Hotel Asset Management Associate (Chicago)

About the Company

Witness Investment is an award winning multigenerational real estate investment firm specializing in hospitality investment and development. Since 1985, weve built a reputation for operational excellence and value creation, with a growing portfolio of premium-branded hotel assets across the Midwest. Our team is the strategic engine behind asset performance and portfolio-level execution.

About the Role

The Associate will report directly to the Vice President of Asset Management and play a key role in the tactical execution of business plans across Witness Investments hospitality portfolio. This role is ideal for those with a background in hotel asset management, operations, revenue strategy, or hospitality consulting looking to transition into or grow within hotel real estate who thrives in a fast-paced, team-oriented environment. The Associate will support property-level oversight, financial modeling, data infrastructure, reporting, and operator engagement to help drive revenue growth, improve profitability, and execute strategic initiatives.

Responsibilities

Portfolio Monitoring & Analysis

• Support weekly STR reviews and R28 topline commentary across the portfolio
• Track forecast, budget, and underwriting performance across all assets
• Prepare Weekly Flash Reports, Monthly Asset Management Evaluation, and Quarterly Performance decks
• Monitor RevPAR index trends, GOP flow-through, and cost efficiency metrics

Operator Oversight & Revenue Strategy

Capital & Compliance Support

Financial Reporting & Investor Support

Technology, Dashboards & Data Governance

Site Visits & Property Evaluations

Qualifications

Education

Experience

Skills

Personal Attributes

Why Join Us?

At Witness Investment, you will have the opportunity to contribute to a legacy of excellence while shaping the future of a dynamic and growing portfolio. We value relationships, innovation, collaboration, and a commitment to achieving exceptional results.