CEO, AI Services

About Toptal

Toptal is a global network of top talent in business, design, and technology that enables companies to scale their teams, on-demand. With $200+ million in annual revenue and team members based around the globe, Toptal is the world’s largest fully remote workforce.

We take the best elements of virtual teams and combine them with a support structure that encourages innovation, social interaction, and fun. We see no borders, move at a fast pace, and are never afraid to break the mold.

Job Summary: CEO, AI Services

As the CEO of AI Services at Toptal, you will lead one of the company's most innovative divisions. Our AI Services integrate world-class expertise in data annotation, forward-deployed engineering, enterprise AI transformation, and a comprehensive AI software development approach. This role is crucial for advancing the next generation of AI and intelligence for enterprises, encompassing all AI-related areas, including AI-driven businesses and AI Service offerings.

You will adopt an engineer's mindset, focusing on solving complex business and operational problems. As the chief architect and operator of Toptal’s AI Services business, you will construct frameworks that enhance operational efficiency and push the boundaries of what's possible in AI Services. This leadership position demands a builder's mindset and a deep sense of ownership, requiring you to create AI frameworks and strategy, ensure functions are fully built out, and drive consistent execution across all AI Service areas.

Acting as the business owner for all AI initiatives, both internal and external, you'll oversee the full AI ecosystem. You will collaborate closely with Product and Engineering to design and scale the systems powering Toptal's AI capabilities and client solutions. Working with 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, and all communication must be in English.

Responsibilities

• 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.
• 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, ensuring alignment with evolving business needs.

Your Journey at Toptal

• In the first week, expect to: Onboard and integrate into Toptal. Learn Toptal’s model, value proposition, and story. Deep dive into the AI Services organization, understanding current structures, key initiatives, and challenges. Meet key leaders and stakeholders across AI, Product, Engineering, and the Executive team to build foundational relationships.
• In the first month, expect to: Conduct a comprehensive assessment of AI Services initiatives, including organizational structure, team capabilities, operational processes, and performance metrics. Engage with senior leaders and stakeholders to validate findings and gather input on critical challenges. Begin shaping a strategic operating model and execution framework. Develop a clear understanding of client expectations and feedback.
• In the first three months, expect to: Begin executing a detailed operational plan aligning with Toptal’s strategic objectives for AI Services, emphasizing scalability and efficiency. Sponsor and oversee initiatives improving AI Services delivery consistency, system scalability, and client impact, ensuring cross-functional alignment. Deepen engagement with clients and internal stakeholders to anticipate future AI Services needs.
• In the first six months, expect to: Achieve significant growth in AI Services-driven business initiatives and impact across Toptal. Drive measurable improvements in operational efficiency, client satisfaction, and delivery scalability across all AI Services. Refine and scale AI Services processes and systems supporting seamless delivery, resource management, and cross-functional collaboration.
• In the first year, expect to: Achieve consistent execution of AI Services strategy through a high-performing, aligned leadership team. Position Toptal’s AI Services as a core driver of competitive advantage through scalable operations, strong client delivery, and sustained business impact. Scale the operational infrastructure including technology process to support anticipated growth. Champion innovation and continuous improvement.

Qualifications and Job Requirements

• Bachelor’s degree is required; Master’s degree in Engineering, Computer Science, Business, or a related field preferred.
• 10+ years of progressive leadership experience scaling complex AI, technology, or service organizations and multiple business units, ideally in technology-driven environments.
• Proven track record 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.
• Experience at a technology, AI, or hyper-growth company strongly preferred; management consulting or investment banking experience a plus.
• Exceptional strategic thinking and problem-solving skills, with data-driven decision-making in ambiguous environments.
• Excellent communication and interpersonal skills, capable of influencing stakeholders at all levels.
• Experience driving cross-functional collaboration across Product, Engineering, sales, marketing, delivery, and support.
• Hyper-organized, efficient, and able to prioritize execution and mentor others.
• Adaptable to changing priorities, learning new skills, and building consensus across senior stakeholders.
• Takes ownership for personal success and the success of the entire AI organization.
• Committed to quality in all deliverables.
• Ability to thrive in a fast-paced, rapidly growing company, managing diverse challenges and deadlines.
• Willingness to travel to meet clients, team members, and stakeholders.
• You must be a world-class individual contributor to thrive at Toptal.

Key skills/competency

• AI Strategy
• Operational Leadership
• P&L Management
• Enterprise AI Transformation
• Data Annotation
• AI Software Development
• Cross-functional Leadership
• Strategic Execution
• Scalable Systems
• Business Growth