RemoteLeaf Logo
Log in Sign up

Chief Technology Officer - US-Based

3 hours, 7 minutes ago
United States
Full-time
Executive
CTO (Chief Technology Officer)
Software Development
Microservices
Apply Now
Toptal

Toptal

Toptal is a curated talent marketplace connecting freelance software developers, designers, finance experts, product managers, and project managers with businesses globally. With a focus on top 3% talent in software engineering, design, and finance, To...

Construction & Engineering
5K-10K
Founded 2010
$4M raised
View All Jobs 23

Description

  • Set and execute Toptal’s AI and engineering strategy, bringing evidence-based recommendations to the CEO.
  • Own the end-to-end technical architecture, including services, data flows, interfaces, infrastructure, security, and system boundaries.
  • Design and operate AI foundations covering model selection, fine-tuning, orchestration, retrieval, context engineering, tools, guardrails, evaluation, and cost control.
  • Deploy agentic systems across matching, vetting, onboarding, delivery, and internal operations, with measurable accountability for outcomes.
  • Establish evaluations, regression suites, and review loops to measure AI quality and reliability.
  • Increase engineering productivity through AI-assisted development, testing, review, and operations.
  • Own workforce planning, team design, headcount, hiring commitments, talent assessment, and performance standards.
  • Lead and develop a globally distributed engineering organization while maintaining high standards for speed, quality, throughput, and reliability.
  • Partner with Product to expose core business logic through modular interfaces and scalable infrastructure.
  • Assess the organization and AI maturity, establish shared architecture and operating cadences, and deliver agents into production against defined milestones.

Requirements

  • Bachelor’s degree in Computer Science, Engineering, or a related technical field; advanced degree strongly preferred.
  • 15+ years of progressive engineering leadership, including substantial experience as a CTO, VP of Engineering, or direct report to one at meaningful scale.
  • Hands-on production experience with foundation models, agentic architectures, harness design, retrieval, context engineering, fine-tuning, and evaluation.
  • Experience deploying agentic systems at scale with measured effects on cost, cycle time, quality, or revenue.
  • Strong understanding of model routing, hosted versus self-hosted infrastructure, inference capacity, latency, cost budgets, and provider portability.
  • Proven experience creating strategy, driving organizational adoption of AI, and communicating effectively with executives and technical teams.
  • Quantifiable experience with workforce planning, hiring, talent assessment, and performance management.
  • Current coding ability and expertise in distributed systems, service architecture, data-intensive applications, and cloud infrastructure at scale.
  • Experience modernizing large existing codebases and replacing critical systems without interrupting operations.
  • Experience leading globally distributed remote teams; marketplace or multi-tenant platform experience preferred.
  • Ability to work independently, manage deadlines, use digital collaboration tools, and reliably attend scheduled virtual meetings on camera.
  • Outstanding written and verbal communication, with a high-ownership, urgent, hands-on working style.

Benefits

  • Fully remote position with team members distributed globally.
  • Full-time, exempt employment classification.
  • Opportunity to lead AI transformation across a global technology organization.

Interested in this position?

Apply directly on the company website

Apply Now

Similar Roles

FutureSight

Technical Co-founder (CTO)

FutureSight 11-50 Internet Software & Services

FutureSight is seeking a full-time Co-Founder & CTO to define, build, and lead a new B2B AI venture from inception through initial traction alongside its venture-building team.

United States Full-time Lead CTO (Chief Technology Officer) Machine Learning Engineer
System Design
3 hours, 52 minutes ago
FutureSight

Technical Co-founder (CTO) - AI Legal Front Desk

FutureSight 11-50 Internet Software & Services

BloomLex, a FutureSight venture, is seeking a technical co-founder to lead product and engineering as it brings its managed AI front-desk platform for law firms from live pilots into reliable, scalable production.

United States Lead CTO (Chief Technology Officer)
3 hours, 52 minutes ago
FutureSight

Technical Co-founder (CTO) - AI for Automotive Retail

FutureSight 11-50 Internet Software & Services

Atrium, a FutureSight venture building an AI-native workforce for used-car dealers, is seeking a technical co-founder to own product and engineering from the first production code through scalable deployment.

United States Full-time Lead CTO (Chief Technology Officer)
DOM
1 day, 3 hours ago
FutureSight

Technical Co-founder (CTO) - AI Legal Front Desk

FutureSight 11-50 Internet Software & Services

BloomLex, a managed AI staffing venture for law firms, is seeking a technical co-founder to lead product and engineering as its AI front-desk platform moves from live pilots toward reliable, scalable production deployment.

United States Full-time Lead CTO (Chief Technology Officer)
5 days, 3 hours ago

You're on a roll! Sign up now to keep applying.

Sign Up

Already have an account? Log in

Used by 14,729+ remote workers