Chief Executive Officer



Technology / Telecom Reform, Education


General Management / Strategic Planning


IL - Chicago metropolitan area
MO - Kansas City, Missouri metropolitan area
WI - Milwaukee metropolitan area

About the Organization

Since its founding in 1998, Inner-City Computer Stars Foundation, also known as i.c.stars, has been creating opportunities for underserved adults with underestimated potential to secure careers in technology and to use systems thinking to affect transformational civic change. Using project-based learning and full immersion teaching, i.c.stars provides program participants with a 4-month technology and leadership immersive training that enables participants to learn by doing. Participants gain on-the-job experience and develop the professional networks needed to jumpstart successful careers in technology. But i.c.stars is more than just a bootcamp. Committed to the long-term success of its participants, i.c.stars also provides paid internship opportunities, career placement, and ongoing coaching, skills-building support, and leadership development opportunities. With a job placement rate of 90%, program participants see an average of 300% in increased earnings.

The program has graduated more than 60 cycles with over 820+ alumni – graduates go on to have successful careers at places like Accenture, Salesforce, and US Foods and others go on to become entrepreneurs, with over 60+ businesses started by i.c.stars alumni! The rigor of the i.c.stars program coupled with its leadership curriculum and wrap-around support has been consistently recognized by employers as one of the strongest in the market – that is why i.c.stars participant retention rate stands at over 81%.

With a $9M operating budget and headquarters in Chicago, i.c.stars has expanded their footprint to Milwaukee and Kansas City with an eye towards future expansion in potential markets like Houston and Detroit. Powered by a deeply passionate staff, committed employer partners, donors, and an active alumni and volunteer base, i.c.stars is well-equipped to empower their program participants – participants who have the power to bring change home to their families, to their community, and to the tech industry itself.

To learn more about the organization and its impact, please visit their website.

About the Position

i.c.stars seeks a Chief Executive Officer (CEO) to take over for the Co-Founder as the organization looks to amplify the impact of its work. With a recently established presence in Kansas City – coupled with a presence in Chicago and Milwaukee – and poised for planful growth, i.c.stars is looking for a CEO excited to build upon i.c.stars' 25-year legacy and, in deep partnership with the Board and leadership team, set the strategy and plan that lead to organizational sustainability and continued scale. The CEO will serve as the organization's lead fundraiser and external representative championing i.c.stars' work across carried audiences and cultivating potential partnerships.

Reporting to the Board of Directors, the CEO will manage a team of five direct reports, this includes the Chief Innovation Officer/Co-Founder, Chief Operating Officer, Chief Revenue Officer, Chief Learning and Program Officer and Executive Assistant as well as oversee a full team of 30+ full-time staff. The CEO will also be responsible for leading i.c.stars in alignment with the organization's core values and ensuring that the organization carries out its vision and mission in service of its program participants, alumni, staff, partners, and champions.

Coming into the role in the first year, the CEO's priorities will be to:

  1. Learn and strengthen the organization's culture and programs with a commitment to racial equity and inclusivity
  2. Develop a compelling strategic vision and support the senior team's leadership driving of the plan
  3. Inspire and lead people through a smooth transition and to work together with a common purpose
  4. Cultivate new partnerships and maintain existing relationships
  5. Position i.c.stars for its next great chapter

The right candidate will embrace the opportunity to leverage this unique leadership platform to broadly and powerfully position i.c.stars' mission, harness and expand its strong, existing network of funders and partners to meet the needs of its program participants, and determine how best to amplify i.c.stars' message toward greater visibility and influence.

Responsibilities include, but are not limited to:

Strategic Leadership

  • Partner closely with senior leadership and the Board to create and implement strategic plan and growth model that sustainably scales the organization's impact
  • Working closely with senior leaders and key stakeholders, articulate programmatic scope and goals at the division and organizational level, including an emphasis on developing innovative approaches to delivery
  • Uphold i.c.stars' mission and vision and foster an organizational culture consistent with i.c.stars' core values, ensuring these are reflected in the day-to-day work of the organization
  • Ensure that i.c.stars actualizes its commitment to racial equity and inclusivity, acting as both a proactive driver and exemplar related to the organization's efforts both internally and externally
  • Champion and integrate DEIBJ in all systems, processes, resources, and functions across the organization and at the Board level and model an inclusive, equitable, and welcoming culture

Organizational Management

  • Manage, lead, and collectively empower team members at all levels of the organization; demonstrate a shared leadership model alongside members of C-suite and the Regional Executive Directors
  • Work closely with Chief Learning and Program Officer to maintain and enhance a data-driven culture in service of programs and institutional learning across functions while maintaining program outcomes tied to a culturally and industry responsive curriculum
  • Oversee and partner with Chief Operating Officer to ensure sound fiscal management that anticipates operating within the approved budget, ensures maximum resource utilization, and maintains a positive financial position
  • Set and tone and expectations for Chief Operating Officer's work in building protocol, systems and processes that support continuous improvement and dynamic innovation across all teams
  • Act as primary liaison to the Board of Directors, engaging Board members in the current and future needs of the organization, soliciting input and support on an ongoing basis
  • Communicate effectively with the Board and provide, in a timely and accurate manner, all information necessary for the Board to function properly and to make informed decisions

Fundraising and Community Engagement

  • Serve passionately as i.c.stars' most senior spokesperson to the organization's funders, employer partners, champions, and public and lead fundraiser, responsible for raising and growing the organization's $9M development target in FY 2024
  • In partnership with the Chief Development Officer, develop and execute fundraising strategies that continue to cultivate existing donors engage new funders, and capitalize on opportunities generated by the success of i.c.stars
  • Personally engage in high-level external fundraising and serve as lead ambassador for i.c.stars in high-level donor meetings and build a culture of philanthropy at the Board level that builds the path to i.c.stars' future
  • Contribute to external messaging strategy, marketing and communications and resource allocation; ensure all marketing and communications are consistent with the i.c.stars' brand and mission

Candidate Requirements:

  • 15+ years of work experience, including at least five years of experience in senior leadership positions within entrepreneurial organizations or teams; prior work experience in technology and/or workforce development highly preferred
  • A track record of leading transformation efforts and/or scaling a team, line of business, and/or organization and the ability to execute change management through organizational layers
  • Passionate about serving historically underserved adults and an unwavering belief in harnessing the untapped potential of program participants and committed to living out i.c.stars' values of: Stewards, Teachers, Agents to Change, Resilient, Solution Finders
  • Demonstrated success developing and implementing multi-year strategic plans with an ability to achieve goals and align interests through influence and collaboration
  • Track record of meeting multi-million dollar development goals in a nonprofit setting and serving as a thought leader in one or more of the following areas: workforce development, technology training, youth development and advocacy and / or related field
  • Robust people management experience, with the ability to inspire, develop, and retain a high performing team, set priorities, delegate responsibilities, let senior leaders drive their work while holding them accountable for outcomes, and provide thoughtful, learning-oriented feedback
  • Experience working in a multi-site or regional organization
  • Comfort and confidence with DEIBJ and racial literacy in different spaces, and prior experience bringing a framework of racial equity to their work
  • Ability to communicate our strategy internally and externally to partners, funders, and key stakeholders in a range of environments and a demonstrated ability balance listening and learning with leading with the ability to act as a compelling advocate for the work of i.c.stars

Location: i.c.stars is headquartered in Chicago with locations in Kansas City and Milwaukee. While there is a preference for a candidate to be local, or within commutable distance, to either of those locations, i.c.stars will also consider exceptional candidates outside of those cities.

Compensation and benefits:

The salary range for this role is $225K-$275K, commensurate with experience. In addition to compensation, i.c.stars also provides a suite of competitive benefits that include health, dental, and vision insurance, retirement contributions, paid holidays, vacation, sick, and personal time.

i.c.stars is an equal opportunity employer. All qualified applicants will be considered for employment without unlawful discrimination based on race, color, creed, national origin, sex, age, disability, marital status, sexual orientation, military status, prior record of arrest or conviction, or current employment status.

Like i.c.stars, On-Ramps is deeply committed to diversity, equity, and inclusion. We believe social change happens when people with a wide range of backgrounds, experiences, and identities come together with a common purpose.

On-Ramps is committed to the inclusion of all qualified individuals in the hiring process, including but not limited to those with disabilities. If you require reasonable accommodation(s) to participate in the application or interview process, please contact