Land your first enterprise SaaS deal?

This past week has been an interesting one. I’ve started getting recognized by some bigger company names - the kind of companies whose founders I’ve admired for years.

They’ve been reaching out for legal help, which has been both humbling and energizing. It’s also a good reminder of how powerful building a personal brand can be when you show up consistently.

On the flip side, I noticed a gap in my own habits. I sometimes forget to extend podcast invites, even when conversations with great guests are right in front of me.

That’s something I need to be more deliberate about, because relationships compound just as much as content does.

The biggest lesson, however, has been around relevance. Whenever I share something fresh - like a draft I’ve been working on or a new regulatory update - it resonates.

People appreciate insights that are both timely and grounded in real-world practice. It reinforced for me that consistency and relevance are what compound over time, not chasing trends or copying others.

Enough about my life updates, now onto today's lesson.

The Trap of Enterprise Support

Landing your first enterprise SaaS deal is a thrilling moment. You celebrate with your team. The client is excited. Everyone feels like they’ve just crossed a major milestone.

But often, the excitement is quickly followed by reality. The late-night calls begin:

“Server’s down.”

“Bug just popped up.”

“Can you fix this right now?”

At first, you respond immediately. It feels like the right thing to do. You don’t want to risk disappointing the client you worked so hard to land.

But the moment you do it once, you’ve set a precedent. The unspoken assumption becomes that you’re on call 24/7. No limits. No boundaries.

And over time, this silent expectation erodes your team’s morale, strains your culture, and creates promises you never meant to make.

The real problem? Nobody ever said otherwise. When support hours aren’t explicitly defined in your contracts, the default assumption is “always available.” And that’s exactly where most SaaS founders trip up.

Why Enterprise Clients Won’t Push Back

Enterprise clients rarely raise the issue of limits because unlimited access benefits them. If you’re willing to answer every call, they will gladly take it.

It’s your responsibility to set boundaries before those expectations drain your team.

This is about being sustainable. Clients respect clarity more than they respect silence. And if you never define limits, you’re giving away something priceless: your team’s time and energy.

How to Fix It

Protecting your company doesn’t just require saying “no” to clients. It requires structure.

1/ Define support hours clearly. Spell it out in your SLA. Is it 9-to-5 on business days? Is it only during local hours? Put it in writing.

2/ Create an escalation ladder. Critical outages deserve urgent handling, but “critical” must be defined. Not every bug is an emergency.

3/ Charge for after-hours coverage. If a client truly needs round-the-clock support, let them pay for it. Many won’t, but the ones who do will make it worth your team’s time.

The truth is, clients rarely object to paying for additional support once you set the terms. But they’ll never be the ones to bring it up. That responsibility falls squarely on you.

TL;DR

Enterprise SaaS clients will assume you’re always available unless your contracts say otherwise.

So define your support hours, create an escalation process, and charge for after-hours coverage. Boundaries don’t hurt relationships - they protect them.

Conclusion

In SaaS, the danger isn’t always in the code, the infrastructure, or even the market competition. Often, it’s in the silent expectations that slowly grow unchecked. Support hours are one of the clearest examples of this.

When you burn out your team to keep one client happy, you don’t just risk losing that client; you risk losing ten others who depend on your stability.

The smartest SaaS companies know that boundaries are not barriers. They are what make long-term relationships possible.

Your job isn’t to be available at all times. Your job is to deliver value consistently, sustainably, and on terms that both you and your clients understand.

And that only happens when you put the boundaries in writing before the first late-night call ever comes in.