Former Seattleite Jon Jenkins, the Head of Engineering at Pinterest, has taken the lead of a “super scrappy, super agile” team of engineers building one of the biggest social networks on the web today. Using billions -- or maybe even trillions -- of data points supplied by users around the world, he and his team are curating personalized experiences for every Pinner, helping to show them new things they didn’t even know they liked yet. I sat down to talk to Jon about solving some of the most exciting challenges of his career in this edition of Nextcast; here are a few of the highlights: This PolySci graduate with a knack for “hacking around” has done the big company and the startup thing more than once in his career. After spending almost 9 years at Amazon in Seattle, he hightailed it to San Francisco to join the Pinterest startup team, who piqued his interest with an intriguing set of problems to solve. Jenkins says he is “fascinated by challenges associated with scaling things...and challenges associated with data mining or deriving useful information from large pools of data.” He adds, “Pinterest has both of those challenges at an even bigger scale.” (4:30) The problems Pinterest is solving for its users are based on huge amounts of data providing huge amounts of value to customers, who may not even know they want that value until they get it. “A pin is an object...coupled with the user’s context about that object,” Jenkins explains. It’s not just about what gets pinned, but what it says about the Pinner’s interests. Jenkins and his team are using that information to present that user with even more things they might enjoy, even if the user doesn’t know they like it yet. “We can tell you things about yourself that you didn’t even know,” based on what you pin, within the context your boards and profile. “That’s something I don’t think anyone has done before.” (7:20) Jenkins shares that his business philosophy is based on always putting the customer first. “In no matter what you’re building, you should absolutely understand how it’s going to positively impact...customers,” he says. If you can’t articulate that in a way a customer will understand, he says, you’re not likely to be successful. He feels just as strongly about APIs -- which helps to explain why there is no Pinterest API yet. “APIs are forever, and you need to treat them that way. You don’t get to release these things to the world and then pull them back, or at least you shouldn’t.” Jenkins adds: “Software is a promise.” (12:02) Though he still loves Seattle, Jenkins admits he wishes he’d moved to San Francisco earlier. The vibrant, connected, sharing-focused community is something he would like to see carry over to other tech communities. Another thing he wishes? That’d he’d pushed himself harder, earlier in his career, to take more risks. “Being successful in technology is really about pushing the boundaries,” he says, advising tech upstarts to not let a fear of failure control them. And though risk-taking and idea-challenging are now part of his daily routine, he explains, “I should not have been afraid to break things or challenge conventional thinking earlier.” (17:00) Jon’s advice to other startups and leaders is concise, but powerful. “You better understand what your customer wants,” he says first. “[Be] incredibly pragmatic in how you deliver,” is his second tip, which is all about the power of fast iteration and agility. The quicker you can notice problems and do something about them, the better off you are. And finally, he says: “[Build] an engineering team that actually wants to deliver stuff.” Not every engineer gets excited by shipping, but you need to make sure your team is staffed with only that kind. Getting your product in front of customers is the difference between success and failure. (24:25)