Starting up in stealth

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, and they didn’t know how to catch up.

“It was really challenging for us to go up market,” she told me in August when I interviewed her in her office. “We nailed SMB, we did a good job moving upstream towards mid-market, but we just really sucked at selling to the enterprise. And by the time we got to $80 million in ARR, it was the only route left.”

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. I was particularly interested in how she developed customer personas and messaging while keeping a low profile.

“If anything, stealth gave us the ability to really go broad in the number of profiles,” she said. ”It gave us the chance to really test out messaging, so that was pretty cool.”

She also shared what she’d learned as a CEO her second time around when it comes to building early teams and managing a hybrid workplace.

“I really like this stage of a startup. You know, the bigger you are, the more middle management there is, and there's just more opportunities for the mediocre person on the team,” said Tracy. “It’s much harder to be mediocre at a small startup.”

Come back tomorrow for the second half of our conversation in which she explains how to run a board meeting in 60 minutes. 

The secret? Replace traditional 80-slide board decks with succinct memos that sum up the company’s milestones and pain points. In our conversation, she laid out how she builds 2-4 page board memos that get finance, R&D and other housekeeping matters out of the way, “and then it's all strategy after that.”

(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 your startup’s 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.

Thanks for listening,

– Walter.