CEO, AI Services

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As the CEO of AI Services, you will lead Toptal’s AI Services business which is one of the most innovative divisions of Toptal. Our AI Services combine world‑class services in data annotation, forward‑deployed engineering, enterprise AI transformation, and an integrated AI software development approach—all aimed at advancing the next generation of AI and intelligence for enterprises. These are just some of the areas that you will own within Toptal’s AI Services business.

Your mindset will be that of an engineer who will work to solve business and operational problems. There will be no problem large or small for you to solve yourself. You will be the chief architect and operator of our AI Services business, constructing frameworks that enhance the operational efficiency and push the limits of what’s possible for AI Services. You will work to build and lead the full‑scale execution of Toptal’s AI Services business—including all AI‑related areas such as AI‑driven businesses and AI Service offerings.

This role demands a builder’s mindset and a deep sense of ownership. You will create the AI frameworks and strategy, ensure the functions are fully built out and working to perfection, and drive consistent execution across all AI Service areas of Toptal. Acting as the business owner for all AI initiatives across Toptal, both internal and external, you’ll oversee the full AI ecosystem while collaborating closely with Product and Engineering to design and scale the systems that power our AI capabilities and client solutions.

Working across a high‑caliber leadership group, you will bring strong AI discipline and strategic clarity to deliver world‑class client outcomes and sustainable growth.

This is a remote position. Resumes and communication must be submitted in English.

• 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 we are tightly aligned to support evolving business needs.

• Bachelor’s degree is required. Master’s degree 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, ideally within technology‑driven environments.
• 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 is 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. You are hyper‑organized, know…