How Infrastructure Kills ISV Deals (Even When the Product’s Strong)

Infrastructure doesn’t usually come up on the first few calls, especially when you’re selling software that’s typically offered as a SaaS.

But that changes fast the moment a buyer says, “Can we run this in our self-managed environment?”

It shows up later.

When the buyer brings in their infrastructure or security lead and starts asking how this thing will run in their environment.

That’s when things change. You’re not just selling features anymore. You’re being evaluated on install, updates, monitoring, support, and whether your team can deliver in more than one setup.

Most ISVs aren’t ready for that shift. They’ve built for the cloud, optimized for speed, and pushed infrastructure planning down the line.

But once you’re in the room with enterprise buyers, that gap becomes the risk. 

That’s when the deal slows, stalls, or stops.

You’re Not Just Shipping Code. You’re Shipping Infrastructure.

Most ISVs still think they're selling a product. 

They’re not. 

The moment a buyer asks, “How does this run on our infrastructure?” you’re no longer in a product conversation. You’re in a delivery conversation.

And if you can't answer those questions with clarity, confidence drops fast. You lose control of the deal.

You know it’s happening when a buyer brings in their security team or infrastructure lead. That’s the tell. They’re not asking if it works. They’re asking how it’s going to live in their world.

The product may have already cleared technical validation. But if delivery isn’t clear, consistent, and supportable, the risk gets passed back to the buyer. Most buyers won’t carry it.

That’s when the sales cycle gets stuck, not during the demo or when they see your roadmap. It happens during procurement, security review, or deployment planning. The part of the process most ISVs don’t prepare for because they treat infrastructure like an implementation detail instead of part of the product.

And if you somehow stumble through and close the deal without solving this? You end up with shelfware. The installation’s too complex, support can’t keep up, and the renewal never comes.

What Enterprise Infrastructure Teams Ask Before Close

Infrastructure doesn’t usually come up on the first call. It shows up later, during procurement or deployment planning when security or infrastructure leads get involved.

Most ISVs aren’t ready for that shift. 

They shortcut delivery planning early on, especially if they come from a cloud-native or SaaS background. So when infrastructure questions start getting asked, the answers aren’t clear. 

That kills momentum.

These are the questions that stall or sink deals:

• Can you support multiple Kubernetes distributions?
• What’s your upgrade and rollback process across environments?
• Can customers monitor deployments without needing to learn Kubernetes?
• How do you manage identity and access in each install?
• Who owns the outcome when the install fails?
• How do you patch security issues in isolated or air-gapped environments?
• What happens when something breaks and the client says it’s your fault?

If your team doesn’t have clear, consistent answers, the buyer starts seeing friction.

It’s not about blame. It’s about confidence. 

The deal doesn’t move forward because no one trusts the handoff.

What Broke When One ISV Tried to Sell On-Prem

We worked with an ISV that came to us thinking the issue was their sales process. It wasn’t. The product was solid. The message was clear. But the second the buyer asked for on-premise support, everything stalled.

They were getting enterprise interest, but buyers wanted self-managed, multi-client deployments. 

And while the platform technically ran on Kubernetes, there was no consistent install process. No monitoring model that worked outside their hosted environment. No real plan for updates, rollbacks, or support once the software left their hands.

They were built for a single environment. And now they were being asked to run in three or four. That’s where things started to break.

We helped them build out a productized delivery layer. Something that could be installed the same way across environments. Something that gave the customer visibility without needing to learn Kubernetes. Something that didn’t fall apart the second it left the cloud.

That dropped install time from weeks to days. But more importantly, it let their team speak with confidence during the deal because they weren’t guessing or scrambling to answer infrastructure questions.

And that allowed them to better serve existing and new customers.

A Lack of Infrastructure Agility Derails Sales Teams

Most of the time, the sales team thinks the sale will go smoothly. The demo lands. The buyer nods. And everyone’s excited.

Then the buyer pulls in their infrastructure team or their security lead. Now they want to talk about how this thing actually runs. Not what it does, but how it gets installed, updated, and supported.

That’s where the problems start.

A lot of ISVs haven’t prepared for that moment. They’ve got one deployment model (usually the cloud). So when the buyer asks about on-premise or hybrid, there’s no install process, support plan, monitoring, or rollback. They have nothing the team can explain with confidence.

Sometimes that kills the deal outright. Other times it closes anyway, but the installation never finishes. The platform sits there as shelfware, half deployed, and the buyer starts looking at something else. Now support is stuck, sales gets blamed, and the hope for renewal is gone.

Delivery teams end up rebuilding installs from scratch. And support can’t train new hires because nothing’s consistent. Each deal becomes a one-off engagement that stretches the team thin.

You don’t fix that with better onboarding. You fix it with infrastructure that works the same way across environments so your sales, delivery, and support teams aren’t guessing every time someone wants to run your product a different way.

ISVs Aren’t Ready for Critical Infrastructure Questions

Enterprise buyers are asking tougher questions.

They want to know how your product runs. Not just in the cloud, but on-prem, in private cloud, or across environments. And they’re not asking because they’re curious. They’re asking because someone on their end (security, compliance, legal) is forcing the issue.

Most ISVs aren’t ready. They were built to run in the cloud (opening the door to risk). Their whole delivery model assumes they control the environment.

So when a buyer asks for on-prem, they shrug. Maybe they’ve tried Kubernetes. Maybe it runs in dev. But there’s no consistent install process. No plan for upgrades or monitoring. No support model the team can explain without guessing.

That’s when the deal starts to slip.

Infrastructure agility is how you stay in control.

It gives you a consistent way to deploy, update, and support your product—regardless of where it runs. So when the buyer brings in their infra team, you’re not scrambling to answer basic questions.

Most teams assume Kubernetes is too complex. That it takes too much to support. But usually, no one’s told them which parts actually matter. The ecosystem is huge. The guidance isn’t.

That’s where teams get stuck. And where we usually step in.

Buyers expect you to be ready.

If you’re not, they’ll move on.

Your Next Move

Before you chase the next enterprise deal, step back and ask:

If three new customers showed up next quarter (each with different infrastructure requirements) could you handle it without breaking?

Most ISVs can’t. Not because the product isn’t good. But because the delivery model wasn’t built for variation.

Infrastructure agility changes that.

One way to deploy. One way to patch. One way to monitor. It doesn’t matter where it runs. The playbook stays the same.

Most teams get there by standardizing on Kubernetes because it works the same everywhere. 

That’s the point.

We tell teams to run a pre-mortem. Not a demo. Not a roadmap review. A delivery premortem:

• What happens when the installation fails?
• What happens when the patch is late?
• What happens when the client says, “This is on you”?

You don’t need every answer today. 

But if you can’t see the shape of the problems, you’re not ready.

If you don’t fix them, it’s not just sales that suffers. Support burns out. Renewals vanish. 

And the product that should’ve worked ends up collecting dust.

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About the author

Derrick Sutherland - Chief Architect at Shadow-Soft

Derrick is a T-shaped technologist who can think broadly and deeply simultaneously. He holds a master's degree in cyber security, develops applications in multiple languages, and is a Kubernetes expert.