Starting up in stealth: A conversation with TigerEye co-founder/CEO Tracy Young

In 2011, Tracy Young co-founded PlanGrid, which made software for construction teams. After scaling the company to 450 people and raising $69 million, it was acquired by Autodesk in 2018 for $875 million. That’s a win, but Tracy and her partners didn’t go for the exit because they’d reached the peak of the mountain. They cut the deal because PlanGrid was behind in the market, and they didn’t know how to catch up. Three years later, during the pandemic, Tracy and her husband, Ralph Gootee, co-founded TigerEye, a RevOps AI agent that lets analysts answer questions and allocate resources based on data that’s updated multiple times each hour.  Last year, TigerEye closed a $30 million Series A. She describes it as “moneyball for business,” the tool she wished she’d had at PlanGrid when she was fighting entrenched competitors who were just better at enterprise sales.  In part one of our interview, she explains why they started their new company up in stealth and how TigerEye reflects her vision of what enterprise software should accomplish. She also shared what she’d learned as a CEO her second time around about building early teams and managing a hybrid workplace. Subscribe now to get part 2: Her approach to work-life balance The unique challenges women founders face while fundraising How to run a board meeting in 60 minutes, and The importance of gaming out worst-case scenarios. Runtime: 23:09 EPISODE BREAKDOWN (2:53) TigerEye’s origin story: “We wanted a second chance, and that became a big desire of ours.” (5:11) “There's certain decisions that only leadership and the CEO can make.” (7:58) “We just really sucked at selling to the enterprise.” (9:53) How to manage customer discovery while you're in stealth. (15:53) Tracy’s tactics for managing a remote-first team effectively. (19:25) When it comes to personnel, it’s “much harder to be mediocre at a small startup.” (21:21) Why she still interviews every new hire at TigerEye. LINKS Tracy Young Why I started TigerEye 5 failure points between 5 and 100M ARR  TigerEye Ralph Gootee SUBSCRIBE 📥 LinkedIn: https://www.linkedin.com/newsletters/7249143254363856897/ 📓Substack: https://fundbuildscale.substack.com Thanks for listening, -- Walter.