Website upwork Upwork

Upwork is the world’s work marketplace.


Upwork ($UPWK) is the world’s work marketplace. We serve everyone from one-person startups to over 30% of the Fortune 100 with a powerful, trust-driven platform that enables companies and talent to work together in new ways that unlock their potential.  

Last year, more than $3.3 billion of work was done through Upwork by skilled professionals who are gaining more control by finding work they are passionate about and innovating their careers.  

The Upwork Sales team brings our on-demand talent platform and services to small, medium and large businesses. We are 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 Enterprise segment. We are looking for a collaborative, deal – centric and data-driven Director of Sales. This position is responsible for leading the account executive team and maximizing new deal acquisition 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. The ideal candidate is a proven performer who has met and exceeded revenue goals, operational goals and is a hands-on coach for the sales organization, and will guide the success of the sales team in areas of account acquisition, accurate forecasting, sales performance analysis, and sales methodology. They will also work closely to provide timely feedback to senior leadership in both sales and marketing for go-to-market strategies. 

Your Responsibilities:

  • Lead and inspire a team of Sales Managers/ front line leaders who run the day to day operations of teams of Account Executives.
  • Create, develop and motivate a high performing team by mentoring, challenging, and developing frontline sales managers and sales representatives.
  • Oversee the sales execution strategies and tactics focused on quota attainment by the Enterprise New Business team. This includes deep knowledge in prospecting, opportunity management, objection handling and closing. 
  • Develop plans and strategies for customer acquisition and achieving the company’s sales goals
  • Create and manage an accurate forecast of monthly and quarterly sales. 
  • Create a culture of continued success goal achievement through talent management, coaching, and training
  • Provide positive feedback and celebrate managers’ and sales reps success;
  • Provide corrective feedback to inspire the team to stretch and perform their best
  • Define and deploy best practice 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
  • Foster cooperation, communication and commitment among team members
  • Encourage collaboration within and across organizational boundaries
  • Partner with marketing and Sales Leadership on the Enterprise SDR and Growth teams
  • Play a critical role in ensuring tight coordination and collaboration across Sales, Solutions, and Services

What it takes to catch our eye:

  • Experience managing Managers is required
  • Consistent and measurable track record of success
  • Ability to sell into multiple departments within a single company
  • Demonstrated experience with recruiting, hiring, managing, and mentoring a successful sales team
  • Demonstrated experience with building and successfully scaling sales processes
  • Ability to adapt quickly depending on the sales need
  • Coaching and mentoring sales people through deals
  • Experience with a “land and expand” sales philosophy highly preferred
  • Experience working closely with cross-functional stakeholders across Marketing, Sales Operations, Enablement and Product team.
  • Expertise with Salesforce, Domo, and Outreach is a plus 

Come change how the world works.

At Upwork, you’ll shape talent solutions for how the world works today. We are a remote-first organization working together to create exciting remote work opportunities for a global community of professionals. While we have physical offices in San Francisco and Chicago, currently we also hire full-time employees in 19 states in the United States. 

Our vibrant culture is built on shared values and our mission to create economic opportunities so that people have better lives. We foster amazing teams, put our community first, and have a bias toward action. We encourage everyone to bring their whole selves to work and grow together through development opportunities, mentorship, and employee resource groups. And oh yeah, we’ve also got amazing benefits – including medical insurance for you and your family, unlimited PTO, 401(k) with matching, 12 weeks of paid parental leave, and a generous Employee Stock Purchase Plan. Check out our Life at Upwork page to learn more about our benefits and the employee experience.

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.

To learn more about how Upwork processes and protects your personal information as part of the application process, please review our Global Job Applicant Privacy Notice.

Tell us about the interview process for this job

Upwork utilizes both phone and video interviews. The first interview is a phone conversation with the recruiter. If selected by the recruiter, you will advance to a phone conversation with the hiring manager. The next step is the video interview, which is a collaboration among team members at Upwork. The number of video interviews you'll participate in depends on the role, but typically you can expect 2-3 interviews. You will also likely be asked to complete a skills assessment during this stage. After your first interview, if you will be moving forward in the process the reference check process will begin.

Tell us about your diversity and inclusion efforts

Diversity, inclusion and belonging (DIBs) is who Upwork is. Our vision for diversity, inclusion and belonging is dignity, purpose, community and fairness at the center of every working moment. We know can't fulfill our company mission - to create economic opportunities so people have better lives - without a dedicated strategic investment in diversity, inclusion and belonging, both within our corporate teams and on the Upwork platform. We approach the work on our inclusion strategy as specific, not singular. We resist the urge to recycle popular practices. We balance impact with practicality. Upwork also has 8 Upwork Belonging Communities (UBCs) which create spaces that center the professional needs and goals of all Upwork employees who identify as LGBTQIA+, Black, Hispanic/Latino/a/x/e, Pan-Asian, veterans, women, caregivers and/or neurodiverse. UBCs make it more possible for team members to find their unique fit within our One Upwork community without having to sacrifice meaningful aspects of their identities.

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