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All About The Users—Todd Olson, CEO of Pendo

Todd Olson is the CEO and co-founder of Pendo. Pendo is a product engagement platform that helps businesses better understand their users and is a Series-D company backed by Sapphire Ventures, Battery Ventures, and Spark Capital. In this Path to PM post, we discuss the importance of connecting with a product's users and the tough aspects of product management.

Tell us about how you broke into product management.
Before Pendo, I was a VP of product at Rally Software. I got there via an acquisition of a startup I founded. At that startup, I was arguably the CTO and head of product.

I had frankly never heard of the role of product management at that time. But later I realized I was effectively also serving as the PM of the company.

It sounds like you ended up in a PM role without even knowing it. Many people describe “falling into product management” as opposed to seeking out product roles.
I think it's really common. It's just treated very, very differently. Back in 2000, product management was much less popular than it was in 2018. The role was very different back then.

What helped you develop your product management career given that you weren’t in a formal PM role?
One of the seminal books that opened my eyes to a lot of product management was The Four Steps to the Epiphany: Successful Strategies for Products that Win by Steve Blank. That's when I first started thinking about the term product-market fit and how to do real customer discovery. Honestly, it was that book that really helped me develop a lot of my thinking around it.

How has your experience with product management informed Pendo?

I think the big issue in product management is that we spend all this time—we come up with this thesis on what to build, we invest on what to build, we apply craftsmanship to it—but then sometimes people just don't use it.

I often talked to customers who either didn't realize it was shipped or they weren’t getting value out of it. That's really what drove me to build Pendo.

Pendo's focus is really about making sure people get full value from the software they use. Pendo is Latin for "value," and that's how it all connects.

What’s something that Pendo does to really connect with its users?
We have a Slack channel for all of our customers. Invariably, when I decided this we got a lot of pushback from our support team. They were concerned about being overloaded with customer service requests. I mean it literally got blocked by the team! I kept asking and asking and eventually, we actually put it out there.

Flash forward to today, and almost 2000 people log into our channel every single day, talking about everything from Pendo to general product management. To hear the voice of the customer in such near proximity has been amazing for Pendo’s growth.

What advice would you give to current PM interviewee?
Product management is ultimately about shipping software. Some people want to be a product manager because they want to "own the roadmap," but I think it's a lot less glamorous than that. The devil's in the details. I think you have to grow a thick skin and be comfortable saying no. You're going to say no way more than you're going to say yes. Way more.

That's the job. We often make zero-sum decisions in product - you're getting something but NOT the other thing, you never get both - that's just not how PM-ing works. If you’re not comfortable saying no, then it's not a good fit for you.

It’s great you mention this - often, aspiring PMs think they can be a “mini-CEO” of a product, which I believe is a bit misguided.
I think that mini-CEO thing is killing it because it makes product management look overly attractive. PM-ing is tough. It is brutal. PMs are really important but it's a really difficult job.

Lastly, what’s a product you love?
I think Tesla’s product is excellent. They do a fantastic job of delivering product delight. Product delight is something that is difficult to programmatically deliver. Because it's typically not one thing - it's many things. And delight doesn't mean perfection. Delight means you do some things really really well and you understand how to deliver an unexpected experience to a user. And I think it shows in the devotion of the user base.


Read more about Pendo on their editorial site, ProductCraft.

Visit PMLesson's Online Course for more great product management interview prep.

Stephen Cognetta

Stephen Cognetta

Hi, I'm Stephen Cognetta, CEO of PMLesson and a former Google PM who has conducted hundreds of interview sessions. I've spoken about product management at Google, WeWork, Duke, Yale, and more.

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