Enterprise Sales Executive, AI Solutions

This is a fully remote position, open to applicants in Canada.

📋 Description

• Identify, cultivate, and secure enterprise client opportunities for Toptal’s AI Solutions division.

• Assist clients in addressing intricate business challenges through advanced AI solutions, software and platforms, services, and transformations enabled by AI.

• Create customized solutions that transition clients from AI strategy and experimentation to implementation.

• Build, prioritize, and develop a focused portfolio of enterprise accounts alongside a self-sourced business pipeline.

• Take ownership of new-logo acquisition, revenue expansion, client outcomes, pipeline development, and forecasting.

• Engage in prospecting, pitching, negotiating, and closing new opportunities in collaboration with Sales Development Representatives.

• Define and implement account strategies, opportunity generation, and multi-year growth plans.

• Spearhead AI solution development and deal execution in partnership with AI Services leadership, Industry GMs, Practice Leaders, Pursuits, Partnerships, and Delivery teams.

• Collaborate with Client Partners to enhance strategic relationships and maximize account value.

• Shape solutions across various domains including AI Strategy & Transformation, Agentic Solutions, Data Services, AI Platforms, Industry Solutions, Joint Partner Solutions, and Managed Services.

• Lead strategic discussions with both prospective and existing clients, including C-suite executives.

• Maintain a disciplined approach to pipeline and account intelligence for accurate forecasting and decision-making.

• Negotiate contracts and work with clients on Toptal’s AI capabilities and specialist offerings.

• Build credibility through consultative engagement linked to client AI priorities, workflows, technology investments, and desired outcomes.

• Develop proposals and finalize deals.

• Expand buyer networks and strengthen executive engagement across accounts.

• Introduce additional AI capabilities, platforms, partners, and managed services while displacing existing providers.

• Implement measurable growth plans and cultivate long-term client relationships.

• Contribute to team rituals, share best practices, and participate in win/loss reviews.

• Mentor new team members and educate them about Toptal, its AI model, and strategies for territory growth.

⛳️ Requirements

• A bachelor's degree is mandatory.

• 7–10+ years of experience in enterprise technology, AI software, professional services, or consulting sales.

• Strong expertise in enterprise account development and complex solution selling.

• Direct experience in selling enterprise AI solutions is essential.

• Extensive background in consultative customer engagement and selling service-oriented, technology-enabled, or outcome-based solutions to enterprise clients.

• Proven success in building a book of business from scratch through self-sourcing, prospecting, and developing new enterprise relationships.

• A solid track record of managing a $5M+ annual gross portfolio and closing complex, multi-phase deals ranging from $250K to $1M+ with enterprise clients boasting $2B+ in annual revenue.

• Comfortable engaging C-level executives regarding AI’s influence on business, technology, operating models, workforce, and the competitive landscape.

• Knowledge of enterprise AI challenges and trends, including generative AI, agentic AI, AI applications and platforms, enterprise data and knowledge, models, workflow automation, governance, evaluation, controls, and managed AI operations.

• Ability to discuss the transition of AI from strategy and experimentation into enterprise workflows and production settings.

• Experience selling solutions that involve leading AI, cloud, data, or enterprise technology platforms.

• Capability to operate in a platform-flexible environment across client technology ecosystems.

• Familiarity with hybrid talent models, forward-deployed delivery models, or alternative consulting delivery frameworks.

• Proven ability to build and execute account plans that support portfolio growth and maintain a healthy pipeline.

• Demonstrated success in collaborative prospecting, both virtual and on-site sales calls, and multidisciplinary sales efforts.

• Experience negotiating complex service agreements with procurement and legal teams.

• Ability to collaborate across multiple internal teams.

• Willingness and ability to travel up to 25%.

• Regular or occasional travel to meet Toptal clients and customers within and outside the geographic area.

• Exceptional written and verbal communication skills.

• Capability to thrive in a fast-paced, rapidly growing company.

• Must be a top-tier individual contributor.

• Resumes and communications must be submitted in English.

• Must be eligible to work without visa sponsorship or assistance.

🏝️ Benefits

• Fully remote workforce.

• Remote position.

• Opportunity to collaborate with a global network of exceptional talent.

• Client-facing fieldwork and exposure to enterprise AI initiatives.

• Travel opportunities to client sites, conferences, and team events (up to 25%).