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