Harper Reed

Harper Reed has made it a bit of a professional habit to be at the crux of digital zeitgeists.

His latest efforts place him on the front lines of the efforts to nail down what is often referred to as contextual commerce, which means enabling transactions in a range of contexts when inspiration — and intent to buy — collide. This might happen on Pinterest, in an e-mail or while browsing a retailer’s mobile web site.

Reed, 38, works in next-gen commerce at PayPal in the PayPal-owned Braintree office in Chicago, where he helps digital merchants of all sizes sell to customers in a range of contexts on web sites and in mobile apps. His official title is entrepreneur in residence, next-gen commerce.

He’s been at PayPal since August 2015, when the company he cofounded with Dylan Richard, Modest, became the first PayPal acquisition since it separated from eBay for an undisclosed sum.

Modest, a mobile commerce platform, also had a prescient mission: mobile commerce. The company, founded in 2012, helped merchants create an app or add a mobile store and let merchants add “buy” buttons into spaces such as e-mails, blog posts or ads.

He wet his whistle in the world of e-commerce in the mid-Aughts when he became the chief technology officer at Threadless, which was an early pioneer of user-generated content. It printed customer-submitted designs on apparel and accessories, and Reed said it inadvertently invented the concept of crowdsourcing. There, he learned about selling online at a time when people didn’t trust e-commerce, in way that felt trustworthy and quick. He also learned the value of hiring a diverse team.

“The team that I had built was all white dudes with the same perspective on things that was at times comfortable and easy, but we weren’t as innovative as our competitors” due to lack of diversity, he said.

Afterward, a year and a half of “wandering the Earth” paid off when he was asked to become the chief technology officer for former President Obama’s reelection campaign.

He considers Obama to be the first tech-friendly president, and admires the former president’s management skills. “He finds people he can trust and lets them do their job,” Reed said. “I think he is technologically inclined, but the success of the campaign in regards to tech was due to the fact that he was not scared of tech — he trusted the decisions that were made.”

He called starting Modest an “aggressive reaction to his own experience” with low conversion rates in e-commerce, at a time when mobile commerce was still considered an outlier.

“We were orbiting around the idea of intent and context. We would take the bus into work, and if you said, ‘here’s a shirt you might like’ and I open it on my mobile phone, I’m not going to pull out my credit card and wallet. We thought, ‘How does someone do this? An e-mail to yourself, or you try to remember?’ This isn’t working, and we are losing so much.”

Today’s efforts at PayPal are a continuation of his mission at Modest to help smaller merchants navigate the increasingly murky world of mobile shopping. It’s a tricky prospect from which retailers as well as shoppers stand to gain, but the recent cancellation of Twitter’s “buy now” button, for example, is a testament to the uphill battle that is contextual commerce.

Reed agrees that it’s “absolutely correct” that there are concerns that social media users might not necessarily be in a buying mind-set while they browse. “That is why ‘contextual’ is a perfect word. Instead of context, we were using ‘intent,’” he said. “What we don’t want and what people are worried about is turning every space into a buy button, because that won’t solve the problem. We have trained our users not to pay attention to those spaces.”

Instead, the hope is that when the user intends to make a purchase, the retailer can facilitate that. He uses Pinterest as an example. “The problem they are trying to solve is when you say, ‘I want this.’ It isn’t that every Pin you look at you want, and that is where it becomes interesting. Not every time you open Messenger do you want an Uber, but when you do want an Uber, it appears. That is the goal.”