CEO, AI Services

Job Title: Chief Executive Officer – AI Services

As the CEO of AI Services, you will lead Toptal’s AI Services business, one of the most innovative divisions of the company. The role encompasses ownership of AI-driven services, data annotation, forward-deployed engineering, enterprise AI transformation, and integrated AI software development. You will act as the chief architect and operator, building and leading the full-scale execution of the AI Services business.

This remote position requires English communication. You will collaborate closely with Product and Engineering to design and scale systems that power AI capabilities and client solutions, while overseeing the full AI ecosystem across internal and external initiatives. Your world-class execution will enable sustainable growth and world‑class client outcomes.

• Own the vision, strategy, and execution plan for Toptal’s AI Services, including all AI‑driven Service offerings.
• Define the organizational structure and leadership model for the AI Services teams, ensuring the right roles and capabilities are in place.
• Provide hands‑on operational leadership, bringing rigor, consistency, and clear accountability to all AI Service lines and functions.
• Translate high‑level AI Services strategy and business objectives into detailed operational roadmaps for all areas of responsibility.
• Establish scalable AI Services processes and systems to ensure delivery excellence, efficiency, and client satisfaction at scale.
• Partner cross‑functionally with Product, Engineering, Marketing, Finance, and Legal to execute on strategic priorities and company‑wide AI Services initiatives.
• Drive a high‑performance culture across all functions and businesses, while ensuring tight alignment to evolving business needs.

• Bachelor’s degree required;
  Master’s in Engineering, Computer Science, Business, or a related field preferred.
• 10+ years of progressive leadership experience in scaling complex AI, technology, or service organizations and multiple business units.
• Proven track record of successfully leading multi‑service or AI‑driven initiatives with accountability for P&L, growth, and operational excellence.
• Demonstrated ability to develop and execute scalable AI strategies and operational frameworks that drive efficiency, client satisfaction, and sustainable growth.
• Experience at a technology, AI, or hyper‑growth company strongly preferred.
• Management consulting experience at a top‑tier firm (e.g., McKinsey, Bain, BCG) or investment banking experience is preferred but not required.
• Exceptional strategic thinking and problem‑solving skills, with the ability to make data‑driven decisions in ambiguous environments.
• Excellent communication and interpersonal skills, capable of influencing stakeholders at all levels, including executives and clients.
• Experience driving cross‑functional collaboration and alignment across Product, Engineering, sales, marketing, delivery, and support functions.
• Excellent organization skills and detail‑oriented; hyper‑organized and efficient, prioritizing execution and mentoring others.
• Adaptable; comfortable managing changing priorities, learning new skills, and building consensus across varied senior stakeholder groups.
• Ownership; dependable leader who takes responsibility for personal and organizational success.
• Quality; takes pride in everything delivered as a reflection of self.
• Ability to work in a fast‑paced, rapidly growing company and handle a wide variety of challenges, deadlines, and diverse contacts.
• Willingness to travel to meet with clients, team members, and stakeholders.
• Must be a world‑class individual contributor to thrive at Toptal; not merely a delegator.

• 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.

US FLSA Classification:
Full‑Time/Exempt

Executive

Full‑time

Business Development and Sales

Technology, Information and Internet