EXECUTIVE DIRECTOR - CHICAGO

EXECUTIVE DIRECTOR

CHICAGO

Who We Are and What We Believe:

For over two decades, Bottom Line has been a relentless ally committed to building strong connections with students, providing them with individual support, and ensuring they have the guidance needed to affordably access college, persist, and graduate career-ready. Particularly for students from low-income, first-generation backgrounds facing systemic challenges, Bottom Line's advisors serve as steadfast allies, guiding them through college selection, supporting them through their degree pursuits, and facilitating successful career launches.

On average, Bottom Line graduates achieve nearly double their family's income in their initial post-college employment, a testament to the organization's profound impact that extends beyond individuals to families and entire communities. As pioneers in college support with a focus on graduation rates, Bottom Line effectively narrows the substantial gap between first-generation, low-income students and their more affluent peers.

Established in 1997 in Massachusetts and expanding to New York City in 2011, Bottom Line has steadily grown to assist thousands of aspiring degree holders from disadvantaged backgrounds on their journey to higher education. Since opening in 2014, Bottom Line Chicago has been a steadfast ally to first-generation college students from systemically under-resourced communities. Serving over 1,500 students across 70 zip codes, the Chicago region is dedicated to helping students navigate their journeys to college graduation and career success.

In partnership with donors, Bottom Line seeks to expand its impact radically: to annually support 20,000 students in their educational journeys by 2030. To realize this ambitious vision, Bottom Line will deepen investment in Chicago, New York, Massachusetts, Ohio and Detroit and will also seek to expand to new regions.

What You Will Do:

The Executive Director role is an exciting opportunity for a Chicago-based leader to drive local impact and ensure an incredible experience across Bottom Line’s local stakeholders (e.g., students, families, donors, partners etc.). This next leader will build upon Bottom Line’s strong foundation in the region and play a transformative role in growing the organization's impact and reach in Chicago. Reporting directly to the Chief Regional Officer and partnering closely with the local Advisory Board, the Executive Director will have the relationship-building, fundraising, team leadership, and strategic thinking skills necessary to fuel Bottom Line’s growth in Chicago, supporting almost 2K+ (and growing) students as they gain access to and through college and launch their careers. The Executive Director will have high emotional intelligence, cultural competence, and a collaborative and relational mindset that allows them to effectively lead a high-performing regional team and be equally comfortable serving as the local face of Bottom Line and engaging with a wide variety of stakeholders, including students, staff, donors, and the external community.

As the lead fundraiser for the region, the Executive Director will have the skills and more importantly, motivation needed to engage a wide range of donors in order to achieve ambitious revenue goals. The Executive Director will also serve as a member of Bottom Line’s Senior Leadership Team, which sets overall organizational strategy, representing the needs of the Chicago region and developing and driving the strategy to implement work regionally.

Leadership & Management

• Advance BL's 2030 vision via leadership of the Chicago Strategic Plan. Lead the overall strategic and operational excellence across Bottom Line Chicago’s staff, programs, and execution in service of the mission.
• Oversee regional results (program, development, staff experience) to ensure regional focus is on highest value work, model continuous improvements, and make data-driven decisions
• Lead and motivate a team of staff who have a wide array of diverse experiences and skills, establish and maintain a vibrant and meaningful work culture at Bottom Line Chicago.
• Balance local and national perspectives; initiate and guide the regional team to encourage collaboration with the National team, ensuring alignment in achieving both annual and long-term strategic objectives for the organization.
• Advocate for and bolster the organization’s foundational principles, policies, and dedication to racial equity, actively steering the organization towards a more anti-racist and multicultural stance.
• Foster a cultural ethos consistent with the organization’s Foundations and Core Values to foster staff engagement and drive the attainment of ambitious objectives.

Fundraising, Partnerships, and Champions

• Lead fundraising efforts and serve as the chief advocate for Bottom Line Chicago, executing a fundraising strategy with the Development Team to achieve both immediate and long-term regional goals.
• Work closely with the Regional Advisory Board, utilizing their expertise to build relationships and secure funding and partners throughout the Chicago area
• Foster relationships and secure substantial, multi-year contributions from individuals, foundations, and corporate entities.
• Identify new opportunities and establish as well as maintain partnerships with donors, thought leaders, and key community influencers, including K-12 schools, colleges, and grassroots organizations.

Thought Leadership and Community Engagement

• Amplify Bottom Line’s prominence as a leading voice within the sphere of college and career accessibility, persistence, and triumph.
• Serve as leader and front-line presence of Bottom Line Chicago, representing BL at high profile community events and in secured media

Duties, responsibilities, and activities may change at any time with or without advanced notice.

Who Should Apply:

The Executive Director must be a visionary and dynamic self-starter who shares Bottom Line’s commitment to changing the lives of students and their families. The Executive Director must value diversity and demonstrate comfort and competence working with and leading a diverse team. They must be a passionate, authentic, ethical, and mission-driven leader. The Executive Director will also be a person who possesses:

• Bachelor’s degree and legal work authorization.
• Proven success in leading and managing high-performing organizations, business units, or teams, especially during periods of growth
• Strong ability to set strategic direction for cross-functional priorities and manage teams (ideally through layers) to drive towards outcomes
• Skilled people manager; adept at identifying strengths in others and nurturing team members to develop and grow while simultaneously holding a high bar for achieving outcomes
• Proven fundraising experience within a relevant scale/context ideally with experience securing funds across a variety of funding streams (e.g., individuals, corporate, foundations etc.)
• Demonstrated experience in building, nurturing, and managing relationships with a wide swath of stakeholders (e.g., staff, donors, corporate partners, high schools, and higher education institutions etc.)
• Knowledge and connections across the Chicago education landscape; a trusted player in the space with the ability to serve as a thought partner to leaders across the local education ecosystem
• Strong alignment with Bottom Line’s mission, vision, and core values.
• Dedication to empowering underserved students by guiding them in selecting appropriate college options and providing support throughout their journey to a successful career launch.
• Demonstrated commitment to Bottom Line’s Mission, Vision, and Core Values

Personal Characteristics:

All employees are expected to demonstrate continued growth within our seven core competencies. Competencies provide Bottom Line with a way to define, in behavioral terms, what it is that people need to do to produce the results that the organization desires, in a way that is in keeping with its culture. Bottom Line defines competency as a cluster of related knowledge, skills, and attitudes that affect a major part of one’s job that correlates with performance on the job, that can be measured against well-accepted standards, and that can be improved via training and development.

• Relationships: Identifies opportunities and takes action to build and maintain meaningful and collaborative connections with various stakeholders.
• Results: Produces quality outcomes; compiles and analyzes data to drive future plans; uses creative solutions.
• Communication: Effectively articulates information in a clear, concise, and timely manner to a wide range of stakeholders.
• Inclusiveness: Creates and maintains an environment that respects and values the identities and cultures of all colleagues and students we serve.
• Talent Development: Actively contributes to the hiring, development, retention, and promotion of a highly effective team.
• Agility: Demonstrates adaptability and openness to shifting priorities, needs of stakeholders, and organizational changes.
• Planning: Effectively and efficiently uses resources (people, time, materials, technology) in order to create, meet, and assess both strategic and task-oriented goals.

At Bottom Line, we have a strong commitment to Community and Belonging. We aim to attract qualified candidates who hold these same values and help us further recognize and celebrate the diversity among us.

How To Apply/Application Deadline:

All applications must be submitted via Bottom Line’s Career Page.

Please share your resume and cover letter.

The application deadline is April 20, 2025.

Start Date:

July 2025

Compensation:

$170,000 – 185,000

Benefits:

Learn about our benefits here.