Designing Espressive, an employee engagement platform for desktop, Android & iOS

Sean Ross
Sean Ross
Jun 15 · 14 min read

What I did, how I did it, what I learned, and why it matters.

Final Result: Co-Branding Espressive
  1. Intro
  2. What’s an Espressive?
  3. Process (What it’s like to design & build a complex MVP in 9 months)
  4. Radical Branding for the Enterprise: Espressive! and Barista
  5. Chatbot Personality
  6. Revolutionary Third Party Branding
  7. Features, Architecture, and Workflows — (Granular Details)
  8. Learnings


In 2016–2018 I was the Head of Design for Espressive, where I was part of the core leadership team (employee #6) building out the MVP Product Experience across web and mobile as well as the Consumer-Facing Brand, both of which centered around Barista, an AI Chat Bot with a friendly and helpful personality. The core team consisted of the CEO, Head of Product, Head of Design (myself) and Head of Engineering.

This is my attempt, a year later, to unpack and distill some of the process-oriented narratives about my time with Espressive, and highlight some things that I think might be applicable to the wider arenas of design and startup culture. My goal is to strike a balance between the pragmatically useful and the more “grey areas” of personal authenticity, which is—for me anyway—where the most flavor resides.

When you’re working in a startup environment, there’s always too much to get done on any given day. So after the fact, I’ve always been highly motivated to quickly move on to the next thing—for me, that might mean some creative downtime to work on a personal project—or in this case, being offered a similar role in another startup venture. As a result of quickly moving trains and timelines, I’ll admit that I’ve struggled with writing case studies and have mostly avoided them in favor of explaining the work in person to my next prospective employer or client.

Although I recognize how important it is, rehashing my old work is my least favorite thing to do as a designer. Learning how to make case studies more interesting for myself is part of my goal, which I hope will mean it’s more valuable for readers—and if you’re reading this because you might be interested in hiring me, perhaps when we meet in person we can spend more time discussing the latest season of Black Mirror, and less time rehashing what I did a year ago, thanks to this effort. :)

So, What’s an Espressive?

Having come from Service Now, (a SaaS provider to IT operations of large corporations, including providing help desk functionality), the CEO and Head of Product had a fairly clear vision for what they wanted Espressive to be from a feature set perspective—my role as Chief Design Officer was to make it consumer friendly. One of my reasons coming aboard is my penchant and mission for making boring things more human and unique—delightful, even. The “hole in the market” Espressive aimed to fill had to do with what was missing from Service Now’s business model—scalable user experiences. While Service Now was great at providing the needed technology, it left building out the actual user experience that interfaced with it to individual organizations—namely IT departments, with little to no experience designing software.

Espressive is designed to replace highly unpopular, oft-avoided corporate web portals with “esperiences”, natural language chat-based workflows designed to resolve simple problems instantly, and more complex issues more efficiently — through automation and machine learning, and interoperability with existing enterprise “systems of record”, such as Service Now. The core concept is one universal touchpoint to get your issue resolved. Behind the scenes, Barista uses natural language processing and neural networks to understand employee requests, and machine learning to predict the right department (IT, HR, Facilities).

Here are some of the problems Espressive solves for the enterprise:

Web Portals and Knowledgebase articles are the standard means for employees to get help at work, but they have an extremely low adoption rate (10–15%), and for good reason — they’re poorly designed, difficult to use and navigate, not well maintained, and lack the simplicity and effectiveness we’ve come to expect from consumer-grade user experiences, but unfortunately are still sorely lacking in the workplace.

When employees can’t find the answer they need, they open a case and wait in line. These issues are usually urgent in nature—meanwhile work responsibilities are put on hold… sort of like being stuck at the DMV. Barista automates many of the most common front-line use cases, allowing employees to get back to doing what they were hired to do, while allowing internal help experts to focus on key business initiatives, instead of soul-destroying repetitive tasks. It’s an important point to make that AI and automation often isn’t setting out to replace or eliminate the jobs of human beings, but to make those existing jobs more viable—to offload the “grunt work” to automated systems that can actually do a better job at it, because unlike humans, software and AI actually love “bullsh*t jobs”.

85 to 90% of employees pick up the phone or send an email to ask a question, rather than searching portals or intranets. I’ve never seen a corporate web portal that didn’t make me want to self-harm.
Instead of learning how to navigate a portal site that was designed by an intern in 1998, I always make an effort to befriend my IT person. Chances are high they will either be saving my ass the next time I spill coffee on my laptop (just before the big presentation)—or telling me to wait in line. Pre-emptively voting Superman over Lex Luthor with Kindness in the right place can make your life imminently more stress-free. Apply this rule with abandon.

Barista provides employees with immediate answers to questions and resolution to issues, easily guiding them through otherwise complex and daunting processes. Employees are less screamy and far more productive as a result.

A primary example — a simple password reset ends up costing companies dearly — in both downtime for employees, as well as in-person help desk assistance. A simple password reset accounts for up to 30% of all IT related service desk calls—an insane waste of human energy. Barista can re-set a password and have an employee back up and running in no time. You won’t even have time to run to the bathroom. But seriously, go ahead, please.

Onboarding of new hires is typically fraught with complexity that companies don’t know how to manage well, if at all. Barista solves this problem by combining complex tasks involving multiple constituencies into easy to complete workflows that allow new hires to get up and running fast. Companies with effective onboarding see a 50% increase in new hire retention. Barista integrates the onboarding process with HR and IT systems — new hires easily complete all onboarding paperwork through Barista and have their systems waiting for them at their desks on their first day in the office. How? Read on, intrepid reader…

An Amazon-like shopping experience allows employees to easily order the equipment and software they need to do their job, without fuss. (That’s how).

Another drain on productivity solved: 30–45% of IT’s time goes to detection and identification of outages after they’ve occurred. Barista identifies outages based on employee issues, notifies employees of the outage, and automatically responds to each outage-related inquiry, resulting in a 40% increase in help desk productivity during these times. Or extra smoke breaks?

Behind the scenes, Barista uses NLP and neural networks to understand employee requests, and machine learning to predict the right department: IT, HR, Facilities and more.

In short:

— Barista Makes it Easy to Get Answers

— Increases New Hire Retention

— Improves New Hire Productivity

Launch of Company to MVP in 9 Months: Not for the Faint

Much has been written (online and off) about what it’s like to work for Silicon Valley startups. After having been on the early stage startup carousel for 2 decades now, from my experience no two are alike. This is because no two founders are the same, and much—if not all—of the cultural “energy field” of an organization emanates—almost exclusively—from the founder.

What I can stand by as a generality, are two things: Working with Espressive was equally rewarding and challenging. Rewarding because Espressive was a high octane no monkey business “get s — t done” workplace, founded by a CEO who was (and still is) on a personal mission to change enterprise software for the better, who thoroughly knows what he’s up against—and is also willing to burn the midnight oil 24/7 and lie his own body down on the railroad tracks in order to get there.

And challenging? For the exact same reasons, of course.

The rewards of working for a founding CEO with a prior successful launch and exit experience are many. I learned a ton from Pat Calhoun, our CEO, about nearly every aspect of scaling up a modern technology company, and I’ve never worked for anyone in my life who worked as hard, and systematically and choreographically accurately as Pat did. He’s a force of nature and coupled with his high integrity, there’s no doubt in my mind that my Espressive stock options will someday be worth every penny I paid for them.

A lot of what can suffer in this type of environment are the same things that designers are actively in charge of delivering, though—creative problem-solving, which isn’t by the numbers and often doesn’t arrive in a “made to order” capacity. As it turns out, I’m not alone in feeling this way. I’ll dissect this more a bit later when I dive into some creative highlights of the project.

My work on Espressive began in a somewhat chaotic fashion, as our Head of Engineering wasn’t due to arrive for several months, and she was a lynchpin in structuring the work in a way that a project manager would. The first several months were mostly about cleaning up the CEO’s early prototype, which was made in (IMHO a dreadful tool), and sketching out early concepts for how the visionaries (Pat the CEO and Fran Fernandez, Head of Product) understood things from a feature-wise perspective, so that our front end engineer could start to architect how the build was going to behave, and so that Pat had a better demo design to present to prospects in the field. This included an initial pass at the onboarding experience, purchasing/catalog, as well as a later abandoned feature we called accolades. Here are some very early examples.

Early Visual Wireframes/Vision: New Hire Onboarding
Early Vision/Wireframes: Existing Employee Accept Existing Gear, & Get Help
Early Vision/Wirefraames: New Employee Accept New Gear, & Get Help, + My Gear, Install Software, Manager Approval, etc.
More Insane Gear Flows
More flows, replete with the earliest iteration of Barista, at this point an extremely unfriendly cup of sorrow.
Early Chat Flows
Onboarding Tasks: New Hire Orientation
Early concept, also later abandoned, for a company leaderboard, replete with asinine fake names.
Early Company Directory Concepts

At this early stage, I considered these functional wireframes, but they had to also be good enough to provide visual design direction so that the working prototype felt legitimate and real. This gave us a proper “test bed” to validate these concepts with potential customers, as well as get feedback from our board. Not having yet begun any work on my vision for branding Espressive, I struck a balance here between visually “believable”, but also intentionally slightly “off kilter” so that nobody would fall in love with the design before I had the chance to think things through, independent of establishing the nuts and bolts of the user experience. In hindsight, I admit it was a slightly weird line in the sand, but one that made sense to me at the time.

The Egregious Misuse of Color

As the early designs progressed, we also realized that we needed to start thinking about mobile and web differently, and the design efforts focused on building a framework to understand the differences in layout and interaction models, and we built out a scalable repeatable system of patterns.

Mobile Vs. Web Design System

A question emerged early on about tenant branding. It was a known fact in the space (using Service Now as the standard) that customers would want to “own” or “skin” the branding of Espressive. The open question was precisely how much, to what extent, and most importantly, whether Espressive could really be branded at all under those constraints—would Espressive be completely subsumed by the client’s corporate branding? How would we then “imprint” the unique value proposition to the end user in such an environment? Was that outcome a potentially huge loss? My sense is that it would be, and that it was imperative to find a way to meaningfully claim it. You don’t invest hundreds of hours innovating unique user experiences and not claim the branding of them.

Co-branding became an ongoing concern that the more screens and flows got worked out, became more top-of-mind. In order for us to not just be another white label generic enterprise product, I knew we needed to find a meaningful way to bake in our branding at the molecular level. This wasn’t simply about logo placement—I knew that battle wasn’t worth fighting over. This was something else, at the time I just didn’t know what it was—but I remember saying “Guys, it’s not about the logos. It’s something else,” to a bunch of confused faces and silence.

Radical Branding for the Enterprise: Espressive! and Barista

Around this time I got a ping over Slack asking about the company logo. It read:

Any progress on the logo? I think the building people want something other than an unprofessional paper on the door.

I had been so busy with architecting features and flows, that I hadn’t had a moment to focus on the brand side of things. But instead of furiously designing logos to appease the building management, I began carving out a design brief focused on clarifying in words what a solid brand should accomplish for us.

From the outset, I’d learned about the nuances of audience segments as it relates to brand from my time at eBay, which utilized a framework that addressed both buyers and sellers differently. Our situation was similar in complexity, in that we had a primary paying customer—the IT/HR “buyer” whom we needed to speak directly to and gain trust with—but our primary user (and therefore likely to become an enthusiastic evangelist) was the enterprise employee. Our competitor was none other than Service Now, who technically-speaking dominated the space, without serving the real needs of either party. These were the personas and business environment which comprised a baseline framework for exploring what would become the consumer-facing brand for Espressive.

It was around this time that “Emoji: The Movie” came out, and I began noticing emoji-everything everywhere—not just in movies, but advertising—and not just advertising for tech, but basically everything under the sun. Emojis had become culturally mainstream. I knew Barista was a great concept, but it lacked a distinctive personality. During a week-long sprint, it all came together under one umbrella. Barista would be the lynchpin of the brand: the purveyor of our tone and voice, and a constant reminder that it was Espressive underpinning the user experience, regardless of the logo that was layered over the top.

Espressive! Branding

The best part? Barista could wear third party brand colors without breaking a sweat. Everything suddenly clicked together inside the user interface as well. Introducing the variable of a primary brand color reduced the clutter that had been accumulated in the discovery phase of the designs—in one fell swoop, I had solved the issue of our brand, co-branding, and ultimately what our UI design system was going to be.

Another HUGE issue that was solved was my fear that Espressive was going to be mistaken as having something to do with coffee beverages. I loved the metaphor of the Barista being a high touch helpful enabler of the modern workforce, but I worried that from a brand perspective the coffee cup was too much for anyone to understand at first glance. So a deal was struck to keep the coffee cup out of the brand, using just the face. The more fully developed iteration of Barista would only occur inside the UX, where it made sense contextually.

Espressive! Co-Branding

The Espressive Logo

Enterprise branding is generally rather stale and uninspired
Consumer-oriented branding in tech has more personality

A lot of brands in the enterprise space are speaking to executives.
Espressive works best when it speaks to humans in an accessible, personable language.
It should be able to be buttoned up, but also casual.
Having a point of view and a personality is more than just icing, it’s the cake.

For the logo, I knew I wanted something that would stand out among enterprise software to be more personable and unique. Humanistic and friendly. In a similar way that Facebook branded their like button, Evernote had that wonderful elephant with the slightly bent ear, I wanted Espressive to have something that no-one else could claim. I’m not sure it can be said that what ended up coming to pass was 100% original, but for the enterprise space, I believe it is—and that’s what matters in the end. The word Espressive simply felt better to me with an exclamation point after it. Since Yahoo! was basically dead to rights, I felt should steal it from them—truthfully I’m not sure anyone would even notice the relation.

I also had to fight pretty hard for the handwritten type—someone on our team said the E looked too… NSFW. My response? Good! People take notice of all things NSFW. (I won the argument).

Early type studies
Early handwritten type studies
Type Variations
Type and Brand Ideations
Co-Branded Mobile & Web

Sean Ross

Written by

Sean Ross

Cross-disciplinary design veteran, MFA @ CCA. High EQ/polymath/stoic philosopher/visual artist/producer/songwriter

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