Director, Proposals

Cresa•Chicago, IL

21h

About The Position

At Cresa, we believe our clients deserve better. A better space to work, create, build, grow. A better outcome for their people and organization. A better partner who puts their needs first, helping them navigate the landscape, tilting the playing field in their favor and giving them an insider’s edge. Our mission is to find and foster the best environment for every business. Our purpose is to think beyond space - strengthening those we serve and enhancing quality of life for our clients and employees. We are built to champion our clients’ aspirations through real estate. When considering partnership, we strive to connect with those who share our values: Work Together, Create Value, Be Tenacious, Enhance Community, and Embrace Diversity . We believe in being the change. We work together to find new ways of doing things that create value for our clients — and for each other. Because there is not much that feels better than collaborating to make a positive difference each day. At Cresa, we offer an opportunity to be part of something bigger. To learn, advance, mentor and be recognized. Your voice will be heard, and you will be valued for both your individual and team contributions. Summary We are seeking an experienced Director with proven experience leading and developing winning real estate solutions for corporate occupiers. This individual understands how Cresa’s suite of services work together and can articulate our unique value add to prospective portfolio clients. Though formally an individual contributor, this role requires a leadership mindset – setting strategic direction for proposal development, managing inputs from across the organization, and empowering more junior team members to contribute effectively. The Director serves as the connective tissue between stakeholders, driving clarity and consistency across the sales cycle. This highly visible and collaborative role requires excellent communication skills, strong stakeholder management, and the ability to coordinate across Cresa’s service lines and offices to deliver high-quality, customized solutions.

Requirements

8–10 years of relevant solutions sales and proposal development experience
Bachelor’s degree preferred
Strong ability to listen to multiple stakeholders, synthesize what was heard, and develop a winning solution – proven experience working with cross-functional teams is a must
Ability to guide and manage junior contributors while taking ownership of the final deliverable
Proven experience managing formal procurement processes for commercial real estate services
Exceptional writing, editing, and proofreading skills with meticulous attention to detail
Strong time and priority management skills with the ability to work independently under tight deadlines
Highly proficient in Adobe Creative Suite (InDesign is a must) and Microsoft Office (Outlook, Word, Excel, PowerPoint)
Comfortable working across multiple time zones to support global pursuits

Responsibilities

Leverage their deep understanding of real estate outsourcing to develop custom solutions for each prospect, evaluating their unique challenges and goals
Lead the bid management process through the development of RFIs, RFPs, and client presentations
Establish a strategic framework for each proposal—leading narrative development, solution design, and pricing strategy while directing junior team members to support execution
Partner with sales leads and subject matter experts to shape differentiated, client-specific approaches
Establish a clear proposal response schedule that outlines action items, responsible parties, and internal deadlines – including pricing templates and MSA redlines
Write original short- and long-form copy (e.g., executive summaries, case studies, bios) and edit submissions for clarity, tone, and strategic alignment
Review, edit, and finalize all work product for quality and consistency before submission
Upload final proposals to procurement platforms when applicable (e.g., Ariba)
Lead the development of post-proposal deliverables (e.g., workshops, YellowPads, final presentations, BAFOs)
Maintain and evolve a knowledge library of solution content, templates, and best practices to improve team efficiency and consistency over time
Identify and implement process improvements and innovation opportunities