About Oilcan

Oilcan is the partnership of Cory Watson and Jay Shirley. We want to share the joint experiences that we’ve had through decades working in various high growth startups and companies. Throughout our work and studies, we’ve faced a common struggle just as the engineering org is hitting their stride and forging their engineering identity and culture. It’s hard to intentionally and deliberately cultivate the engineering practices that allow a company to focus on the challenges of today while increasing the capacity to handle customer needs in the future. Some companies do this well from the beginning, but most struggle to find the balance of one hand in the moment and the other in the future.

Our shared enjoyment over studying highly consequential events, whether incidents or significant infrastructure migrations, and determining what went into making them a success brought us together to curate our insights and share them. Through Oilcan, we’ve formalized a lot of conversations we’ve had and hope to be more valuable and focused for busy quickly growing companies.

Cory Watson was steeped in regulatory-scoped ecommerce, learning to keep an eye on key metrics. He helped shape the idea of observability in the industry, joining Twitter as one of the first Site Reliability Engineers and, later, managed the observability team. He joined Stripe to bootstrap observability and reliability efforts. After Stripe, Cory worked as a field CTO at SignalFx and a Senior Principal Engineer at Splunk, learning the vendor side of the industry. Throughout his career Cory has managed large migrations, built observability stacks, and led teams. From his dozens of talks over the years you can see Cory's passion about how computers and humans work together in complex systems. Most recently Cory's work at Jeli honed his focus on learning from incidents.

Jay Shirley worked in a variety of early, high growth startups through the .com bubble, including leading an engineering team bringing the Amazon platform to other large scale merchants. It was then that he started to look at how people work together, and how highly effective teams, rather than individuals, deliver outsized impact. That eventually led him to cofound a startup focused on leveraging proven coaching techniques to help high potential people achieve deeper, meaningful goals. After that, he spent 7 years at Stripe helping to build the infrastructure org, and launched and led several core platform teams, and then worked directly with the CTO and his staff to understand, and expand, the practices of the most productive and engaged technical teams.

We believe in upfront, visible pricing and transparent partnerships. We want to work with you, and we firmly believe trying to replicate one company's culture into another is as unlikely to work as stitching a third arm to your torso so you can type 33% faster. If there is part of our process that adds friction, please let us know because we are failing in our most important goal. Removing friction is often the best path for higher performing engineering teams.