Todd Olson

Todd Olson, Business and Pleasure

Todd Olson, Founder, and CEO of Pendo. Pendo compiles and analyzes data that product managers need to make the right decisions about the development of software. It helps those product managers make sure customers actually use the features developers spend the time to create. Todd has raised over $11 million to help his customers create more engaging products. Todd recently served as Vice President of Products at Rally Software Development Corp. Mr. Olson led the evolution of Rally’s proven Agile ALM platform for enabling software and product-driven enterprises through its public offering. He co-founded 6th Sense Analytics, Inc., served as its President and Chief Technology Officer and led the fundraising of $7 million in seed capital. Mr. Olson was Chief Scientist of the Together business unit of Borland Software that he joined as a result of the successful acquisition of TogetherSoft. Mr. Olson co-founded Cerebellum Software Inc. and served as its Chief Technology Officer. He frequently speaks at leading industry events on the topics of Agile software development, Product Management, and entrepreneurship. He has a Bachelor of Science degree from Carnegie Mellon University in Electrical and Computer Engineering and is a graduate of its Entrepreneurial Management program.  

Q. Tell me about Pendo?

Pendo extends your product to capture all user behavior, gather feedback, and provide contextual help. There are a lot of products in the market that helps collect feedback such as Uservoice which is another Raleigh/SF based company. There is a host of solutions that focus on collating, collecting and synthesizing feedback directly from end customers, salespeople and all sorts of stakeholders. At Pendo, our vision is to help answer the question “what do people want in their product,” and to ultimately help filter the noise bias vs actual behavioral engagement. I was head of product of a publicly traded SaaS biz, and would hear all sorts of anecdotal feedback (both positive and negative) on a product. However, when we actually saw the data the results were quite the opposite. At Pendo we focus on using quantitative information by collecting very rich analytics on what people are doing and what they aren’t doing.  If the first problem is understanding, the second is how do you drive engagement and encourage behavior? We create features that are specific to certain sets of users to contextualize their experience based on role and persona. A new user who is an admin will have a different on-boarding experience than a customer returning the system after 3 months.

“we focus on using quantitative information by collecting very rich analytics on what people are doing and what they aren’t doing.
Pendo, Business and Pleasure

Q. Is Data always right?

I like the quote said by the founder of Netscape, Jim Barksdale “If we have data, let’s look at data. If all we have are opinions, let’s go with mine.” That pretty much sums up my views around data.  Data is just one piece of the pie when making a decision. It would be irresponsible to solely rely on quantitative data to make any decision.

Q. What do you think about Intercom? 

Intercom is fantastic. They are aiming at being the enterprise communication platform of the future. We often get compared to them as we both do in-app messaging, however, the use cases are different. Pendo is focused on automated campaigns. While Intercom is focused on direct communication to teams. I see Intercom competing more and more with the likes of with Desk and Zendesk.

““If we have data, let’s look at data. If all we have are opinions, let’s go with mine.”

Q. How does Pendo increase its hooks within organizations?

We do not gate users. By observing user behavior we quickly saw that although we were selling directly to Product Management departments an another natural customer persona is the Customer Success department. They can see which customer uses what feature, which is invaluable to CS teams. Not introducing barriers to our product early gave the option to invite CS teams to use the product. About 1/3 of the audience of Pendominum, our annual product conference, was CS teams and last month. More CS [teams] signed up than product teams! You can't anticipate what is going to happen when until you put it in someone's hand.

Todd Olson, Business and Pleasure

Q. How do you view consumerization of the enterprise? 

For the first time in a long time we are seeing more intuitive interfaces being applied to legacy enterprise functions. This adoption has really helped Pendo enter the market (this is outlined in our Series B funding deck). In my opinion, I see the future of the enterprise as the world where people are consuming platforms and not single applications. When you segment every function of your enterprise to different SaaS companies what happens when things go down? Do you really want to get 25 emails from all your different vendors? I think a few players will win in the consumerization of the enterprise, specifically the firms that have the highest compliance and security built to scale.

Q. How do you build a great company in Raleigh (non- major market city)?

The first core principle to build a good company anywhere is to first find product market fit.  I learned from Brad Feld, a famous institutional investor in Silicon Valley and a friend, to never overlook product market fit. After you have found PM fit, have a religious dedication to maintain it. Always be listening to your customers and delivering them value. Beyond that, hire great people. We are intense, focused, and very choosy. We go outside the area to recruit if need be, I actually hire recruiters outside the area to avoid any bias. Additionally, we are fortunate in Raleigh to have three exceptional universities that help keep a steady pipeline of top-tier talent. 

“The first core principle to build a good company anywhere is to first find product market fit.

Q. Your a PM focused CEO, when do you hire a someone with a complimentary skill to you?

You can't offload management. We don't have an HR function, I invited a Chief People Officer from the bay area and she confirmed we do not need an HR function We use PEO (professional employer organization) to do on boarding benefits etc. The "soft stuff" is important information that employees should be able to discuss with their direct report, I see HR as an excuse as an area for people to bitch about things. If people can't go speak with their managers about something at our size, that's a problem. We need to have dialogue. I do a 90 day 1:1 with everyone in the company. I did 3 this week alone. Some last 10 mins and some are 45 mins. My version of checking in and a chance for people to discuss the latest.

“I do a 90 day 1:1 with everyone in the company. I did 3 this week alone. Some last 10 mins and some are 45 mins. My version of checking in...
Pendo, Business and Pleasure

Q. How do you balance a growth and your personal life in a startup?

You have to be intentional. Having dinner with my family is important to me, so I I leave at 5:30 or 6. I have dinner with my family and plug back in when kids go to bed. My family is a priority so I make time for it. I try to travel only twice a month.

“You have to be intentional.

Q. Do you recommend a sabbatical for entrepreneurs after they exit?

Ohh yes. Take a break! I took the summer off to travel, consult and taste a different culture. I got to plug myself into communities that helped change my perspective.

Q. How do you travel for B&P?

Hotel Tonight is my app. In San Francisco, I get an Airbnb if I'm staying more than two nights if less I'll do hotels. I like to get groceries and make it feel like home, the routine is important to me when traveling. I'm an evangelist of public transit and try to use it in every city I go to. I enjoyed my time in Tokyo but love to always return to SF. The access to nature and the incredible food is hard to beat.


Todd's Raleigh Recommendations

Coffee: Morning Exchange, Jubala, Videri ( for their mocha!)

Restaurants: Poole's Diner, Crawford & Son's, Bida Manda

Cocktails: Foundation Bar, Fox's Liquor Bar