Description

Vision and Mission:

Chicago Loop Alliance (CLA) leads the community by creating and supporting inclusive programs that attract people and investment to the Loop. CLA secures this vision through planning & advocacy, enhanced services, activation of public spaces, and economic development. Learn more at LoopChicago.com. 

Reports to:

President & Chief Executive Officer

The Opportunity:

The Chief Strategy Officer (CSO) is a newly created senior leadership role that will provide specialized focus on the future growth and expansion of Chicago Loop Alliance (CLA) – aligning the organization's priorities while envisioning a clear path forward. Partnering with the President & CEO, the CSO will serve as strategic architect — layering strategy with vision, accelerating mission; laying the foundation for deepened relationships with government, corporate, and civic stakeholders while positioning the Loop as a preeminent destination.

Organizational strategy will focus on shaping culture, climate and mutually benefiting alliances for transformative success. This opportunity is for an innovative, results-oriented leader deeply anchored in Chicago's civic, corporate, and public-sector communities to help define and expand the future of downtown Chicago.

Assignment Competencies 

• Connected Leadership: Empowers staff and elevates the performance of the whole team.
• Relationship Intelligence: Employs diplomacy; builds trust-based, durable relationships across diverse stakeholder groups.
• Grit + Drive: Identifies and pursues new revenue, partnership, and programming opportunities.
• Mission Alignment: Deeply committed to an inclusive, economically vibrant downtown Chicago.
• Strategic Vision: Sees the big picture and connection to long-term organizational goals, creating conscious, integrated systems.

PRIMARY RESPONSIBILITIES

In collaboration and guidance from the CEO:

Organizational Strategy

• Develop and implement a comprehensive, multi-year strategic plan.
• Align broader business objectives with mission - transforming vision statements into actionable strategies:
• • Design and implement an annual plan that drives progressive, systematic impact; scales productivity; enhances brand integrity; and fuels ongoing growth.
  • Develop and implement sustainable tactics that increase brand exposure and partner engagement.
  • Employ partnership and social impact campaigns to fuel development initiatives, strengthen messaging, and demonstrate mutual benets for current and potential stakeholders.
  • Identify remedies for process and service gaps to ensure organizational outcomes are achieved.
  • Work collaboratively with stakeholders to foster goals and mission alignment.
  • Lead, mentor, and develop sta across the government aairs, membership, and development functions.
  • Contribute to the development and monitoring of CLA's strategic plan, ensuring alignment across all programmatic and operational priorities.

Membership & Board Development

• Lead strategy for recruiting, retaining, and elevating CLA's member base across corporate, retail, hospitality, real estate, and cultural sectors.
• Develop tiered membership structures, value propositions, and engagement programming that deepen member participation and satisfaction.
• Partner with the CEO and Board Chair on board recruitment, governance best practices, and committee alignment to strengthen CLA's leadership pipeline.
• Identify and cultivate prospective board members who represent the Loop's evolving economic and demographic landscape.

Government Aairs & Advocacy

• Cultivate and manage relationships with elected ocials, city departments, and regulatory agencies at the local, state, and federal levels.
• Develop and execute a proactive government aairs agenda that advances policies supporting the Loop's economic vitality, public safety, transit access, and quality of life.
• Represent CLA in city planning processes, budget hearings, and legislative forums with a unied voice for Loop stakeholders.
• Monitor and respond to emerging policy developments that affect the downtown business environment and CLA's programmatic work.

Corporate Partnerships

• Identify, cultivate, and steward a portfolio of high-value corporate partners aligned with CLA's mission and key initiatives — including Sundays on State, the Loop Ambassador Program, and research publications.
  • Maximize existing corporate, community and governmental relationships, boosting partner currency.
• Design and execute a diversied revenue strategy encompassing membership growth, corporate partner and sponsorships, grants (where appropriate) and earned income from programming and events.

Strategic Relationship Building

• Be forward-facing and grounded in Chicago's civic, philanthropic, real estate, tourism, and business communities.
  • Build a strong coalition of cross-industry support.
• Build and maintain relationships with peer downtown management organizations, regional planning bodies, and national urban district networks.
• Represent CLA on coalitions, task forces, and public forums that shape downtown Chicago's future.
• Support the CEO in high-level stakeholder engagement, including board cultivation, funder stewardship, and civic diplomacy.

Placemaking, Programming & Promotions Strategy

• Provide strategic insight and partnership development support for CLA's signature programming, including Sundays on State.
• Create framework for new programming and hallmark Loop initiatives.
  • Where appropriate, lead complex, multi-disciplinary projects from start to nish — working with cross-functional teams and stakeholders to plan, manage project schedules, identify challenges and mitigate risks.
• Ensure that CLA's placemaking and marketing activities align with the organization's advocacy goals and member interests.
• Champion the Loop as a premier destination for business, culture, and tourism — working with regional and national media, tourism boards, and economic development entities.
• Leverage CLA research assets — including the State of the Loop report — to inform programming decisions and tell a compelling story about downtown recovery and vitality.

WHAT SUCCESS LOOKS LIKE – YEAR 1

• CLA's board pipeline is strengthened, with new prospects identied and cultivation underway.
• Membership base has grown and retention rates have improved through a clearly articulated value proposition and strengthened member engagement strategy.
• At least two signicant new corporate partnerships or sponsorships are secured, directly supporting CLA programming and nancial sustainability.
• A government aairs agenda is in place, with active relationships across City Hall, Springeld, and relevant federal offices.
• The CEO has become a recognized local and national voice in arenas of downtown economic recovery and civic leadership topography.
  • Convene organizations and community leaders.
  • Identify opportunities to participate in cohorts, panels, working groups, and committees that position the brand and reinforce support, commitment and investment (voice/vision).

Salary: $150,000-$175,000 commiserate with experience.

Benefits: Medical, dental, vision, and life insurance; holidays, vacation, sick, and personal time; employer contributed 401(K); transit benefit program; partial cell phone plan reimbursement; and annual Divvy membership available

Close Date: July 17, 2026

Contact: Please send your cover letter and resume with the subject line “CHIEF STRATEGY OFFICER” to [email protected]. Include how and where you learned of this position in your cover letter.