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