTO/VP Engineering experience (or direct report at meaningful scale) - Deep, hands-on
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