[Remote] Chief Executive Officer, AI Services

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Note: The job is a remote job and is open to candidates in USA. Toptal is a global network of top talent in business, design, and technology that enables companies to scale their teams, on-demand. As the CEO of AI Services, you will lead Toptal’s AI Services business, focusing on innovative solutions in data annotation and enterprise AI transformation.

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 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.
• Onboard and integrate into Toptal.
• Learn Toptal’s model, our value proposition, and our story.
• Deep dive into the AI Services organization to gain clarity on current structures, key initiatives, and challenges.
• Meet key leaders and stakeholders across AI, Product, Engineering, and the Executive team to build foundational relationships and understand cross-functional dependencies.
• Conduct a comprehensive assessment of AI Services initiatives, including organizational structure, team capabilities, operational processes, and performance metrics.
• Engage with senior leaders and key stakeholders to validate your initial findings and gather input on critical challenges and growth opportunities.
• Begin shaping a strategic operating model and execution framework tailored to the unique needs of Toptal’s AI Services function.
• Develop a clear understanding of client expectations and feedback to align AI Services initiatives with market demands.
• Begin executing a detailed operational plan that aligns with Toptal’s strategic objectives for AI Services, emphasizing scalability and efficiency.
• Sponsor and oversee initiatives that improve AI Services delivery consistency, system scalability, and client impact, ensuring cross-functional alignment and sustainable operational excellence.
• Deepen engagement with clients and internal stakeholders to anticipate future AI Services needs and proactively adapt offerings.
• 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 that support seamless AI Services delivery, resource management, and cross-functional collaboration.
• Achieve consistent execution of AI Services strategy through a high-performing, aligned leadership team.
• Have positioned Toptal’s AI Services function 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 AI Services growth.
• Champion innovation and continuous improvement initiatives that keep Toptal agile and ahead of market trends.

Skills

• Bachelor’s degree is required.
• 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.
• 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 how to work efficiently, and prioritize execution, as well as mentor others to do the same.
• Adaptable. Comfortable managing changing priorities, learning new skills, and building consensus across varied senior stakeholder groups.
• Ownership. You are a dependable leader who takes responsibility for your success as well as the success of the entire AI organization.
• Quality. You take pride in everything you deliver as a reflection of yourself.
• Ability to work in a fast-paced, rapidly growing company and handle a wide variety of challenges, deadlines, and a diverse array of contacts.
• Willingness to travel to meet with clients, team members, and stakeholders.
• You must be a world-class individual contributor to thrive at Toptal. You will not be here just to tell other people what to do.
• Master’s degree in Engineering, Computer Science, Business, or a related field preferred.
• 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.

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