As an AWS Enterprise Strategist, Jake works with enterprise technology executives to share experiences and strategies for how the cloud can help them increase speed and agility while devoting more of their resources to customers.

Throughout his career, Jake has led large-scale IT transformations, which today are the basis for his firm belief that any enterprise can successfully adopt the cloud and save money at the same time. While he was VP of IT Operations at Live Nation, he led a large data center consolidation project that was heavily focused on cost reduction. That experience paved the way for when, a few years later, the Live Nation CEO kicked off a modernization effort across the company, which included a mandate to go “all in” on AWS. Jake reoriented his team to form a new Cloud Services function at the company, and successfully migrated 118 applications, 668 servers, and 1PB of storage to AWS in 17 months. The migration reduced IT costs by 48% in the first year and a half—all without any migration bubble costs.

For Jake, a critical element for a successful migration to the cloud is focusing on people to ensure that teams have the necessary skills to get the job done well. When Jake first started the Live Nation migration to the AWS, he had no budget for additional resources, increased headcount, or outside help. To get there with his current team, he needed to upskill them—and quickly—so they could be confident enough to migrate all corporate IT to AWS, including a few very challenging systems that were less compatible with cloud infrastructures. For that reason, he focused on training his people (and himself) on the new skills they’d need. The experience taught him that the cost of cloud migration is directly proportional to the expertise your team has with the cloud, a lesson he shares with customers today.

Another important career lesson for Jake is a bias for action. Getting his people equipped early with new skills freed them to get started trying and learning about the cloud. Today he advises customers not to wait (because your competitors never do) and just start trying new things. At the same time, he reminds customers that failure is a normal part of learning. He likens the innovation process to what’s involved in capturing the perfect, eye-catching photo for the cover of National Geographic. Most photographers will take hundreds of photos (and discard them) before they land on that perfect shot. The goal for customers today is to get through those 100 experiments (and failures) quickly so they can find that one successful innovation that works—in weeks, not years. The way Jake sees it, that kind of agility can only happen when organizations experiment quickly at low cost and with low risk.

Outside of work, Jake applies the same thirst for learning and trying new things to his hobbies (he considers himself a “knowledge junkie”). When choosing a new pastime, he has two criteria: one, they must be tough enough that he’s forced to grow, and two, their difficulty must force him to concentrate completely on the activity—a condition he finds meditative, as it quiets his mind. That philosophy has led him to learn Brazilian Jiu-Jitsu, non-competitive motorcycle racing, becoming a licensed airplane pilot, and, most recently, working towards earning a helicopter license.