Ignorance Is Bliss. Sometimes It's a Competitive Advantage.

Sometimes not knowing the rules changes everything.

We all have ways of doing things. The way we sell. The way we lead. The way we make decisions.

And somewhere along the way, we stop questioning why.

When I joined ParentSquare as a co-founder in 2014, the company had already been developing its technology for several years. I came on board to complement our technical expertise with sales, marketing, fundraising, and go-to-market strategy.

I knew software sales. I knew how to connect with people, understand their needs, and earn their trust.

What I didn't know was how technology was supposed to be sold to schools and districts.

That experience reinforced something I've always believed: Trust can open doors that assumptions have closed.

Nobody told me how it was supposed to work.

I quickly discovered that selling technology to schools could be complicated. Budgets, committees, board approvals, lengthy sales cycles, and implementations that sometimes took months.

But I hadn't spent years in that industry learning all the reasons things couldn't be done differently.

So I started asking questions.

Why couldn't a school get started right away?

Why did every purchase have to become such a lengthy decision?

What if we found price points that worked within existing approval thresholds? Helped schools think creatively about their budgets? Made it easier for decision-makers to move forward?

And what if we simply showed them how easy the product was to use?

While schools were accustomed to technology implementations that could take months, I could demonstrate how ParentSquare could be up and running in just a few days.

Imagine that. An opportunity to make an immediate difference.

No complicated pitch. Just a clear solution to a real problem.

And it worked.

The freedom of not knowing

I wasn't setting out to disrupt an industry. I simply hadn't learned all the reasons why things supposedly couldn't be done differently.

Of course, there were rules and processes to respect. But there were also habits and assumptions worth questioning.

That mindset shaped much of what followed at ParentSquare.

Over the years, I helped build and scale our revenue organization, contributing to fundraising efforts and experimenting with pricing, messaging, product ideas, sales approaches, and new ways of reaching customers.

Some ideas were mine. Others came from colleagues. I was open to all of them.

Try it. See what happens. Learn. Adjust.

Over my eleven-some years with ParentSquare, I had the privilege of helping grow the company from three people to more than 400 employees.

But what fascinated me most wasn't just the growth.

It was the people.

It always came back to people.

Listening to what mattered to a superintendent. Understanding the pressures facing a school administrator. Making complicated technology feel simple for teachers and parents. Building enough trust that someone felt comfortable trying something new.

And inside the company, bringing different perspectives together, finding common ground, and keeping things moving when frustrations ran high.

I learned that some of the biggest obstacles to progress aren't a lack of intelligence, talent, or good ideas.

Sometimes we're simply so accustomed to the way things are done that we stop questioning them.

And sometimes a fresh perspective is exactly what we need.

A new chapter. The same curiosity.

After more than 20 years in technology sales and startups, I'm bringing that curiosity into my next chapter with Fail Fast Consulting.

Exploring the fascinating intersection of human behavior, leadership, coaching, and organizational growth.

Whether we're building a company, leading a team, or navigating our own lives, perhaps the most interesting question is:

What else might be possible if we stopped assuming we already knew the rules?

That's the spirit of Fail Fast.

Try things. Learn quickly. Adapt. Keep moving.

Be More Human. Especially When It Matters.

Linn Sillers joined ParentSquare in 2014 as a co-founder, served as VP of Sales & Marketing from 2014 to 2017, and continued contributing to the company's growth through January 2026.

A little piece of history: ParentSquare's early company profile on Gust which identifies Linn as VP of Sales & Marketing and Co-Founder and includes an early product demonstration she presented. A classic example of simple, human approach to selling that helped shape the messaging and sales process for years to come.

Understand what matters. Make the complicated simple. Build trust.