Job Opportunities

• Department: Membership, Learning, and Professional Growth
• Supervisor: Chief Operating Officer
• Location: Chicago, IL | Full Time, Exempt
• Salary Range: $140,000 – $165,000

Description

Chicago REALTORS® is seeking a Vice President of Membership, Learning & Professional Operations to lead the integration and performance of Membership Services, Learning (RRES), Professional Standards, and Broker Relations. This role focuses on operational excellence, lifecycle alignment, staff leadership, and service consistency across the member journey, from student engagement through active membership and professional advancement.

The Vice President will ensure that systems, processes, and teams operate cohesively to deliver a high-quality member experience while maintaining compliance, financial discipline, and organizational integrity. This position is ideal for a strong operational leader who thrives in multi-function environments and is committed to performance, accountability and continuous improvement.

Essential Duties & Responsibilities

Division Leadership & Operational Alignment

• Lead and integrate Membership Services, Learning (RRES), Professional Standards and Broker Relations into a coordinated, member-centered division.
• Supervise managers and professional staff, establishing clear performance expectations and accountability structures.
• Align workflows, systems and service standards to ensure consistent, high-quality member experiences.
• Identify operational improvement opportunities and implement process enhancements.

Member Lifecycle Coordination

• Lead the coordination and optimization of the member lifecycle experience, ensuring alignment across departments at each stage of engagement.
• Strengthen onboarding, engagement and renewal touchpoints to improve member satisfaction and retention.
• Monitor lifecycle performance metrics and recommend operational adjustments as needed.
• Align school advising and student engagement processes to create a clear transition into membership.

Learning (RRES) Oversight

• Provide leadership for the Association’s real estate school operations, ensuring regulatory compliance and service excellence.
• Oversee student advising and enrollment operations to ensure consistent follow-up and administrative efficiency.
• Evaluate staffing, workflows, and operational effectiveness to support sustainable service delivery.
• Collaborate with Communications to support visibility and enrollment consistency.

Renewal & Financial Oversight

• Lead the planning and coordination of the annual membership renewal and billing cycle.
• Oversee divisional budgets, forecasting and resource allocation.
• Ensure accurate reporting and data integrity to support informed decision-making.
• Monitor operational performance against financial targets and recommend adjustments where necessary.

Professional Standards & Compliance

• Ensure compliant, fair, and timely administration of ethics, arbitration, mediation and ombudsman processes.
• Maintain alignment with NAR Core Standards and applicable regulatory requirements.
• Ensure risk management practices are consistently applied within the division.
• Coordinate with legal counsel as appropriate.

Brokerage & Stakeholder Coordination

• Support brokerage relationship management efforts in partnership with the Broker Relations function.
• Maintain clear communication channels between brokerage leadership and Association services.
• Participate in industry meetings and stakeholder engagements as appropriate..

Governance & Reporting

• Prepare and present regular operational performance reports to Executive Leadership.
• Provide data-driven insights regarding member trends, service effectiveness, and operational risks.
• Support Board committees as assigned, ensuring clarity and follow-through on initiatives.

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, nonprofit leadership, education operations, or related fields.
• Demonstrated experience supervising managers and professional staff.
• 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 & Competencies

• Strong operational leadership and organizational alignment capability.
• Demonstrated ability to lead multi-function teams.
• Analytical mindset with experience using data to guide performance.
• Clear and effective communicator across staff and volunteer leadership.
• Ability to manage complexity while maintaining service excellence.
• Collaborative leadership style with strong accountability standards.

Working Conditions & Expectations

• Occasional evening and weekend commitments for meetings or events.
• Limited travel for conferences, training, or outreach as needed.
• Full-time, exempt position with competitive benefits and professional development opportunities.

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.

• Department: Membership, Learning, and Professional Growth
• Supervisor: Vice President, Membership, Learning, and Professional Growth
• Location: Full Time, Exempt
• Salary Range: $70,000 – $85,000

Description

The Broker Relations Partner serves as the Association’s strategic relationship lead for its largest and most influential brokerage firms, representing offices that account for the majority of the Association’s membership. This role exists to ensure brokerage leaders feel seen, heard, supported and deeply connected to the value of the REALTOR® organization.

Acting as a trusted advisor and primary liaison to brokerage owners, managing brokers, and office leadership, the Broker Relations Partner builds long-term partnerships that strengthen engagement, improve retention, and inform the Association’s strategy and services. Through proactive relationship management, consultative support, and continuous feedback gathering, this position protects and grows the Association’s most critical member segment.

This role delivers a consistent, high-touch and data-informed experience for brokerage partners while serving as the internal voice of the broker, ensuring brokerage insights directly shape programs, communications and strategic priorities.

Essential Duties & Responsibilities

Strategic Broker Partnership & Engagement

• Own and advance strategic relationships with a defined portfolio of the Association’s largest brokerage firms, serving as their primary advisor and point of contact.
• Build trusted, consultative partnerships with brokerage owners, managing brokers, and office leaders to understand business goals, challenges, and opportunities for collaboration.
• Develop and execute intentional engagement strategies that strengthen connection to the Association and demonstrate clear member value.
• Proactively identify at-risk or declining offices and implement targeted relationship-based retention strategies.
• Represent the Association in the field through regular on-site visits, leadership meetings, and brokerage events to maintain a visible and accessible presence.

Retention, Growth & Member Value

• Partner with brokerage leadership to support recruiting, onboarding, and professional development efforts that connect agents to Association resources early and consistently.
• Equip offices with tools, insights, and programs that enhance agent success, engagement, and long-term membership.
• Identify opportunities to deepen participation across education, events, leadership pathways, and non-dues offerings.
• Monitor engagement trends, satisfaction signals, and participation data to surface risks and growth opportunities and recommend strategies to leadership

Communications & Internal Alignment

• Serve as the internal advocate for brokerage partners by capturing feedback, needs, and market insights and translating them into actionable recommendations.
• Collaborate cross-functionally to ensure timely resolution of brokerage requests and a seamless service experience.
• Inform Association strategy, communications, and program design through continuous brokerage intelligence and relationship insights.
• Maintain a CRM or relationship-management database to track actionable relationship records and engagement activities to support strategic decision-making.

Leadership & Community Building

• Facilitate forums and networking opportunities that connect brokerage leaders with one another and with the Association.
• Support leadership cultivation by identifying and encouraging broker and agent involvement in committees, governance, and volunteer opportunities.
• Champion initiatives that elevate broker engagement, satisfaction, and long-term partnership with the Association.

Qualifications

• Demonstrated strength in building trust-based relationships and influencing stakeholders at the leadership or executive level
• Strong consultative, communication, and presentation skills
• Ability to work independently, manage a portfolio of partners, and operate effectively in both field and office environments
• Strategic thinker with the ability to analyze engagement trends and translate insights into action
• Professional presence with strong follow-through and accountability

Education & Experience

• Bachelor’s degree or equivalent professional experience required.
• 2+ years of experience in relationship management, account management, membership engagement, real estate operations, or partnership development
• Experience working with brokerage leadership, REALTORS®, or membership-based organizations strongly preferred
• Proven success managing external partners or clients and driving engagement, retention, or growth outcomes

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.