What I Wish I Knew Before Our First Enterprise Deal

I run a small SaaS company. Two years in, we landed the meeting every founder dreams about. A well-known enterprise wanted to roll our product out across several of their teams. The call went great.

Written by: Lily James

Published on: June 4, 2026

I run a small SaaS company. Two years in, we landed the meeting every founder dreams about. A well-known enterprise wanted to roll our product out across several of their teams. The call went great. I was already counting the revenue in my head.

Then, their procurement team sent over a security questionnaire, a spreadsheet with more than ninety questions. How often do you scan for weaknesses? How do you track and fix them? What’s exposed to the internet? I stared at it and realized I couldn’t honestly answer most of it. We had been so busy building that security had become the thing we would handle someday. Someday had finally come, and with a deadline.

The Two Weeks I Didn’t See Coming

What followed were two stressful weeks. We pulled engineers off real work to run checks we should have been running all along. We tried a few free tools, drowned in confusing reports, and argued about which problems were serious. Most of the issues turned out to be minor. But working this out by hand, while the deadline loomed, took a real toll.

Somewhere in this mess, a fellow founder told me to stop reinventing the wheel and pointed me to https://topscan.me/. I was skeptical. I had already lost days to tools that promised a lot and delivered noise. Still, we were short on better ideas, so I gave it a shot.

What I Learned the Hard Way

Looking back, the true lesson wasn’t about any product. It was about timing. Security reviews aren’t really about being perfect. They are about being able to show your work. Here’s what I would have done differently from day one:

  • Start scanning early, so there’s a record to point to instead of a frantic snapshot.
  • Keep notes on what you found and how you fixed it, since buyers care about the process as much as the result.
  • Watch what’s reachable from the internet, because that’s what a buyer worries about most.
  • Make the whole thing automatic, so it runs on its own.

The Part That Helped

I’ll be honest about why TopScan stuck with us after the deal closed. It did the boring work without fuss. It checked our servers, APIs, and software using well-known open-source engines, then sorted the results so the serious issues stood out and the routine noise stayed out of the way. This alone saved us hours of staring at confusing reports.

Here are things that mattered most for a small team like ours:

  • The setup had to be quick. Nobody had time for a tool that needed its own planning meeting.
  • It had to keep running as we rolled out updates, so new problems didn’t slip past us between releases.
  • It had to fit into how we already worked, sending alerts to Slack, so they reached us instead of sitting in a dashboard we ignored.

None of this replaces good judgment, and I would never pretend it does. But for a company with no dedicated security person, just having a clear, current picture of our weak spots changed how calmly I could handle the hard questions.

read more : The Moving Mistakes That Create the Most Stress — and How to Avoid Them

What I Tell Other Founders

When friends ask me about getting ready for a big customer, I keep it simple. Don’t wait for the questionnaire to start thinking about security. By then, you will be negotiating under stress, which shows. Put the basics in place while the stakes are still low. Run regular checks, keep a tidy record, and let software handle the repetitive parts.

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