Upwork
Upwork is the world’s work marketplace connecting businesses with independent talent.
Chicago, IL

Vice President, Leadership and Development at Upwork

| Chicago, IL
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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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Technology we use

  • Engineering
    • JavaLanguages
    • JavascriptLanguages
    • PerlLanguages
    • PHPLanguages
    • PythonLanguages
    • ScalaLanguages
    • SqlLanguages
    • AngularJSFrameworks
    • Node.jsFrameworks
    • SparkFrameworks
    • SymfonyFrameworks
    • TensorFlowFrameworks
    • Vue JSFrameworks
    • MongoDBDatabases
    • PostgreSQLDatabases
    • AWS RedshiftDatabases
    • PrestoDatabases
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What are Upwork Perks + Benefits

Upwork Benefits Overview

Upwork proudly offers a comprehensive set of benefits to ensure employees are able to bring their whole selves to work. To allow for that, we aim to deliver world-class offerings and perks that cover your medical, dental, vision, emotional and family well-being. If you are an active, regular, full-time employee working a minimum of 20 hours per week you are eligible for all lines of coverage.

Culture
Volunteer in local community
In addition to company organized opportunities, we offer paid time off for volunteering at your favorite local organizations.
Partners with Nonprofits
The Upwork Foundation is Upwork's social impact arm–our goal is to make sure the future of work is inclusive, especially for communities at risk of being left behind by changing technology.
Friends outside of work
Eat lunch together
Intracompany committees
Open door policy
Pair programming
Open office floor plan
Diversity
Dedicated Diversity/Inclusion Staff
Diversity Employee Resource Groups
Our employee resource groups include Up & Out (LGBTQ), Women at Upwork, Black Initiative Network, Que Tal (Latinx), Upwork Veterans, Upwork Family and Asian Professionals for Excellence.
Hiring Practices that Promote Diversity
Health Insurance & Wellness Benefits
Flexible Spending Account (FSA)
Upwork provides an annual HSA contribution. You may also contribute pre-tax dollars to a Health Care FSA and Dependent Care FSA account.
Disability Insurance
Upwork offers both short term disability (STD) and long term disability(LTD) insurance.
Dental Benefits
Upwork provides your dental coverage through MetLife with a PPO plan offering.
Vision Benefits
VSP Vision offers a broad array of services for employees at Upwork.
Health Insurance Benefits
We offer Anthem Blue Cross PPO and HSA plans and you may choose the best plan for you and your family.
Life Insurance
Life Insurance coverage of 2X up to $300,000. Employees can also purchase coverage for a Spouse/DP and child(ren).
Pet Insurance
Nationwide Pet Insurance now provides coverage to all pets within your life!
Wellness Programs
Upwork offers an on demand mental health platform, Ginger.IO, along with a parenting support tool, Cleo.
Onsite Gym
Mental Health Benefits
Retirement & Stock Options Benefits
401(K)
Upwork offers a traditional pre-tax 401(K) along with an after-tax Roth IRA option.
401(K) Matching
Upwork matches 50% of every dollar contributed by employees into their 401(k) up to $5,000 per year. Employers match is fully vested after 1 year of service.
Company Equity
Upwork offers equity as part of our standard compensation package.
Employee Stock Purchase Plan
We allow qualified employees to purchase company shares at a discounted price.
Performance Bonus
Child Care & Parental Leave Benefits
Child Care Benefits
Upwork offers dependent care flexible spending accounts. In addition, we offer a $100 monthly credit from Trusted for backup and emergency child care services.
Generous Parental Leave
Upwork provides employees time to bond with their newborn and family. We offer up to 12 weeks of fully Paid Parental Leave.
Remote Work Program
Upwork encourages a healthy work-life balance. For your convenience we allow you to work from home on Wednesdays.
Family Medical Leave
For eligible employees, FMLA provides up to 12 weeks of unpaid leave for any circumstances regarding your personal health condition or to take care of a family member.
Adoption Assistance
Upwork will reimburse up to $3,000 for eligible fertility or adoption related expenses per plan year.
Company sponsored family events
Vacation & Time Off Benefits
Unlimited Vacation Policy
Generous PTO
Paid Volunteer Time
The Upwork Foundation has asked that 1% of employees time be used for giving back to the community and volunteering.
Paid Holidays
Paid Sick Days
Perks & Discounts
Beer on Tap
Casual Dress
Commuter Benefits
You can elect up to max of $260 pre-tax for transit and parking. Upwork will match 50% of your pretax contributions each month.
Company Outings
Free Daily Meals
Upwork provides lunch on a daily basis from local Chicago restaurants.
Game Room
Stocked Kitchen
Upwork has a fully stocked kitchen including unlimited snacks, coffee, tea and all of the flavored LaCroix you can handle.
Happy Hours
Fitness Subsidies
We reimburse employees up to $50 per month for fitness related expenses. We have a corporate partnership with 24 Hour Fitness, but you can apply to your preferred gym or approved wellness expense.
Home Office Stipend for Remote Employees
Professional Development Benefits
Job Training & Conferences
Diversity Program
Lunch and learns
Promote from within
Time allotted for learning
Online course subscriptions available

An Insider's view of Upwork

What's something quirky about your company?

The best part of our company culture is our Work Online Wednesdays, it gives me a better understanding of the experiences many clients and freelancers have using Upwork to grow their business. It's also important to me that Upwork values championing the future of work by empowering its employees to work flexibly each week.

Maggie

Mid Market Account Executive

What's the biggest problem your team is solving?

The Enterprise team is solving for how organizations engage talent and how talent finds opportunity. In an "on-demand" economy, technology has changed the way we commute, lodge, and shop. The workforce is rapidly evolving and technology is fundamentally changing work now, too.

Mandela

Enterprise Account Executive

How does the company support your career growth?

I started my professional life in HR and due to the shifting labor market, I saw an opportunity to be part of something special with Upwork. I took a leap into the unknown as the second sales rep in the Chicago office. Fast forward a year and a half later, I’ve been able to grow my career from sales rep to leading the first Mid-Market sales team.

Angela

Sales Manager

How do you make yourself accessible to the rest of the team?

Making myself available before and after working hours demonstrates commitment to seeing them grow and succeed. Casual sit downs over coffee outside the office to get to know individual contributors and managers on a more personal level allow me to further understand what drives and motivates them inside and outside of work.

Natalie

VP, Enterprise Solutions

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