Director of Sales Development 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. 


 Upwork is voted #1 place to work in Chicago! - 2019


The Upwork Sales team brings our on-demand talent platform and services to small, medium and large businesses. We’re hiring an SDR Director for our fast-growing Sales Development Representative (SDR) team. As a leader, you will be responsible for leading a high-performing team of individuals who master the lead qualification and opportunity qualification process. The SDR Team will book meetings and source early-stage sales opportunities and be instrumental in maintaining strategic partnerships with Marketing and Sales leadership. You will also develop content relevant to potential clients, support go-to-market activities, promote targeted campaigns and cultivate qualified opportunities that will funnel into Upwork’s sales teams. If you thrive in a dynamic environment where you have the freedom to build and implement new sales processes, focus on business verticals, and target new customers for Upwork to acquire and grow.

In this role, you will:

    • Lead, encourage, and train a team of SDRs whose role consists of prospecting, booking meetings and opportunity identification and qualification.
    • Develop SDRs into strong, highly capable team members for further development within the organization
    • Develop and coach to a best-practices framework of persona-based prospecting with personalized pitches
    • Hold each SDR accountable to defined metrics and KPI's
    • Lead weekly call reviews with SDR team, both in team and 1:1 setting
    • Own SDR "Sales Qualified Opportunity" number
    • Measure and continually find ways to improve process and performance
    • Refine SDR standards, process & metrics
    • Build and document scalable systems and processes to grow SDR team
    • Ensure that team has high quality account and lead/contact information
    • Motivate individuals and teams to exceed objectives through coaching, regular broadcast of results, and creative incentives
    • Regularly report on team/individual results – approved meetings, opportunities created and pipeline to the VP of Sales
    • Partner with Marketing for MQL conversion/event/campaign promotion and follow-up
    • Ensure disciplined use of, Salesloft, Gong and other sales tools


To win in this role, you need:

    • 4+ years' experience in a Sales Development Role or quota-carrying sales role
    • At least 5 years' experience managing managers within an SDR organization
    • Experienced with high-volume outbound, phone-based lead generation (Cold Calling)
    • Experience with technical products in the tech industry
    • Process-oriented in lead and opportunity management
    • Ability to create a sense of urgency & identify needs/pain with prospects
    • Ability to present value-based messaging
    • Solid Communication skills (written and verbal)
    • Familiar with CRM (SFDC) system for managing leads
    • Meeting deadlines and commitments



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.