Jenny Ji—Why I joined Orb
On the heels of our Series A funding announcement, we’re sharing a bit more about the humans building Orb. I sat down with Orb’s Head of Design, Jenny Ji, to learn about how she's developed her design skills, and what has informed her approach to work.
I’m curious to hear what sparked your interest in design. Were you an artist? Or did you always know that you wanted to do technical product design and build startups?
(Laugh) Neither! As a kid, I took lots of art classes, but it was a hobby that fell by the wayside as I got older. Still to this day, I don't draw well. But I liked graphic design - really what it comes down to is problem solving. I was 100% committed to being a print designer.
Print! What? Not interactive?
Web design was so limited at the time! Digital was clearly the future and I was fortunate enough to be at a studio where they were willing to invest in me. I got a crash course in interactive design and learned enough code to build everything I designed; that’s really served me well over the course of my career.
So how did your early work in agencies get you to where you are today?
I got to learn. I wasn’t restricted to any single medium or industry. I did a ton of brand and communications work, experienced the ups and downs of e-commerce, worked on integrated campaigns, dabbled in exhibit design, and made the jump to freelance. Being in SF also meant I had a front row seat to the rise of apps. Definitely got thrown into the deep end on a couple of projects, but those experiences really shaped me as a designer.
Freelancing provided you with growth opportunities, but it can be a pretty tough gig, especially in San Francisco where there is a lot of talent, and it’s not cheap to live here. How did you make it work?
I've been really blessed to work with a lot of people in my career that have been my advocate. Clients that have pulled me aside after I shared a bid and said “No, no, no. We are gonna pay you what you're worth.” I’ve had a client tell me “I’d love to hire you full time, but I can tell that your heart’s not in it, and you’re not going to be happy unless you’re passionate.” And that client continuously connected me with new work. And I’ve really tried to carry that forward, because that's what we should be doing with talented folks who are helping us build our businesses.
So how did you go from agency/freelancing to in-house in the tech space?
Completely by accident! I knew one of the co-founders at Path, and he asked me to come by for lunch to talk about design. We finished up and I left and said to myself “I think I just interviewed for a job except I don't know what job I interviewed for and what I'm getting myself into.” I spent two years at Path - my first experience at a startup, but also my first job where I really believed in what we were building. And two years of continued learning–the first time I worked with a product manager (not the kind of PM I was used to!), finding product market fit, what’s a monetization strategy–I could go on and on. Looking back, it should have been terrifying but everything was moving so fast that it was mostly just exciting.
After spending your entire career in the consumer space, how did you end up in B2B?
I had returned to freelancing when I got connected to the CTO at BuildingConnected. They weren’t sure about bringing on a full-time designer and I wasn’t ready to go back to in-house. A short term contract to get them set up with a design system seemed like the perfect fit for both sides. About three weeks in, I had this moment where I just thought to myself, “These are amazing people. There's an opportunity here if this company continues to grow in scale.” BuildingConnected was building something that directly impacted the way people tackled their work. It’s not a flashy or sexy problem, but it’s tangible and impactful.
The downside of freelancing is that you often move on before you get to see the results of your work. As a freelance designer I can't build a company. I can't scale a company. I can't build or scale a team. I can maybe lead a project team from time to time, but the impact won’t be the same. I joined in 2015 and 3.5 years later, we were acquired by Autodesk. In that time, I’d built out and led a team of 26. The company had gone from 20 people to 250. And that was a great arc - start from nothing, build a design system, build a design team, transition the company into a larger organization.
And staying on in the corporate environment wasn’t where your heart was?
There is a lot to be said for doing the executive leadership work in a large corporation. I really appreciate what I was able to learn and do there, but I missed the hands-on work. At my core, I’m still a designer and I love designing products and solving problems that way. So I went back to freelance again, taking on project work, which is when I was introduced to Orb’s CEO, Alvaro. And we started off similarly to the way I started off with my last company: with a small freelance project.
And you were immediately thrilled with the usage-based billing and pricing space?
Yes and no. I took the project because it was intriguing - another opportunity to learn. On the other hand, I was really burnt out from the acquisition and managing/sustaining through the pandemic so I don’t know if I would have been “thrilled” with anything. But I really loved working with Alvaro and Kshitij—they’re just great human beings—and then as I dug into the work at Orb, the more I found that the problem space started to get really interesting.
So you start on this freelance project and start seeing the opportunity. What did it take for you to end up as Orb’s Head of Design?
We hit an inflection point after a few months when it became clear that Orb was ready for a dedicated full time designer. The big question was around the role. I can't shut off the part of my brain that thinks about strategy and scaling and everything else that goes into building a company. Orb made a distinct choice to pull forward a key executive hire knowing that it's not a decision many seed stage companies would make. That speaks not only to our commitment to design, but also the importance of design to our product’s success. As we add layers of complexity, we could just slap some solutions on it. But that’s going to create a mess. And that’s just not the kind of product Orb is committed to building.
What is the biggest challenge for design right now?
Complexity. It would be one thing if we were just building a metering product because only certain people care about metering and how it works. But we aren't. We're building an end-to-end solution. And while it’s really important to get metering done correctly, and it’s important that we make it easy to set up plans and pricing options - those are parts of the revenue workflow that engineering and product folks care more about. But the true surface area for Orb touches RevOps, Finance, your CRO, your CGO.
Building something that recognizes revenue correctly is not just a technical challenge, it’s a communication challenge. How do we show how revenue is recognized? And how will that differ for the finance teams at, say, earlier stage companies, vs. those getting ready for an IPO, vs. a more established public company? All of these touch points across the entire revenue workflow. It’s not just who's interacting with what, but also what are the ramifications of actions upstream and downstream. Then add in all of the different pricing models that we're trying to account for… it’s complicated. But the solution can’t be complicated. It has to be intuitive without sacrificing accuracy. Big gnarly problems for design to solve.
If this kind of big, gnarly work sounds interesting to you, we’re hiring.