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Director of Transaction Management

Cushman & Wakefield

North Chicago, ILJob$162–190K/yrSeen todaySeen in employer's feed today

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At a glance

Compensation
$162–190K/yr
Location
North Chicago, IL
Work Authorization
Not specified

Olive focuses on jobs in the United States, including remote roles you can work from there.

Requirements

Credentials this posting asks for.

State Real Estate Salesperson License, requiredBachelor's degree, required

Job overview

The Transaction Management Director leads strategy and execution for complex client real estate portfolios and enterprise initiatives across multiple asset classes. The role develops market optimization and transaction plans, guides negotiations and brokerage resources, partners with client stakeholders, and oversees reporting, financial analysis, governance, and process improvement. It also leads transaction teams and direct reports while using technology and AI-enabled solutions to improve execution and client outcomes.

Skills & qualifications

RequiredNice to have

Skills

Transaction Management, requiredContract Management, requiredCompliance, requiredLegal Documentation, requiredProject Management, requiredTeam Leadership, requiredOrganizational Skills, requiredFinancial Analysis, requiredFinancial Modeling, requiredStrategic Planning, nice to haveBusiness Case Development, nice to haveValue-Add Analysis, nice to haveOccupancy Cost Analysis, nice to havePortfolio Optimization, nice to haveReporting Templates, nice to haveProcess Documentation, nice to haveMicrosoft Office Suite, requiredCommercial Real Estate Platforms, nice to haveCoStar, nice to haveHypREspace, nice to haveLeaseCalcs, nice to haveAI Solutions, requiredRelationship Management, nice to haveClient Focus, nice to haveCommunication, nice to havePresentation Skills, nice to haveCommercial Acumen, nice to haveNegotiation, nice to haveStrategic Thinking, nice to haveData Analysis, nice to haveProcess Governance, nice to haveContinuous Improvement, nice to haveCross-Functional Collaboration, nice to have

Qualifications

10+ Years Real Estate Experience, requiredState Real Estate Salesperson License, requiredBachelor's Degree, requiredFinance, Real Estate, Business, Economics, or Related Field, nice to have

Benefits

Medical Insurance
Vision Insurance
Dental Insurance
401(k) Match
Paid Time Off

Full job description

Job Title

Director of Transaction Management

Job Description Summary

As the Transaction Management Director, you will lead transaction management strategy and execution for large, complex client portfolios and enterprise real estate initiatives across multiple asset classes. This role translates client business objectives into market optimization strategies, transaction plans, portfolio opportunities, and high-quality execution outcomes while leading brokerage resources, transaction teams, and cross-functional partners.

Job Description

This role will primarily:

  • Lead market optimization planning, strategic transaction initiatives, and portfolio execution strategies that align with client real estate goals and business priorities.

  • Lead and oversee aggressive negotiations to deliver favorable outcomes on behalf of the client while guiding internal and external brokerage resources through complex transactions.

  • Partner with client corporate real estate teams and senior operational stakeholders to identify real estate needs, areas of opportunity, and portfolio optimization strategies.

  • Drive governance, operational consistency, and continuous improvement across transaction management delivery.

Success in this role looks like:

  • Large, complex transactions and strategic initiatives are executed with strong governance, consistent work quality, clear stakeholder alignment, and measurable client outcomes.

  • Portfolio strategies, business cases, financial analyses, value-add calculations, and occupancy cost savings recommendations support client decision making.

  • Brokerage resources, direct reports, field agents, service partners, and cross-functional teams are aligned around transaction priorities and execution standards.

  • Reporting tools, templates, process documents, playbooks, and post-transaction reviews improve consistency, transparency, and continuous improvement across account delivery.

As a member of Cushman & Wakefield’s Portfolio Advisory Group, the Transaction Management Director will be dedicated to one or more of Cushman & Wakefield’s most dynamic client accounts. In this role, you will collaborate closely with peers and the account team to support a client's strategic real estate vision. The Transaction Management Director will embody our team philosophy “Client First, Insight Always, Execution Excellence”, ensuring every deliverable reflects the team’s commitment to innovation, collaboration, and measurable impact.

Key Responsibilities

Strategic Portfolio & Market Optimization

  • Lead market optimization planning and strategic transaction initiatives that align with client business goals, portfolio objectives, and real estate priorities.

  • Lead development of strategic real estate plans and provide strategic real estate advice to clients.

  • Identify occupancy cost savings strategies, pull-forward opportunities, expansion and contraction strategies, and other portfolio optimization opportunities.

  • Produce and support business case development, reporting, data analysis, and financial analysis required to complete strategic plans.

Complex Transaction Leadership & Execution

  • Initiate new transactions, dispositions, and renewals, and guide transaction delivery through execution.

  • Manage internal and third-party brokerage resources through the course of transactions, providing strategic direction to brokers and client stakeholders.

  • Lead and oversee aggressive negotiations to deliver favorable outcomes on behalf of the client and support consistent transaction management practices.

  • Execute complex, large transactions with high-level transaction knowledge and oversee legal review of client leased documents.

  • Engage project managers, facility managers, environmental consultants, and other partners as needed to support transaction execution.

Client Relationship & Transaction Governance

  • Partner with client corporate real estate teams and local business unit leaders to understand requirements and build transaction strategies that support client needs.

  • Lead and facilitate client presentations, business reviews, key client meetings, and transaction governance discussions.

  • Partner with clients’ senior-level operational groups to identify real estate needs, transaction priorities, and areas of opportunity.

Reporting, Financial Analysis & Value Creation

  • Maintain and monitor process reporting to clients using a variety of tools and ensure accurate transaction data using various systems.

  • Perform market and financial analysis to support transaction strategy, portfolio recommendations, and client decision making.

  • Manage revenue projections and tracking to support account-level visibility and performance management

  • .

  • Prepare close-out reports and value-add calculations for transactions.

Process Governance, Technology & AI Enablement

  • Coordinate reporting requirements and provide guidance to field agents, service partners, and clients to maximize reporting effectiveness.

  • Modify and adapt process documents and playbooks to meet client requirements.

  • Identify and implement process improvements, innovations, post-transaction reviews, and client survey practices that support continuous improvement.

  • Leverage AI-enabled and technology-driven solutions to improve transaction execution, reporting quality, analysis, workflow efficiency, and client outcomes.

People Leadership & Team Development

  • Manage direct reports through coaching and mentoring to support an engaged, high-performing transaction management team.

  • Lead transaction teams, brokers, field agents, service partners, and cross-functional contributors through complex transaction activity.

  • Maintain a cohesive, performance-measured team environment that supports client satisfaction, work quality, and consistent delivery.

Qualifications

Must-Have Requirements

  • 10+ years of experience in corporate real estate, transaction management, corporate services, or a related commercial real estate function.

  • Must obtain and hold state real estate salesperson license.

  • Experience with high-level, complex transaction management, including contract management, compliance, and legal documentation.

  • Demonstrated project management skills, including the ability to identify tasks and coordinate timely completion of transaction components.

  • Ability to lead a team in a cohesive, performance-measured environment.

  • Strong organizational skills with the ability to balance multiple responsibilities and deliverables while maintaining client satisfaction.

  • Well-developed financial analysis and modeling skills.

Preferred Experience

  • Experience leading large strategic initiatives, enterprise transactions, or transactions across multiple asset classes.

  • Experience leading direct reports, brokerage resources, field agents, service partners, and cross-functional transaction teams.

  • Demonstrated success developing strategic plans, business cases, value-add analyses, occupancy cost savings strategies, and portfolio optimization recommendations.

  • Proven ability to develop and improve reporting templates, process documents, playbooks, and account-specific workflows.

Technology & Tools

  • Advanced proficiency with Microsoft Office Suite, including Word, Excel, PowerPoint, and Outlook.

  • Experience with commercial real estate technology platforms.

  • Experience with CoStar, HypREspace, or LeaseCalcs is a plus.

  • Demonstrated ability to identify and leverage AI-enabled solutions that improve transaction execution, reporting quality, analytics, workflow efficiency, and business outcomes.

Capabilities

  • People leadership and team development

  • Relationship management and client focus

  • Communication and presentation proficiency

  • Financial and commercial acumen

  • Negotiation and transaction leadership

  • Legal documentation knowledge

  • Strategic thinking and curiosity about data and innovation

  • Process governance, continuous improvement, and cross-functional collaboration

Education

  • Bachelor’s degree required. Finance, Real Estate, Business, Economics, or related field preferred.

Cushman & Wakefield also provides eligible employees with an opportunity to enroll in a variety of benefit programs, generally including health, vision, and dental insurance, flexible spending accounts, health savings accounts, retirement savings plans, life, and disability insurance programs, and paid and unpaid time away from work. In addition to a comprehensive benefits package, Cushman and Wakefield provide eligible employees with competitive pay, which may vary depending on eligibility factors such as geographic location, date of hire, total hours worked, job type, business line, and applicability of collective bargaining agreements.

The compensation that will be offered to the successful candidate will depend on factors such as whether the position is covered by a collective bargaining agreement, the geographic area in which the work will be performed, market pay rates in that area, and the candidate’s experience and qualifications.

The company will not pay less than minimum wage for this role.

The compensation for the position is: $ 161,670.00 - $190,200.00

Cushman & Wakefield is an Equal Opportunity employer to all protected groups, including protected veterans and individuals with disabilities. Discrimination of any type will not be tolerated.

In compliance with the Americans with Disabilities Act Amendments Act (ADAAA), if you have a disability and would like to request an accommodation in order to apply for a position at Cushman & Wakefield, please call the ADA line at 1-888-365-5406 or email [email protected] . Please refer to the job title and job location when you contact us.

INCO: “Cushman & Wakefield”

How this job compares

Set against the 518 open Real Estate jobs on Olive Jobs, counted November 13, 2026.

Pay
  • This posting$162–190K/yr
  • US median$133–217K/yr336 salary ranges

This range's midpoint, $176K, is 5% below the US median midpoint ($185K) — in the middle half of Real Estate salary ranges across the US.

Openings
Olive Jobs lists 16 open Real Estate jobs in Illinois and 518 across the US. 6% of them nationwide are listed as remote or flexible.
Hiring the most across the US
Experience
This posting asks for at least 10 years of experience — more than three in four Real Estate postings that state a minimum ask for (median 6 years, across 415 postings).
Education
This posting asks for a bachelor's degree; 181 of the 518 open Real Estate jobs (35%) ask for a bachelor's degree or higher.

Counted across the open, public US postings on Olive Jobs on November 13, 2026. Figures based on too few postings are left out.

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