Vice President, Leadership and Development


Chicago, IL, USA Remote

Full time

People Operations / Entry level

Jan 26

This job is no longer accepting applications.

Upwork ($UPWK) is the world’s work marketplace. We help connect companies large and small with top independent talent from around the world. Simply put, our mission is to create economic opportunities so people have better lives.

Every year, more than $2 billion of work is done through Upwork by skilled independent professionals who want the freedom of working anytime, anywhere.

We're seeking an experienced, imaginative, driven and proven leader to join as our Vice President of Learning and Development. Reporting to our Chief People Officer, you will drive Upwork’s success by bringing your business acumen, mastery in building diverse high performing teams, and people centric growth strategies to our leadership team to help us scale. 

You will utilize and continue to develop your high growth company experience, management and individual contributor development expertise, coaching skills, quantitative and qualitative data insights, and communication skills to understand Upwork’s business priorities, and create scalable, impactful growth strategies and experiences for our team to accelerate our business performance. You will build a culture of engagement and drive business results by delivering measurable and sustained value-added solutions. As a consultative and trusted advisor to the most senior leadership of Upwork’s team, you will be the first point of contact on developing and most effectively challenging our distributed team.

Your Responsibilities:

  • Be the beacon of our people centric employer brand cornerstones, especially growth without compromise.
  • Develop and drive best in class learning experiences which engage participants intellectually, emotionally, and personally for transformative growth and development at all levels of our organization.
  • Be a thought leader for tip of the spear development approaches. You will craft the future of work and push our talent to stretch. 
  • Partner actively with senior leadership throughout the business to assess their organizations, be out ahead of their organizational growth needs.
  • Design, execute and evolve initiatives which improve our high performance culture as we bring on new talent.
  • Actively partner with and amplify Diversity, Equity, and Inclusion efforts and ensure Upwork is an incredible place for anyone and everyone.
  • Drive continuous improvement in how we onboard, ramp our team, communicate our business priorities, and set new team members up for success. 
  • Drive analytical rigor and deep analysis on effectiveness and competitiveness of existing efforts; establish and drive key metrics which measure business impact at the macro and micro levels.
  • Innovate and react quickly as business realities change, staying up to date on best practices and trend, while maintaining a long term focus on our talent development as a strategic competitive advantage. 
  • Build strong partnerships throughout the HR Leadership team and the VP+ cohort within the organization.

What it takes to catch our eye:

  • 10+ years experience in progressive HR roles in high growth rapid change environments. 
  • Strong communication and influencing skills; effective listener, ability to connect and influence actions and outcomes with employees at all levels in the organization.
  • Track record of strong business partnership with leadership within a dynamic, fast paced environment, including a reputation as a passionate positive agitator.
  • A strong perspective on the learning and growth experience landscape and where Upwork should be headed.
  • Development thought leader and creative subject matter expert: you have in-depth knowledge relevant strategies, world class program, and practices and are able to represent Upwork in external situations. You have demonstrated your ability to deliver custom tailored development based on the needs, stage and personality of your organizations.
  • Deep analytical skills with the ability to translate data and trends into key insights and recommendations.
  • Proven ability to design, track, prioritize and drive to success multiple concurrent projects with a strong operational background and mission centric emphasis.
  • Hands-on leader. You’re resourceful, forward-thinking, drawn to building from ambiguous and unsolved problems and have an "own the outcome" mindset. 
  • Influence and partnering with a diverse group of stakeholders, able to partner with deeply technical as well as operational, business-minded leaders on key people issues. You excel at openness and flexibility with internal clients, balanced with maintaining consistency and equity in people philosophies and practices.
  • People leader and developer: you are experienced across the full spectrum of people management and development. You’re able to build the leadership bench strength on your team. You are able to zoom in and assess where people can be coached, empowered, and focused. You also know when it’s time to pivot your approach and organization to deliver for the business, and aren’t afraid to make bold calls.

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 support hiring of corporate full-time employees in 15 states in the United States. Please speak with a member of our recruitment team to determine whether you are located in a state in which we are hiring corporate full-time employees. 

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. Oh yeah, we’ve also got amazing benefits.

Check out our Life at Upwork page to learn more about 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.

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the world’s work marketplace, connecting millions of businesses with independent talent