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Chicago, IL


The Bail Project is a new non-profit organization designed to combat mass incarceration by disrupting the money bail system ‒ one person at a time. Over the next five years, The Bail Project will work with local partners to open dozens of sites in high-need jurisdictions and pay bail for tens of thousands of low-income people, reducing the human suffering caused by unaffordable cash bail and building on the work of grassroots groups and movements for decarcerationand racial justice.

Our organization is comprised of a central support team and a network of Bail Disruptors who work in local jurisdictions to identify community members at risk of pretrial detention, pay their bail, and provide support throughout the legal process. Our model leverages the fact that bail money is returned when people make their court appearances, allowing us to maintain a revolving bail fund and maximize our impact.

In addition to posting bail, The Bail Project seeks to partner with local advocacy groups, collect stories and data from our sites and work with universities to measure the socio-economic impacts of unaffordable cash bail with the goal of informing legislative reform.

Through these efforts, The Bail Project will be the largest non-governmental decarceration of Americans in history — reducing human suffering, restoring the presumption of innocence, and adding to the growing momentum to end mass incarceration.

Position Summary:

Bail Disruptors are community members across the country committed to racial and economic justice. They are the core of The Bail Project, securing people’s release, disrupting the criminal legal system, and fighting mass incarceration.

Our Chicago Site Manager will oversee day-to-day site operations in Cook County and an additional county outside of Cook County, and work alongside Bail Disruptors to ensure that the sites run smoothly: that clients are supported to return to court and that data entry (including client data in Salesforce, bail receipts and other expenses) is recorded accurately and in a timely fashion.

The Chicago Manager will facilitate staff meetings, monitor client relationships, conduct regular check-ins and evaluations and oversee bail disruptor schedules to ensure the Chicago sites are functional. This role acts as a bridge between the Central Team and the site-by-site Bail Disruptor network. As part of this bridge, the Manager will monitor local bail policy, coordinate gathering client stories and lead efforts for change alongside partners and the Central Team.

The Chicago Manager will report to our Director and Associate Director of Operations and work alongside our CEO as needed. Occasional travel in-state is required to jails, courthouses, and stakeholder meetings.


Managing site operations

  • Manage all aspects of Chicago site operations, enabling Bail Disruptors to prioritize posting bail and supporting clients to return to court
  • Communicate Chicago team needs and act as the main liaison between Chicago and Central Team
  • Monitor the Chicago budget and cash flow and ensure receipts are recorded daily
  • Ensure that client data is uploaded accurately and thoroughly in Salesforce each week
  • Ensure compliance with other relevant organizational policies, such as those governing expenses, client selection, etc.
  • Coordinate staff schedules and PTO to ensure full site coverage
  • Maintain inventory of Chicago sites and manage requests for resources
  • Identify systemic barriers affecting bail operations and work with Central team to develop solutions

Monitoring team dynamics and Bail Disruptor performance

  • Coordinate Chicago team meetings and cultivate an environment of trust and accountability in line with TBP’s mission
  • Facilitate check-ins with Bail Disruptors to oversee team dynamics, monitor client relationships, ensure the upkeep of data entry, and creatively resolve interpersonal issues on staff
  • Complete bi-annual formal performance evaluations
  • Track performance metrics at the level of the individual and for the Chicago sites at large

Building partnerships

  • Partner with Central Team and community advocacy groups on local efforts for policy reform and implementation
  • Create and nurture partnerships with local community and social service organizations that support TBP’s work
  • Participate in and support the development of the National Bail Disruptor network
  • Monitor and track local criminal justice movements and legislation and identify opportunities to leverage TBP’s data and work to effectively decarcerate and thereby reduce or eliminate the need for a local fund


You are driven, highly organized, and have a deep commitment to The Bail Project’s mission to eliminate race- and wealth-based disparities in our criminal justice system. Applicants must be willing to work independently as well as in collaborative teams. A sense of humor, innovative spirit, and willingness to adapt to the change inherent to a rapidly scaling startup are essential.

To excel in this role, you likely bring the following:

  • Background working in operations, especially handling finances and data
  • Experience managing direct reports and conducting formal performance reviews, especially for staff in a client support or criminal justice context
  • Experience in advocacy, community organizing and building strategic partnerships
  • Strong investment in the local community and in the fight for racial and economic justice
  • Self-motivated, flexible, and hard-working
  • Access to a reliable vehicle
  • Excellent organizational abilities and ability to handle multiple projects
  • Strong decision-making and communication skills
  • Basic ability in GSuite (Word, Excel, Powerpoint) or willingness to learn

Compensation: This is a full-time exempt position. Salary is commensurate with experience. The Bail Project offers competitive health benefits, dental and vision plans, flexible PTO, life insurance and a 401(k) plan.

How to Apply:

Interested applicants should submit a resume and cover letter to careers @

by March 1, 2019 with “Chicago Site Manager ” in the subject line. In the cover letter, please address the following:

  • Why do you want to work for The Bail Project?
  • Please share 1-2 experience(s) that highlights why you would be a strong candidate for the site manager position.

No faxes or phone calls please. Applicants will be notified regarding whether or not they have been selected for an interview. Applications without cover letters will not be processed.

The Bail Project is proud to be an equal opportunity/affirmative action employer and actively seeks the candidacy of people of color, women, and formerly incarcerated individuals. We are committed to inclusive hiring and dedicated to diversity in our work and staff.

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