Jack Pearson
Real estate and technology professional, passionate about how the physical world is built and operated. My career has been centered on understanding complex real-world workflows and solving them with technology.
Chicago, IL · jackwpearson1@gmail.com ·LinkedIn ·GitHub
Experience
Multifamily Investment Sales, Broker · Interra Realty
2025 – Present
Licensed broker representing owners, investors, & developers in the purchase and sale of mid-market multifamily properties.
- Responsible for full sales cycle including prospecting, cold calling, underwriting, marketing listings, contract negotiations, and managing transactions through closing. Built custom CRM and underwriting app to reduce redundant manual work.
- Member of 3 broker team completing $31M in closed sales in 2025 and $37M YTD in 2026.
Construction Project Management - Contract Basis · Independent
2024 – 2025
Provided construction project management consulting services, including budget/estimate development, proposal creation, permitting processes, and on-site project oversight.
- Projects include commercial interior renovations, facade repair/replacement, and apartment renovations.
- Began working on coursework for real estate licensing at this time.
Senior Product Manager · Homebound Technologies
2022 – 2024
Lead product development for two engineering/design squads at homebuilding proptech.
- Owned the product domain for procurement from estimating through payouts & a greenfield external vendor platform.
- Led development of trade partner platform for managing POs, invoicing/payments, and schedules from concept to launch. 98% of payment processes automated as a result. Work included accounting automation with Sage Intacct to support three-way matching.
- Reduced estimating/buyout time by 63% (from 120+ days to 45 days) by developing platform capabilities for reusable workflows for takeoffs, master contracts/pricing, and purchase order automation.
- Led discovery with estimators, project superintendents, trade partners, & accountants both in-field and remote. In-depth sessions sitting with users to understand their workflows and where the product needed improvement.
Product Manager · Procare Solutions
2019 – 2021
Managed full product lifecycle from discovery through delivery for B2B SaaS shipped on both web & native mobile.
- Engaged with existing and potential enterprise customers as the product expert, participating in client discovery sessions & leading tailored demos.
- Mapped client requirements to capabilities, workarounds, and gaps to inform roadmap strategy.
- Attended industry conferences to support sales and share product expertise through live demos.
- First employee & product manager introduced from parent company (Procare) into acquired startup (Kinderlime).
Software Engineer · Intelivideo
2018 – 2019
Designed for and developed SaaS software in a legacy code base building a suite of tools and themes for white label subscription video products used by clients such as Title Boxing, Pure Barre and MELT Method.
Web Developer · Freelance
2018
Worked directly for clients on the development of new websites. Responsible for all phases of design and development.
Architectural Intern · Piekarz Associates
2016
Assisted in all phases of the design process from conceptual design to producing construction documents
Education
University of Kansas
Masters of Architecture (M.Arch)
2012 – 2017
DevMountain
Web Development Bootcamp, Certificate of Completion
2017 – 2018
Licensed Real Estate Broker, Illinois
License 475.216275
2025 – Present
Skills
Sales & product: Enterprise discovery & product demonstrations, Sales, negotiation & stakeholder management
Technical: Technical/software product development, Data analysis / SQL
Domain: Construction & real-estate technology, Construction procurement/financial workflows