Future Position
VP of Enterprise
Future Position

VP of Enterprise

About Toptal

Toptal is a global network of top freelance talent in business, design, and technology that enables companies to scale their teams, on-demand. With $100+ million in annual revenue and over 40% year-over-year growth, Toptal is the world’s largest fully remote company.

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.

Position Description

As Toptal’s VP of Enterprise, you will be the General Manager of our Enterprise business responsible for accelerating Toptal’s expansion into the space, leading and scaling a world-class sales organization that is changing the way the world’s largest companies leverage professional services. You will work closely with Toptal’s Executive and Senior Leadership Teams and will lead Toptal’s Enterprise team to target, develop, and close high-value clients across the enterprise landscape. Sitting on Toptal’s Executive team, this role oversees sales, relationship management and delivery for new and existing enterprise clients.

To be successful in this position, you will need to be an exceptionally creative and well-organized sales leader with a track record of building and scaling high-performing sales functions supporting enterprise business in the services space.

This is a remote position that can be done from anywhere. Due to the remote nature of this role, we are unable to provide visa sponsorship. Resumes and communication must be submitted in English.


  • Work closely with Toptal’s Executive team and Senior Leadership Team to accelerate the expansion of Toptal’s business in the enterprise space.
  • Manage all of the team’s inbound and outbound sales processes and continuously improve these processes leveraging data-driven, results-oriented evaluation and experimentation.
  • Develop account prioritization criteria and work with members of the Enterprise team to prioritize their target client portfolios.
  • Regularly meet with members of the Enterprise team to review activity, guide further direction, evaluate performance, and develop coaching plans.
  • Work closely with Toptal’s Director of Strategic Accounts, Regional Directors, Head of Enterprise Sales, and Head of Partnerships to evaluate and evolve the team’s short-, medium-, and long-term tactics for establishing Toptal as the leading provider of professional services in the enterprise space.
  • Build deep and productive relationships with the teams responsible for client delivery, ensuring cohesive partnerships and timely pairing of resources with the needs of our clients.
  • Define geographic focuses or vertically assigned industries for members of the Enterprise Team, and work with them to develop strategic enterprise sales playbooks tailored to each client segment.
  • Develop and execute a plan for scaling the team structure and goals, as well as the interviewing standards and hiring plans needed to achieve these goals.
  • Build, maintain, and grow C-level relationships with multiple executives from clients in your team’s portfolio.
  • Set aggressive sales goals for your team and take full ownership over leading the team to meet those goals.
  • Be in constant communication with team members via Zoom.

In the first week, expect to:

  • Onboard and integrate into Toptal.
  • Rapidly begin learning about Toptal’s history, culture, and vision.
  • Shadow key teams across Toptal to learn the core of our operations and capabilities.
  • Build a fundamental understanding of Toptal’s Enterprise operations.
  • Meet with the leaders within Enterprise to better understand the current state of the team.
  • Learn about the essential OKRs and goals that have been set forth for this role’s function.

In the first month, expect to:

  • Go through deeper onboarding in key areas of the company for which Enterprise is of strategic importance, including beginning to do real work with the associated team leads and individual contributors.
  • Develop a comprehensive understanding of our enterprise client lifecycle, including new sales, contract negotiation, delivery, relationship management and account growth.
  • Onboard onto ongoing and upcoming initiatives that are relevant to Enterprise.
  • Plan out a roadmap for the long-term success of Enterprise at Toptal.
  • Partner with the CEO and other members of the Executive team to understand the initiatives and relationships that are the keys to success.

In the first three months, expect to:

  • Launch an enterprise roadmap, setting up the Enterprise team for high standards, durability, and scale.
  • Drive real impact for Toptal, building its reach and credibility with new and existing customers, with a particular focus on enterprise and what the future holds for all types of work.

In the first six months, expect to:

  • Build and implement strategies for long-term relationship building and enterprise engagement.
  • Develop Toptal’s long-term initiatives for success in the enterprise space.
  • Be fully responsible for the sales, delivery, and relationship management for all of Toptal’s enterprise clients.


  • 10+ years of proven success leading and managing professional service sales teams including staffing and/or project sales, with relationships ranging from director-level to C-level contacts.
  • Successful experience as a sales team leader at a rapidly growing professional services organization.
  • Ability to build strong relationships and collaborate with Executive leaders across multiple business units within the organization.
  • Exceptional developer of talent who can both work with salespeople on the front lines and also develop and execute coaching plans for the team’s continued development.
  • Strong understanding of how to navigate a large organization to assess which accounts/projects are in need of our specific resources, as well as a strong ability to evaluate the merit of creative new tactics.
  • Extensive experience leading teams responsible for closing deals in the $1M to $50M+ range, including experience with service agreements ranging from a few team members to 20+ team members.
  • Exceptional discipline, attention to detail, and motivation. You must be fully capable of leading the team in responding to consistent challenges and going above and beyond as needed.
  • Highly capable of motivating a team towards the prospect of growing an innovative, world-changing business with us.
  • Excellent written and oral communication skills. This includes being fully capable of building and maintaining a respected boardroom presence.
  • 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.

Note: This is a role that, while not open at the moment, highlights skill sets that are consistently in high demand within Toptal. We encourage interested applicants to apply - as a rapidly scaling company, we end up developing innovative new roles often. We regularly review the applicants for this position to find matches for these unique opportunities.

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Who You Will Work With

Sean Middleton

Sean Middleton

Chief Revenue Officer

As Toptal's Chief Revenue Officer, Sean is responsible for strategy, sales, and client success. He works closely with the executive team to ensure their growing client portfolio has access to the best talent in the world. Before joining Toptal, Sean spent ten years at Cognizant, where he played various roles, including President of their new Accelerator business division and COO of their Digital Business transformation service line. Sean earned a BS in Computer Science from Cornell University and an MBA from the Wharton School at the University of Pennsylvania.

Taso Du Val

Taso Du Val


As Toptal’s Chief Executive Officer, Taso manages Toptal’s core team of hundreds of team members distributed throughout the world, with a focus on innovation. Since Toptal was founded in 2010, Taso has led it to become the largest high-skilled, on-demand talent network in the world. Taso serves on the board of multiple organizations, advising on talent strategy and innovation for Fortune 100s and nonprofits. Taso has guest lectured at Harvard Business School, Wharton, and Oxford on talent management and entrepreneurship.

View The Whole Team

Working at Toptal

We're changing the way the world works. Toptal is not only a place to progress your career and design your own lifestyle, but also a company where you'll learn how to develop innovations that push business and technology forward.
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Working at Toptal has been the best experience of my career. Every day I'm surrounded by intelligent, thoughtful, and hard-working colleagues that push me to be better.

Jordan Lyons

SEO Manager