Sales Development Manager 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. 


The Upwork Sales team brings our contingent staffing solutions to mid-market and large enterprises. Many leading analysts predict that 50% of the workforce will be freelancing by 2020. As a result more companies are moving towards flexible workforce solutions and many are using online staffing platforms to embrace this shift. Today 30% of the Fortune 100 are already using Upwork to get more work done. We are looking for a Team Lead to join our Chicago team. This is a ground floor opportunity for a leader with a startup mentality who can roll up their sleeves, or an individual contributor who wants to move into leadership to build our teams and grow the business.

Your Responsibilities

  • Recruit and manage a team of Sales Development Representatives and create a culture of continued success and goal achievement through talent management, coaching and training.
  • Develop plans and strategies for converting inbound activity into revenue or identifying Enterprise opportunities within team’s book of businesses to achieve the company’s sales goals.
  • Create a detailed, accurate and predictable sales forecast.
  • Monitor and report on quota attainment on a weekly, monthly, quarterly and annual basis.

What it takes to catch our eye

  • You are an individual contributor who has a track record of success and quota achievement in sales or staffing.
  • You have the drive, the organizational and interpersonal skills to manage a group of sales reps that make a high volume of daily outbound calls and emails to multiple audiences for multiple product lines and multiple campaigns.
  • You are an excellent communicator. You are strategic with a creative mindset. You are both competitive and collaborative.
  • You have a basic understanding of two-sided marketplaces and Enterprise SaaS products.

How to really knock our socks off

  • You have experience with building and successfully scaling sales processes.
  • You have coached and mentored sales people through top of funnel outbound activity.
  • You have experience with a “land and expand” sales philosophy.
  • You have at least 1 year of experience managing a team of SDRs.
  • You are proficient with CRM & prospecting tools, e.g. SFDC, Salesloft, Zoominfo, LinkedIn Sales NavigatorYou have knowledge of the Upwork platform.


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.