Chief Operating Officer Job Posting

The Chicago Association of REALTORS® (“CAR”) is seeking an experienced, collaborative leader as Chief Operating Officer, taking CAR to the next level of member success.  CAR unites all facets of the real estate industry as a leading advocate, driving REALTOR® business success and supporting the economic development of our communities. Since 1883, CAR has been the 'Voice of Real Estate' in Chicago, representing over 16,000 members across all real estate specialties.  As the ninth-largest local REALTOR® association in the country, CAR has a visible national footprint, with its leadership team serving at the state and national levels. We are steadfast in our commitment to promoting diversity, equity, and inclusion within the real estate industry, and actively work to advocate for fair housing practices that ensure equal opportunities for all individuals.  CAR’s culture is built on a foundation of excellence, where we strive to set the example; leadership, as architects of careers and communities; diversity, embracing differences in people, thoughts, and values; respect, valuing our people; collaboration, breaking down barriers to achieve shared goals; and advocacy, championing our people, members, initiatives, and industry.

CAR’s next COO will be passionate for making a positive impact, a strong communicator, an expert in the art of interpersonal skills, and has a proven track record of effectively managing teams and executing projects.  The position will be in person/on site in Chicago, Illinois. 

Key Responsibilities

People/Teams

  • Serve as a member of the Executive Leadership Team (ELT) and oversee the development, structure, and facilitation of ELT meetings to ensure strategic alignment and collaboration.

  • Supervise and manage departments including the REALTORS® Real Estate School, membership and professional standards, Commercial Forum, sustainability, and information technology.

  • Build, develop, and manage strong teams and team leaders to deliver outstanding member experiences and operational excellence.

  • Build trust with leadership and staff by demonstrating a genuine commitment to CAR’s mission, values and a collaborative, transparent leadership style.

Strategic Oversight and Organizational Management 

  • Lead the implementation and tracking of CAR’s strategic plan, ensuring alignment with short- and long-term organizational goals.

  • Prepare executive updates on organizational initiatives and programs for the Board of Directors and other leadership bodies when needed. 

  • Oversee the association's Leadership Accelerator Program, a leadership academy designed to refine and accelerate members' leadership capabilities through various trainings, programs, and projects.

  • Serve as the staff liaison to the Public Policy Committee, Chicago Association of Realtors Political Action Committee (CARPAC), Coffee with the GADs program, and the Property Management Forum in collaboration with the Illinois Realtors government affairs team. Ensure the CEO remains informed on emerging political issues and key policy matters impacting the city that require the association’s position, advocacy, or lobbying efforts. Additionally, maintain clear and effective communication channels to align internal messaging before public statements.

  • Attend all relevant meetings and events, including CAR Signature events and programs, Board of Directors, Finance, Audit, and State and National events, as assigned.

  • Ensure the CEO is kept fully informed on conditions and operations of the Association and assist with day-to-day management.

  • Assist the CEO in planning, formulating, evaluating, and recommending policies and programs to the Board of Directors that further the Association's objectives.

  • Assist in the preparation of the Association budget, with direct accountability for the executive office budget and oversight of additional departmental budgets under the COO's purview.

  • Oversee and maintain Association, Foundation and CARPAC Bylaws, Operating Policies and Procedures, and the Employee Handbook, in conjunction with Association legal counsel, human resources, and the Member Policy Division of NAR.

Leadership

  • Act as a thought partner to the CEO, providing high-level strategic support, foresight, and counsel on key initiatives.

  • Exhibit executive presence, embodying confidence, professionalism, and a solutions-oriented mindset that inspires trust and respect.

  • Be a proactive, self-directed leader who thrives on organization and autonomy without requiring constant oversight.

  • Display strong analytical skills and creative problem-solving capabilities to deliver results.

  • Foster strong relationships with volunteer leaders and members, ensuring a collaborative approach to advancing the Association’s mission. Provide guidance and support to volunteer committees, task forces, and leadership groups, while serving as a visible and approachable point of contact for members.

Culture Fit & Impact

  • Demonstrates alignment with CAR’s core values of excellence, leadership, diversity, respect, collaboration, and advocacy, ensuring these values are consistently reflected in decision-making and leadership practices.

  • Actively fosters an inclusive and supportive environment by embracing diverse perspectives and promoting equity within the organization and the membership.

  • Values transparency and open communication, ensuring staff and volunteer leaders are informed and engaged.

  • Practices collaboration and teamwork, breaking down barriers to achieve shared goals and advancing the Association’s mission.

  • Respects time and resources, setting clear expectations for meetings, deadlines, and deliverables while prioritizing efficiency and purpose.

  • Leads by example through recognizing and celebrating success, uplifting colleagues and encouraging a culture of positivity.

  • Demonstrates compassion and understanding in addressing challenges, emphasizing a problem-solving mindset.

  • Maintains a focus on accountability and trust, ensuring operational excellence and a commitment to continuous improvement.  

Innovation & Future-Readiness

  • Develop and implement a forward-thinking staffing strategy that ensures long-term organizational sustainability and growth.

  • Design and execute a structured succession plan to cultivate leadership talent and maintain institutional knowledge.

  • Lead the development and execution of a digital transformation strategy, enhancing member services and internal operations through the integration of emerging technologies such as automation, AI-driven analytics, and CRM improvements.

  • Oversee IT leadership to ensure the adoption of cutting-edge technology solutions that optimize member engagement, streamline workflows, and enhance decision-making.

  • Identify and implement non-dues revenue opportunities, leveraging technology, innovation, and strategic partnerships to ensure long-term financial growth and sustainability for the Association.

Qualifications 

  • Proven leadership with a track record of leading digital transformation and successfully implementing new technologies, automation, and data-driven solutions that have a measurable impact on both member experience and organizational efficiency.

  • Strong business development mindset, with a proven ability to identify, evaluate, and implement new revenue streams, particularly in non-dues areas.

  • Experience with financial strategy and budgeting, particularly in the context of revenue diversification.

  • Proven ability to work independently with minimal supervision, demonstrating strong initiative, accountability, and sound judgment in achieving organizational goals.

  • Ability to make sound, timely decisions in high-pressure situations, sometimes with limited information or time for extensive deliberation.

  • Proven project management skills with the ability to lead people and cross-functional teams at various levels within the organization.

  • Outstanding written, oral, and presentation communication skills, with a high level of proficiency and comfort using technology.

  • Demonstrated strong emotional intelligence and interpersonal skills.

  • Consistent track record of delivering measurable and impactful results to an organization.

  • Experience driving cultural improvements and enhancing the organization’s value proposition.

  • Willingness and ability to attend evening events, participate in occasional overnight travel, and represent the Association through business-related travel as needed.

  • Certified Association Executive (CAE) designation preferred. Realtor Certified Executive (RCE) designation a plus.

  • Familiarity with the real estate industry or experience within a real estate association is a plus but not required.

  • Bachelor’s degree required or equivalent years of related experience. A Master’s degree in business administration, technology management, or a related field, or equivalent experience is preferred.

  • A minimum of five years of senior management experience, preferably in a professional trade association environment.

  • Proven experience in a supervisory role, including direct management of staff, teams, and departmental functions.

  • Demonstrated experience in creating, managing, and overseeing budgets.

Compensation                                                                                                                                         

Base Salary of $200,000 - $230,000.  CAR additionally offers a robust benefits package, including health insurance and a variety of other benefits.

To Apply                                                                                                                                         

Candidates interested in this exceptional career opportunity must submit a detailed resume, cover letter, and three professional references electronically to:   phippsmalta@gmail.com 

CAR is an equal opportunity employer and encourages candidates of all backgrounds to apply.