Mental Health & Safety of Enterprise Software Sales

I should probably admit it: I’m an Optimizely addict. I’ve been using since 2007.

My role has always been about customer care - trying to understand the three people who live inside every client:

1. The buyer — who has to justify the spend.

2. The supporter — who has to keep it upright when it wobbles.

3. The user — who presses publish.

I listen, I try to connect the dots. And I’ve seen how differently the same product lands with each of them. And it’s always different. Good, bad or otherwise.

Of course, Optimizely is hugely successful. It’s the market leader by all measures. And like any good tech leader, it has an annual conference. Opticon is part showcase and part pep rally. Tote bags, rooftop vibes, lots of clapping.

I go, I learn, I catch up with people. I do sip the Kool-Aid, but I don’t swallow. Not because I’m cynical, but because there’s one small problem that’s bugged me for years. It’s about the disconnection between the target persona and the actual one.

The Buyer

Enterprise software is usually bought by IT, not marketing. Marketing attend the pitch, but IT has to live with the consequences. They support it. They field the tickets. They get the late-night call when a deployment needs a rollback.

Which is why IT doesn’t buy hype or the theatre of software promises. Truth is, they roll their eyes at it. They buy resilience, extensibility, interoperability. They buy safety, predictability and value for money.

Yet much of the positioning is written for CMOs.

It’s an awkward mismatch which maybe explains why adoption stories stall and why true blockbuster case studies are rare.

Outcomes are claimed:

"Our business grew by 50%"

But few truly believe. More often than not - it’s correlation dressed as causation.

The User

The day-to-day users definitely aren’t CMOs either. They’re usually a handful of editors, trained to publish content.

Meanwhile, marketing are genuinely stressed out - their calendars are littered with unmissable, immovable urgent deadlines: campaigns to launch, assets to wrangle, logistics to lockdown, approvals to secure from stakeholders who feel impossible to please, multiple-agencies to herd, media to buy, analytics to analyse that never quite line up.

When every day is fire-fighting, nobody is queuing up to create six variants of a page. Nobody is logging in to tweak a button colour. For most marketers, the CMS is someone else’s job.

So while the line says “marketers will love it,” the truth is more like: marketers barely touch it.

Too Slow to Value

The best platforms need skilled people to unlock them. That’s expected. What isn’t expected is the fog that follows.

• Personalisation is powerful… once the data’s all integrated and wired up properly.

• Experimentation is slick… once engineering has the bandwidth to configure it just so.

• Analytics are detailed… though most teams still prefer GA4, however flaky the baselines are.

A software product’s ‘potential’ doesn’t get an IT Director’s heart racing. Ease of operation does. More bluntly, if it takes a month of config and a set of training courses to ‘enable’ a feature, it probably won’t happen. If personalisation means opening up Jira, its DOA.

The problem isn’t that the platform is bad, it's not, it's best-in-class. It’s that the funnel of tasks - from hope to idea to execution - is too complicated for the rhythm of real marketing teams, and it’s made even harder in organisations where marketing is decentralised globally.

Meanwhile in IT…

IT didn’t buy a dream. They bought a product. They’re watching to see how it’s used, how brittle it is to maintain, how well it integrates with the rest of their stack. If a younger rival arrives with cleaner interoperability, stronger support, more predictable pricing, and an interface as easy as ChatGPT (or whatever comes next)… it’s gonna be of interest.

So What Now?

We know, and we accept that selling to the marketplace demands a degree of showmanship. Who doesn’t secretly want to be like Steve Jobs announcing the iPhone to great rapture? But I'd argue that selling to the enterprise customer isn’t about dazzling features. It’s about trust and clarity - as well as confidence.

Make it easy to launch.

Easy to measure.

Easy to iterate.

Easy to prove impact.

Make it feel like a tool teams want to use, not one they’ve been trained to tolerate.

Because there’s still too little compelling evidence that digital experience platforms solve the day to day pain of marketing (or IT) teams:

• Does it help us make better content?

• Does it make attribution easier without having to dial in the BI team?

• Does it save us time, reduce risk, and cut the cognitive load?

Yes or no?

If yes. Show me how. Now. Right now.

If the answer is “it depends… on the version… on the implementation,” we’re losing the room.

Our Approach

At First Three Things, we don’t pitch fantasies.

We make Optimizely work the way enterprise buyers expect: stable, extensible, interoperable, and well supported.

We start with the platform, not a PowerPoint deck of beautiful slides.

We design the architecture.

We build what’s needed.

And we strip out the friction until buyers, supporters, and editors all see value.

That’s what mental health and safety really looks like in enterprise tech.