Key Takeaways

  • Pendo is a software company that enhances the user experience of other software applications through data-driven personalization and optimization. The platform integrates with daily use applications, captures data on their usage, and leverages this information to improve the user experience.
  • Pendo’s PENG System is a reward system based on Pendo’s seven core values. Employees recognize their peers for extraordinary work or for embodying these values. Awards for each core value are given out every quarter.
  • Todd Olson is a hands-on leader who prioritizes customers and direct, transparent communication. He is committed to sharing information widely within the company and is willing to “roll up his sleeves” to solve problems.
  • Todd’s strategy for Pendo includes transitioning to a multi-product company, integrating cultures during acquisitions and international expansion. As Pendo expands globally, Todd is mindful about the importance of understanding different societal and work cultures.

Executive Summary

Hey folks, thanks for joining us on a brand new episode of The Leader Show with Lou Carter. Today, we are joined by Todd Olson, the CEO of Pendo, a comprehensive product experience platform that empowers businesses to prioritize product-centric strategies.

So, without any further delay, let’s find out what makes Pendo a Most Loved Workplace®. 

Delving into Todd Expounds on Enhancing User Experiences through Data-Driven Software Personalization

Lou sets the tone for the conversation by asking Todd about his company, 

In reply, Todd describes as a software company that enhances other software applications by using data-driven personalization and optimization. It does this by integrating with applications people use daily, capturing data on how these applications are used, and leveraging this information to improve the user experience. 

Pendo also provides analytics and personalization features to enhance user interaction. Mr. Olson concludes by stating that Pendo serves as an infrastructure for better user experiences in a world where software transforms how we interact with brands.

Cultivating a Thriving Work Culture: Todd Olson Explores the Pillars of Employee Satisfaction at Pendo

On a similar note, Lou asks Todd about Pendo’s work culture and why employees love working there. The latter explains that one of the key factors is being intentional about creating a positive and engaging work culture. Since the early days, Pendo has understood that to deliver excellent customer service, they need happy and engaged employees. 

Todd highlights that the company emphasizes living its values, not just stating them. Pendo operates peer recognition systems to reward employees who embody these values and also uses their values to inform business decisions.

Mr. Olson also underlines Pendo’s commitment to continuous improvement and openness to feedback. He mentions meeting with every employee after their first 90 days, and despite the company growing to nearly a thousand people, he continues to engage with staff at various levels. Also, regular surveys are conducted to assess if the company is living its values and to gauge employee sentiment.

Todd on Pendo’s PENG System and its Impact on Cultivating an Engaging Work Culture

Moving on, Todd highlights the reward system at in response to Lou’s query about their ‘awards for living values.’ The system, known as the PENG system, is based on Pendo’s seven core values, which include a focus on the customer and direct, transparent communication. Employees can give shout-outs to colleagues who have done extraordinary work or exemplified these values through Slack, their collaboration tool.

For example, if someone has exceptionally focused their efforts on customers, they are recognized through the PENG system. At the end of each quarter, they tally these recognitions, and the person with the most recognitions for customer focus receives the ‘maniacal focused customer’ award.

Similarly, they have an award for directness and transparency given to those who provide valuable feedback, even to Mrs. Olson. This feedback-driven culture encourages everyone to speak up and contribute to making the company a better place.

Awards for each core value are given out every quarter, with plaques in their office showcasing the winners. They also have an overall award for the person who has been recognized the most. According to Olson, this system has significantly maintained its culture as the company scales.

Hands-On and Transparent Leadership Philosophy at Pendo

In response to Lou’s question about his leadership philosophy, Todd mentions that many of his personal values align with Pendo’s core values. He strongly prioritizes customers and maintains direct, honest, and transparent communication. 

Mr. Olson notes that his commitment to transparency might make traditional managers uncomfortable, but he firmly believes in sharing information widely within the company, as it fosters a healthier work environment.

He describes himself as a hands-on leader, refusing to shy away from tasks simply because of his title. Whether coaching a team member, helping with a sales or customer issue, or brainstorming with an engineer or product person, Todd is willing to “roll up his sleeves” to solve problems.

Additionally, he values his 20 years of experience in tech and encourages the company to leverage his insights. Rather than restricting himself to a few major decisions, Mr. Olson prefers being in the trenches and part of the team. He believes this inclusive, collaborative approach influences the rest of the company, reinforcing the perception that everyone is part of a united team working towards common goals.

Pendo’s Future Strategy – Product Diversification, Cultural Integration in Acquisitions, and International Expansion

When asked about Pendo’s future, Todd outlines a few key areas of focus. First, he plans to transition Pendo from a single-product company to a multi-product company. This involves launching new product lines and exploring potential acquisitions.

Additionally, Todd underscores the delicate process of merging cultures during acquisitions, emphasizing the need to combine the best aspects of both companies to create a unified and evolved culture. He stresses that they do not want to stifle the existing culture of the companies they acquire, as it’s not beneficial for either party.

Another significant area of focus is international expansion. While Pendo is predominantly US-based, Olson recognizes the need to think more like a global organization to continue their growth. They currently have employees in three additional countries, but Olson acknowledges the challenges of expanding into regions with different societal and work cultures. 

He is keen on investing in understanding how Pendo can operate effectively within these cultures to ensure it’s a great place to work, not just in the US but also in countries like Japan and the UK.

Challenge and Importance of Adapting Core Values in Different Cultural Contexts

Subsequently, Todd talks about the importance of understanding and respecting different perspectives. He points out the challenge of applying their core values across different cultures. For example, he mentions Pendo’s value of “directness and transparency” and acknowledges that it may have different implications in Japan than in the US or Europe.

Mr. Olson also emphasizes the need for Pendo to adapt its values in a comfortable and natural way for people in different cultural contexts. This is crucial for Pendo’s success as they strive to be a loved workplace globally, based on his belief that employees who love their work are more likely to perform their best and take care of customers effectively. 

He sees this as a key strategic goal and an interesting area for innovation as Pendo expands internationally.

Aligning Values with Global Diversity

Todd concurs with Lou about the complexities of international cultures and how they can differ significantly. Olson points out the evolution of Pendo’s core values to better accommodate these cultural differences, making them universally applicable and understandable.

Originally, Pendo began with four values in 2014, which expanded to seven in 2016. In the current year, Pendo refreshed these values again, particularly focusing on the language used to express them. For example, he mentions how Pendo’s value of “directness” was previously expressed as “brutal honesty,” a phrase that translated very differently in international contexts.

Recognizing the potential for confusion and misunderstanding, especially as Pendo grew and employed more people from diverse backgrounds, the company revised its values to ensure clarity, translatable words, and explainability. This enhances understanding and provides a rubric for assessing potential hires’ cultural fit with Pendo’s values during the interview process.

Lastly, Todd emphasizes the importance of investing time and energy into refining these crucial cultural aspects of a company, akin to investing in any other essential aspect of the business. This, he believes, has been a significant accomplishment for Pendo this year.

The Power of Language and Cultural Nuances

Next, Lou and Todd delve deep into the implications of language and its potential to impact how people feel and perceive others. Lou points out that the phrasing of a question or statement can significantly affect the listener’s response. He uses the example of the shift from a direct question like “Who are you?” to a more inviting phrase like “Tell me more about who you are,” which could provoke less defensive reactions.

Discussing the concept of friendship and respect prevalent in many Asian cultures, Lou acknowledges that Todd is diving into these cultural nuances as Pendo goes global. He further emphasizes that the lessons learned from this expansion could be applied internally in the company’s existing setup, fostering a culture of acceptance and respect.

Lou and Todd go into much greater detail throughout this conversation.

Thank you for listening!


Lou Carter : It's great to be here today in, Most Loved Workplace, today with Todd Olson, Todd's the CEO of, and it's an awesome time because he has not only a Most Loved Workplace, but he is doubling in size and he has more growth. He's gotten a lot of success, and the company itself is just wonderful. Todd, welcome.

Todd Olson : It's great to be here. Thanks for having me.

Tell me about What do you do? What is Pendo all about? What drives Pendo?

Revolutionizing Software Applications Through Data-Driven Personalization and Optimization  [01:08]

Yeah, we basically are a software company that makes other software better. So, we install ourselves an application that people use, whether it's, you know, your application for your favorite bank or maybe an application use at work. And we capture data on how people use it to help build a better experience for you in that software application. We also complement that analytics with the ability to personalize the experience message you and really it's just about look, software is changing a lot of the way we engage with brands that we work with, that we use on a regular basis. And Pendo is, you can think of us as infrastructure that help make those experiences better.

LC : That's awesome. And tell me more about how with Pendo, people just love working there, right? This is kind of love, this belief. What is it that makes Pendo a place that employees love?

Measuring Employee Sentiment And Nurturing A Thriving Workforce [02:01]

TO : Well, I think the first thing is being intentional and focusing on it. You know, I think there is no like, oh, we're just going to create a culture and magically things will be okay. I think from the early days we've decided that in order to build the kind of company we want and to serve customers the way we want to serve customers, we need employees that are engaged and happy and love being here because that will come through with the customers and, so to do that, I think part of being intentional is, one, writing down what your values are and then focusing on living them. So many times I hear from employees that Pendo is one of the few places that actually lives their values. They're not just words written on a wall or on a website. We do that by having peer recognition systems where if you see someone living a value, you can recognize them.

And we give out awards for living values. We also make sure that when values are used to help us inform business decisions, we're really communicative around why we made decisions and how our values influenced those. The other thing that we do a lot is just constantly focusing on being better and getting feedback. For years I did a one-on-one with every employee in the company after their first 90 days. Now it shifted to kind of a group setting, because we're almost a thousand people, but I still meet regularly across the company in different levels. Just soliciting feedback, like, is the experience what you expected? Is it what you heard it was like? And are constantly looking for ways to ingest and tweak. We do surveys regularly to capture are we living the values. Like EMPS is something that we have. It's a corporate measure that we report to our board of directors, which EMPS you know, is employee health or employee sentiment. So I think those are some of the reasons I'd say it's really, really intentional.

LC : Todd, I love what you had mentioned about awards for living values. Wow. Tell me how that manifests. How does that, examples of that and what are the awards and what have people done to show that?

A Culture Of Recognition And Honoring Values In Action [04:10]

TO : Yeah, so, you know, so we have seven core values and so one of them is my focus on the customer. So it's a very customer-focused organization. And every day I say someone at Pendo, because we have, you know, again, nearly a thousand people are doing extraordinary things for customers that look, if it was reliant on like me to see each and every one of these people doing it, it certainly wouldn't scale or work.

But when anyone sees anyone doing an amazing thing for a customer, they can do a shout out. They basically do a recognition, it's actually, we call it our PENG system and it shows up in Slack, which is our employee collaboration tool. Then we tally these things. So if you've been, you know, recognized for being really focused on customers the most, in a quarter, you'll win the ‘maniacal focused customer’ award for that quarter.

So every quarter retaliate of all these recognitions and give away awards based on doing it. And it could be, that's one value. Another one is around being direct and transparent. I'm a big believer that feedback's a gift and it's valuable to be direct with people, to know where they stand and to make each and every one of us better. That includes being direct with me. So if we, if someone comes up to me and says, Hey, I really didn't like what you did there, you know, this would've been slightly better.

We'll recognize that sort of behavior. We want people to speak up and make this place a better place. So, that's an area where, you know, when people do that, they get recognized and we give out a ‘be direct and transparent’ award every single quarter. And, you know, you can go in our office, we have plaques, we have, you can see every quarter who's won which award per value. And then there's an overall award winner. The person that's been recognized the most gets rewarded as well. But it's, big part of our culture and how we've continued to maintain it as we scale.

LC : Well, let's talk about you Todd, Todd Olson and the leader. The leader himself. Tell me about your leadership philosophy and values as a person and as a CEO.

Top-Down Collaborative Team Culture: A Unified Approach To Success [06:15]

TO : Well, look, I think, you know, I've already touched on some of them. I mean, and some of them are codified in our core values. I really care about customers. I really care about direct and honest and transparent communication. I think transparency is one of the things that does probably set myself and us apart. And it, you know, I'll say being transparent is uncomfortable to managers, specifically from traditional organizations.

I like to share everything. We have very few secrets, you know, very few situations. Only people are in the know. And I think it's really made it a better place. I think you'll also, you know, I think people describe me as a very hands-on leader.

So, I like, I just don't believe that, you know, my title means that certain jobs are too small for me or I shouldn't be doing, you know, so I think I'm willing to roll up my sleeves and whether it's coaching someone in an organization on how to deal with another colleague, or whether it's working with someone in a sales or customer capacity to help take care of a customer better, whether it's whiteboarding with an engineering or product person.

Just like, I actually enjoy that. I enjoy just solving real problems and being with the team and like, look, I've had the fortunate pleasure of being in tech for over 20 years in my career and I've seen a lot of stuff [laugh] and the company should use that [laugh]. You know, I'm just an experienced person and I, you don't want to just relegate to me to like, making a few big decisions or what have you. I like being in the trenches and really being part of the team. I think that's a big part of my leadership style. And I think that cascades down. I think everyone who works for me and down feels that way. That we're all in this team together. We have an aligned set of goals and that it takes each and every one of us to succeed.

LC : I like that a lot. and you know, you see that with Elon Musk. He's down there and he is actually doing the work, right? He's creating, he's thinking, he's innovating, he's developing because he has that experience, you know, back from, you know, PayPal, the software development. I mean, why not your experience, you do a great job, you lead developers and that's what should happen, right? That's your expertise. That's really cool, you said that, and that's a lot of, you know what Most Loved Workplace is all about, the book, and it's about, you know, getting into the work, collaborating, being part of the ecosystem, and really digging what you're doing every day. And, so that sounds just spot on. It really does. So just, you know, sort of finally, where do you see Pendo going? Like, you know, in the future? Where do you see it going in the next year or so? What's next?

Merging Cultures: Navigating Acquisitions And Preserving Organizational Identity [08:55]

TO : Well look, it's a lot. I mean,[laughs] we're growing really rapidly. And I think there's a couple areas of focus for us. One, we started as a, it's a single product company, you know, as an entrepreneur, I wanted to solve a problem and solve a pain. We built a product around that. And as we grow and scale, I want to continue maintaining growth, we have to become a multi-product company. So we're starting to launch new product lines, we're starting to look at more acquisitions and look, we've done a few acquisitions and those are always interesting, but that's always an area where we have to meld two cultures together because we obviously don't want to acquire a company who's great and then kill that culture. Like that's not good for those people or for us. We want to take the best bits and combine it with the best bits of ours and kind of unify it and evolve both cultures.

The other big piece is international. You know, we are predominantly a North American or even US-based business. And in order to continue growing and scaling, we need to act and think more like a global international organization. And so we do have folks in an additional three countries and I think we need to continue to look at how we expand that. And it's challenging, expanding internationally where there's different cultures at work, like different, you know, human cultures, societal cultures, but understanding how Pendo operates within those areas is I think something that I'm particularly keen on exploring and investing in to make sure that is a great place to work. In Japan and the UK and in other foreign countries.

LC : Funny you mentioned Japan. That's our next list. Also, Poland and the UK. So that's interesting. You mentioned that and yeah, Japan it's a different culture we'd say, right? It really is. They would also agree and I think many people in Japan and as well as companies in Japan have a unique culture. And it's about like melding, you know, and seeing in looking out from here, right? You kind of, you explore it from in front of you and different perspectives of that culture. And then how do we find those elements that are really strong and magnetic that we all can really become part of that we want to become part of and makes us both better, right? Things that we can do better and things that we appreciate about what we already are, what you're really doing.

And when, in your international approach is saying, oh, I really appreciate that about your culture and here's what we do. Perhaps it could make it even better. Would you be aware of that? Would you be accepting of that, right?

Evolving Values: Crafting Clear And Globally Understandable Principles [11:34]

TO : Yeah. Look, this is all about adaptation and you know, I mentioned that we have a value of be direct and transparent. What does it mean to be direct and transparent in Japan? Probably different than what it means in the US or even Europe, you know? And so, exploring that and making sure that it's comfortable for those individuals and natural is, I think, a really, really interesting area that we can innovate on. And because yeah, we want to be a loved place to work in Japan, obviously. Because I think it's core to our success as a business is people who love where they work, ultimately do their best work, ultimately take care of customers the best. I mean, it's part of the strategy. So I think it's critical for us to find ways to scale internationally.

LC : And, the cultural elements internationally are very different too. That there is, a lot of the research before is the McClellan Power Index. There's the way power is perceived differently in Japan as it is in the US and Eastern versus Western. There's other constructs too, of high trusts, low trusts. High context, low context cultures that have high, in Asia more high sometimes in the US more low context. There's numerous studies that show the differences.

And then you have to test those studies again because they change, they shift with new generations with a new influx of talent. And whether there is really, the living of that research and behaviors or they're just perceptions is a big question too, right? There could be more similarities than there are dissimilarities perhaps due to language differential. There's so many questions, isn't there?

Investing In Clarity: Building A Rubric For Cultural Fit Assessment [13:12]

TO : Oh, a hundred percent. And actually, and interesting, just a fact is that, as I mentioned, our values are important. A big, big important, way that we live our culture. and we refreshed our values early this year, so, as I said, we have seven, we've had seven since about 2016. We started the company actually in 2014, early 2014 with four values. So twice we revisited these. These things that are very, very, very important. We've made adjustments, we've changed them, we've adapted them. The refresh in many ways was to help address some of the issues you're talking about, which is, are these words that we're using, so I keep talking about being direct before the value is ‘be direct’, It used to say ‘brutal honesty’. What we found is the word brutal honesty in English translates very different when you look globally.

And it's one of these things like, yeah, yeah, yeah. When it's, I don’t know, when you're 400 people, 500 people and everyone kind of knows what it means, like it's fine. It's like, it's fine, you know? But as you grow really, really fast and people don't know what it means and they're just reading these words, they're getting confused.

It's not helping the culture. So we adjusted the words, refreshed all the values to make sure the words translated well, the words were explainable, they were clear. And I think we've came up with a rubric for, through interviewing process, like what questions you can ask, which can help test whether this person is a good fit or not with respect to our values, right?

A lot of investment here just to make sure it's clear and understandable by a global audience. And I think that's, you're touching on something I think very, very important. But if these things are important, you have to invest time and energy into it. Just like you invest time and energy and everything else. So that's one of the cool things I think we've done this year specifically.

LC : Absolutely. And people don't realize it's, you know, time, energy, investment, [laugh], you know, there's also monetary. These are very important things. And where you're touching on too, the word brutal honesty can be, goes back to the way in which people feel within government regimes. Are they being brutal with me? Are they going to harm me? This, that question and then the question itself can be actually, are people being placed into defensive positions with a question versus a statement. So you're shifting the statement really to, so you're saying this is the question. Say, I would say to you, “Hi, Todd, tell me more about who you are”, right? Versus “who are you”, you know, how do they feel? You know, who are you is a lot like saying give me your passport and identity

TO : Yep.

LC : Versus, Todd, tell me more about who you are. Right? And, even the directive could be seen as brutal honesty. So me saying to you, tell me versus Please let me know you better. Please help me understand. You know, that's now we're getting even deeper to this concept of friendship, which is pervasive in Asia. Friendship is very pervasive and respect, honesty. You know, the whole concept of really loving another's way of being, respecting their way of being. It's really deep in their culture.

TO : Hundred percent, hundred percent.

LC : You’re going there. You're going there, Todd, it sounds like you're doing this. This is so exciting. You're literally going international.

TO : It's fun. It's fun. Look, it's a journey. And we're early in that journey. But yeah, I think, look, I mean, I'm sure we'll learn a lot [laugh] as we can get down this path.

LC : You know, what’s cool though, Todd. Even if, you know, that's [inaudible] two away, right? The lessons can be learned in the here and now, inside of your company now. Even the concept of respect that you're doing, and you're already leading around. You know, how we accept and love another person.

That's a good point.

LC : Todd Olson, Pendo, awesome person, leader, done great jobs instead of Pendo doubling in size, doing amazing things going international. Thanks for joining me today.

TO : My pleasure. Thanks for having me, Louis. Take care.