Director of Enterprise Solutions at Upwork
Chicago, IL, US

Upwork ($UPWK) is the world's largest freelancing website. Each year $1.7 billion of work happens through Upwork, allowing businesses to get more done and helping professionals break free of traditional time and place boundaries and work anytime, anywhere on projects they love. At Upwork, you'll help build on this momentum. Together, we'll create economic and social value on a global scale, providing a trusted online workplace for businesses to connect with extraordinary talent and work without limits. 


As a Director of Enterprise Solutions you will hire, develop and coach a team of Solutions Architects to identify solutions to address customer pain points from sale to widespread adoption. You will provide leadership and oversight to our “special team” members as well as address the pre-sales activity for our staffing offerings to large enterprises.  This is a cross-functional role that will partners cross-functionally with our enterprise sales, product, services, and talent teams to define and articulate the Upwork value proposition.

Your Responsibilities:

  • Hiring, developing, coaching and directing a team of Solutions Architects that focus on both landing new accounts as well as expanding existing accounts.   
  • Partnering with internal teams to understand product offerings and capabilities as well as streamline new product features and releases. 
  • Design methodologies and processes that support customer growth in innovative and scalable ways.
  • Play a critical role in supporting the sales team to develop material and articulate Upwork’'s offerings to prospective customers.
  • Provide subject matter expertise on either (A) the talent & staffing or (B) digital marketing and agency industries and incorporate that knowledge into the solutions built.

What it takes to catch our eye:

  • Expertise designing solutions within (A) the contingent labor and staffing space OR (B) the digital marketing and agency space and are familiar with the technology and policy landscape.
  • Creative problem solving solving skills. You will implement new approaches to solving old problems through the Upwork platform and balance the requirements of a complex industry with building to scale and simplicity.
  • Customer-Centric Mindset: You obsess over customer success and design solutions that meet enterprise needs.

How to really knock our socks off:

  • Stellar written and verbal communications skills that allow you to communicate in a way that is simple and credible.
  • Experience with technical implementations and ability to speak the language of our customers.
  • Motivation to drive through programs and achieve results. You are a self-starter with a track-record of executing for results—that suits you perfectly.
  • Strong leadership skills that motivate both our clients and the team you manage.  You will play a critical role in forming our offering and strategic thinking and the ability to transform that strategy into tactical action is essential.
  • A relentless drive to make a mark in this world and know that it’s up to you alone to do so.


Come change how the world works.


At Upwork you’ll help shape the future of work. From our offices in San Francisco, Mountain View and Chicago, together we’re creating exciting new opportunities for a world of professionals. You’ll be part of a vibrant culture built on shared values: Inspire a boundless future of work, Put our community first, Have a bias towards action, and Build amazing teams. Along the way you’ll have fun and enjoy the perks of a people-first company: Work from Home Wednesday's, daily breakfast and lunch, regular in-office happy hours, top-notch benefits … and more. Check out Upwork’s spotlight on The Muse for a glimpse of our daily work/life balance.


Upwork is proudly committed to recruiting and retaining a diverse and inclusive workforce. As an Equal Opportunity Employer, we never discriminate based on race, religion, color, national origin, gender (including pregnancy, childbirth, or related medical condition), sexual orientation, gender identity, gender expression, age, status as a protected veteran, status as an individual with a disability, or other applicable legally protected characteristics.