Position: Regional Executive Director, Midwest

Position Type: Internal-External

FLSA Classification: Exempt

Reports to: Jonathan Paul, Chief Regional Operations Officer

Start date: May/June 2026

Location: Chicago, IL

Location Classification: Location-specific

Salary Range: $180,000 – $200,000 is the hiring salary range (i.e. the range a candidate would be offered to start). Please note: OneGoal aligns salaries to Cost of Labor, so the actual salary offered would be dependent on the Cost of Labor in the candidate’s living location.

About OneGoal

OneGoal transforms postsecondary advising and support so that every student can define their own future. Together with our partners, we’re building a movement to close the opportunity gap. We work side-by-side with partner schools and districts to build their knowledge and capacity. The result is more effective support for all students. Our unique approach, honed over 15 years, prioritizes strong human relationships. And it’s proven to deliver real student impact: An independent study by the University of Chicago found that OneGoal students are about 40% more likely to earn their postsecondary degrees than students from similar backgrounds. At OneGoal you’ll be immersed in a culture of collaboration, shared purpose, and collective impact.

The Person

The Regional Executive Director (ED) serves as the face of OneGoal in the Midwest and is charged with building trust and credibility among funders, partners, and key regional champions. They build OneGoal’s brand, and advocate for our mission and vision for postsecondary advising in the local community. They do this while ensuring strong programmatic outcomes, securing the financial resources to achieve our mission, and creating a strong and rewarding staff experience for their teams.

The Regional ED is both the Midwest’s regional leader and a member of the OneGoal Leadership Group. They author and communicate a compelling vision for OneGoal’s work in the community that will inspire internal and external stakeholders to engage with, invest in, and believe in what’s possible for young people.

You will do this by:

Fundraising, Partnerships, Outreach, and Brand-Building (60%): Lead the Managing Directors of External Affairs and Partnerships and Growth, and their teams to hit or exceed our revenue and district and state partnership goals respectively.

Lead External Affairs planning and strategy, in partnership with National Development and Regional Operations colleagues.
Cultivate individual and institutional donors and serve as primary solicitor for all major gifts.
Steward a diverse, engaged, and active group of Advisory Board members committed to supporting fundraising and program expansion.
Develop and execute a plan for OneGoal to expand both within Illinois and across Midwestern states via advocacy, lobbying, and partnerships with state government, education departments, anchor funders, and local districts.
Steward district leaders, state education leaders, and other influencers to invest and partner with us around shared goals for impact and growth.
Position OneGoal as a thought leader and go-to partner for postsecondary planning and success through advocacy and coalition work.
Engage with the media, and speak at events (OneGoal events as well as others) to raise awareness and build champions.
Partner with the Midwest Leadership Team to track and manage growth of our school and district partnership health, and create a clear multi-year, comprehensive funding and growth plan.

Team Leadership (25%): Lead the Midwest regional team to hit or exceed target KPIs in program impact, partnership growth, staff engagement, and financial efficiency & health.

Set a clear and compelling vision for the Midwest regional team, investing both the Midwest regional team and national partners.
Provide timely management and coaching support to the Regional Vice President (RVP), MD External Affairs, and MD Partnerships and Growth to ensure they are achieving strong results with their team, including our program impact goals and growth efforts at the district, city, and state level.
Effectively oversee the management of budget, including identifying opportunities and approving trade-offs connected to our overall priorities.
Cultivate a strong, trust-based team culture that fosters trust and belief in the Midwest region and broader organization, and empower People Managers to do the same
Support the leadership team in development of a team culture plan centered around our Core Values and cultural commitments

Executive Leadership of OneGoal (15%): Serve as a collaborator and partner to five other Executive Directors, National teams, and Regional teams across the country

Ensure alignment between regional vision/activities and our organizational strategic direction.
Support the health of the organization specifically through National/Regional collaboration initiatives at the senior level, including cascading change management.
Create, share, and refine a comprehensive annual plan, incorporating strategic objectives, personnel, and budget.
Contribute to OneGoal’s strategic plan and provide input to key organizational decisions as part of our Leadership Group.
Liaise with state and district leaders to build brand awareness and harness ideas to inform our local and national strategy.

The Regional Executive Director, Midwest is likely to see themselves in the following examples as they are designed to help you determine if this opportunity aligns with your own passion, purpose, skills, and experiences.

You believe deeply in the brilliance of all students and in their ability to earn a postsecondary degree.

You believe that our Fellows face real systemic barriers to postsecondary completion and that empowering families, teachers, and students to own their unique path will help them to overcome those barriers.
Your hope is coupled with a strong understanding of postsecondary readiness, access, and success research and the barriers that first-generation, low-income, and students of color face in pursuit of their postsecondary goals.

You are an opportunity generator – and a seasoned fundraiser who inspires others to invest in us.

You are driven by a bold vision of what’s possible, and can quickly and effectively build momentum around that vision across diverse constituencies.
You have an exceptional ability to create and refine a clear, compelling vision. You are able to take an inherited, big-picture vision and break it apart to crystalize the critical steps necessary to actualize that vision (e.g. set benchmark goals and time-bound key actions).
You bring deep experience and relationships with the Chicago and Illinois funder community.
You can see connections across lines of work and open lines of communication and forming strong collaborative partnerships.
You understand and can connect today’s strategic choices to the long-term financial viability.

You have a remarkable ability to compel and inspire.

You have tremendous ability to adapt messages to different audiences in order to inspire stakeholders and build champions.
You believe your impact can be greater when you empower others. You believe that all individuals have the ability to be great, and that even great executors can achieve more with additional resources and support. You build relationships quickly, consistently, and authentically.
You are driven by the belief that we cannot move the needle on the postsecondary completion movement without talented individuals from diverse backgrounds working together.
You are able to influence, cultivate, and inspire action due to an exemplary ability to build coalitions, lead from a position of inquiry, and be empathetic and flexible to the needs of others.
You actively work to uproot the barriers and mindsets that impede opportunity for our Fellows and our work. You are committed to influencing others to gain and act on an understanding of the barriers our Fellows face and become champions of addressing those injustices.

You are highly effective at building authentic, long-lasting relationships and coalitions.

Your relationships with key stakeholders are authentic and grounded in honesty, integrity, and trust.
You are persistent and understand that building relationships across Midwest funder, state, and district leaders will take time. You will put in the work and strategize with team members to help more Fellows have access to OneGoal.
You are energized by uncovering and understanding the unique interests and needs/motivations and barriers to increasing our fundraising efforts and effectively managing and engaging our funder base.
You enjoy collaborating with others to leverage their knowledge and are eager to work across functional teams and internal and external audiences to ensure everyone is invested in what is happening in the Midwest region.

Qualifications:

Deep fundraising experience, with a strong preference for specific connections and context with the Chicago funder community (Required)
Experience building partnerships with school, district, and state education leaders (Required)
Lived experience of the Fellows we serve (Preferred)
Ability to travel up to 20% annually (Required)
Experience leading and managing teams and serving on an organization’s leadership team (Required)
Experience in Midwest education and/or the postsecondary landscape (Preferred)
Located in the Chicago area and able to be in the Chicago office 2-3 days per week, along with occasional evening events.

Our Team

Guided by a clear set of core values and beliefs, you will join an impressive group of more than 200 OneGoal staff across the country who believe in the untapped potential within students. The OneGoal team challenges themselves and others to regularly ask, “Is there a better way?” We believe that in order to create the change we seek, each person we hire brings a remarkable and diverse set of experiences, skills and characteristics that individually and collectively, will contribute to the radical change needed to move us towards a more just nation.

The Tangible Good

OneGoal offers competitive compensation based on the market for nonprofits our size. Our benefits package* includes: over eight weeks of paid time off (or 43 business days), between vacation days, wellness time, and holidays; paid medical or parental leaves should you have need; medical, dental, vision, short-term and long-term disability, and life insurance; as well as a 401(k) with a 3% match.

We believe in compensating staff members fairly in relation to each other, their qualifications, and their impact on behalf of the organization, and take internal and external fairness seriously. OneGoal does not negotiate salary offers; instead each salary offer is determined carefully using external and internal benchmarking. You will have an opportunity to discuss salary in more detail after you begin the hiring process.

*OneGoal reserves the right to change benefits at any time according to business need.

If you require a reasonable accommodation to submit an application or to participate in the application or interview process, please reach out to our Human Assets Team to request an accommodation. Our Human Assets Team can be contacted at 773-321-2630 or HumanAssets@onegoalgraduation.org.

OneGoal does not discriminate against any employee or applicant for employment because of actual or perceived sex, race, color, ancestry, citizenship, ethnicity, national origin, religion, age, disability (mental or physical), sexual orientation, gender identity or expression, marital status, pregnancy, breastfeeding or related medical condition, parenthood, genetic characteristic or information, military or veteran status, marital status, or any other characteristic protected under federal, state, or local law.

OneGoal

Latest Jobs

Regional Executive Director, Midwest