Learning And Development Officer Jobs (NOW HIRING)

As it enters its next phase of growth, Hope Chicago is seeking a Chief Development Officer to architect the fundraising and partnerships needed to scale a radically different approach to economic mobility.

Organizational Overview

Hope Chicago is a nonprofit pioneering a radically different approach to advancing economic mobility for families and neighborhoods. The organization partners with five neighborhood high schools in historically underserved communities on Chicago's South and West sides and guarantees debt-free pathways through postsecondary education for every graduate, as well as one of their parents or guardians.

In just four years, Hope Chicago has supported more than 2,600 students and 300 parents in pursuing college or career credentials, with its first wave of graduates expected in Spring 2026. Working in partnership with 29 colleges and a growing network of workforce training providers, Hope Chicago has emerged as a national leader in using postsecondary access and completion as a lever for advancing economic mobility for families and entire communities.

Hope Chicago's model is distinct in several key ways:

• Placebased and comprehensive: Every graduate of the five partner high schools is eligible-no GPA cutoffs, no merit screens.
• Multigenerational: Scholarships extend to one parent or guardian for every Hope Scholar, recognizing that families are engines of economic progress.
• Family-centered support: Access is paired with wraparound support and engagement with entire families, helping Scholars complete programs and transition to careers.
• Multipathway: Scholars choose college or workforce routes aligned to their individual goals, strengths, and aspirations.

Hope Chicago is now entering its next chapter of growth, impact, and influence. It is leveraging its early results to reimagine the systems beyond individual scholarships-working to shape new opportunity at the intersection of families, postsecondary institutions, workforce partners, and employers. Hope Chicago aims to demonstrate what is possible when the talent in every community is fully unlocked.

More information about Hope Chicago can be found at www.hopechicago.org.

Hope Chicago is seeking a dynamic and entrepreneurial Chief Development Officer (CDO) as it enters its next phase of growth and scale. This is a rare opportunity for a senior development leader to help shape how a bold, proven model is funded, communicated, and scaled-playing a defining role in securing the resources and partnerships needed to propel families' economic futures.

The CDO serves as the chief architect of Hope Chicago's fundraising and partnership strategy, making the case for sustained investment in a fundamentally different approach to postsecondary access and mobility. Reporting to the CEO and serving as a key member of the Executive Leadership Team, the CDO leads a development operation that currently raises approximately $21 million annually. In close partnership with the CEO, Board of Directors, and senior leadership, the CDO will chart a bold and sustainable path forward-deepening major donor relationships, securing transformative gifts, and expanding revenue beyond traditional philanthropy.

The CDO manages and develops a team of seven, including four direct reports, spanning prospect development, donor relations, communications, development operations, and systems. The role requires both strategic vision and strong operational leadership to ensure the team is aligned, accountable, and positioned to meet ambitious goals.

Externally, the CDO serves as one of the most visible ambassadors for Hope Chicago-building trust, inspiring confidence, and inviting partners to play a role in reshaping economic futures for students and families across Chicago.

For a development leader motivated by scale, significance, and the chance to help define what equitable opportunity can look like in practice, this role offers a uniquely meaningful platform.

Provide Strategic Leadership and Vision 

• Serve as a key member of the Executive Leadership Team, contributing to organizational-wide strategy and direction.
• Assess and refine Hope Chicago's current fundraising and partnership strategy.
• Deliver a clear, measurable fundraising plan in close collaboration with Executive Leadership.
• Drive long-term revenue sustainability by exploring innovative and nontraditional funding opportunities in addition to traditional philanthropy.
• Ensure alignment of fundraising strategy with organizational, programmatic, and financial priorities.
• Champion and embed a culture of philanthropy across the organization.

Cultivate and Lead a High-Performing Development Team 

• Provide strong, human-centered leadership to a talented, mission-driven development team of seven, fostering a culture of trust, collaboration, and continuous learning.
• Build team capacity through coaching, clear expectations, and professional development opportunities.
• Enhance systems, processes, and workflows to increase efficiency and support future team scaling.

Strengthen Mission-Forward Communication and External Engagement

• Serve as a compelling public ambassador for Hope Chicago, communicating its mission and impact across diverse audiences.
• Partner with data and communications teams to shape clear, emotionally resonant messaging grounded in storytelling and impact metrics.
• Lead high-touch donor communications, events, convenings, and stewardship that deepen engagement and build long-term relationships.
• Elevate the organization's brand and visibility, positioning Hope Chicago as a thought leader in postsecondary access and multigenerational economic mobility.

Advance Major, Principal, and Transformational Fundraising 

• Partner with the CEO and Board to cultivate, solicit, and steward major and principal gifts.
• Set fundraising priorities and portfolio strategies in collaboration with the CEO.
• Work closely with the development team to help them achieve individual and team fundraising goals.
• Manage a portfolio of major donors, partners, and prospects while guiding the organization's broader philanthropic efforts.

The CDO must be a leader who resonates both personally and professionally with the mission of Hope Chicago and the partners they serve. The ideal candidate will be an accomplished leader and fundraiser, skilled at innovative strategy, and ready to work in a fast-paced, high-impact environment with stakeholders from a broad range of sectors.

Additionally, candidates should have the following personal and professional skills, qualities, and competencies.

• 10+ years of professional fundraising experience at a non-profit organization of similar size and scope to Hope Chicago, with a track record of meeting or exceeding fundraising goals and growing a development program creatively and strategically.
• 5+ years' experience managing fundraising professionals.
• Demonstrated success securing six and seven-figure gifts from individuals and institutions.
• A track record of energetic and creative approach to leadership with a passion for organizational development.
• Proven expertise operating with deep relational integrity to cultivate, solicit, and steward individual and institutional donors and partners.
• Ability to galvanize a team around a clearly articulated vision and strategy, with an eye toward cohesive team function and professional development of departmental colleagues.
• Strong analytical skills and the ability to partner effectively with data and information teams to inform donor strategy and decision-making.
• Experience collaborating with communications colleagues to deploy media and marketing strategies in service of organizational advancement.
• Excellent public presentation skills.
• A posture of positivity, hope, and joy that can inspire and motivate people - internally and externally - to participate in the organizational mission.

The salary range for this position is $230,000 to $280,000, commensurate with experience. Hope Chicago also offers a generous benefits package.

This is a hybrid role based in Chicago with the expectation for in-person work a minimum of 3 days a week.

Hope Chicago is a tax-exempt 501(c)(3) organization and values its diverse and inclusive workplace. We do not discriminate on the basis of race, religion, gender identity or expression, age, sexual orientation, national origin, or marital status, and are committed to a welcoming, respectful environment for all who work for and engage with Hope Chicago.

Hope Chicago has retained Orr Group to lead this search. Nominations and inquiries can be submitted to:

Jesse Bryan

Vice President, Orr Group

jbryan@orrgroup.com