In March 2020, right after leaving Autodesk following the $875 million sale of construction software company PlanGrid in 2018, Tracy Young and Ralph Gootee found themselves at a sudden standstill as COVID-19 shelter-in-place orders began. Having worked together since 2011 and married in 2013, the two founders transitioned abruptly from managing high-velocity corporate teams to confinement at home. Rather than immediately launching another business, they used the lockdown months to conduct a detailed retrospective on their decade at PlanGrid, systematically dissecting their past operational mistakes, successes, and key professional relationships.
Rebuilding with Familiar Talent
This period of analysis laid the groundwork for their next startup, TigerEye. Young and Gootee mapped out the workplace dynamics they wanted to recreate, defining their core team values before settling on a specific product idea. When building the initial team, they drew directly on their past networks. According to Y Combinator's account, the first 24 or 25 hires at TigerEye were people Young and Gootee had worked with previously. By bringing in trusted colleagues from their PlanGrid years, they established an early engineering and operations culture rooted in established trust and shared past experience.
An Unexpected Enterprise Realization
In between PlanGrid and TigerEye, the co-founders also served as Visiting Group Partners at Y Combinator, reading thousands of applications and interviewing ambitious founders. During one interview, Young and Gootee spoke with an 18-year-old engineer building a video application. When they asked why he was not building software for real workplace productivity, the founder candidly replied that enterprise software was for old people. The remark underscored a key realization: young developers frequently avoided corporate back-office software, leaving enterprise modernization to experienced founders who had spent years dealing with broken software tools inside large organizations.
Applying Applied Physics to Business Revenue
During their post-acquisition tenure, Young and Gootee had seen firsthand how costly corporate software could be. Their unit spent millions of dollars annually on enterprise tools, plus hundreds of thousands more on administration, yet still relied on fragile spreadsheets for financial forecasting. To address this, Gootee proposed applying simulation theory—a framework he had previously utilized at the Johns Hopkins University Applied Physics Laboratory—to enterprise revenue modeling.
Standard CRM databases such as Salesforce operate as flat databases; when a sales representative saves an opportunity, the system overwrites the record's history without retaining change logs. To fix this, TigerEye snapshots CRM data every 15 minutes, capturing every minor modification as it occurs. Machine learning models and advanced statistics then process these snapshot sequences to run automated business simulations, offering continuous revenue predictions based on historical behavior rather than manual spreadsheet calculations.
Dynamic Enterprise Forecasting
By snapshotting CRM changes every 15 minutes and applying statistical simulation model theory, TigerEye turns flat record-keeping systems into dynamic predictors for enterprise revenue management. Replacing static spreadsheets with continuous temporal tracking allows companies to analyze underlying sales behavior over time, bringing defense-derived simulation techniques directly into daily business operations.
AI-generated editorial illustration; not a documentary photograph.
Source: Dissecting the past to predict the future: Tracy Young on building TigerEye
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