This former Google exec is out to prove the on-demand model can scale. Can she do it?

Stacy Brown-Philpot had what you might call box-level seats to the last dot-com bubble burst.

An M&A analyst for Goldman Sachs, Brown-Philpot was working on tech deals in New York when the NASDAQ peaked and then plummeted thanks to the Internet boom. It was then that the 24-year-old Penn grad did something unusual: She decided to jump right into the fire.

“I was curious how these companies were creating all this value,” said Brown-Philpot, now 40 years old. “What are they actually doing? Who are the people that are doing it? That piqued my interest in tech.”

Soon after the collapse, she left the East Coast for Stanford to learn more about the unstable industry she had by then only watched from afar. After graduating with her MBA in 2002, she went on to Google, first working in finance and then in operations where she helped the tech giant grow from 1,000 employees pre-IPO to a team of 50,000.

This year, she once again finds herself where the action is. She is the newly appointed CEO of TaskRabbit, an online marketplace that matches freelance labor with local projects. Founded in 2008, TaskRabbit was among the first companies to enter the now overcrowded cohort of on-demand startups.

With funding in the on-demand space skyrocketing from $57 million in 2010 to more than $4 billion in 2014, many argue that on-demand is at the epicenter of the irrational startup valuation problem now plaguing Silicon Valley. While on-demand startups collectively — minus Uber — have raised $3.89 billion to date, fewer than 10 have gone through a successful exit and dozens have closed down along the way. As on-demand has suffered, so has TaskRabbit: The startup has gone through at least one major product pivot as well as a series of layoffs.

Investors and critics alike are sitting and waiting for on-demand to implode and Brown-Philpot is being put to the test. Can the math wiz-turned-operations manager prove on-demand is a sustainable and scalable business model? Former and current colleagues say that if anyone is up to the task — pun intended — it’s her.

“She is a remarkable human,” said Google’s Head of People Operations Laszlo Bock. “It is rare in your career to come across people who are exceptionally good at many things like Stacy is.”

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Before I heard Brown-Philpot’s voice, I heard her laugh. A short woman with a petite build, she was a few minutes late to our interview. As she came through the door, she was giggling at something said by a coworker in the hall. It was a late Friday afternoon and with a party to attend right after our chat ended, she was wearing a Diane Von Furstenberg-style wrap dress and wedge heels. The first thing that struck me was how relatable and easy she was to talk to — somewhat uncommon traits among startup CEOs. Within minutes of our interview at TaskRabbit’s headquarters in downtown San Francisco, she had me laughing too about how both our partners use the app to get chores done around the house that they can’t accomplish solo.

It is in this setting that Brown-Philpot begins to demonstrate that social skills are not her most remarkable attribute. The daughter of a single mother living in Detroit in the ‘80s and ‘90s, she tells me all the successful people in her hometown grew up to be doctors and lawyers. For sometime, she assumed she’d do the same. Then in high school she took an accounting class and realized not only was she good at math — a topic that other students scoffed at — she enjoyed it.

From then on she couldn’t get enough of working with numbers. Even when her high school guidance counselor told her that she should really diversify her course load if she wanted to be a doctor, she ignored him.

“I could’ve probably been a good doctor or lawyer, but I didn’t like biology,” she said. “People say you should follow your passions because you’ll be more successful at something you are passionate about. In my case it’s true.”

Rebelling against convention is a theme that would follow Brown-Philpot throughout her career. When she made the move out West after the Internet bust in 2000, she recalls her mother raising her eyebrows at the decision. In 2003, it was still very unclear that the search engine company would become the colossal success that it is today.

“When I took the offer at Google, my mother said to me, ‘Google, what’s Google?,’”  Brown-Philpot recalled with that same laugh I heard out in the hall. “After I explained it to her, she said that if that didn’t work out, ‘you can always go back to public accounting.’”

Things did work out — for the company and for Brown-Philpot. After 13 interviews — including one with now Facebook COO Sheryl Sandberg — Brown-Philpot became a sales finance director. She was initially responsible for forecasting, budgeting, and revenue analytics for Google’s then relatively small operation, but she quickly moved up in the ranks. During her tenure she did everything from managing Google’s operations out of India to ultimately all of global consumer operations, which includes products like Google+ and Chrome.

Google’s Bock said that Brown-Philpot’s operational capabilities are unparalleled — even for Google’s infamously high standards. Yet he also attributes Brown-Philpot’s success to her people skills. It would be easy for her to go around and “act like the smartest person in the room,” Bock said, and in many cases she would be. Instead she had a “warmth and a way of engaging people that brings out the best in people around her,” he said.

Interestingly enough, the people around her were what kept Brown-Philpot at Google for a decade.

“I had this moment where I realized that this was the best set of people that I have ever interacted with,” she said. “I didn’t really know what we are doing at the company, but I knew it would be a fun ride.”

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When TaskRabbit founder Leah Busque initially approached Brown-Philpot to consider joining her team as chief operating officer, Brown-Philpot immediately said no. It was 2012 and Busque, an engineer by trade, needed to bring in a business mind to help her scale the platform. After five years in operation TaskRabbit was still only available in nine domestic markets.

Brown-Philpot insisted the role wasn’t right for her — even offered up several candidates that she thought would be interested — but Busque wouldn’t take no for an answer. She convinced Brown-Philpot to get informally involved in the business, at first advising the founder on her presentations to her board of directors. A little more than a year later, after Busque had vetted hundreds of candidates for the role, Brown-Philpot officially became COO. As Busque said, “she was hooked” on what TaskRabbit was trying to accomplish.  

(TaskRabbit Founder Leah Busque)

Brown-Philpot’s decision to leave Google prompted another deja vu-like conversation with her mother, Shirley. Back at home in Detroit where TaskRabbit is still not available, Shirley had no idea what the startup or on-demand services really were. But this time around, Brown-Philpot found herself able to explain the growing startup in terms she knew her mother would understand. Shirley had to forgo finishing college to take care of a young Brown-Philpot and her older brother Damon. Hardly passionate about insurance, Shirley worked at BlueCross BlueShield as a claims adjustor because it provided enough money to support her two children.

“[TaskRabbit] could’ve helped my mom so she didn’t have to work so many hours and fall asleep reading to me at night because she was tired from working,” Brown-Philpot said. “It was this opportunity to create every day work for everyday people and be the life support that every day people need to thrive.”

To call a startup CEO “mission driven” at this point is cliche, but Google’s Bock says that in Brown-Philpot’s case, it's genuine. When Bock recently went to visit Brown-Philpot at TaskRabbit's headquarters, all he had were logistical questions for his former colleague: “What happens when someone needs a handyman, but none are available? What about when there are tons of workers seeking jobs that don’t exist?”

Each of Brown-Philpot’s responses to Bock were rooted in the fundamental idea that TaskRabbit allows both workers and users more freedom to do what they want with their time. Later in his visit, Bock recalls Brown-Philpot going around the office and introducing him to the some 30 or 40 TaskRabbit employees around the office. He was impressed not only that the CEO knew all their names, but their stories as well.

It’s this attention to TaskRabbit’s impact in the community and employee culture combined with her “flawless” execution of the platform’s growth that made Brown-Philpot’s recent transition to CEO so obvious to Busque. Within a year of Brown-Philpot joining the team, Busque was pregnant with her first child. Right when she was ready to have the baby, the startup was launching a brand-new product in London, TaskRabbit’s first international market. Busque was unable to be there every day to see the plan come to fruition, yet the rollout was a huge success.

On her first day at TaskRabbit, Brown-Philpot told Busque that in five years her goal was to become CEO of a mid-to late-stage startup. At the time, Busque didn’t think that startup would be TaskRabbit, but in less than three years Brown-Philpot proved that there was no one more capable to take the founder’s idea to the next level.

“She is always going to do the right thing. Not just for the business, but whoever is involved,” Busque said. “She isn’t going to sacrifice one area of the business for another and in a business like TaskRabbit’s, that’s really, really hard.”

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Brown-Philpot’s experiences as a leader seem bulletproof, but the business she is taking over may still be in danger. While the CEO says that they quadrupled the business last year — declining the request to unveil the size of their user base — TaskRabbit faces competition from several competing services including Handy, Hello Alfred and Thumbtack. TaskRabbit also hasn’t had a major funding round since 2012, a reality that could put them in a precarious situation given a slowdown in the on-demand funding market.

When I brought up these factors to Brown-Philpot, she seemed largely unfazed. Last year was the platform’s “best year ever” and she confidently projects that they will be profitable by the end of the year. They are available in 18 U.S. markets, plus London, and are experiencing 20% month-over-month growth. Her biggest challenge now is to take some of the lessons she learned at Google and scale the business even further — something she says she can accomplish with or without more investment.

[A Tasker delivering balloons and flowers]

“TaskRabbit should be everywhere and as long as we focus on unit economics, we will have the freedom to decide when that will happen,” she said. “If we want to be in four markets next year, we could do that ourselves. If we want to be in 14, we would probably have to raise to do that, but that would be our choice.”

Inevitably, at one point our conversation turned to the fact that Brown-Philpot is working toward this goal as one of a few — if not the only -- Black women running a startup at TaskRabbit’s scale. When the news came out that she would succeed Busque as CEO, she said the response was overwhelming. Despite giving the press release to just two reporters, coverage poured in from countless outlets who more or less only focused on Brown-Philpot’s gender and race. She says that one day that won’t be the case, but for now, she sees herself as the best person to build TaskRabbit — regardless of her background. No check box needed.

“I only know how to be me. I only have ever been Black and a woman,” she said. “I can’t deny any part of who I am. I have to talk about who I am. It is part of my existence and personality. It has shaped how I grew up and how I make decisions. I embrace it.”

At this point in the saga that has become the on-demand industry, Brown-Philpot might be exactly the leader that TaskRabbit needs. And if the critics are proven right and the model is doomed, I get the feeling Brown-Philpot will be on the ground floor of tech's next big idea.