From Glossier to Chord Commerce: Lessons in Building Enterprise Software for Operators

From Glossier to Chord Commerce: Lessons in Building Enterprise Software for Operators

Most enterprise software companies start with a product idea and look for customers. But what happens when you build software after spending years in your customers’ shoes? In a recent episode of Category Visionaries, Bryan Mahoney shared how his experience as Glossier’s CTO shaped Chord Commerce’s approach to building enterprise software.

The Operator’s Journey

The path from operator to software builder wasn’t planned. Bryan recalls a pivotal conversation with Henry Davis at Glossier: “I remember one day debriefing on a candidate that I’d recently interviewed with Henry, and we agreed that it wasn’t the candidate they wanted to hire. And he made this joke, boy, it’d be great if we could hire you. And then we’d both laugh uncomfortably.”

That uncomfortable laugh led to Bryan becoming Glossier’s CTO, where he spent four years building the technology that would shape his understanding of what commerce operators really need.

Building from Experience

When Bryan and Henry later started Arfa (which would evolve into Chord), they approached software development differently from typical enterprise companies. As Bryan explains: “We really believe that we’re operators. We had created a system as operators for other operators… we know where the hard parts are and we really felt like we’ve been able to productize, like I said, sort of decades of experience.”

Understanding Real Pain Points

Their operational experience helped them identify problems that weren’t obvious to traditional software companies. Bryan notes: “Each one of these apps creates a data silo that makes it increasingly difficult for you to have a really holistic view of your entire customer.”

The Evolution of Product Focus

This deep understanding led to multiple iterations of their product. Bryan describes their latest focus: “Recently, we have decided to focus almost exclusively on that latter part, the commerce data platform, where we’re more agnostic to your storefront technology and your order management system or commerce back office technology.”

Building with Early Adopters

Instead of building in isolation, Chord engaged early customers as development partners. Bryan advises: “Find some brands that are willing to build with you… willing to exchange the fact that we’re riskier and we’re early stage in exchange for having some amount of influence over our product roadmap and build with them.”

Key Lessons for Operator-Led Software

1. Start with Real Problems Don’t start with technology looking for a problem. Start with problems you’ve personally experienced and solved.
2. Focus on Core Challenges Bryan emphasizes looking beyond surface-level issues: “The hard parts of commerce used to be the storefront experience and the checkout experience… commerce is really a part of like all of our experiences.”
3. Build for Sophistication Their ideal customers are “brands that want to connect with their customers and deliver these differentiated experiences… brands that want to collect first party data, that want to have all of their first party data in one place.”
4. Stay Connected to Operators Maintain close relationships with customers to ensure your product evolves with their needs.

The Future View

This operator-led approach shapes how Chord views the future of commerce. As Bryan notes: “If you’re not collecting great data, if you’re not leveraging your own channels to learn more about your customers, then you’re going to be left behind. I just don’t think you can build a great and durable brand without doing that.”

For founders building enterprise software, Chord’s journey offers a crucial lesson: deep operational experience isn’t just helpful for product development – it’s transformative. It changes how you identify problems, build solutions, and engage with customers.

The key isn’t just building features that operators want – it’s understanding the strategic challenges they face and building solutions that give them “superpowers” to solve those challenges more effectively.