Jack Pearson

Product manager in proptech and B2B SaaS who became a licensed multifamily broker, then designed and built the AI-native software that broker needed.

Chicago, IL · jackwpearson1@gmail.com ·LinkedIn ·GitHub

Experience

Broker, Multifamily Investment Sales · Interra Realty

2025 – Present

Licensed broker representing clients in the purchase and sale of multifamily properties.

  • Underwriting, rent-roll and T-12 analysis, and offering memoranda.
  • Owner outreach and negotiation.
  • [Deals closed / volume / notable transactions to confirm.]
  • Became the customer for the software I later built: every Everre feature started as something I needed on a live deal.

Contract Project Management · Independent

2024 – 2025

Construction project management on a contract basis for commercial projects. Began coursework and licensing for real estate brokerage during this period.

  • Interior renovations and retail facade repair and replacement.
  • Estimating and permitting.

Senior Product Manager · Homebound

2022 – 2024

Owned procurement product for a technology-backed single-family homebuilder offering personalization at scale.

  • Delivered contracting capabilities that cut the buyout period for new developments from 120+ days to 45.
  • Introduced itemized takeoffs for every plan and option, backed by an integrated product catalog tracking bids, historical pricing, and line-item specifications.

Product Manager · Procare Solutions

2019 – 2021

Full product lifecycle, discovery through delivery, for childcare B2B SaaS on web and native mobile. Heavily involved in the enterprise sales cycle as the product and demo expert.

  • First employee and first product manager placed by Procare into acquired startup Kinderlime. Took over product strategy and backlog from the founders and integrated the team's development process into the parent company.
  • Continuous user engagement; qualitative and quantitative data for decisions and communication.

Software Engineer · Intelivideo

2018 – 2019

Built tools and themes for white-label subscription video products used by Title Boxing, Pure Barre, and MELT Method.

Angular.js · Ruby on Rails · PostgreSQL

Architectural Intern · Piekarz Associates

2016 – 2016

All phases of design from concept through construction documents.

Founder projects

Everre · Founder

2025 – Present

AI-native CRM for commercial real estate brokers, designed and built end to end. The AI does the analyst's work; the broker keeps the relationships.

  • Agent capability registry with risk-graded policy (105 capabilities), an MCP server and OAuth authorization server so brokers connect Claude or ChatGPT to their own data, and email agents at *@ai.everre.co.
  • Financial-document extraction that verifies every figure against the source text and never commits without a person. Usage-based billing on Stripe meters with a spend guard that fails closed. E-signature with an ESIGN/UETA audit trail.
  • Nationwide public property dataset (4.16M parcels) built with a Python ELT pipeline over county ArcGIS and Socrata endpoints.
  • ~690 API routes, 2,600+ tests. Ran founder-led outbound and diagnosed the result honestly: clicks, no conversions, and a repositioning from all-in-one CRM to AI analyst plus open API.

TypeScript · Hono / Bun · Postgres · TanStack Start · Anthropic API · MCP · Stripe · Cloudflare Workers · Python

FifthYear · Founder

2026 – Present

Registration, payments, teams, brackets, and results for adult recreational athletes and the organizers who run their competitions. Web, iOS, and Android.

  • Stripe Connect with the organizer as merchant of record and a fee pass-through gross-up so payouts equal the listed price to the cent.
  • 886 merged pull requests and 152 migrations since March 2026. Native mobile app shipped to both stores through Expo.

TypeScript · Hono / Bun · React · Expo · Stripe Connect

Education

University of Kansas

Master of Architecture

2012 – 2017

DevMountain

Web Development Bootcamp

2017 – 2018

Licensed Real Estate Broker, Illinois

License 475.216275

2025 – Present

Skills

Domain: Multifamily brokerage, Underwriting, Rent rolls & T-12s, Offering memoranda, Homebuilding procurement

Product: Discovery, Positioning, Roadmaps, Analytics, Pricing & GTM

Engineering: TypeScript, React / React Native, Postgres, Python, Stripe, Auth & security

AI: Agent architectures, MCP servers, Document extraction, Prompt-injection defense, Spend guards & metering