Over the past several months, I’ve had the rare privilege of building a company from the ground up. Opportunities like this don’t come along very often. Every decision we make today—every process, every system, every technology platform—will become part of the foundation upon which we hope to build a company that lasts for decades.

That foundation matters.

Not just because the right technology can make a company more efficient, effective and scalable, but because every application ultimately becomes part of the customer experience. Every CRM, every AI platform, every support system, every marketing tool and every internal process becomes an extension of the company itself.

Naturally, evaluating software has been part of our journey over the past few months…a LOT of software.

CRM platforms. Marketing automation. AI tools. Video creation. Product demo software. Customer support platforms. Analytics. Project management. Development tools. Accounting systems. If there was a category that could help us build a better company, we probably researched it, watched the demo, signed up for the trial and, more often than not, paid for a subscription so we could experience it the way a real customer would.

Like everyone else, we started with Google. We asked ChatGPT, Claude and Gemini for recommendations. We read reviews, watched YouTube videos, compared feature lists and looked at analyst reports.

We expected to learn which software was best.

Instead, we learned something much more important.

We learned about the companies behind the software.

That was never our intention.

In fact, I don’t think it’s what most buyers intend. When we evaluate software, we naturally ask questions like: Does it have the features we need? Will it integrate with our existing systems? Can it scale with us? Is the pricing reasonable?

They’re all valid questions.

After hundreds of hours evaluating products, however, I’ve become convinced there’s another question that’s even more important.

If everything goes wrong after I become a customer, why should I trust this company to do the right thing?

Software Has Bugs. Character Is a Choice.

Let’s get one thing out of the way.

Software is hard.

Every meaningful application has bugs. Every engineering team makes compromises. Every roadmap is longer than the available resources. AI has only accelerated the pace of innovation and, with it, the opportunity for things to break in unexpected ways.

None of that bothers me.

I’ve been around business long enough to know perfection doesn’t exist.

What surprised me wasn’t the bugs.

It was how many companies seem to have accepted bugs as inevitable while simultaneously making themselves virtually impossible to reach when you need real help.

Somewhere along the way, parts of the software industry seem to have forgotten that they aren’t simply shipping code.

They’re building relationships.

Relationships are built on trust, and trust is rarely tested when everything is working perfectly. Trust is tested the first time something goes wrong.

The Pattern Became Impossible to Ignore

As the months went on, a pattern began to emerge.

The demos were polished.

The marketing was exceptional.

The websites were beautiful.

The messaging was compelling.

Then reality showed up.

Support requests measured in days instead of hours.

No weekend support.

Pricing that somehow became much more complicated after you’d invested your time learning the platform.

AI agents that seemed more interested in preventing you from talking to a human than helping you solve a problem.

Generic contact forms.

No visible phone number.

No obvious way to contact leadership.

Companies that appeared to have invested enormous amounts of time and money making it easy to become a customer—and considerably more effort making it difficult to reach someone after you were one.

At first, I assumed these were isolated experiences.

Eventually I realized they reflected something deeper.

They reflected not only a culture, but a culture that is becoming endemic to the world of AI SaaS.

Three Companies, Three Different Attitudes

One particular company (we’ll call this one SL) delivered one of the best software demonstrations I’ve seen in years. The product looked polished, intuitive and incredibly capable. We were excited. The entry-level pricing seemed reasonable and they advertised startup discounts, which immediately caught my attention.

Then we discovered that the capabilities we really needed required a minimum five-seat commitment at more than double the price. The “startup discount” turned out to be little more than selling fewer seats at exactly the same per-seat cost. After forty years in sales, I have a difficult time calling that a discount.

Then we started using the software.

It was buggy.

Support responses often took days.

There was no meaningful weekend support.

Eventually I found myself doing something I should never have had to do—using Seamless.ai to locate executive email addresses because I couldn’t get the help I needed through normal channels.

Not one responded.

The software disappointed me.

The company disappointed me even more.

Another company (let’s call this one “HG”) showcased genuinely remarkable AI technology. When it worked, it was nothing short of amazing. I decided to create a birthday video for my fiancée and built a project consisting of roughly thirty scenes.

It should have been simple.

Instead, every time I rendered the project, four, five or six scenes would randomly change. The voice would no longer sound like me. I’d tell the software, “Leave everything alone except these scenes.” It ignored the instructions, fixed a few scenes and broke several others.

I rendered the same project over and over again.

Ten times.

Maybe more.

I still couldn’t produce a usable video.

Curious whether upgrading to a higher-tier plan would improve the experience, I attempted to schedule a demonstration with a human being. Instead, I was greeted by an AI sales agent that asked a handful of qualifying questions, determined I wasn’t planning to spend enough money, and impolitely directed me back to the self-service option.

Conversation over.

Ironically, after I stopped using the product, I began receiving emails from what appeared to be real salespeople. I replied. I asked to schedule a meeting.

Nothing.

Silence.

Then there was Ultimo Bots.

Their software impressed me immediately, but that isn’t why they’re in this article.

While I was interacting with their AI assistant—which, incidentally, was excellent—a senior executive joined the conversation. I hadn’t requested a human. I wasn’t frustrated. Nothing was wrong. They simply wanted to introduce themselves, answer any questions I might have and make sure everything was going well.

A week later I had another question.

The same thing happened.

Then I looked at their website more carefully.

Their people are visible.

Their leadership is visible.

Their address is easy to find.

They’re proud of who they are.

Ironically, the company with one of the best AI products I evaluated also seemed the least interested in hiding behind AI.

That left an impression.

Before You Buy the Software, Buy the Company

This article isn’t really about any of those companies.

They’re simply examples of choices.

Every software company eventually chooses what kind of company it wants to become.

Some optimize almost exclusively for customer acquisition.

Others optimize for customer relationships.

Some see customer support as a cost to minimize.

Others see it as an investment.

Some build walls between themselves and their customers.

Others build bridges.

As buyers, I think we need to become much better at evaluating the company, not just the product.

Before you buy software, spend ten minutes evaluating the people behind it.

Can you easily find a real address?

Is there a phone number?

Do they introduce their leadership team, or do they seem determined to remain anonymous?

Is the pricing transparent?

Can you talk to a real person before becoming a customer?

Do they appear proud of who they are, or are they hiding behind chatbots, contact forms and generic email addresses?

Most importantly, ask yourself one simple question.

If everything goes wrong tomorrow, why should I trust these people to do the right thing?

The answer to that question will probably tell you more about your future experience than any feature comparison ever could.

A Reminder to Ourselves

I didn’t write this article to criticize an industry.

I wrote it because building a company forces you to think carefully about the kind of company you want to become.

This isn’t a promise that we’ll never ship a bug or disappoint a customer. We will. Every software company does. The standard isn’t perfection.

The standard is character.

Character is answering the phone when it’s inconvenient.

Character is responding to an email you wish you hadn’t received.

Character is admitting a mistake instead of explaining it away.

Character is making it easy for customers to find you instead of designing systems that keep them at arm’s length.

Character is remembering that behind every support ticket is a business owner, an employee or a customer whose day probably isn’t going very well.

If we ever become the kind of company that makes customers hunt for an executive’s email address just to be heard, I hope someone sends this article back to me.

Not because they’ll have misunderstood it.

Because somewhere along the way, we’ll have forgotten what we were trying to build.

Software solves problems.

Character determines whether customers stay.

If I ever forget this I hope you will remind me!!!

Jim Boudreau is the founder of Studio 1119 and Managing Partner of Nautilus Growth Partners. After four decades in B2B sales, leadership, and entrepreneurship, he writes about building businesses, technology, leadership, and the principles that create enduring companies.

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