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Life after Obama: Why the president’s 2012 campaign CTO left politics

Published Apr 13th, 2015 1:10PM EDT
Obama CTO Interview

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For the next chapter of their careers, two prominent technologists from the Obama 2012 re-election campaign decided to trade politics for the startup life, building some of their experiences and insights from the campaign into the foundation of their newly launched Chicago-based venture called Modest.

Modest’s co-founders are Harper Reed, the highly regarded CTO of the Obama 2012 campaign, and Dylan Richard, the campaign’s director of engineering. Reed tells BGR that he and Richard had been “hovering around ideas” about how to improve the e-commerce experience on mobile for a while now, well before the campaign. Outside of politics, for example, Reed’s past experience includes a stint as the CTO at T-shirt design company Threadless, while Richard is, in addition to a fellow Threadless vet, a former developer for Crate & Barrel.

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Reed says moving to the campaign put them inside “the world’s biggest e-commerce lab,” given things like the amount of individual donations that came pouring in, which itself was only one piece of the puzzle that Obama’s techies were focused on. The whole experience got Reed and Richard thinking about some of the ideas they’d kicked around for a while, and when the dust from the campaign settled, a plan began to take shape.

They decided to build a company with which they’d try to make a dent in the e-commerce experience. The goal of their new enterprise: it would help businesses give their customers “the ability to buy from anywhere in just a few taps.”

“It’s actually a pretty simple to explain problem,” said Reed about the motivations for launching Modest at the end of January. “Have you ever tried to buy something on a phone? There’s not really a compelling solution. Interfaces usually aren’t made for the screen. It kind of takes a lot of work, you’re entering your credit card a bunch of times – there are many paths for things to go wrong.

“On the campaign, we did a lot of work to make sure the mobile device was a first-class device that was treated with the same attention, the same everything as your regular desktop Web. One of the things driving us is – how do we make it so that every retailer in the world can have a very, very good mobile experience for their retail technology.”

Modest does that by helping create mobile shopping experiences in the form of an app, working with businesses like Chicago coffee company Intelligentsia whose app is built on Modest’s platform. Modest also can easily drop its solution into a retailer’s existing mobile application.

The company picked up backing from the likes of Google chairman Eric Schmidt, as well as Greylock Partners, 500 Startups and Base Ventures. Modest says its platform integrates with any commerce platform, along with automatic Shopify and Magento integrations as well as more to come. Support for Android, ApplePay, and PayPal also are coming soon.

In a statement about his support of the company, Schmidt said Modest seems poised to “create major shifts in the mobile shopping experience.” One of the platform’s major changes, he noted: no shopping carts, which Reed says don’t have a place on mobile devices. Moreover, Modest believes that customers making one purchase at a time results in them making a bigger overall spend.

“It’s a SaaS platform, so what this allows is any retailer in the world to go ahead and log in to Modest and generate an app for their usage,” Reed said. “It can be any kind of business, and you can pretty instantly – and when I say instantly, I mean very instantly – get that user experience that’s focused on mobile. If you were to go to, you could click through and sign up, and in a handful of minutes you can download an app to your iPhone and demo and see our tech.”

Reed and Richard started work on Modest in December 2012, and it has about 18 employees right now.

The name of the company, it should be noted, isn’t so much a tongue-in-cheek descriptor of its personality or that of its people – after all, “I am pretty awesome” is the first sentence of Reed’s (@harper) Twitter bio – as it is something of a reflection of its ambitions.

“Most of us at Modest,” Reed reflects, “are not necessarily the most modest people. “In naming the company, we thought if we can bring mobile and make it a first-class citizen for e-commerce, then we will have done something really great. And the first thing about e-commerce is, the market size is bananas. So we thought, if we have a successful company, how much of the market does it get?

“One of the things we like to talk about is, you can make a really great company that’s changing lives and how mobile commerce works for millions of people and still be only a small part of the industry. We could make modest changes to e-commerce and still be greatly affecting it.”

Andy Meek Trending News Editor

Andy Meek is a reporter based in Memphis who has covered media, entertainment, and culture for over 20 years. His work has appeared in outlets including The Guardian, Forbes, and The Financial Times, and he’s written for BGR since 2015. Andy's coverage includes technology and entertainment, and he has a particular interest in all things streaming.

Over the years, he’s interviewed legendary figures in entertainment and tech that range from Stan Lee to John McAfee, Peter Thiel, and Reed Hastings.