Drake Orser
Chicago,IL
Summary
Graduate of University of Iowa with dual degrees in Business and Entrepreneurship. Experience with Chicago Bulls, Chicago Bears, and a Chicago-based start-up fostered a collaborative, relationship-driven business approach. Currently at Essex Realty Group, specializing in multifamily investment sales and contributing to underwriting and valuation of over $799 million in assets across Chicagoland.
Overview
2026
2026
years of professional experience
1
1
Certification
Work History
Associate
Essex Realty Group, LLC
Chicago, Illinois
01.2022 - Current
- Underwrote and prepared Broker Opinions of Value (BOVs) for over 300 multifamily assets, supporting senior brokers in pricing strategies and presentations worth an estimated $799M.
- Conducted comprehensive rent surveys and market analyses across 20+ Chicago submarkets to ensure accurate valuations.
- Developed Excel templates for valuation and underwriting, enhancing analysis efficiency.
- Managed due diligence, escrow, and closing processes by coordinating with attorneys, lenders, and clients to assure timely contract execution.
- Oversaw fieldwork initiatives, including property tours, inspections, and site walk-throughs to assure reliable valuation inputs and efficient communication.
- Maintained CRM and investor database of over 9,800 contacts, segmenting owners and investors for targeted outreach.
Head of Client Success
FanFood
Chicago, Illinois
01.2019 - 01.2022
- Negotiated proposals and restructured agreements, expanding business to over 350 venues across four countries.
- Surpassed year-over-year growth goals by identifying and entering more than 10 new markets.
- Developed client success framework, implementing forecasting and retention programs with over 90% renewal rate.
Premium Sales and Service Representative
Chicago Bears
Chicago, Illinois
2018 - 2019
- Executed 80 to 120 outbound touch-points daily, focusing on face-to-face sales appointments and stadium tours to secure new business.
- Surpassed premium seat and licensing revenue targets through strategic sales campaigns, leading all sales staff.
Sales and Service Representative
Chicago Bulls
Chicago, Illinois
2016 - 2017
- Prospected new season ticket, group ticket, and premium seating sales through telephone, email, and in-person outreach.
- Led sales staff in achieving highest number of premium seats sold.
- Generated over $4 million in new business within team, ranking among top three in NBA.
Education
Bachelor of Science -
University of Iowa
Iowa City, IA01-2015
Entrepreneurial Certificate -
University of Iowa
Iowa City, IA01-2015
Skills
- Excel modeling and valuation analysis
- Market research and due diligence
- Broker opinions and customer relationship management
Certification
Licensed Real Estate Broker
Illinois Department of Financial and Professional Regulation
Affiliations
Committee Member
Breakthrough T1D Illinois YLC
References
References available upon request.
Timeline
Associate
Essex Realty Group, LLC
01.2022 - Current
Head of Client Success
FanFood
01.2019 - 01.2022
Premium Sales and Service Representative
Chicago Bears
2018 - 2019
Sales and Service Representative
Chicago Bulls
2016 - 2017
Bachelor of Science -
University of Iowa
Entrepreneurial Certificate -
University of Iowa