Masha

Maybe just for my context then, tell me a little bit about you. Tell me a little bit about your role at Calendly. But also your background. How did you end up in Customer Success?

Colby

Yeah, that's a good question. So if we want to take it back to sort of my first job out of college, I wasn't really sure what I wanted to do. And I ended up spending four years in Japan doing Education and Sales for English tutoring for children. And during that process, I got 1000s of hours in the classroom. I got a lot of practice just teaching people and working on on-boarding and training and a lot of these sorts of things. And when it came time to come back to the United States, I knew I wanted to work in software, because my father works in software. He's an engineer, and I always thought it was something that I was always interested in. And so what I was able to do is get a job in an operational team at a software company. And I didn't even know what an operational team was or what they did. My first job was at a company called UserTesting, which I think is a fantastic company. I'm a big fan of qualitative research because I studied anthropology in school. I joined the Sales Operations team there,and one of my first tasks was to build out their first on-boarding and training program for the Sales department. And so from that job, I've worked at a couple different software companies, and I've had the opportunity to work in Operations and Enablement for all the different customer facing teams. So I've done Sales and Customer Success and Support. And here at Calendly, I sit in the Customer Experience organization, which is both Support and Customer Success. My team is responsible for enabling them on everything from product information, and internal systems and tools, through maintaining the customer facing Help Center and creating some of that customer facing content as well. So, we wear a lot of hats here, and I've intentionally tried to work on taking all that information I learned from working in all the customer facing departments and try to find a way to build things internally that reduce duplication and silos. Traditionally, a lot of those teams would have completely separate and duplicative ops teams in some sense. I've tried hard to prevent a little bit of that where I can. That's the big arc.

Masha

That's fantastic. And how big is the success team now? And I guess, I mean, my follow-up question, because there's some provocative questions later about it, is how big is the success team and how you folks organized within Calendly? Because we've seen a lot of different configurations. 

Colby

Yeah, absolutely. So what I can say is, the Customer Experience department is going through massive growth right now. 

Masha

Wow. That's amazing. And so where do you kind of roll into organizationally?

Colby

So I run the CX Operations and Enablement team, and then we have somebody who runs Support and somebody that runs Customer Success. All three of us roll up to the Chief Customer Officer, Tina, who we just brought on board, maybe about a month ago.

Masha

Very cool. And that's so maybe that's my first provocative question or controversial question. In your experience across these variety of companies—and sorry, the assumption there was Chief Customer Officer reports directly into the CEO. Is that fair? 

Colby

Yeah.

Masha

So what have you seen as the best way to set up Customer Experience and Customer Success? And what is the worst, organizationally, like structurally? [Laughs]

Colby

We're gonna have to vet this answer. [Laughs] So what's interesting is I think, if you kind of set support aside and you think about Customer Success specifically, the fight is always does that team sit in the Customer side and roll up to somebody like a Chief Customer Officer or Head of Customer Success? Or do they sit on the Sales side and they roll up to something like the Chief Revenue Officer? Right? And I've worked in both paradigms. And I've seen the duties of that job, like a Customer Success Manager type of role split several different ways. Sometimes they're responsible for renewals. Sometimes they're not. Sometimes they need to expand accounts and close deals, and sometimes they don't. That's maybe an Account Managers job or something. And I think that's the biggest question, right? So for me, if I have to make a choice, I prefer the Customer Success Managers, and Customer Success broadly sitting outside of Sales, and really being focused on making our customers get the best experience they can and get the most value out of the tool. I don't prefer that those roles be quota carrying roles that are commission driven. I think you can build a really great system where the Customer Success Manager partners with somebody on the Sales side, and they can handle owning accounts together. But that is my answer because I think the way you build the team depends on what you want to focus on in terms of outcomes. And for me, the outcome is, have happy customers that use the tool the right way, and get a ton of value out of it. And so I really believe that Customer Success Teams are focused on that, instead of on dollars, like the dollars come if you're doing it right. But I like their minds to be on really helping the customer to be successful. And I think our Head of Customer Success would probably say the same thing. 

Masha

Maybe I can actually—I forgot to ask you this first. But if we just zoom out a level, what is Customer Success in your perspective? And how do you know that it's working?

Colby

Yeah, that's a good question. So for me, Customer Success is a set of individuals at the company who are really responsible for owning the customer relationship, right? I really think of the Sales side of the business as owning the relationship with prospects—or something different than customer– future customers, if you will.

Masha

Not yet customers.

Colby

Not yet customers, right. And so once somebody becomes a customer, there needs to be somebody to own that relationship, and there are a lot of different scales at which you can do that. And I think it depends on who your customers are. It might be that you have enterprise customers, and there's a person responsible for owning the relationship between a couple of companies. But then, you can go all the way to the other end, where you sort of have a scale Customer Success that's really responsible for doing things like on-boarding webinars and that sort of stuff. And so any software tool, no matter how simple it is(Calendly is not a complex tool compared to other places I've worked) a lot of people just need help, and they need a way to get that help. And I think of the Customer Success organization doing that in as proactive a way as possible, where the support team tends to be a little more reactive.

Masha

And so if I kind of double down on that, or dig into that a little bit, what would you say is a good way to tell then with that kind of positioning, that Customer Success is working?

Colby

Sure. I mean, I think there are a couple different ways you can do it, and measuring whether or not Customer Success is working is a problem a lot of companies have. But there are a couple key things that I would think about. One is just product and feature adoption. Is the customer using the tool the way that they should be to get the most value out of it? If you've got a large customer, they could be spending a ton of money, but if they're using 50% of the features, they're leaving stuff on the table. And so increasing product adoption is a big one. But then also, when customers are happy, they don't leave. And that doesn't need to be stated or tracked from a dollars perspective, although it often is, but that's sort of the reality of it is if if you're getting the most value out of the tool, and you're enjoying the relationship you have with your vendor, you don't leave and go find another one. And so product adoption is a really granular thing you can track down to the feature level but just retention of a customer is super important. If that's happening, you know it's working.

Masha

That's great. And so, I want to ask you, dig a little bit more, because people have been using this word “value” a lot, like if the customers getting “value” right? Does value mean the same thing as revenue to you?

Colby

I don't think they're synonyms, no. For me value really comes down to is the product or service making your life easier in a meaningful way. Like it's not necessarily about dollars. It might be about something that you could eventually do a bunch of algebra to get to dollars if you wanted to, right? With Calendly, a lot of the value is it saves people time. It reduces the number of emails you have to send, it reduces friction. So that is valuable to people. And you could find a way to algebra that into dollars, but I don't think you need to. You can track it through other types of measurements. So time saved is a huge one for us at Calendly, number of emails prevented is another one. I hate those conversations where you're talking about, *'Are you free on Tuesday at 1? No? How about Thursday at 3?' And you have to do that like nine times. [Laughs]

Masha

Totally. That's why I'm a huge fan and definitely a big user. Cool. That makes a lot of sense. Thank you for sharing that. How in your experience across these different companies, and I guess more broadly as a field, how have you seen Customer Success sort of evolve in the past couple of years, let's say.

Colby

I would say that focusing on a couple of different areas, one being Customer Success, and the other being sort of Customer Experience, Operations and Enablement, those disciplines have really grown and evolved. And they’re something that companies more widely recognized as being important and crucial, and something you're willing to invest in. I think when I got into the operational space, if you were looking for a new job in Operations or Enablement, or one of these types of things, you were likely to find it in a Sales department, it kind of landed there first. And then as people started to realize that Customer Experience was going to be the differentiator for businesses moving forward, they realized that that was a thing to sort of carve out space for and carve out budget for. And so we talked a lot about that at other companies I've been at, because I've been in the Customer Experience Optimization space for a lot of my career at both UserTesting and FullStory, and we've seen the adoption of tools like those grow, because companies are willing to build out these teams. And so you started to see things like, Chief Customer Officer, or Chief Customer Experience Officer. These weren't really positions you heard too much about 10 years ago, I don't think, as I was just getting started. And so it's been really cool to see that, especially for me, as somebody who cares about these things and works in this discipline, to see it gain adoption. I think that's really neat. I don't know if that really answers the question.

Masha

No, that's fantastic. Absolutely. Were their key events that you could point to or changes that sort of drove that? Because you kind of mentioned, you know, companies started to realize. What was the aha moment for companies?

Colby

So, one thing I have observed just from having spent time at the companies that I did, is that I think a lot of the aha moment came from a really big point of friction that companies were having. And that was friction around how to handle customers through all the new channels that emerged by the addition of not only the internet, but then eventually, smartphones and apps and all of those things. You started to hear a lot about these words very early on. Omni-channel experience and multi-channel experience. And people were really wondering, like, how do we get a holistic understanding of our relationship with our customer? And people weren't really doing that. So I think part of the adoption of Customer Experience came from the need to start paying attention to the whole view. Support had one understanding of customer relationship and maybe the Retail folks had a different one and the Sales guys at Head Office had a different one. And they really needed a way to stitch all those together and make sure somebody was thinking about the entire umbrella. And I think once people started thinking about a solution to that problem, you started to see a focus on these types of customer-centric departments and roles pop up.

Masha

And that's an interesting sort of keyword that you're mentioning too, like this customer-centric thing seems to be gaining some recognition or some speed as well. And I wonder if that's related?

Colby

I think so. And I also think—I mean, I've paid pretty close attention to this just because of where I've worked, but people are really starting to understand the importance of user experience or usability research more broadly. So you're starting to see that customer-centric word. It sort of goes hand in hand with collecting data in that way. If you're wanting to make decisions about what to do as a business based on what your customer wants, or needs, or thinks or feels, you have to be collecting the information and leading with that. It used to be the case, (especially 10+ years ago) that you wouldn't really measure what customers thought of something until you've gone all the way through the process of five years of research and development and building. Then you'd bring your product to market, and then you would sort of measure how people receive the product once it came into the marketplace. And I think because of the success of companies, especially like Apple, people started to push where you pay attention to what customers think as early into the development lifecycle of things as you can. And so, a lot of times, I think that's what people are getting at when they're talking about customer-centric. How many of the decisions that we are making along the way are actually being made using real customer data? 

Masha

That's brilliant. Could you maybe speak to—pretend I just handed you a crystal ball, could you speak to—

Colby

I’ll hold it.

Masha

There you go. How do you see it changing in the next five years?

Colby

I don't know. That's a really big question. I've spent a lot of my career in SaaS, and I try to think about the other industries out there as well, but a lot of my mind is sort of focused on the SaaS world. So if I try to think more broadly about what all the companies are doing, I think we're just going to continue to see a shift towards the digital. I think COVID made the reality of where we're going apparent to people who I think were ignoring it. But for a really long time, we've seen a trend where, whether it's retail or any other type of business, people weren’t paying attention to all the channels. But then they've started to see like, *'Oh, my brick and mortar is dwindling and so we're going online.' And now we're moving even more towards the mobile app space. If you look at companies like Chipotle, they do a massive amount of business just through their mobile app. And I think we're just gonna see that trend continuing. So customer focused teams, I think, are going to spend more and more of their time thinking about those digital channels. It's not that the other channels aren’t important too, but it'll be really interesting to see how this all goes, especially in a world where everybody's working remote. Something my team thinks a lot about, is how are we supporting our customers in a world where our own teams are distributed? And how do we prepare the company to give amazing service even though we're scattered all over the country or all over the world? 

Masha

I'm curious, I wonder if that actually almost makes your predictions, whatever they might be, in the SaaS world, like more broadly applicable because it kind of sounds like essentially most industries kind of have to move towards the digital and the SaaS and whatever, right?

Colby

That's really true. One of the things I've talked with some of my friends who aren't in this space about is the fact that in SaaS, we've been using the tools that everybody's using now for at least 10 years. So all my friends who don't work in the SaaS space started to use products like Zoom and other things over the last two years and they'd never heard of them before, which for me is really interesting because we've been thinking about how to use these tools and build to handle remote work and multiple offices for a really long time in SaaS and I think we were lucky in that way. Like we had all the tools already. So that change was less drastic for us. But I think other people are going to work more like we have been.

Masha

What would you say is the most controversial opinion that you hold about Customer Success that you wish other teams or other companies would just hurry up and catch up to?

Colby

Oh man, that's a good question. Controversial opinion... You're stumping me. So I will say one of the things that I think is really interesting about the type of work that my team does to enable these customer facing teams, whether it's Support or Customer Success, or even Sales is that companies have just been really bad at it for a really long time, internally. And I'm not going to claim to have all the answers or know all the secrets. But I think my opinion on this topic is that people should spend money on it way earlier than they do. I was really pleased to join Calendly at the time that I did, but it was actually, it was pretty uncommon for a company to hire somebody like me to think about operational and enablement problems as early as they did, in terms of headcount. A lot of companies will wait until they have hundreds of employees. And by that point, it's just a lot harder to come in and try to build information pipelines between Product and Engineering and your customer facing teams and to get all that stuff in place. And so I don't know if it's controversial, but I think people should spend money on supporting roles for these customer facing teams a lot sooner than they do. I just think that's enormously crucial. And I think companies are starting to get a little better about it. But yet companies get to hundreds of employees before they've ever sat down and thought about, where do we store information? How do we train new employees? And all that stuff, it's really important.

Masha

I totally feel you. In our last couple minutes, I wanted to ask you this cheeky question, which is, you know, we've heard a lot about customer success folks sort of loving to be either superheroes for their customers and sort of save the day for them, or they love to make their customers feel like superheroes. If you had a Customer Success related superpower, what would yours be?

Colby

I mean, it would have to be something like seeing the future, I think. I think that would make everything easier, if I could see even a week in the future. I think that that would help a lot. And to point specifically to what you said, I think most folks I know who are really passionate about Customer Success and Customer Experience, are in the bucket of the latter. They like the people they help to be the superstars. If we can help make people awesome at the jobs that they're doing, you know, they're going to be happy, we're going to be happy. And that's super important. So if we could predict what these people are going to need from us, right? That'd be really helpful if we could tell the future. The best we can do though is do the research. So I think in lieu of having the ability to see the future, we just have to do research. So we try to.

Masha

Totally, that makes a ton of sense. Look, we've got a couple of minutes left. I want to be respectful of your time and let you go on time. But do you have any questions for me before we wrap up? This was really awesome. Thank you for taking the time.

Colby

Yeah, no, of course. No, I don't think I have any questions. If you're ever looking for other folks to chat with, I know a few people that you probably think are interesting in this space. And so I'm always happy to make introductions to you, if that's helpful. Hopefully I didn't ramble too much. 

Masha

No, this is amazing! Colby, this was really great. And just so you know—and super appreciate your generous offer and we'll definitely take you up on that. Just so you know, sort of the next steps on our end. We're very fortunate to now have a little bit of a backlog, which means that it'll take me probably three-ish weeks to kind of get our transcript all done up. So the next step will be I'll do that and then I'll send it over to you so that you can run it by your folks. And after that, we'll publish and see where that goes.

Colby

Okay, yeah, that sounds great. I'm looking forward to it. This is a lot of fun. 

Masha

Yeah, I really enjoyed it. Thank you so much for taking the time again. 

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