How the Structure that Defined Wistia Almost Broke Us...Then Made Us Stronger Than Ever

Once upon a time, 18 years ago, Brendan and I started Wistia, and the early days were all about fun. A big reason for this was our flat organizational structure.

It didn't matter if you were a founder or had just walked in the door. You could make a real difference quickly. I loved showing off our team dynamic to new employees and was proud of our egalitarian approach.

Flat was startup-y and awesome, while structure felt BigCorp-y and boring.

As we grew from 2 to 30 people, the flat organization that defined our early days became an Achilles heel.

Letting go of our "flat" management style was tough. Never in a million years had I imagined us creating an org chart, but we did—and it was one of our best decisions. The shift allowed us to double in size while keeping the energy, creativity, and risk-taking that characterized Wistia's early days.

Here's a look at the evolution of Wistia's org structure, where we fumbled, how we recovered,  and some unexpected things we learned along the way.

The Flat Years: 2 to 30

My pre-Wistia management experience was limited mostly to restaurant jobs where I hated being told what to do. That spirit inspired Wistia's flat structure. We didn't want to create a company that required rigid management. Autonomy reigned over defined decision-making frameworks.

When we were under 30 team members, constant communication and defining ownership were mission-critical.

We constantly asked: "Who is responsible for getting this done?" 

Clear ownership balanced responsibility across the team, allowing for quick movement and confidence that all bases were covered. This individual ownership motivated our team to push projects forward faster without micromanagement or decision-making bottlenecks.

At this stage, we learned that letting people make their own decisions could be scary, especially for a startup founder ("What if they make mistakes?")

Spoiler alert: People will fumble, but by giving them the authority to make their own mistakes, you also provide them with the freedom to learn from them, which is a good thing.

When A Flat Structure Became a Flat Tire

Early on, our lack of explicit decision-making processes worked in our favor. Everyone dabbled in every decision, fostering creativity.

But as we grew, our flatness broke down.

There was an implicit structure even though we said that things were flat. People came to me or Brendan to make decisions. We weren't truly flat.

Things slowed down, people got risk averse, and things felt a lot less dynamic.

We realized that building a company with a flat org structure had done the exact opposite of what we had intended. We had centralized all the decision-making and relied on a secret implicit structure to make progress.

Every company has a structure. If you don't explicitly define your structure, you are left with an implicit one, which can stifle productivity. We had hoped that being flat would let us move faster and be more creative, but as we grew, we ended up with an unspoken hierarchy that slowed down our ability to execute.

Embracing Explicit Structure: 30 to 60

It took us too long to realize that an organization is ever-evolving. I associated flatness with our identity, which made changing it hard. 

We needed to evolve beyond it. We drew out an org chart, explicitly defining ownership and authority, which did wonders for us.

An organizational chart is never set in stone. It’s a map of the growing organism in your company. Communication and decision-making become more manageable with a precise map, and everyone feels more comfortable navigating their roles.

Delegating, Not Centralizing Authority

Rather than setting up a command-and-control structure, our org chart clarified ownership. Each team had defined roles, and managers ensured their reports had the resources needed to own projects. This delegation empowered teams to move faster with fewer bottlenecks.

Structure in action.

For the launch of our enterprise plan — typically when companies opt for a buttoned-up, risk-averse approach — we went with a parade, complete with a waddling penguin.

Our new team structure bolstered this creative approach. Everyone had clear responsibility and ability to own their area of the business.

The video was one of the most ambitious things we've ever done, and the entire launch required coordination across product, engineering, design, creative, operations, customer happiness… everyone. What's inspiring is that rather than ending up with a watered-down compromise, we produced something we were all super proud of.

We announced our plan just before I took paternity leave for one month. After the team pulled off the launch, it felt amazing knowing that things would motor on for the next month without needing me around.

Looking Ahead: 60 and Beyond

It's easy to get caught up in buzzwords like "flat." Effectiveness is what matters. Our org structure, grounded in our principles, helps us work efficiently.

Creating the org chart meant letting go of a stale part of our identity, reflecting on what truly matters, and building something new. It was a painful process, but necessary for growth. Our current structure works well today but requires active maintenance. 

As we add more people and the work grows in complexity, we must rebuild it again.

And I can't wait.