software sales trainer - contract role

Salary: $30-45/hour (depending on experience) 

Application Deadline: April 14th, 2017

We’re looking for a high-energy, level-headed software sales trainer. We’re a young nonprofit, and you’ll be the second part-time hire. We’ll pay an hourly wage (based on experience), but you should be in it for the mission, rather than the money. You’ll work directly with leadership.

You will be training our 3rd cohort, preparing them for entry-level software sales careers.

Phase 1: Curriculum Development

  • May 1 - May 21

  • ~3 hours/week

Phase 2: Training Sessions

  • May 27 - July 23

  • Saturdays & Sundays

    • 1pm-4pm (6 hours/weekend)

  • Mid-week digital exercise administration & grading

    • ~2 hours/week

Phase 3: Recap

  • July 22 - August 4

    • ~2 hours/week

So, what would you be doing?

  • Reviewing and understanding each candidate’s background/experience

  • Teaching a pre-built sales development curriculum through live sessions

  • Administering and grading digital lessons through LearnCore

  • Tweaking the current curriculum to improve it

  • Communicating with candidates on their strengths and weaknesses

  • Running Q&A sessions with guest speakers

What do we need from you?

  • To embody our values: perspective, merit, respect, courage, communication, flexibility

  • Experience. You have experience in sales development and/or inside sales

  • Energy. You bring it each and every class

  • Patience. You keep a level head, and always prioritize the candidate’s well-being

  • experience

Bonus points for:

  • Experience with LearnCore/LMS systems

  • A diverse personal, professional, and educational background

How to apply:

Interested? Send your LinkedIn profile/resume to, along with a note on why you’re interested, and why you’d do well.

About us:

re:work training is a 501(c)3 that trains people with nontraditional backgrounds how to sell software. We then get them entry-level sales jobs at Chicago tech employers. More at