An Undercover Boss, Elaine Chao, Amy Hood: Broadsheet July 18th

EVERYONE'S TALKING

• Undercover boss. TaskRabbit CEO Stacy Brown-Philpot recently spoke to the New York Times about being one of the few black executives in Silicon Valley—"No one thinks I’m a CEO," she said. Brown-Philpot gave another interview yesterday to Fortune's Leigh Gallagher at the Brainstorm Tech conference and touched on her company's recent acquisition by Ikea.

TaskRabbit, which let users hire independently-contracted “taskers” to perform household chores, is now a built-in option for Ikea shoppers in the U.S. and the U.K.'s largest markets who want help assembling their new furniture. But more growth is planned.

“Part of our expansion strategy is new markets in other cities,” Brown-Philpot said. “Ikea’s in 49 countries—we want to be in all of them, with them, eventually.”

Brown-Philpot joined TaskRabbit as COO in 2013 and got the CEO gig in 2016 when co-founder Leah Busque stepped down. Two years into the job, Brown-Philpot is still trying to better understand both her customers and her contractors. One way she's done it? By going undercover as a tasker herself.

Brown-Philpot on Tuesday told the Brainstorm audience about her experience as a tasker; she had two hours to clean an apartment well enough that the customer would get a security deposit back. “That was a lot of pressure,” she recalled. “It was a good experience to not just feel what it’s like to be a client sometimes but also feel what it’s like to be a tasker.”

The client's dirty oven was especially challenging, but he did get his money back, and Brown-Philpot never revealed her ruse. “I didn’t want to freak him out,” she said.  Fortune

ALSO IN THE HEADLINES

• Rubber meets the road. U.S. Transportation Secretary Elaine Chao was on the hot seat at Fortune's Brainstorm Tech conference on Tuesday, fielding pointed questions about the delay in the administration's promise to spend $1 trillion on infrastructure (she blamed disagreements about how to pay for the proposal) and the raucousness of the Trump White House (she blamed the proliferation of the Internet).  Fortune

• Battling the unknown. How will the U.S. prepare for the war of the future? Lt. Gen. Nadja West, U.S. Army surgeon general, explained the branch's "Future Command" at Brainstorm Tech on Tuesday. The project will assess how the Army's troops and technology can prepare for later conflicts that won’t resemble prior wars. “The tactics, techniques, procedures, and capabilities that we had post-Cold War may not take us to 2028 and beyond,” she said.  Fortune

• Popping the Bitcoin bubble. Also on Tuesday, Stripe COO Claire Hughes Johnson told the Brainstorm audience why the digital payment giant unveiled a tool for merchants to accept Bitcoin in 2015, only to pull the plug on it in April. Bitcoin and other blockchain-based payment services are slow, impractical, and overhyped, she said, noting that clearance times for a Bitcoin transaction right now are 60 minutes; last December they were three to five days.  Fortune

• Looking within. Andreessen Horowitz has promoted Connie Chan to general partner, in a rare move for the venture firm that signals a break from its long-standing requirement that general partners need to have operating experience prior to joining. Chan is the first general partner to get promoted from within and the second female GP to join the ranks of the firm. Fortune

MOVERS AND SHAKERS: Navy Federal Credit Union has promoted EVP of Delivery Channels and Communications Mary McDuffie to the role of COO. USA Today Network is bringing on Kate Gutman, former VP of strategy and digital media at A+E, to lead content ventures

IN CASE YOU MISSED IT

• Too distant for comfort. Hospital statics show that medical help is growing dangerously distant for women in rural America, with at least 85 rural hospitals having closed since 2010. But what does that mean in real terms? The NYT's Jack Healy writes about what it's like for affected women and their families who "struggle to afford the gas, child care and time off work to drive hundreds of miles for an ultrasound, shots or hospital tests" and the risks the crisis poses to mothers whose babies arrive unexpectedly.  New York Times

• Under the Hood. Microsoft Chief Financial Officer Amy Hood tells company recruits that her role is "about creating an environment in which you all remember that you still want to pick us every day." That's a job description that goes far beyond the normal duties of a CFO, but the approach has made Hood—along with CEO Satya Nadella—integral in convincing employees, customers, and investors to return to Microsoft after the tech giant spent more than a decade losing its way.  Bloomberg

• Pumping problems. Despite the recent public discourse about breastfeeding—and the Trump administration's stance on it—nursing, or rather pumping in particular, is a private struggle that millions of women face in a society that's unprepared—and often unwilling—to accommodate them. "There was just never a good spot to do it. Ever," one female professional told Harper's Bazaar. Harper's Bazaar

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