Director of Development

About College Bound Opportunities

College Bound Opportunities (CBO) empowers and inspires low-income, first-generation Scholars to graduate from college and achieve their full potential. Through mentoring, college access and persistence support, and an emphasis on community, CBO helps Scholars thrive in college and beyond. We envision a future where every first-generation student has the support and resources needed to achieve a postsecondary degree and lead a life of purpose and possibility.

Now entering its third decade, CBO is at an exciting inflection point—building on a strong mission and community support base while investing in the strength of systems and structure with an eye on long-term sustainability. The organization is implementing a FY26 Strategic Framework designed to stabilize operations, modernize infrastructure, and position CBO for future growth and impact.

More on CBO appears at the conclusion of this document.

Position Overview

The Director of Development (DD) is a key member of CBO’s leadership team and is responsible for executing a comprehensive fundraising strategy to grow and diversify revenue in support of our mission. This individual will lead all development activities—including individual giving, foundation and corporate fundraising, special events, donor communications, and campaign planning—while also building the infrastructure required for a more robust, scalable development operation. The DD will determine how best to activate the Executive Director, Board of Directors, and staff in the service of the organization’s Advancement goals. Where pertinent, the DD will recommend external vendors to assist with the execution of Development priorities.

This is a unique opportunity for a strategic, hands-on, experienced development leader to shape and strengthen CBO’s philanthropic engine, steward a loyal base of donors, expand our institutional support, and position the organization for sustainable growth in the years to come. CBO has embarked upon a path of ambitious organizational modernization and change. The ideal candidate is an active listener, combining creativity, persuasive communication skills, and a knack for relationship-building with a proven track record of success in raising revenues through diverse channels and a deep belief in the potential of first-generation college students.

Key Responsibilities

Strategic Leadership & Development Planning

Inherit, assess, evolve, and manage a multi-year development strategy with clear goals across all fundraising channels in partnership with the Executive Director and the Board of Directors.

• Collaborate with the Executive Director and Board to build a strong culture of philanthropy where everyone plays a role.
• Create and track fundraising dashboards, campaign pipelines, and performance metrics to monitor progress.
• Build and document development systems, calendars, policies, and workflows.
• Draft and institutionalize a development operations manual outlining policies, timelines, and best practices for appeals, grants, pledges, sponsorships, and gift processing.

Individual Giving & Major Gifts

Lead individual giving strategy, cultivating relationships across CBO’s base of donors—with a particular focus on legacy donors, prospective major donors, and new supporters aligned with our mission.

• Manage and augment a major gifts pipeline; identify, qualify, cultivate, solicit, and steward individual donors with the capacity to give $5,000+.
• Develop strategies and programs to encourage alumni, mentors and committee volunteers to financially support CBO.
• Launch or enhance systems to better manage donor stewardship, including segmentation strategies, personalized touchpoints, and impact reporting.
• Ensure timely gift processing, including use of online donation forms and point of sale options, check processing and deposits, providing regular updates to the accounting team.
• Oversee annual appeal strategy, digital campaigns, and donor communications.
• Activate a nascent planned/estate giving program to engage aging legacy donors and steward long-term philanthropic commitments.

Foundation and Institutional Fundraising

Develop a comprehensive grants calendar and strategy to diversify and grow foundational support.

• Research and identify aligned foundation prospects and funding trends; develop a case for institutional investment in CBO’s work.
• Oversee a grants management clearinghouse for proposals, deadlines, reports, and compliance documentation in collaboration with program and finance teams.
• Develop compelling grant templates, logic models, theory of change documentation, evaluation frameworks, and collateral aligned with funder expectations.
• Partner with staff to ensure programmatic outcomes and organizational impact are well-documented.

Corporate Giving & Sponsorships

Enhance an existing corporate engagement strategy that marries workplace giving with and employee engagement opportunities.

• Cultivate relationships with CSR departments, local businesses, and corporate foundations to establish long-term partnerships.
• Leverage an existing toolkit for corporate engagement that includes sponsorship tiers, partnership packages, and employee volunteer opportunities.

Events & Campaigns

Provide strategic leadership for all fundraising events, including CBO’s annual benefit, cultivation events, and donor appreciation gatherings.

• In partnership with the Executive Director and board-led committees, lead planning for CBO’s 20th Anniversary Celebration campaign in the fall of 2026, using this milestone to elevate visibility, reengage lapsed donors, and inspire philanthropic investment using the stories of student and alumni success.
• Manage event logistics, timelines, donor outreach, and marketing efforts; collaborate across departments and with volunteers as needed.
• Develop and implement strategies for pre- and post-event donor engagement to maximize fundraising potential and retention.

 Marketing, Collateral & Donor Communications

Develop consistent, mission-driven messaging across channels that elevate CBO’s visibility and impact.

• Conduct a comprehensive audit of CBO’s constituent relations management database (CRM) to ensure accurate donor records, gift tracking, and reporting capabilities. Where prudent, automate workflows for gift acknowledgment.
• Guide the development of donor-facing content and collateral, including case statements, impact reports, appeal letters, stewardship packets, and web content.
• Ensure all donor touchpoints—emails, print pieces, thank-you letters, and reports—are timely, professional, and aligned with best practices in donor stewardship and relationship management.

Ideal Candidate Profile

The ideal candidate is a compassionate, influential people-person—a leader who can translate vision into systems, build authentic relationships through shared values, stay motivated through change, ramp up quickly, and enjoys making compelling asks.

Leadership Competencies

• Strategic & Systems Thinker: Connects mission to operations through measurable outcomes. Develops a clear vision aligned with organizational mission, and works towards that vision by setting metrics/goals. Refines vision when called for. Analyzes information effectively through selecting the right data for the situation; choosing the right analytical technique; and applying reasoning skills to the analysis. Ensures data integrity and quality.
• Effective Communicator: Effectively communicates by choosing the right mode of communication; writing with clarity; and verbally communicating clearly and persuasively.
• Fundraising Strategist: Proven success cultivating major donors and building diversified revenue streams. Identifies new prospects, builds rapport and connections, deeply engages to learn information, maintains relationships, and gains critical support and long-term investment; develops champions and partners.
• Cultural Leader: Makes sound decisions by considering situations through multiple lenses; prioritizing what matters most; and moving forward in a timely way. Improves team performance by providing feedback and longer-term mentoring and learning opportunities.
• Financially Astute: Skilled in budgeting, forecasting, and managing organizational resources. Familiar with the nuances of non-profit financial budgeting.
• Community Connector: Engages authentically with donors, alumni, mentors, and partners. Active listener with a curious mind. A true ambassador for the brand.
• Resilient & Adaptive: Thrives in dynamic, evolving environments; balances vision with disciplined execution. Demonstrates an entrepreneurial spirit and growth mindset. Leverages strengths and mitigates areas of growth through feedback, reflection, learning and doing.

Qualifications and Experience

Required

• Bachelor’s Degree
• 5+ years of nonprofit leadership experience, including and especially as an executive or in senior management roles, or equivalent experience in a parallel sector.
• Proven record of raising $1M+ annually through diverse fundraising channels.
• Experience managing budgets, financial systems, and reporting in alignment with GAAP principles.
• Demonstrated commitment to educational access for first-generation students.

Preferred

• Master’s Degree
• Background in college access, persistence, youth development, or related fields.
• Familiarity with CRM platforms, data dashboards, and impact reporting tools.
• Experience in small to mid-sized nonprofits undergoing growth or transition.

Work Environment and Benefits

CBO operates in a hybrid model, with offices located in Highland Park, Illinois. Staff typically work a blend of in-person and remote schedules aligned with organizational needs and team collaboration. This role requires full-time residence in the Chicagoland area, commuting regularly to our office and schools in Lake County, Illinois.

CBO offers a competitive compensation package including:

• Salary range of $75,000–$100,000, commensurate with experience.
• Health insurance, PTO, and professional development support.
• Flexible work environment that values balance, accountability, and connection. The role does require periodic attendance at evening events, weekend engagements, and other ‘off-hour’ commitments to students and families.

To Apply

Interested candidates should submit a resume and a cover letter highlighting qualifications and why this role, right now, in your career trajectory to:  mark@spacebarprojects.com  (Attention: Mark Haggarty*). Clarifying questions may be directed to the same email address. Applications will be reviewed on a rolling basis until the position is filled. All applicants will receive correspondence in return.

*Mark Haggarty is a consultant to CBO under the auspices of SpacebarProjects, LLC, managing the Director of Development search process on behalf of the organization. 

CBO is an equal opportunity employer and strongly encourages candidates from historically underrepresented backgrounds and nontraditional leadership pathways to apply. We believe that diverse lived experiences, identities, and perspectives strengthen our work and deepen our impact for first-generation students and their families.

Since 2006, College Bound Opportunities (CBO) has succeeded with the help of mentors, supporters and staff who are passionate about increasing educational equity and economic justice for students in six partner schools in Lake County, Illinois: Cristo Rey St. Martin College Prep in Waukegan, and Buffalo Grove, Deerfield, Highland Park, Lake Forest, and Vernon Hills high schools. Ensuring every student reaches their goals for high school and college graduation is central to educational equity.

Annually, CBO supports about 200 high school and college students who are asked to maintain a 3.0 minimum grade point average. CBO students have attended over 100 four-year colleges and universities across the country. Overall, 98% of CBO’s students have graduated or are on track to graduate college. CBO’s 304 alumni are working, pursuing graduate degrees, and raising families in their communities.

Relationships are at the heart of CBO’s success. The 1:1 mentor/student relationship and the consistent presence of staff in our Scholars’ lives builds trust with our students and their families, making the college journey a shared experience. The unparalleled support each student receives is at the core of our successful graduation rate. Because we know our students and their families so well, we can adapt programming to better support them and address the challenges they face in a holistic way.

During the 2025-2026 school year, CBO is supporting 70 high school students and 126 college students.

To Apply

Interested candidates should submit a resume and a cover letter highlighting qualifications and why this role, right now, in your career trajectory to:  mark@spacebarprojects.com  (Attention: Mark Haggarty*). Clarifying questions may be directed to the same email address. Applications will be reviewed on a rolling basis until the position is filled. All applicants will receive correspondence in return.

*Mark Haggarty is a consultant to CBO under the auspices of SpacebarProjects, LLC, managing the Director of Development search process on behalf of the organization. 

CBO is an equal opportunity employer and strongly encourages candidates from historically underrepresented backgrounds and nontraditional leadership pathways to apply. We believe that diverse lived experiences, identities, and perspectives strengthen our work and deepen our impact for first-generation students and their families.