We are building AI-native cloud operations from the ground up. If you want to work on genuinely hard problems alongside a team that has done it before, we want to hear from you.
Cloud operations is broken for most companies. Teams spend 20-plus percent of their time on manual ops work that should not require a human. Oscar changes that, and you will be part of building it.
Brian and Jason have built, scaled, and exited transformational technology companies together. They know how to navigate the early stage and help you grow fast alongside the company.
This is not a team where you will be a small cog in a large machine. The work you do in your first weeks ships. Your ideas shape the roadmap. Your relationships define the culture.
We are not bolting AI onto a legacy product. Oscar is built from scratch around a live context graph and AI-driven orchestration. The engineering and GTM problems here are genuinely new.
We have the runway to build and the investors and advisors to help us scale. Roo Capital, Gray Ventures, and leaders from Google, Starbucks, Pendo, and Intuit are in our corner.
We believe the best work happens when people genuinely enjoy what they do. We keep it simple, strive for excellence, and take the work seriously without taking ourselves too seriously.
We do not have formal postings open for every role right now, but we are actively building out these areas and talking to strong candidates. If something below resonates, reach out.
We are a small team doing big things. Everyone is close to the customer, close to the product, and close to the decision-making. That is by design.
We hire the best people regardless of where they are, communicate clearly in writing, and respect focused work time.
We give people real responsibility and trust them to run with it. There is no bureaucracy between you and shipping great work.
We move quickly, learn from what we build, and share that knowledge across the team without hoarding it.
We tell each other the truth, give real feedback, and do not waste time on political maneuvering. The work is the point.
Competitive base salary, meaningful equity, and benefits. We structure comp to reflect that early team members are taking real risk and deserve real upside.
Health, dental, and vision coverage. Flexible PTO. A home office setup stipend to make sure you can do your best work wherever you are.
At this stage, growth is not a perk program. It is a function of working on hard problems alongside people who push you. You will learn more here in a year than most environments offer in three.
We get together in person a few times a year. Good food, good conversations, and the kind of relationship-building that makes remote collaboration actually work.
Drop your email and tell us a bit about yourself. When the right role opens, you will be the first to know. We read every note.
No spam. Just a heads up when something opens that might be the right fit.