Sales Training Program Manager

Chicago | Illinois | United States

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.


The Sales Training Program Manager will play a pivotal role on the Sales Training & Effectiveness Team. This team influences & drives strategic sales initiatives via training, onboarding, coaching, enablement and learning programs; empowering our sales teams to achieve their goals.

The core responsibility of this role will be to develop, facilitate and refine world class continuing education programs to develop the sellers and leaders in our sales organization. It will be your mission to develop training programs to upskill our existing teams and provide unique development experiences based on tenure and role. The Sales Training Program Manager should take ownership over mastering the key sales tools, methodologies, and technologies that enable our teams to produce every single day. We expect that you will thrive in a fast-paced environment, possess a strong degree of executive presence and the ability to develop strong relationships with internal partners.

Your Responsibilities:

  • Design, develop and launch “Upskill” program to provide consistent sales development and learning opportunities to the sales team, addressing needs based on tenure and role.
  • Facilitate “Upskill” programming, ongoing training initiatives and leadership development content across the sales organization based on business needs.
  • Create and facilitate a leadership development program for current sales leaders and individuals looking to pursue leadership. Programming to be complemented with learning opportunities from external partners. I.e. Sales Assembly
  • Manage existing relationships with external sales training providers and seek out opportunities where needs require engaging new partners.
  • Work with sales coaches, instructional designers and internal partners to continually assess and understand training needs, define options, and translate them into meaningful and measurable learning objectives and goals.
  • Design and develop training in a variety of delivery modes (e.g., instructor-led, in-person or virtual training, self-paced training, eLearning, supporting guides, etc.).

What it takes to catch our eye:

  • Demonstrated ability as an Enterprise level Sales Trainer and Program Manager within B2B, SaaS based organizations.
  • Expertise in sales training methodologies and experience training both direct sellers and sales leaders. Experience with MEDDPICC is a plus.
  • Demonstrated ability to successfully develop and execute an ongoing leadership development program.
  • A successful track record of developing internal relationships with learners, managers, partners, and SMEs.
  • Experience with all aspects of training, including needs assessment, building lessons and job aides, working with SMEs, and facilitation.

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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Life at Upwork

We believe in a workplace in which all employees are empowered to see themselves in our One Upwork community. 

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