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Director of Sales

Director of Sales

Full-Time | Chicago | Illinois | United States

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. 


The Upwork Sales team brings our on-demand talent platform and services to small, medium and large businesses. Upwork is looking for a Director of Sales to join our team and continue building on our sales strategy, world-class sales process, and our success within the Middle Market segment. This position is responsible for owning the account management team and maximizing account expansion opportunities to meet overall company goals, ensuring an exceptional team environment through strong leadership. The Director of Sales will be responsible for the growth, training, and development of highly motivated sales team members. Upwork is seeking a proven performer, hands-on coach for the sales organization, and will guide the success of the sales team in areas of account growth, accurate forecasting, sales performance analysis, and account growth methodology.

In this role, you will:

  • Lead and develop a team of Sales Managers who in turn handle the day to day operations of teams of Account Managers.
  • Build, develop and motivate a high performing team by mentoring, challenging, and developing frontline sales managers and sales reps
  • Develop plans and strategies for growing existing customers and achieving the company’s sales goals
  • Craft a culture of continued success goal achievement through talent management, mentorship, and training
  • Provide positive feedback and celebrate managers and sales representatives success; Provide corrective feedback to inspire team to stretch and perform their best
  • Create a detailed, accurate and predictable sales forecast
  • Demonstrate deep understanding of Upwork’s customer portfolios and current sales cycle
  • Define and lead sales training programs that enable your team to achieve their potential while supporting company objectives
  • Define and deploy standard methodology, prospecting methodologies and processes across all aspects of the lead generation workflow
  • Monitor team performance, provide ongoing feedback and apply clear, consistent performance standards aligned with sales goals
  • Develop collaboration, communication and dedication among team
  • Encourage collaboration within and across organizational boundaries
  • Partner with marketing for Account Based Marketing Efforts and Sales Leadership on the new logo acquisition teams
  • Monitor and report on quota attainment on a weekly, monthly, quarterly and annual basis
  • Define the characteristics of a successful sales team and build on it
  • Play a meaningful role in ensuring tight coordination and partnership across Sales, Solutions, and Services

To win in this role, you need:

  • A minimum of 8 years of sales experience, with 5+ years in a leadership role, 2+ years leading sales managers
  • Experience managing managers is required
  • Ability to sell into multiple departments within a single company
  • Proven experience with recruiting, hiring and developing teams
  • Experience in a startup environment, selling a service that is new to the marketplace
  • Demonstrated experience with building and successfully scaling sales processes
  • Ability to adapt quickly depending on the sales need
  • Experience with a “land and expand” sales philosophy highly preferred

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.

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