Senior Director, Membership, Learning, and Professional Growth

Senior Director, Membership, Learning, and Professional Growth

Supervisor: Chief Operating Officer

FLSA Status: Exempt

Status: Full-Time

Department: Membership, Learning, and Professional Growth

Salary Range: $115,000–$135,000

To Apply

Please send your resume and a brief cover letter to [email protected] .
The Chicago Association of REALTORS® is an equal opportunity employer and encourages candidates of all backgrounds to apply.

Position Summary

The Senior Director, Membership, Learning, and Professional Growth is a senior leadership role responsible for stewarding the Association’s full member lifecycle—from first engagement as a real estate student through long-term professional growth, brokerage partnership, and sustained member retention.

This role unifies Member Care, the Association’s real estate school (RRES), Professional Standards, and Broker Relations into one cohesive, member-centered division. The Senior Director designs and drives strategies that strengthen recruitment, improve student-to-member conversion, increase engagement, and deepen relationships with brokerages and members at every career stage.

Blending strategic vision, operational excellence, and people leadership, this position ensures the Association delivers measurable member value, protects critical revenue processes, safeguards organizational integrity, and remains an indispensable professional partner throughout a REALTOR®’s career.

Essential Duties & Responsibilities

Strategic & Organizational Leadership

• Lead the integration of Membership, Learning (RRES), Professional Standards, and Broker Relations into a unified 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, collaboration, and continuous improvement across all functions.

Member Lifecycle Strategy & Growth

• Own the strategy and outcomes for the full member journey: student to licensee to new member to engaged member to brokerage leader.

• Design and implement a cohesive student-to-member conversion strategy leveraging the Association’s real estate school as a primary recruitment and relationship-building channel.

• Partner across Learning, Member Care, and Broker Relations to ensure seamless handoffs, consistent touchpoints, and a connected experience at every career stage.

• Identify and implement initiatives that drive 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 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 evaluation and implementation of technology and process improvements that enhance 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 through the Broker Relations Partner, ensuring intentional relationship management with the Association’s largest firms.

• Strengthen partnerships with brokerage leadership to support recruitment, retention, and long-term 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 as the function evolves, establishing 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 innovation 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 & Executive Communication

• Prepare and present 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.

QualificationsEducation & 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 strongly preferred.

Skills & Competencies

• Strategic leader with strong business acumen and the ability to translate vision into operational execution.

• Proven success leading multi-function teams and complex service operations.

• Skilled in stakeholder management and influence across brokerage, executive, and governance levels.

• 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.

Job Type: Full-time

Pay: $115,000.00 - $130,000.00 per year

Benefits:

• 401(k)
• Dental insurance
• Flexible schedule
• Health insurance
• Paid time off
• Vision insurance

Work Location: Hybrid remote in Chicago, IL 60611