CEO, AI Services - US-Based

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:

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 as to 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.

Responsibilities:

The following information is intended to describe the general nature and level of work being performed. It is not intended to be an exhaustive list of all duties, responsibilities, or required skills.

·        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.

In the first week, expect to:

·        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.

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 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.

In the first three months, expect to:

·        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.

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 that support seamless AI Services 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.

·        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.

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 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 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.

Essential Job Functions

·        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