Designing for trust and complexity in the high-stakes world of billing

I didn’t join Orb because I had a background in billing or finance. I joined because I had seen what happens when pricing systems break down.

Before Orb, I worked as a product designer across different B2B industries for nearly a decade. My last project at a previous company involved working closely with the finance team on pricing operations, and it was one of those moments where you see how the sausage is made.

There were mega spreadsheets with multiple tabs and hundreds of rows. Files were sent back and forth among five stakeholders, who were manually updating rates based on geography, market conditions, and competitive inputs.

This wasn’t a minor workflow. It was core to revenue.

Pricing updates could only happen twice a year because the process was so manual and painful. It blocked growth, consumed months of the team’s time, and introduced risk at every step.

When I learned about Orb and how they’re bringing structure, flexibility, and trust to billing, it immediately resonated.

Every design choice impacts customer revenue and trust

At Orb, we ingest usage data and translate it into subscription logic, invoices, and reporting that companies depend on to run their businesses.

I work on the main billing platform, which oversees pricing and packaging changes, new pricing models, subscription migrations, and workflow improvements. These are all the things that make it possible for our customers to evolve their pricing safely and accurately.

Designing in this space means every change can have big downstream effects. If we make a mistake, it can affect invoices, revenue, and our customers’ customers.

Trust is everything, and that reality shapes how we work.

We often discuss “one-way door” decisions, or changes that are hard to reverse. In a sensitive domain like billing, we carefully consider our potential paths forward, and if there’s a reversible way to learn, we’ll take it.

Proximity to customers is our superpower

One of my favorite parts of working at Orb is how close we are to customers.

We communicate directly with many of them on Slack. I can search through conversations and see how often someone has struggled with a migration flow or lacked visibility into which subscriptions will receive a pricing override.

That signal is powerful.

From there, I’ll sit down with customers on Zoom to dig deeper and ask them to walk me through how they’re using Orb. What’s confusing? Where do they hesitate? What feels risky?

Sometimes the issue is clarity, missing functionality, or a deeper constraint in the data model.

The process usually looks like this:

• Talking to customers and our customer success team
• Framing the problem with product
• Sketching workflows
• Whiteboarding with engineering and product
• Stress-testing ideas against the data model
• Moving into detailed Figma workflows

We also have customer design partners who iterate closely with us. We show them early concepts to get candid feedback, and this ongoing relationship is invaluable to the product.

Designing in a system, not just a screen

Design in billing requires systems thinking.

You can’t just design a single screen. You have to think about how upstream event ingestion impacts billing workflows or how a decision affects downstream invoices and reporting.

If we now require invoices for certain actions, how might that affect revenue recognition later? If we adjust how pricing configurations are updated, what does that mean for the underlying data model?

As a designer, you don’t have to write code here, but you do need to understand how the system works.

I’ve grown to really enjoy digging into the architecture, whiteboarding concepts with engineers, and understanding constraints deeply enough to make responsible design decisions.

It’s complex, but it’s satisfying.

We move at the pace of our customers

Our customers are among the fastest-growing SaaS and AI companies. They’re launching new products, introducing new pricing models, raising funding, and scaling quickly.

That pace influences us.

Some of our internal mechanisms worked well when customers were smaller, but now they need to evolve. We’re currently working on foundational changes that touch nearly every part of the product. We’re evolving parts of the data model, rethinking workflows, and making sure we can support customers at the next stage of growth.

It’s the largest scoped project I’ve worked on in my career, and it’s truly exciting.

When you’re designing in this environment, you’re helping shape the infrastructure that lets companies experiment, launch, and scale confidently.

High ownership, agency, and velocity

We’re a small design team, and that creates a real sense of ownership.

If I see something that’s impacting customers, I bring it up, pitch why we should tackle it, and help shape the solution.

There’s a lot of collaboration between product, engineering, and design. We jam on ideas and debate tradeoffs together. We look at our options and ask which one helps us learn fastest without compromising trust.

The culture is experimental, but not reckless. It’s fast-moving, but thoughtful.

The kind of place for curious, driven designers

If you’re a designer who loves complexity, you’ll love Orb.

You have to be excited to dig into technical domains, understand how data models influence UX decisions, and think about the downstream impact.

You also have to be comfortable moving fast, since our customers move fast too.

For me, that combination of ownership, systems thinking, and real-world impact is what makes this work meaningful. We’re designing infrastructure that companies depend on to run their revenue, and that’s a challenge worth taking on.

If this type of environment sounds like a good fit for you, check out our careers page to learn more.