Enterprise Fun and Games

Adam Hecht
5 min readNov 16, 2020

A Different Way to Think About “Gamifying” Enterprise B2B Software

There are many things I don’t understand about myself. The one I want to focus on today is why I continue playing a video game that I’ve already beaten. Specifically, I am referring to From Software’s incredible Sekiro: Shadows Die Twice.

For those unfamiliar, From Software is notorious for making games featuring brutally difficult enemies with mechanics that punish the player for dying too frequently, with a storyline that is convoluted at best and inscrutable at worst. Indeed, they created (some say revived) a highly addictive experience that kept gamers of all skill levels coming back to play over and over again for the sheer sake of playing itself— not to collect all the items or experience the story for a second or third time.

Generating an emotional response from users has always been the bread and butter of gaming. Sekiro pulled me in because of its incredible challenge, and made me want to be better than the AI. After I beat it the first time, I had to beat it on higher difficulty. Then I had to beat it without using this-or-that ability. Why? For the love of god, why? Why play the same game over and over again if the only thing that changes is the difficulty?

The rush of triumphing over a massive challenge was enough to keep me coming back, and even had me creating my own artificial challenges as part of my own perceived progression. There was no award, no commission check, no bonus tied to me beating the game for the 5th time, and yet I wanted to do it despite the hours it would cost. In short, it was fun to beat the game over and over.

How can we as product managers build software that creates the same emotional response of wanting to “conquer the game” for the fun of it? Especially B2B software?

For strictly consumer software and for software with blended consumer/B2B uses (like Superhuman, Basecamp, and Asana), creating emotional responses and gamification features is a bit less complex. In fact, Rahul Vohra, CEO of the aforementioned Superhuman, gave an incredible interview to Patrick O’Shaughnessy where he touches on this topic (in addition to dozens of others). I highly recommend a listen.

For enterprise B2B software though, where I’ve spent my entire career, it’s a little bit different. After all, business is…well, serious business. But gamification doesn’t necessarily mean “give users badges for stuff” or cheesy leveling mechanics. It can be as simple as recreating the best parts of video games within a B2B context. There are several key things you can do as part of your app’s product vision that will inherently create the same pull to use your software that gamers feel when wanting to defeat the final boss for the umpteenth time.

  • Max Out Ability Points in User Experience

Game designers can (and do) run clinics on user experience for good reason. From menu design to input reaction to information presentation, video games are the gold standard in solid UI/UX. When users push B or Square or X on their video game controller, they have a VERY good idea of what might happen. The first time a user loads up the latest first-person shooter on their PC, they know exactly what WASD will cause their character to do. And this is all without instructions, as control schema are typically hidden away in submenus of the game pause screen. As Donald Norman puts it, “Any time you see signs or labels added to a device, it is an indication of bad design: a simple lock should not require instructions.” By this definition, video games are exquisitely designed.

As such, you should try as best you can for a simplified/streamlined user experience for your B2B software. Automate, templatize, and standardize across you entire app while minimizing required clicks and inputs. For example, make sure that the “Create” button means the same thing for one object as it does for another. Even more important, don’t call it “Create” on one screen and “Add New” on another. And if your analytics tells you that 95% of your users click the same 5 options after clicking “Create” for a given object, offer them a template!

If all else fails, an in-app tutorial with dummy objects and workflow walkthroughs is always an option.

  • Achievement Unlocked: Great Communication

Open world games like Skyrim and Grand Theft Auto have massive maps for the player to explore. Some quests take the player from one side of the world to the other, and while old-school games might not have offered directions, waypoints, hints, and guide markers are ubiquitous now. And for good reason! If I only have one hour to play a game, I want to make progress. Endless searching for a town with no name isn’t progress! Tell me to go east then north.

Users of B2B software are equally pressed for time, and want to make progress on whatever task they’ve logged in to do. Give them waypoints, directions, hints, and markers. In my own career I’ve focused quite a bit on error messages. As Director of Product Management at Boostr, one of my core design principles was always, “If it didn’t work, tell the user why.” Let’s clarify that to say, “If it didn’t work, tell the user why in plain english.” No one wants to read “The app encountered an error,” or “Error Code 23341212: Invalid JSON Object received by server.” Give them their hint: “Error Code 23341212: Missing Required Field “Contact Name.”

  • Reward the Explorers

This may seem obvious, but it’s worth stating outright: if you have power users, make them feel, well, powerful. Games love giving their most dedicated players some incredible gear. It’s their reward for fully exploring the world the designers created.

Aim to build software with a low barrier of entry but a high skill ceiling. That doesn’t mean “build hyper-complex functions,” but if you are working on true enterprise tools, you should have robust capabilities that allow your users to power most if not all of the aspects of their business your software purports to solve.

If you’re building a CRM, make sure you can manage contacts, pipeline, forecasts, and more. A good example of a “power user” feature for a CRM would be the ability to customize the revenue recognition separately from the bookings as part of your forecasting functionality. Maybe you book business and give your sellers quota/commission credit in the quarter where the deal closes, but you recognize the revenue as customers pay quarterly. You would potentially want two separate forecasts if your software is designed to power both sales AND finance.

Building B2B software is simultaneously more and less straightforward than consumer tools, which really just reveals that builders of all types of software face unique challenges. There are lessons on both sides, and while “gamifying” and building addictive features are usually considered to be in the consumer domain, there are ways to apply those learnings in the B2B in a way that leads to better, more robust software.



Adam Hecht

Lover of Product Management as a discipline, software as a service, data science as a hobby, and Iron Maiden as a band.