TigerEye
Summer 2022AcquiredAI for Construction
Pressure-test this opportunity
Turn this teardown into a decision-ready prompt for ChatGPT, Claude, or your agent.
AI for Construction
Turn this teardown into a decision-ready prompt for ChatGPT, Claude, or your agent.
If you only have a few minutes to spare, here’s what investors, operators, and founders should know about TigerEye (S22).
TigerEye began as a planning system for sales leaders and ended as a construction-AI team inside Lennar. Tracy Young and Ralph Gootee founded the company in 2021 after selling PlanGrid to Autodesk for $875 million. They raised $35 million before public launch, spent two years building a temporal business-simulation engine, and emerged in March 2024 with tools for forecasting, territories, hiring, and pipeline management.[1][3][5]
The original product solved a real executive problem: CRMs preserved current state while leaders needed to understand how their business had changed. TigerEye recorded that missing history and let operators test a plan before committing people and budget. The harder commercial question was ownership. Forecasting, business intelligence, revenue operations, and planning already had established systems, internal analysts, and fast-moving AI entrants.
By late 2025, TigerEye had returned to the founders' construction roots. Lennar completed the acquisition on January 14, 2026.[9][10] The deal kept the team together and gave its technology a large operating environment. Its security treatment also shows an uneven exit: preferred holders received Lennar shares and pre-closing payments, while common shares were canceled without consideration.
Young and Gootee had worked together since PlanGrid's earliest years and married in 2013. Young had been a construction engineer at Rudolph and Sletten and Turner Construction; Gootee had worked as a Pixar animator and later used simulation theory at Johns Hopkins Applied Physics Laboratory.[14][2] PlanGrid gave them an unusually complete enterprise-software apprenticeship. TechCrunch reported that the company reached $100 million in annual recurring revenue before Autodesk bought it for $875 million in 2018.[3]
They left Autodesk in March 2020 and used the lockdown to dissect their first company. Young said the starting impulse was “The desire to keep building.” The couple mapped decisions, systems, and former colleagues; the first 24 or 25 TigerEye employees were people they already knew.[2] That recruiting strategy reduced team risk and brought shared context into a difficult data product.
The product idea came from an operating scar. PlanGrid could digitize a construction site while its CEO still relied on static Salesforce reports and analyst-built spreadsheets to run the company. Gootee's pitch was, “I think I can build a business simulator.” Young later compressed the thesis to “Moneyball but for business.”[2] The pair believed a system that remembered change could model future performance better than a spreadsheet assembled for one planning cycle.
TigerEye joined YC's Summer 2022 batch. That September, it announced a $30 million Series A led by Initialized Capital and Next47 after an earlier $5 million seed.[5][6] The funding arrived while the product remained in stealth and gave the returning founders time to build a large surface before asking the market to judge it.
TigerEye's core technical insight was temporal. A typical CRM record exposes the latest opportunity amount, stage, owner, and close date. When a sales representative updates the record, earlier values can disappear from the operational view. TigerEye snapshot the CRM every 15 minutes, preserving the sequence of changes needed to study rep behavior and replay a past state.[2]
Read the complete post-mortem, the rebuild playbook, and the exact reasons TigerEye is still worth studying now.