ceo/executive director

Chief Executive Officer / Executive Director

Start Date: Early 2018

We’re looking for an ambitious, passionate, and experienced leader to bring re:work to the national stage. Someone who cares deeply about economic equality.

We’re a young nonprofit, and you’ll join a team of one full-time employee and five part-time employees . You’ll work directly with the founder, full-time staff, freelance staff, volunteers, and the Board of Directors.

You will be taking our organization to the next level.

So, what would you be responsible for?

  • Execution:

    • Ensure our Chicago operations are functioning at a high-level (i.e. hit our KPIs)

    • Analyze our current operations and personnel, then increase our efficiency and impact

    • Serve our primary customers (candidates, employers, partners) with exceedingly high quality

    • Explore options for new revenue streams, expense-reduction, and business model adjustments

    • Ensure the accuracy, integrity, and timeliness of all financial accounting and reporting

    • Report quarterly results to the Board of Directors

  • Scale:

    • Increase our current growth rate across recruiting, training, placement, and support functions

    • Explore new cities/markets for expansion and create a repeatable model for expanding into those markets

    • Establish a national presence for our brand (e.g. board members, communications, partnerships, etc.)

    • Evaluate and implement technology that will increase our efficiency without diluting our quality of service

    • Maintain a supremely quality service despite growth

  • Fundraising:

    • Sustain the organization’s financial health through contributed (grants) and earned (staffing fee) revenue
    • Understand the landscape of local and national workforce development grantmaking

    • Seek and land grants: major gifts, corporate, foundations, government

    • Nurture existing relationships with foundations and donors

    • Consistently grow our annual revenues

  • Business Development:

    • Develop and maintain partnerships with:

      • Employers/corporations

        • Nurture our existing partnerships and ensure a high satisfaction rate

        • Sign contracts with new partners and maintain our staffing fee

        • Create new partnership options by type of employer

        • Formalize national partnerships with national employers

      • Nonprofit partners

        • Nurture our existing partnerships and inform them about candidate outcomes

        • Formalize national partnerships with national nonprofits

        • Grow the number of referring organizations and number of referrals per cohort

    • Find and establish national partnerships for colocation or shared real estate (nonprofits, corporations, or community colleges)

    • Understand the landscape of software sales communities, groups and organizations and leverage their network/resources

    • Explore M&A opportunities that could drastically increase our impact

  • Recruiting:

    • Staff the organization with diverse talent from both the nonprofit and for-profit sectors

    • Build and manage a diverse, top-tier executive team

    • Grow our Board of Directors based on the 3 W’s (ask for more info!)

    • Hire only team members who live and breathe our values (

  • Communications:

    • Bring our vision and mission to the world (

    • Increase local and national awareness of our brand through PR

    • Refine our web presence through pro bono marketing services

    • Oversee thoughtful, creative marketing campaigns that tell the stories of our people

What do we need from you?

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

  • Leadership. You inspire with action and words

  • Execution. You do what it takes to produce great results

  • Experience. 5+ years in leadership and/or entrepreneurship

  • 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

Bonus points for:

  • MBA in a relevant field (nonprofit management, entrepreneurship, education, etc.)

  • Experience in workforce development or alternative education

  • B2B software experience

  • Sales management experience

  • A diverse personal, professional and educational background

What do you get?

  • Control. This will be your organization to run and grow

  • To actually change Americans’ lives

  • A competitive salary

  • Medical, vision, and dental coverage

  • A blank canvas (company) on which to ‘paint’ (your work)

  • 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 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