Episode 17: Todd Olson and Andrew Waitman

In our 17th episode, Gil discusses category creation with two experienced B2B leaders from the product management and supply chain categories.

Panelists for this episode include:

  • Todd Olson, CEO of Pendo and one of the influencers behind the product experience management category
  • Andrew Waitman, CEO of Assent Compliance and creator of the supply chain transparency category

Or watch the video

You’ll walk away from this episode with insights about branding, content strategy, and measuring product-market fit.

Here are the key takeaways from this episode:

Takeaway 1. Use leading indicators to calculate your TAM

There are many unknowns to creating a category.

The biggest one of all is figuring out whether there’s a big enough market for your product in the first place.

You can’t simply Google your TAM or look at an analyst report to find an answer.

The category doesn’t exist yet.

So where do you start?

A good strategy is to find out whether your target market can generate at least $100 million in ARR.

You need to look at a variety of leading indicators to figure this out.

For Todd Olson and his team at Pendo, this meant looking at the growth in Chief Product Officer roles and their average deal size to gauge the potential demand for their platform.
The great thing about TAM is that it’s not a static number.

You can expand it by broadening your features to appeal to different segments (enterprise, SMB, etc.) or through acquisitions.

Another approach is to invest heavily in your technical team and innovate.

Takeaway 2. Always invest in a quality engineering team

Building an engineering team will probably already be on your list of priorities if you’re a technical founder.

But what if you’re not a technical founder?

How do you go about figuring out what good technical talent looks like and what it doesn’t?

To answer that question, you’ll need help from your CTO.

Your CTO will have a better understanding of what it takes to source, hire, and manage engineers.

In addition to helping your build your team, they will also help you set the vision for your product and ensure your innovative ideas are technically feasible.

For Andrew Waitman and his team at Assent Compliance, one of the lessons they learned early on was the importance of hiring great engineering talent.

The company had historically relied heavily on sales and marketing teams to gain traction.

But it was only until they refocused their priorities on retaining engineering talent that things really took off.

It just goes to show that regardless of TAM, prioritizing your engineering team from day one is always a good idea.

This isn’t something you can put off until later, as it directly affects your ability to deliver a quality product.

Takeaway 3. Leverage your content strategy to bridge the gap between brand promise and reality

You also need to keep in mind that a great product isn’t all that’s required to dominate an entire category.

Your content strategy is equally as important.

It can be the difference between a 10M and a 100M+ company.

A well-executed content strategy is ultimately what allows you to communicate your brand promise with greater effectiveness.

It positions you as the ideal solution to your audience’s most significant challenges, while simultaneously opening the door for word-of-mouth marketing.

As you’ll learn from this episode, developing and implementing a content strategy is just as hard as anything else you do when creating a category.

But the long-term benefits are worth the challenges.


Andrew tells us how being an introvert helped him become a better leader.

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