Espressive
Head of Design, employee #6
Espressive was founded by two ServiceNow executives who’d watched their old company win the enterprise and lose the employee. ServiceNow shipped the plumbing; the experience was left for each company’s helpdesk to design, and helpdesks are not designers. Pat Calhoun and Fran Fernandez wanted to keep the business model and replace the experience with something people would actually use: a conversational assistant, Barista, that understood a request in plain language and resolved it or routed it. They found me through AngelList’s A-List in the fall of 2016. I joined as Head of Design and the sixth employee, designed the MVP from zero, and stayed through the launch that carried the company to its Series B. Gartner named it a Cool Vendor in 2019. It’s still shipping.
The problem
Employee portals get used by 10–15% of the people they’re built for. Everyone else calls or emails, and a password reset alone can be 30% of a service desk’s tickets. Onboarding a new hire touches IT, HR and facilities and is coordinated by nobody. The product idea was one touchpoint, a chat, that handles the simple thing instantly and walks the person through the complex thing, using the systems of record that already exist. My job was to make that touchpoint something an employee would choose over picking up the phone.
Six months of throwing things away
We started at General Catalyst’s offices with a whiteboard and no engineering team; the head of engineering wasn’t due until the following summer. So the first six months were concept work: competitive study of the service-desk world, sketches, Proto.io prototypes in front of prospective customers, and a lot of debate with two founders who knew the vertical cold. Most of it we threw away, on purpose. By the time engineering arrived we knew what resonated and what didn’t, and we built the real thing fast.
Building the MVP
With a staffed team and an aggressive timeline, the work became rapid sprints: specify a feature cross-functionally, prototype it, test it with a customer, ship it with engineering. In parallel I designed the company’s brand and launch marketing. The MVP shipped in nine months with onboarding for new and existing employees, case management, task routing, an equipment store, outage detection and notification, a service catalog, workflows, admin, and the co-branding system described below.
One system, two screens
Mobile and web wanted different layouts and different interaction models, so I built a framework that codified the differences and a design system of repeatable patterns that spanned both. The icon set was drawn as SVG so it could be recolored by the customer at runtime (that mattered; see next section).
The brand problem nobody wanted to solve
Enterprise software gets skinned. Customers put their own logo and colors on it, and the vendor disappears. Following ServiceNow’s model, everyone assumed Espressive would be white-label too. But our whole pitch was a better experience, and if the experience carried no trace of us, we’d be investing hundreds of hours in something the end user would attribute to their own IT department. Then the CEO pinged me on Slack: “Any progress on the logo?”
The answer was a character. Barista, an emoji-native assistant built on the barista-and-coffee metaphor for high-touch service, could wear the customer’s colors and still be unmistakably ours. The customer brands the environment; Barista brands the relationship. Barista also had two audiences with different needs: the IT/HR buyer who needed to trust us, and the employee who needed to like us. So there are two Baristas, an in-app one with the cup (it makes sense when you’re talking to it) and a marketing one without (outside the app the coffee just confuses people).
The wordmark’s mark is drawn from my daughter’s handwriting, which is the kind of thing you can do at employee six.
Designing for trust and for many hands
An enterprise assistant is used by more than one kind of person at once, and it’s wrong some of the time. Both facts shaped the product. Barista routed each request to IT, HR or Facilities with a confidence it didn’t hide: when it was sure it acted, when it wasn’t it asked one clarifying question, and when it couldn’t help it opened a case and handed the person to a human without losing the thread. Managers saw their team’s requests and could delegate; admins taught Barista new answers and saw where it was failing; employees only ever saw a conversation. Designing those three views as one system, with the same information showing up differently depending on who you were, was most of the interaction design work, and it’s the part of the MVP I’d build the same way today.
The team
One rogue CEO with a Proto.io license, two design reports, two VPs and a designer-developer. Consensus was walks around the block, one-to-one, added up over time. There was a bell for when meetings went off the rails.
What happened
Espressive raised its Series B on the MVP and kept going. The product I designed went on to be named a Gartner Cool Vendor in 2019, win gold for IT Service Management at the 2019 IT World Awards, a Bronze Stevie at the 2020 American Business Awards, a Forrester New Wave Leader recognition in 2020, Best IT Management Solution at the 2022 SaaS Awards, and Best Overall Bot Solution at the 2023 AI Breakthrough Awards, and it’s still selling Barista to enterprises. I left in February 2018, before any of them. They went to the product as I designed it and as the team kept building it, which is the point: a brand and a product built so they’d survive their designer. The thing I’d tell a founder now is that the brand question I nearly didn’t get to is the one that made the product defensible.
The mark Espressive runs today is mine too, one of the explorations above, still on the job.
In their words
