Remote Enterprise AI Sales Executive at Toptal — Columbus

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 an Enterprise Sales Executive at Toptal, you will be a key driver of growth within our AI Solutions business. In this role, you will identify, develop, and close opportunities with enterprise clients by helping them solve complex business challenges through forward-deployed AI solutions, AI software and platforms, AI services, and AI-enabled transformation.

You will develop tailored solutions that help clients move from AI strategy and experimentation into production, combining Toptal's capabilities across AI Strategy & Transformation, Agentic Solutions, Data Services, AI Platforms, Industry Solutions, Joint Partner Solutions, and Managed Services to achieve measurable business outcomes.

This role is designed for true hunters who thrive in a high-performance, client-facing environment. It is ideal for individuals who have successfully sold enterprise AI solutions and are passionate about building a book of business from the ground up, forging executive relationships, and creating long-term client value. Success in this role is measured by your ability to convert new enterprise relationships into durable revenue and establish Toptal as a core AI services provider embedded in your clients' most critical initiatives.

Enterprise AI has shifted rapidly from experimentation to execution. Companies are investing in models, agents, AI platforms, data infrastructure, and AI-enabled applications, but many are struggling to translate those investments into production systems and measurable business outcomes.

The challenge is no longer simply selecting an AI model or platform. Enterprises must identify the right workflows, connect AI to their proprietary data and knowledge, integrate existing systems, build and deploy agents and applications, establish evaluation and control frameworks, drive adoption, and continuously operate and improve AI in production.

Toptal brings together world-class AI and domain talent, forward-deployed solution delivery, AI platforms and capabilities, strategic technology partners, expert-in-the-loop operations, and managed services to help enterprises move from AI promise to production.

This role exists to convert that market opportunity into new enterprise relationships and position Toptal as a strategic partner for companies deploying AI across their organizations.

This is a remote position with significant client-facing fieldwork across the US. Applicants who reside within commutable distance of a major metropolitan area are strongly preferred. We do not offer visa sponsorship or assistance. 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.

You will be responsible for building a targeted portfolio of accounts by identifying, prioritizing, and developing your own book of business rather than inheriting an existing one. Once you have signed net new customers, you will partner with Client Partners to deepen and expand those strategic relationships over time.

Net new accounts may begin with a specific AI initiative, workflow, platform implementation, or business problem requiring a disciplined approach to defining the opportunity and matching the right Toptal capabilities to the client's needs. As relationships mature, accounts become more complex, with deeper engagement across multiple business units, workflows, technology platforms, and senior executive relationships.

These accounts demand a highly consultative, strategic approach that includes navigating cross-functional priorities, understanding the client's AI and technology environment, aligning solutions to evolving business objectives, and demonstrating credibility at the C-suite level.

• Own and build a portfolio of enterprise AI accounts, with direct accountability for new logo acquisition, revenue growth, and client outcomes.
• Prospect, pitch, negotiate, and close new opportunities in close partnership with our Sales Development Representatives (SDRs), while expanding the relationships you establish.
• Define and execute account strategy, including opportunity creation, pipeline development, and multi-year growth planning.
• Lead AI solution development and deal execution in partnership with AI Services leadership, Industry GMs, Practice Leaders, Pursuits, Partnerships, and Delivery teams.
• Partner with Client Partners to drive coordinated account expansion and maximize total account value as accounts mature.
• Shape AI solutions that apply Toptal's capabilities across AI Strategy & Transformation, Agentic Solutions, Data Services, AI Platforms, Industry Solutions, Joint Partner Solutions, and Managed Services to clients' most important business and operating challenges.
• Maintain disciplined pipeline and account intelligence to support accurate forecasting and informed decision-making.
• Lead strategic conversations with prospective and existing clients, while exercising discretion and independent judgment.

In the First Week, Expect To:

• Onboard with Toptal and meet your TopPal.
• Learn the core of Toptal's model, our value proposition, and our deep capabilities.
• Familiarize yourself with the tools and resources needed to be successful.
• Dive into our sales methods, our selling processes, and playbooks.
• Become familiar with our contracting and legal methodologies, templates, tools, and processes.

In the First Month, Expect To:

• Meet key Toptal stakeholders who will support your success and the success of the overall team.
• Learn about the Toptal AI Go-To-Market Strategy, our key sales plays, solution portfolio, partner ecosystem, and client engagement model.
• Work with AI Services leadership to establish a portfolio strategy and build account plans.
• Shadow key calls and client meetings.
• Begin to meet with clients, leveraging your existing enterprise AI network and relationships, to articulate Toptal's capabilities and identify where we can help organizations move AI into production.
• Begin prospecting and actively engaging target accounts within your portfolio.
• Meet with SDRs, Client Partners, and cross-functional team members to align on joint account strategies.
• Collaborate with Pursuits and Delivery teams to understand how we design AI engagements.

In the First Three Months, Expect To:

• Exercise discretion and independent judgment in the negotiation of contracts, work collaboratively with clients, and help them engage with Toptal's AI capabilities and specialists.
• Begin shaping AI solutions that resonate with your target accounts, including forward-deployed AI solutions, Outcome Agents, agentic workflows, enterprise data and knowledge solutions, AI platforms, and managed AI services.
• Establish credibility with client stakeholders through informed, consultative engagement tied to their AI priorities, business workflows, existing technology investments, and desired outcomes.
• Own your pipeline and forecast with confidence.
• Develop proposals and close your first set of deals.
• Actively contribute to team rituals, best practice sharing, and win/loss reviews.

In the First Six Months, Expect To:

• Have an initial base of active clients while continuing to build your overall portfolio.
• Expand your buyer network and deepen executive engagement across your accounts.
• Drive net new opportunities by introducing additional AI capabilities, platforms, solutions, partners, and managed services and displacing incumbent providers.
• Shape and influence client priorities, aligning Toptal's AI solutions to critical business objectives and measurable, validated outcomes.
• Execute against a defined growth plan tied to measurable outcomes.

In the First Year, Expect To:

• Have built a list of incredible client accounts, advising them on how to utilize Toptal's AI capabilities to address their priorities and key business challenges.
• Establish and expand a strong executive network across your portfolio, building a foundation of advocates and sponsors.
• Begin to mentor new members of the team, teaching them about Toptal, our AI model, and how to successfully grow their territory.
• Be recognized for your subject matter expertise in enterprise AI solutions, leveraging your existing network and relationships as well as your proven consultative selling skills to drive meaningful results for your clients and the overall AI Services team.

Qualifications and Job Requirements

• Bachelor's degree is required.
• 7–10+ years of experience in enterprise technology, AI software, professional services, or consulting sales, with a strong foundation in enterprise account development and complex solution selling.
• Direct experience selling enterprise AI solutions is required, ideally including forward-deployed AI solutions, AI software or platforms, AI consulting and professional services, or managed AI services.
• Extensive experience in consultative customer engagement and selling service-oriented, technology-enabled, or outcome-based solutions to enterprise clients.
• Demonstrated success building a book of business from the ground up (self-sourcing, prospecting, and developing new enterprise relationships rather than relying on an inherited portfolio).
• Proven track record managing a $5M+ annualized gross portfolio and closing $250K–$1M+ complex, multi-phase deals with enterprise clients with $2B+ in annual revenue.
• Must be comfortable engaging C-level executives on how AI is changing their business, technology environment, operating model, workforce, and competitive landscape.
• A well-rounded understanding 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 how AI moves from strategy and experimentation into real enterprise workflows and production environments, including context, data, integration, validation, governance, adoption, and ongoing operations.
• Experience selling solutions involving leading AI, cloud, data, or enterprise technology platforms, with the ability to work in a platform-flexible environment across client technology ecosystems.
• Exposure to hybrid talent models, forward-deployed delivery models, or alternative consulting delivery models.
• Ability to build and execute account plans that lead to consistent portfolio growth and a healthy pipeline.
• Proven success in collaborative prospecting, running virtual and on-site sales calls, and leading sales pursuits backed by a multidisciplinary team.
• Experience negotiating complex service agreements with procurement and legal departments within enterprise accounts.
• Ability to partner effectively across multiple internal teams to shape innovative solutions that drive client success.
• Willingness and ability to travel to client sites, conferences, and team events (up to 25%).
• Passion for solving client problems with creativity and urgency.
• Regular or periodic travel to meet and engage with Toptal clients and customers both inside and outside of your geographic location.
• Outstanding written and verbal communication skills.
• Ability to work in a fast-paced, rapidly growing company and handle a wide variety of challenges, deadlines, and a diverse array of contacts.
• 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.