Opportunity Snapshot

Overview: Brave Space Alliance (BSA), a community-anchored LGBTQ+ center on Chicago’s South Side, is seeking a courageous and operationally skilled Chief Executive Officer (CEO) to lead the organization into its next era of stability, cultural cohesion, and expanded community impact. Founded in 2017 to fill a profound gap in affirming, culturally competent services for trans, gender-expansive, and LGBTQ+ people, particularly throughout Chicago’s South Side, BSA has become a vital hub for health, housing, food justice, and mutual aid.

Today, BSA stands at an inflection point. The organization has reinforced financial stability, strengthened program operations, and renewed donor momentum, while continuing to build the internal infrastructure needed to sustain its growth amid a shifting political landscape for trans communities. BSA’s staff, leadership, and Board describe this moment as one of possibility and alignment: an opportunity to deepen organizational clarity, nurture a warm and cohesive culture, and further elevate BSA’s role as a trusted community anchor.

Building on the leadership of Channyn Lynn Parker, former CEO and Board Emeritus, BSA’s next CEO will be a values-led, trauma-informed, systems-building leader who can pair strategic vision with operational execution. They will be deeply relational and visible within community spaces, while also bringing the clarity, direction, and steadiness needed to strengthen internal systems, develop staff, enhance partnerships, and guide the organization with integrity.

While knowledge of Chicago’s South Side communities is an asset and will help ground the work in place-based history and context, this national search welcomes candidates from outside Chicago who bring the humility, cultural fluency, and curiosity to learn from the community BSA serves.

Compensation: The salary range for this position is $140,000-$180,000, commensurate with experience, along with a competitive benefits package.

Submissions will be reviewed on a rolling basis, with a priority deadline of Friday, February 27th at 5:00 PM CT.

Full details about the role can be found in the Position Profile, which is available for download, or detailed below.

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About Brave Space Alliance

Brave Space Alliance (BSA) is an LGBTQ+-focused center on Chicago’s South Side that provides affirming and culturally competent services for all who enter its doors. Founded in 2017 to address the significant gap in programs, resources, and community spaces centering trans and gender-expansive people, particularly on the South Side, BSA exists to meet essential needs with dignity, care, and connection.

Rooted in its Four Pillars of Dignity, which include Health, Housing, Food, and Identity, BSA provides holistic services that strengthen individual and collective well-being. Through these pillars, the organization offers preventive and behavioral health services, HIV/STI testing and treatment, housing support, food access and justice programs, assistance with essential items, and community-based events and supports that affirm self-expression and personal agency.

BSA is recognized locally and nationally as a vital community anchor: a place where LGBTQ+ people, especially those most impacted by systemic inequities, can access care without judgment, experience belonging, and build power together.

As BSA grows, it remains guided by its founding belief: that liberation is built collectively through care, dignity, and the creation of brave spaces where all people can thrive. In the years ahead, BSA will continue to build power alongside the community by broadening its reach, forging new partnerships, and continuing to create spaces where all people are supported and affirmed.

To learn more about BSA, visit: bravespacealliance.org

Organizational Structure

BSA operates under a team structure designed to support responsive, community-centered service delivery across its programmatic pillars. The CEO will lead a committed staff of approximately 15 staff members, including a core group of full-time roles supported by part-time and fractional positions in community engagement, development, and operations. This structure allows the organization to remain responsive to community needs while retaining flexibility as programs evolve.

The Moment

Brave Space Alliance enters this leadership transition from a position of renewed strength, increased visibility, and growing momentum. The organization has strengthened its financial footing, expanded its donor base, delivered consistently high-impact programming, and deepened relationships within LGBTQ+ communities across the South Side.

As BSA looks ahead, stakeholders see a moment of opportunity and alignment. Staff, Board members, and community partners describe excitement for continued growth, strengthened internal systems, and expanded community presence. With core programs thriving and community needs evolving, the next CEO will have the opportunity to build on BSA’s current foundation by enhancing infrastructure, nurturing staff development, broadening partnerships, and advancing a clear, community-informed vision for the future.

This transition is a natural next step in BSA’s evolution: an opportunity to stabilize what has been built, support a talented team, and guide the organization confidently into its next chapter of impact.

About the Role

The CEO will serve as BSA’s chief strategist, organizational builder, and relational leader, responsible for translating BSA’s mission and values into sustainable infrastructure, trusted community presence, and long-term organizational stability.

Partnering with staff and the Board of Directors, the CEO will prioritize:

Strategic Vision & Adaptive Leadership

• Articulate a clear, community-aligned vision for BSA’s next phase.
• Guide organizational priorities and decision-making pathways through transparent, values-aligned leadership.
• Navigate complex political relationships and civic environments while remaining grounded in community needs.

Organizational & Operational Leadership

• Stabilize and strengthen internal systems, including Standard Operating Procedures, performance management, data/evaluation processes, supervisory structures, and cross-team communication.
• Build sustainable workflows that reduce burnout, clarify expectations, and support staff development.
• Ensure compliance with legal, regulatory, health, safety, and reporting requirements.
• Strengthen facilities management and support long-term planning for space needs.

Community Engagement and Visibility

• Maintain a visible, relational presence within community spaces and programs.
• Lead with humility, cultural fluency, and trauma-informed practice.
• Build authentic trust with program participants, staff, volunteers, and partners.

Fundraising, Advocacy & External Relations

• Continue to build fundraising momentum through strong donor stewardship, compelling storytelling, and partnership development.
• Maintain and strengthen relationships with civic partners, funders, elected officials, public health agencies, and community coalitions.
• Engage in measured, mission-aligned public positioning in moments where organizational interests or consistent service delivery could be impacted.

People Leadership & Talent Development

• Cultivate a warm, relational, cohesive staff culture that prioritizes care, accountability, and clear communication.
• Provide coaching, mentorship, and professional development pathways for staff.
• Balance being hands-on with empowering staff through shared accountability and role clarity.

Leadership Attributes

Ideal candidates will bring many of the following qualities:

Strategic, Visionary & Adaptive: The CEO will bring the ability to look ahead and anticipate what BSA needs to thrive in evolving political, civic, and funding landscapes. They will guide the organization with clarity and purpose, helping staff and Board members align around shared priorities. This leader will be skilled at adapting to changing conditions at the federal, state, and local levels while protecting organizational focus, ensuring that growth is grounded in both mission and operational capacity. They will cultivate a vision that is ambitious yet attainable, one that honors BSA’s history while opening doors to new possibilities. This leader will value collaboration and open communication without losing sight of executive responsibility, creating a balance that empowers others while keeping the organization aligned. Their transparency will strengthen trust internally and externally, positioning BSA as an organization grounded in integrity.

Operationally Rigorous & Systems-Minded: The next CEO will bring the clarity, steadiness, and follow-through needed to strengthen BSA’s internal infrastructure. They will bring experience building and refining systems that help staff do their best work and ensure organizational consistency. This leader will understand how to translate mission-driven aspirations into sustainable operational practices. Their approach will balance urgency with thoughtful pacing, helping the organization grow without overextending its capacity.

Community-Rooted & Relational: Grounded in humility and cultural responsiveness, the CEO will be a visible, present leader who builds trust through genuine connection with community members, staff, and partners. They will understand the importance of being accessible, not as a symbolic gesture, but as a core leadership practice for a community-centered organization. While knowledge of Chicago’s South Side is a valuable asset, this leader will also recognize the importance of learning from those with deep roots and lived experience. They will engage with community spaces in ways that honor existing relationships and strengthen BSA’s credibility.

Humble, Trauma-Informed, and Reflective Practice: The CEO will understand trauma-informed leadership not as a clinical framework but as a way of showing up with consistency, compassion, and respect for the range of life experiences within the organization. They will bring emotional intelligence and warmth to their leadership, creating environments where people feel safe, valued, and able to communicate openly. Comfortable acknowledging what they don’t know, they will seek feedback, adapt their approach, and model work practices that support staff sustainability. Their reflective leadership will help cultivate a culture grounded in curiosity, accountability, and ongoing growth, strengthening relationships and fostering internal cohesion.

Equity-Driven, Intersectional, and Values-Aligned Leadership: This leader will be deeply committed to anti-oppressive practice and able to navigate complex dynamics across race, class, gender identity, disability, education, and lived experience. They will understand how inequities show up in nonprofit spaces and work proactively to reduce harm, elevate those most impacted, and strengthen internal collaboration. Their leadership will reflect an understanding of intersectionality, particularly as it relates to the communities BSA serves, and will help cultivate a culture rooted in dignity, accountability, and shared power. Their approach will invite dialogue and reflection while guiding the organization toward more equitable practices.

Courageous Navigator of Political & Civic Relationships: Given the organization’s visibility and the current political climate affecting LGBTQ+ communities, the CEO must be comfortable navigating civic, governmental, and coalition-based relationships with both confidence and care. They will represent BSA with integrity, ensuring the organization’s public engagement reflects its mission, values, and responsibilities as a nonprofit organization. This leader will understand when to build alliances, when to set boundaries, and how to communicate BSA’s role in broader civic conversations. Their approach will be thoughtful, measured, and grounded in community trust.

Staff Developer, Mentor & Culture Builder: The CEO will be a leader who prioritizes staff development and creates clear pathways for professional growth across the organization. They will guide, coach, and mentor team members, supporting them in strengthening their skills while establishing consistent supervisory and communication practices. This leader will cultivate a work environment that values collaboration, transparency, and shared accountability, strengthening morale and nurturing cross-team cohesion. By modeling healthy conflict engagement and celebrating staff contributions, they will help BSA continue to evolve into a supportive, connected workplace.

Ideal Experience

Strong candidates will bring a range of the following experiences and perspectives. We recognize that exceptional leaders emerge along varied pathways and may not reflect every listed qualification. With this in mind, we encourage candidates to apply even if their background does not match every listed qualification.

• Senior leadership experience in a nonprofit, community-based, public health, or social service context.
• Proven ability to build and strengthen organizational systems, infrastructure, and operations.
• Experience developing anti-oppressive, trauma-informed, and community-accountable leadership practices.
• Experience strengthening staff culture, supervisory structures, and team cohesion.
• Fundraising experience with individual donors, foundations, and/or corporate partners.
• Experience navigating political and civic relationships, ideally within contexts involving LGBTQ+, public health, or community-based services.
• Experience implementing ethical, culturally grounded evaluation and data practices.
• Deep alignment with BSA’s mission and communities, including the dignity, safety, and liberation of trans and Black LGBTQ+ whose lives and experiences shape the heart of BSA’s work.

An understanding of Chicago’s South Side is valuable for grounding this work, though candidates from beyond Chicago are equally encouraged to express interest. Candidates who are newer to the city will be expected to approach this learning with humility, curiosity, and respect for the community’s history and leadership.

Compensation and Benefits

The salary range for this position is $140,000-$180,000, commensurate with experience.

Brave Space Alliance offers a competitive benefits package, which includes the following:

• Medical, dental, and vision insurance, with 75% of medical premiums and 100% of dental and vision premiums covered by BSA, along with gender-affirming care, short- and long-term disability coverage, and life insurance.
• Generous paid time off, including 20 discretionary PTO days, 12+ days of office closure for observed holidays, and 3 floating holidays annually.
• Sabbatical benefit of three months after five consecutive years of employment, eligible for use beginning in the sixth year.

About Avra Search Partners

We believe in turning moments of transition into moments of transformation.

Avra Search Partners is a national executive search and leadership advisory firm committed to placing transformative leaders in mission-driven organizations. We partner with a wide range of nonprofits and impact-focused businesses, including foundations, advocacy organizations, associations, and artistic and cultural institutions, to design search strategies that honor organizational values and help institutions thrive.

We specialize in high-touch, selective engagements that combine evidence-informed evaluation with a relational approach, helping institutions build stronger futures through exceptional leadership.

With a deep commitment to inclusion, resilience, and leadership excellence, Avra helps clients identify and attract outstanding candidates from a range of backgrounds, including individuals who have historically had limited access to executive opportunities. Our work centers on expanding the leadership pipeline, strengthening governance, and ensuring organizations are supported by leaders equipped to guide their next chapter.