Senior Enterprise Sales Trainer

Chicago | Illinois | United States

Upwork ($UPWK) is the leading tech solution for companies looking to hire the best talent, maintain flexibility, and get more done. We’re passionate about our mission to create economic opportunities so people have better lives. Every year, more than $2 billion of work is done through Upwork by skilled professionals who want the freedom of working anytime, anywhere. Top companies connecting with extraordinary talent around the globe? Upwork is how.


The Senior Enterprise Sales Trainer 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 refine, develop and facilitate a world class new hire training program for our sales organization. It will be your mission to help increase sales productivity and decrease ramp time for new hires, as well as develop training programs to increase the overall effectiveness of our sales teams. This role 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:

  • Facilitate and manage the sales new hire onboarding program, delivering meaningful and engaging training on-time in a fast-paced environment
  • Make ongoing iterations and improvements to curriculum and delivery methods for both the new hire onboarding program and our ongoing sales skill development program
  • Work with sales coaches and internal stakeholders to continually assess and understand training needs, define options, and translate them into actionable 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.)
  • Create sales training documents and playbooks as required for specific programs

What it takes to catch our eye:

  • Demonstrated ability as an Enterprise Sales Trainer within B2B, SaaS based organizations
  • Expertise in sales training methodologies including MEDDPICC and experience training sellers on value and solution based selling
  • Deep knowledge of executive level buyer personas within technology organizations including Marketing, Tech and CX executives
  • A successful track record of developing internal relationships with learners, managers, partners, and SMEs
  • Experience designing, developing and executing sales training materials and programs

Come change how the world works.

At Upwork, you’ll shape talent solutions for how the world works today. We’re a remote-first organization supported by offices in Santa Clara and Chicago, working together to create exciting remote work opportunities for a global community of professionals. 

Our vibrant culture is built on shared values and our mission to create economic opportunities so that people have better lives. We build 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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