How Octopus Deploy Stopped Debating Messaging Internally and Started Asking Buyers

‍How one company stopped letting internal opinion drive messaging decisions.

At Octopus Deploy, a messaging disagreement used to mean the team went back and forth until someone gave up. Two people could look at the same page, hold different perspectives on what wasn't working, and have no mechanism to settle it. Eventually a version went out the door. Not because anyone was convinced. Because everyone was done.

The disagreements ran deeper than word choices. Octopus Deploy spent its first decade as a product-led company built by and for developers. Over the past several years, the business has shifted toward enterprise sales, and with that came a fundamental tension: should the website speak to the practitioners who use the product hands-on, or to the decision-makers who approve the purchase? Both camps had a legitimate read. Neither could prove the other wrong.

They tried AB testing. But Octopus Deploy isn't Amazon. They don't run millions of visits through a page. A test would run for weeks and come back: 20 conversions versus 19. Nothing. The team would interpret the results through whatever they'd already believed, and the cycle would start again.

But there was one thing nobody was even questioning. The feature they called "multi-tenancy."

Octopus Deploy has a platform capability that lets customers deploy software to hundreds or thousands of endpoints, each managed as a separate tenant. Retail kiosks, distributed infrastructure, that kind of thing. They'd called it multi-tenancy for close to ten years. In the knowledge base, on every relevant page, in sales conversations, in onboarding. Nobody questioned it because there was nothing to question. It was just the word for the thing.

Then they surveyed people who had never heard of Octopus Deploy.

"I personally don't know what 'multi-tenancy' means, but that just could be because I don't have enough context on the tool." — Jair, Software Engineer III, Enterprise (Wynter survey respondent)

The responses didn't come back with notes about the phrasing. They came back confused about what kind of company Octopus Deploy was. In most of the tech world, multi-tenancy means shared database architecture. A hosting model, not a deployment capability. The respondents thought they were looking at a completely different product.

Not a meeting. Not another round of debate. The marketing team shifted to "tenanted deployments" across positioning and messaging. A term in use for nearly a decade changed in days.

The language wasn't the point. If the one thing nobody questioned turned out to be wrong, what did that say about everything they had been going back and forth on?

That question changed something structural. Wynter surveys now happen before internal review, not after. A new page or campaign goes in front of real practitioners in the right roles while there's still time to act on what comes back. Two days, not two months. The opinions still form. They just form after the market has had a say, not instead of it.

The different perspectives haven't gone away. People at Octopus Deploy care about how the company talks about itself. They should.

What's changed is that there's a new voice in the room.

"The people we're really trying to get this in front of is ultimately prospects and customers. They will be the one who decides whether the messaging is right or not. Not really internal debates where it goes through six rounds before anyone's actually seen it — and you're like, who knows? Maybe the second one was right." — Tony Kelly, Director of Marketing, Octopus Deploy

Results at a Glance

Replaced AB testing entirely. The team hasn't run an AB test in roughly two years. Fast qualitative feedback from Wynter surveys gives them more actionable direction than traffic-based testing ever did.

Surfaced a terminology blind spot in marketing. After Wynter survey respondents consistently misinterpreted "multi-tenancy," the team repositioned around "tenanted deployments" in marketing messaging. A term that had anchored nearly a decade of customer-facing marketing changed based on clear market signal.

Shortened the path from draft to launch. By front-loading external feedback, the team reduced the cycle of internal revision that previously delayed launches. Late-stage objections can now be addressed with data rather than reopening the debate.

Produced a high-performing landing page. An ad landing page tested through Wynter became the team's best-performing paid landing page for approximately six months, outperforming pages built through the traditional multi-stakeholder review process.

Expanded into product development. The product team independently adopted Wynter surveys for feature prioritization, surveying non-customers to understand what the broader market is trying to solve rather than relying solely on existing customer feedback.

About Octopus Deploy

Octopus Deploy is a deployment automation platform that helps software teams deploy applications reliably across complex environments. Used by thousands of organizations worldwide, Octopus Deploy simplifies release management for development and operations teams.

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