[Remote] Chief Executive Officer, AI Services

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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. Company OverviewToptal is a network of talent in business, design, and technology that enables companies to scale their teams, on demand. It was founded in 2010, and is headquartered in San Francisco, California, USA, with a workforce of 1001-5000 employees. Its website is https://www.toptal.com.Company H1B SponsorshipToptal has a track record of offering H1B sponsorships, with 2 in 2024, 1 in 2021, 1 in 2020. Please note that this does not guarantee sponsorship for this specific role.