After ESTEEM: John Flatley

Author: Gene Stowe

When the Bay Area company SharePractice closed a few months after he joined, John Flatley viewed it as another item checked off his bucket list -- experiencing being among the 9 out of 10 startups that fail. That’s how fully the 2011 ESTEEM graduate embraces the entrepreneurial mindset and the “middle space” bridge between technology, entrepreneurship, and business. “Even though things changed, it didn't scare me away because I still wanted the experience,” he says. Flatley already had four fast-rising years at Google and a break to explore Asia, Europe, and, on a motorcycle, North America. So he set a new goal – move to Chicago – and achieved it through a job with Raise Marketplace, the world’s largest gift card marketplace, where he’s working now.

Goal setting brought Flatley, who grew up near Tampa, to Notre Dame in the first place: when he was in high school, he decided to get out of Florida and go to a Catholic university. Waitlisted at Notre Dame, Flatley spent a year at Boston College before getting accepted to his dream school as a transfer. (He spent two undergraduate years and his ESTEEM year on the cheerleading squad.) During his senior year, facing doubts about his goal of becoming an orthopedic surgeon, Flatley decided to join ESTEEM, figuring that the business experience would serve him well in a medical practice or any other career.

After those intense years, Flatley decided to leave Google and see the world. He visited Tokyo, Shanghai, and Hong Kong with a coworker, then Rome, Zurich, Paris and Amsterdam with his girlfriend. He planned a self-challenging solo, all-camping motorcycle ride from San Francisco to Anchorage and then to Florida, although he finished in Chicago when he felt the trip (blogged at had accomplished its purpose. “I felt like I had really found my niche,” he says. “I love solving problems. I wanted to be a consultant.” He applied to 100 companies and landed interviews with two – a small firm in Seattle that turned him down and Google, where a Notre Dame alum he met on LinkedIn supported his application and he was offered a tech support job based in Austin. Flatley told the recruiter that he’d prefer California, so he was placed in Google Wallet Risk Operations in the Bay Area as an analyst. Working with an engineer, he automated parts of the repetitive job, an experience that let him to grasp the technical perspective and learn Python. He was promoted twice in three years, first to Strategist where he helped bridge the technical and business needs, then to Technical Project Manager, where he managed 12 projects across three engineering teams in the United States and India.

“It was one of the most difficult things I had ever done, and it made me feel the most proud of myself,” says Flatley, who persevered through cold, heat, rain, and hail despite a traffic accident in Vancouver and battery problems that left him stranded in a desolate area until a passerby gave him a jumpstart. “If I ever have a problem in work or life, I can think, ‘this is easy compared to what I had on that trip.’”

After the ride, Flatley joined SharePractice to experience the startup life. The firm planned a Yelp-like app where doctors could rate procedures, combining their real-life experience with evidence-based studies, a return to Flatley’s health care interest. Within a week, the company cut its staff from 12 to three and pivoted to a new product before it ran out of money. That’s when Flatley, who had visited Notre Dame and Chicago frequently, decided to leave the Bay Area and return to the Midwest. Despite the West Coast’s beautiful weather and great personal and business opportunities, he says, “It didn’t feel like home to me. I didn’t like the culture. It felt like a ‘what can you do for me?’ culture.”


Flatley set the goal to be a product manager and found the job with Raise, an e-commerce company with a familiar business model. During the interview, he opted to try front-end consumer work, but the experience was unrewarding. “We ran probably 10 experiments and none of them led to any increase,” he says. “Even the best idea might not change people’s behavior.” Flatley accepted an offer to oversee a team in California as product manager also responsible for the back end and a bulk seller tool. The team in California is responsible for risk products, and the teams in Chicago are responsible for the bulk seller tools and administration.”

“The culture feels like a Silicon Valley tech – I think it would fit in quite well,” he says. “The people are different. They’re Midwesterners. You leave a meeting, and everybody says thank you. You hold doors open for people. It’s just a different vibe. It’s a good mix between my past experience and the experience I want now. I’ve slowly gotten myself into the position I’m in. I’m pretty happy with where I am.”