sales enablement program manager

Sales Enablement Program Manager (Training, Placement, & Support)

Start Date: November 27th, 2017

We’re looking for an ambitious, organized, and proactive Program Manager. Someone who can manage various projects, people, and programs at once. Someone with software sales training and management experience.

We’re a young nonprofit, and you’ll be the first full-time hire. You’ll work directly with the founder, freelance staff, volunteers, and the Board of Directors.

You will be managing our entire cohort-based programming.

So, what would you be responsible for?


  • Schedule and organize all 2018 cohorts
  • Ensure we have quality, committed sales trainers for all sessions
  • Recruit and evaluate technology sales experts as guest speakers for sessions
  • Improve curriculum based on role and industry trends
  • Add to digital coursework in our LMS (Learncore)
  • Finalize training decks, with presenter notes
  • Evaluate students’ performance and deliver feedback on areas for improvement
  • Track learning and development, and tweak curriculum accordingly


  • Build and maintain employer relationships; ‘sell’ re:work’s program to employers
  • Guide the matching process for candidates with compatible employers
  • Define and document hiring profiles for each of our employer partner
  • Manage interview preparation with mentors and volunteers


  • Work with staff and volunteers to match and coordinate mentorship
  • Develop programming for re:work alumni to empower ongoing training and collaboration with the program
  • Track progress of candidates post-placement and assess areas for improvement
  • Communicate with partnering employers to understand needs & wants
  • Work with employers of re:work alumni to assess progress and provide feedback


  • Manage a thrifty P&L and report on all program-related expenses
  • Execute on KPIs surrounding retention, placement, and training success
  • Attend and participate in quarterly board meetings
  • Help recruit contractors, volunteers, and candidates

What do we need from you?

  • To embody our values: perspective, merit, respect, courage, communication, flexibility
  • Execution. You do what it takes to produce great results
  • Experience. 3+ years experience in software sales (preferably in management & training)
  • Energy. You fuel yourself and others around you
  • Flexibility. You can change course without skipping a beat, assuming it makes sense
  • Resourcefulness. You do a lot with a little
  • Ideas. We are not perfect. You bring fresh ideas on how we can improve
  • Ability to commit to some night and weekend work

Bonus points for:

  • B2B software sales management experience
  • B2B software sales training/enablement experience
  • Nonprofit volunteer and/or professional experience
  • experience
  • A diverse personal, professional and educational background
  • Sales and/or bootcamp experience
  • Funny stories

What do you get?

  • To actually change Chicagoans’ lives
  • A competitive salary
  • A healthcare stipend (or COBRA coverage)
  • A blank canvas (company) on which to ‘paint’ (your work)
  • A very flexible schedule (a week off between cohorts), though it will be involved. We’re a startup...
  • To work with great people
  • Networking with Chicago leaders across multiple industries

How to apply:

Interested? Send your LinkedIn profile to, along with a note on why you’re a great fit for the role and organization.

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