Forward Deployed Operator

About CloudCruise

CloudCruise builds computer-use infrastructure for healthcare. We automate the administrative and clinical workflows that still require people to manually navigate legacy healthcare systems with deterministic browser agents that self-heal when systems change.

We serve dozens of healthcare customers running tens of thousands of automations every day. CloudCruise has grown quickly through customer demand and word of mouth, and is backed by a $5M seed round from investors including Floating Point, Meridian Street Capital, Twine, and Refract Ventures, with angels like Zack Lipton (CTO Abridge) and David Singleton (fmr. CTO Stripe).

The Role

You'll own the workflows CloudCruise builds for our customers - from figuring out what needs to be automated to getting it into production and keeping it running reliably across multiple customers and workflows at once.

You'll work directly with customers to understand how their operations work, translate messy real-world processes into clear requirements, and use CloudCruise and AI coding tools to build the automations themselves

This isn't traditional customer success, and you don't need to be a software engineer. We're looking for someone who is great with customers, extremely detail-oriented, and unusually effective with AI tools - someone who can move quickly without dropping details.

What You'll Do

• Own customer implementations end-to-end. Work directly with customers from the first discovery call through launch and production
• Build automations. Use CloudCruise, AI coding tools, and internal tooling to build and configure customer workflows.
• Maintain production workflows. Investigate failures and adapt workflows as requirements and external systems shift underneath them.
• Manage multiple implementations at once. Keep several customers, projects, and workflows moving forward simultaneously without dropping details.
• Shape the product. Push recurring failure modes, customer needs, and coverage gaps back into the roadmap. You'll see patterns nobody else in the company can see.

You Might Be a Fit If

• You're extremely detail-oriented. You notice edge cases other people miss. When something fails 1% of the time, you want to understand why.
• You're great with customers. You're clear, responsive, organized, and comfortable working directly with both technical and non-technical stakeholders.
• You're AI-native. You use tools like Claude, Codex or similar products constantly and are unusually good at getting useful work out of them.
• You're technically curious. You don't need an engineering background, but you're comfortable learning new software, debugging problems, reading logs, working with structured data, and figuring out how systems behave.
• You're excellent at juggling multiple threads. You can manage five different workflows for three different customers and always know what needs to happen next.
• You move quickly and take ownership. You prefer getting into the tool and figuring things out, and you stay on problems until they're solved.

Nice to Have

• Experience in implementation, solutions, technical customer success, operations, consulting, or a similar customer-facing role
• Experience working at an early-stage startup
• Familiarity with browser automation, APIs, SQL, or developer tools
• Experience in healthcare, health tech, revenue cycle management, or healthcare operations

Why CloudCruise

• Real ownership. You'll own the workflows our customers depend on every day, not just manage a project plan around them.
• A new kind of role. AI is changing the boundary between engineering, operations, and implementation. You'll be using AI to do work that would have required a team of engineers a few years ago.
• Ground floor. You'll help define how implementation works at CloudCruise as we scale from dozens to hundreds of customers, with the opportunity to eventually build a team around that.