Join Our Team
The Chicago Association of REALTORS® 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, the Chicago REALTORS® 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, the Chicago REALTORS® 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.
The Chicago Association of REALTORS®’ 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. Our workplace culture led us to earn the award of one of the Best Places to Work by Crain’s Chicago Business in 2021.
Open Positions:
Senior Director, Membership, Learning, and Professional Growth
- Department: Membership, Learning, and Professional Growth
- Supervisor: Chief Operating Officer
- Location: Chicago, IL | Full Time, Exempt
- Salary Range: $115,000 – $135,000
Description
Are you a strategic leader who thrives at the intersection of education, service excellence, and long-term professional growth?
Chicago REALTORS® is seeking a Senior Director, Membership, Learning, and Professional Growth to lead and strengthen the full member lifecycle, from first engagement as a real estate student to long-term success as a brokerage leader. This is a high-impact leadership role focused on alignment, systems, and delivering measurable value at every stage of a REALTOR®’s career.
You will unify membership services, education, professional standards, and broker relations into a cohesive, high-performing experience that supports members, protects organizational integrity, and sustains long term growth.
Essential Duties & Responsibilities
Strategic & Organizational Leadership
- Lead the integration of Membership, Learning (RRES), Professional Standards, and Broker Relations into a unified, member-centered division with shared goals, systems, and service standards.
- Develop and execute departmental strategy, goals, and performance metrics aligned with the Association’s strategic plan and growth priorities.
- Serve as a key member of the leadership team, advising the COO and Executive Leadership on member trends, risks, opportunities, and investment priorities.
- Establish a culture of service excellence, accountability, continuous improvement, and collaboration across all functions.
Member Lifecycle Strategy and Growth
- Own the strategy and outcomes for the full member journey: new student to new licensee to new member to engaged member to brokerage leader.
- Design and implement a cohesive student-to-member conversion strategy that leverages the Association’s real estate school as a primary recruitment and relationship-building channel.
- Partner with Learning, Member Care, and Broker Relations to ensure seamless handoffs, consistent touchpoints, and a connected experience across every career stage.
- Identify and implement initiatives that increase recruitment, retention, engagement, and non-dues participation.
- Monitor lifecycle metrics, including conversion, onboarding effectiveness, satisfaction, renewal, and retention, and adjust strategies accordingly.
Division & Operational Leadership
- Provide leadership and oversight for a multi-level team, including managers and professional staff roles across Member Care, Learning, Professional Standards, and Broker Relations.
- Align workflows, systems, and staffing models to ensure efficient, high-quality service delivery and a consistent member experience.
- Oversee budgets, forecasting, and resource allocation across all functional areas.
- Ensure strong data integrity, reporting, and performance dashboards to inform decision-making.
- Lead the evaluation and implementation of technology and process improvements that enhance both staff efficiency and member experience.
- Provide executive oversight of the Association’s annual membership renewal and billing cycle, ensuring proactive planning, cross-functional coordination, risk mitigation, and successful execution of this critical revenue process.
Brokerage & Stakeholder Engagement
- Oversee strategic brokerage engagement efforts through the Broker Relations Partner, ensuring intentional relationship management with the Association’s largest firms.
- Strengthen partnerships with brokerage leadership to enhance recruitment, retention, and overall member value.
- Represent the Association with industry stakeholders, partners, and leaders to advance collaboration and visibility.
Professional Standards & Risk Management
- Ensure compliant, fair, and timely administration of ethics, arbitration, mediation, and ombudsman processes in alignment with NAR requirements.
- Oversee risk mitigation practices that protect the integrity and reputation of the organization.
- Monitor trends and recommend proactive policy or process improvements.
- Coordinate with legal counsel as appropriate.
Learning (RRES) Strategy & Oversight
- Provide strategic leadership for the Association’s real estate school, ensuring regulatory compliance and a best-in-class student experience.
- Provide hands-on leadership and direct supervision of school staff while the function evolves, establishing processes, priorities, and performance expectations.
- Position the school as a gateway into membership by aligning curriculum, advising, and engagement with the broader Association journey.
- Lead student recruitment, advising, and enrollment strategy, ensuring proactive lead follow-up, strong conversion, and a seamless transition from student to member.
- Evaluate the school’s structure, staffing, financial performance, and operational effectiveness; implement a sustainable, right-sized service model aligned with long-term growth.
- Champion innovations in education delivery, digital learning, and student engagement.
- Oversee instructor partnerships, curriculum development, and compliance requirements.
- Collaborate with Communications to strengthen the school’s brand positioning and recruitment impact.
Governance, Reporting and Executive Communication
- Prepare and present regular performance reports, insights, and strategic recommendations to Executive Leadership and the Board of Directors.
- Proactively surface risks, trends, and opportunities impacting membership, learning, and professional standards.
- Ensure compliance with NAR Core Standards and applicable regulatory requirements across all functions.
Education & Experience
- Bachelor’s degree or equivalent required; master’s degree in business, public administration, education, or a related field preferred.
- Minimum of seven (7) years of progressively responsible leadership experience in association management, membership services, education operations, or related fields.
- Demonstrated experience managing compliance-driven functions, operational systems, and cross-department workflows.
- Experience interpreting or implementing policies related to education regulation, professional standards, or member governance is strongly preferred.
Skills and Competencies
- Strategic leader with strong business acumen and the ability to translate vision into operational execution.
- Demonstrated success leading multi-function teams and complex service operations.
- Skilled in stakeholder management and influencing across levels, including brokerage and executive leadership.
- Strong analytical mindset with experience using data to guide strategy and performance.
- Excellent communication, presentation, and change-management skills.
Working Conditions & Expectations
- Occasional evening and weekend work required for meetings, programs, or events.
- Limited travel may be required for conferences, training, or outreach.
- This is a full-time, exempt position offering competitive benefits and opportunities for professional growth.
To Apply:
Please send your resume and a brief cover letter to talent@victoriagillespieconsulting.com.
The Chicago Association of REALTORS® is an equal opportunity employer and encourages candidates of all backgrounds to apply.