Innovating travel experiences: A dive into Product Leadership

Join us as we sit down with Kristin Dorsett, the Chief Product Officer at Viator, the world’s largest experiences marketplace. Delve into Kristin's remarkable journey, from her early career exploration to her pivotal role in shaping the product landscape at Viator.

Discover how Kristin's passion for product was ignited and fueled over the years, paving her path to becoming a trailblazing leader in the industry.

Explore Kristin's transformative work and achievements at Viator, where she spearheaded initiatives to enable massive scale of supply, revolutionized the business model for operators through the "Accelerate" program, and cultivated customer loyalty through innovative app development strategies.

Gain insights into Kristin's leadership style, navigating a remote-first, globally-located tech organization. Learn how she harnesses the power of autonomous cross-functional teams to solve complex challenges and fosters a culture where "we strive for better, not perfect.”

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Transcript

Speaker 1: 0:01

Hello everyone and thank you for tuning in again. I am Kayleigh Bateman, the content director at Sheet and Code, and today we are discussing innovating travel experiences a dive into product leadership with Kristen Dorsett. With me today I've got Kristen Dorsett, the chief product officer at Viator, which is the world's largest experiences marketplace, and we're going to dive into her remarkable journey, from her early career exploration to her pivotal role in shaping the product landscape at Viator. Welcome, kristen, thank you so much for joining us. Thank you for having me. We'd love to kick off, if it's okay, with a little bit about you and your background and right through to how you entered the world of product management at Viator. That's okay with you.

Speaker 2: 0:46

Sure. So I have a bit of a convoluted journey to get where I am today, and so I studied at university PR and literature, really with a high focus on writing, and I really thought that I wanted to get my MFA in creative writing and be a writer as my career. But to get an MFA you have to have a manuscript, and so that was going to take a couple of years, and so I was going to work for a couple of years and I just happened to have my first job be at a company called HomeAway, which is now Vrbo, which at the time was the leading marketplace for vacation rentals, and I joined in a PR role and loved it Like I loved working in tech. I love the energy, I love the products, I loved all the people I worked with and really I just kind of like the idea of becoming a writer just left me and I'm like, nope, this is, this is what I want to do. I love tech and this is what I want my career to be and I want to build tech businesses, and so that's basically what I've done.

Speaker 2: 1:48

So at HomeAway, I started in marketing and then ended up expanding my role to include more of sales and then a bit of product management, and then I had an opportunity to become a product manager for our property managers part of our business, and so it was a pretty property managers part of our business, and so it was a pretty nascent part of the business and it was an opportunity to kind of do a zero to one build. And I'd never been a product manager before, but I knew the customers really well, coming from a sales and marketing background, and so I knew exactly what our customers needed and I just had to learn the vocabulary of product management and the process of product management, to take what I knew as a subject matter expert and convert it into a backlog and a roadmap and all the things you have to do as a product manager. And once I found product management, I loved it and I felt a bit like I'd found my calling because it was. I think I'm a good opportunity or problem spotter and so I could always spot the problems and then being a product manager put you in a position to help solve them, and so for me it was the best of both worlds. I got to use both sides of my mind and I loved it.

Speaker 1: 2:57

Yeah, I love that, that you completely just changed careers after you discovered tech, and this is what I'm going to do, and that's that's where I want to go.

Speaker 2: 3:07

And I actually. So I changed again a couple of times. So I went to business school after HomeAway and really thought that I wanted to start a company. I definitely. I took a lot of courses in entrepreneurship and had the academic discipline of entrepreneurship, I think pretty well understood. But then when I got out there to do it in the real world, it's really, really hard. And so I joined to start a very, very early stage startup in the UK and it was really hard work and I learned that if you are not really passionate about the problem you're solving, you're going to burn out as a founder. You have to really live and breathe that problem and I just really didn't, having joined someone else's startup. And so after that I decided to go back into product management and move back to the States at an early stage startup called BookBub, which is a daily deal site for eBooks, and that was really really fun. Again, it was a lot of zero to one product management, building new products from scratch.

Speaker 2: 4:12

But I found that I was living in Boston and I couldn't handle the Boston winters and I wanted to live somewhere sunnier. So I actually moved to Las Vegas and in Las Vegas there weren't a lot of interesting product management opportunities, and so what I found instead was a customer support leadership role at TripAdvisor, and I'd never run a customer service team before, but it was a good company and I was like this is a new challenge and they had really interesting problems to solve within the customer service team. And so I took a customer service role, a very operational role, and so I've been at TripAdvisor for almost eight years now. I found myself at TripAdvisor leading a support team for the B2B customers which are tour and activity operators, for the B2B customers which are tour and activity operators, and I really got to have a lot of empathy for those operators, listening to their calls every day and having to take escalations, and I really had a lot of empathy and I wanted to help solve those problems for them, because often they were in our product. And so I found myself getting more and more involved with the product team, saying, hey, did you know about this problem? Again, back to I see the opportunities and I want to help find solutions for them.

Speaker 2: 5:30

So I started partnering very, very closely with the product management organization at Viator and we did a lot of big changes on the supply side of our business in my first couple of years. So we automated a lot of the publishing of products to actually make my support team no longer had to review products manually, we would auto publish them, which was an enormous change for our marketplace. So we went from a pretty curated marketplace of about 50,000 products to over 400,000 at one point in time Wow, so an enormous, enormous change in our marketplace. And that was partnering very, very closely with our product teams to do that. And then eventually there was an opportunity for me to move more officially into a product role and I did it and eventually ended up taking over all the product for Viator and where it stands right now, I actually look after all of R&d, so I look after product in engineering, design, research and data amazing.

Speaker 1: 6:29

All right, uh, on this um podcast, we love people that have very we call them squiggly career routes and people that, um, just find their way into the tech industry, um, and then take an unconventional and way around it as well. So we absolutely love that and yours is very squiggly, very squiggly. I love that.

Speaker 1: 6:49

I saw when you said that you went into project management, that you felt that you had to learn the vocabulary and the process and I was wondering at the time, did you feel like when you were moving into tech, did you think that was going to be quite? Did you think that was quite, was going to be quite a daunting move, that it was going to be very technical? Or actually I've had ladies say that about product management on this podcast before and they say a lot of it is just about being a good communicator, knowing how to talk about your projects, being able to communicate to the board or who, or stakeholders or whoever it is, about that project and actually, and then, as you said, a lot of it is just knowing the vocab and the process, not necessarily being technically minded.

Speaker 2: 7:34

I think it depends on what product you own within a company. So I was lucky that the first product that I owned was a product for property managers that was a UI UX based product, and so I think those are a little bit easier to kind of enter into. I actually, after a year or so in product management at HomeAway, I ended up taking over some connectivity API products which were much more technical in nature, and I read a lot of books to get the vocabulary at least so I could have the conversations with the engineering counterparts. To be speaking the same language. I would know the functional requirements that were needed, but I needed to put that in the right language so that they understood the technical requirements. And it's easier, when there's a UI that you're working with, to sort of work with the designer and say, hey, this is what we want it to look like, this is roughly how we want it to work. It's much harder when you're like, ok, I want this endpoint, to do these things with these SLAs.

Speaker 1: 8:34

Yes, yeah, and as well. You now have moved into a large role. You lead quite a large team. You lead quite a large team, so finding that being able to work together is obviously is incredibly important to find a way where you can communicate across a very large team. So I wanted to ask you about that, because Viator is remote, first, and globally located, so obviously that can present very unique challenges for yourself. How do you effectively foster collaboration and communication among your teams across different time zones and also cultures.

Speaker 2: 9:15

It's hard, it's definitely hard. I mean it would be easier if we were all sitting co-located in one office, but it would also be less fun and there'd be less diversity of opinions. Yeah, and we definitely we'd be less global. We're a global company, we have global customers and therefore having global perspectives is actually really, really powerful for us when we're making product decisions. But it's not easy.

Speaker 2: 9:38

I mean, we, like everybody in COVID, we had to move to remote out of necessity, and then it really just became something that became part of our DNA. I mean, our entire executive team basically moved around the world and it just like no matter what. We were going to be on Zoom every day and we found, as we were hiring remotely, that the talent pool we had access to just got broader and broader, and so it was working for us. And so, where some companies have moved to trying to bring people back into the office, we really doubled down on remote first, and flexibility and I think it is really a core part of our value proposition as an employer is that we are flexible and we do want you to have that balance of work and life that works for you. And I think we don't just say it. I think we actually live it.

Speaker 1: 10:28

Yes, living it, especially if that comes from the executive team, because that's normally where companies fall short that you don't see it from the top down or the executive team might be doing something different to everybody else, but if you see it from the top, then everybody just knows that's okay and I can be okay and I can be flexible and I can be remote and I'm valued just as much as everybody else, whether or not they go into an office or not. But actually seeing your leadership team do it.

Speaker 2: 10:55

So so so I work from home, from Austin, texas. There is no one else at Viator in Austin. So no matter what, I am sitting on zoom for eight to 10 hours a day. Yeah yeah, so if I'm doing it, I have to be comfortable that everybody can be effective, like I can be effective, so I trust my teams to be effective Exactly exactly and a little bit more.

Speaker 1: 11:16

I wanted to ask you about your teams. Autonomous cross-functional teams are a cornerstone of modern product development. No-transcript.

Speaker 2: 11:32

Sure, I'm definitely a big believer in cross-functional teams. We're organized into roughly 30 pods that are all cross-functional in nature, and the people within the pod may be different. The different roles B2B and B2B could be either operator-facing products or also partner-facing products. So Viator actually has a big third-party distribution network, and so we have teams that are focused on different kinds of distribution partners, from travel agents to e-commerce partners like Bookingcom and Expedia. So, just for example, one of the teams focused on partners is focused on an initiative related to growing our affiliate network, and so that pod is composed of a product manager and an engineering leader, as well as an engineers.

Speaker 2: 12:27

Product marketing. There is usually I mean, we have a designer in place an analyst, as well as user research, and that cross-functional group of people are looking at, okay, what are the opportunities for us to grow our number of affiliates, as well as the experience for the affiliates we already have on board and how we can increase retention from those accounts. And so they work very, very closely together to identify, okay, what's the next opportunity to go after, how do we validate that it's a real opportunity and how do we ultimately come up with a solution that's going to solve that opportunity and so it's very, very, very, very cross-functional and we actually one of the projects that team has worked on we launched an influencer storefront product in soft launch a few weeks ago where influencers who are going to be talking about Viator hopefully on their social media channels also, can now have one link that goes to one link on Viator that showcases all of the different experiences that they want to highlight and potentially have their readership or their social media followers have access to.

Speaker 1: 13:33

Amazing, and there is this misconception that, working in tech, you're very siloed and actually you work on your own and that's it. From what you just described there, that is complete rubbish and that you do work with lots of different teams across one project. So yeah, did you think that tech was going to be like that? Were you quite surprised when you realize, actually, the amount of teams and cross-functional teams that you would be working with for one project? Was that quite a surprise to you?

Speaker 2: 14:05

I don't know if I would say it was a surprise. I mean, I did start in marketing and so I would say my first year or so I was working by myself quite a bit. I mean, you would do meetings where you talk about broader strategic things, but a lot of what I was doing was writing articles for the website, writing email newsletters, and so it was a lot of IC individual contributor work. But definitely, once I moved into a product role and was part of a cross-functional product pod, it was where, every single day, I was talking to people across the business. I mean, because you have a wide array of stakeholders in different functions, as well as the different people in your pod itself, and so, yes, the number of different types of people you interact with every day is very high in a company that's doing product the right way.

Speaker 1: 14:50

Yeah exactly I wanted to ask you a little bit about. We spoke about some of the challenges, but what have been some of the most rewarding challenges you've faced during your time at Viator?

Speaker 2: 15:03

I think one of the most challenging things was my very first role at Viator leading the supplier support team, because, like I mentioned, I'd never led a support team before, so I had to not only learn a new company, a new industry, I had to learn a new function and figure out okay, what does a good support organization actually look like? What are the metrics, how big does my team need to be? And so I was learning a lot, really really fast, and that was very, very challenging but also incredibly rewarding. So I think, anytime you're able to be building a skill from scratch, you're just growing so fast, and that's why I look back fondly on that time, because I was learning so much so fast even though at times I definitely felt like I was underwater.

Speaker 1: 15:50

Yes, I'm pleased you said that, because a lot of ladies that are guests on this podcast they tend to say, when stepping into a leadership role or managing a new team, they have this feeling as if they're meant to have all of the answers to everything, because that that they're suddenly looking after a team and that's they're meant to know everything, um. But I love the fact that you just said that you saw it as a learning experience and that you know it was challenging but you learned a lot, um, and that basically you didn't have to know everything. You have a team there that is there to fill in um all of the blanks and to teach you a lot, lots of things, and it sounds like that you did learn a lot from that experience, just just by asking your team, I'm assuming.

Speaker 2: 16:32

Yeah, I definitely learned a ton from my team because they've been again, again. They were the industry expert, they knew our customer, they've been running an operation, so they knew, roughly, I mean, what we should be doing. But what they didn't necessarily see was the bigger picture of how should the product be working together with the team to build an overall better experience, and I think that's where having a product background as well as an operations background is what I brought to the table. I was actually able to say, ok, these are how the two things should be fitting together and not working in silos.

Speaker 1: 17:03

Yeah, yeah. I love that, and could you highlight some key strategies or approaches that you've implemented to build your customer loyalty through the Vital app? I'm assuming customer loyalty through that app is incredibly important, so how did you and your teams work together to build some key strategies or approaches to build that customer loyalty?

Speaker 2: 17:26

Sure. So travel is a generally low frequency category, and so we have to work even harder to get repeat customers and loyalty, because sometimes there can be such a distance between that first booking and their second booking. But what we found is that our users who use the app actually repeat at much higher rates and are much more loyal. And so whether that was chicken or egg, if they were self-selecting into our app, or whether our app had some magic to it, we may never know, but we definitely have doubled down on that strategy and we are trying to get as many of our users as possible, whenever they have, after they booked the first thing, to actually download the app to cater to all the post-booking use cases that they have.

Speaker 2: 18:13

So if you book an experience, you're sitting from home in Austin, texas, and you're booking an experience in Rome, it may be two months away, and so whenever you book it, you have certain ideas in mind of how it's all going to work.

Speaker 2: 18:25

But once you get there on the ground, in destination, you actually have a different set of problems than what you necessarily anticipate. It's things like okay, I need to message the operator because I'm going to be 15 minutes late. Okay, well, how are you going to do that? Or I need to find the meeting point. How do I quickly plot that into Google Maps and find the meeting point to meet the operator at the right place? And so there's a number of these use cases that are really well suited for the app because of the native app functionality that's available, and so we want every single booker to have the app in their hands when they're in destination to solve those problems and then, while they're there, we also can give them suggestions of other things they might want to book while they're in destination, and we've seen this strategy really go well, where we're seeing a lot more people using the app while they're in destination and a lot more people booking that second thing.

Speaker 1: 19:16

Yes, yeah, I'm assuming as well from that having a very diverse team in that sense really helps with coming up with new ideas and just lots of different backgrounds and cultures where people can chip in on ideas like that from lots of different experiences, instead of keep having the same idea, keep coming up for the app. I'm assuming that with quite a diverse team you have quite a diverse range of ideas that come up for things like what you just described.

Speaker 2: 19:46

We do, and we really encourage dogfooding with our employees. So we give every single employee Viator credit to use and we want them to sort of act like they're a customer and give us feedback. And so definitely, they're going to a diversity of places. Their family makeup may be different, the reason of their trip may be different, and so we actually get a lot of valuable insights from our own employees using our products. I did, actually. I went on vacation three weeks ago and I did a big write-up for the teams of sort of everything I liked and didn't like so much in our product, and that's something that's really important for building customer empathy is just to use the be your own customer, because where we have the opportunity to use our own product and not every product person can, yeah, I think that that's what's fun about working on a travel travel app is that every single one of us can be a traveler yes, exactly yes, and that most people at some point have used, um, something from vi Viator and would be familiar with it, especially TripAdvisor.

Speaker 1: 20:54

When I heard that you were coming on here and that you had this mantra about done is better than perfect I have said that to so many people since I have read that and I absolutely love that you stand by that how do you strike a balance between delivering high quality products and embracing a culture of iteration and rapid innovation.

Speaker 2: 21:16

Yes, I will correct you a little bit. Our value is we strive for better, not perfect, I would say. My perspective is a product is never done and you should constantly be iterating, and so for me, that's what that value really means is that you don't have your first release, doesn't have to be perfect, because there's always a next one and the next one, and so it's better to get something out in a customer's hands and let them tell you if it's solving their problem than for you to stay internal and just be thinking about all the different permutations of what could be. Instead, just put it in customer' hands and they'll tell you. Or, through experimentation, the numbers will show you. And so we definitely push to getting that first MVP minimum viable product out as quickly as possible, but knowing it's not going to be perfect and that we're going to need to have many fast follows to get it to where it's actually hitting all the numbers that we do want it to have.

Speaker 1: 22:11

Yes, I love that. Yes, just getting out there and people trying it, that must be a really, a really great place to work mentally, because I've worked at places where there's lots of talk of things and things never get pushed out and you never feel like you're moving forward. Or you might reach the end of the year and you think, actually, what did we actually do this year year other than lots of meetings, about meetings, and we never actually, you know, push things out for people to use and people to experience? Um, but actually that is the mantra and it's just just, you know, just pushing things out, getting people to experience them. Mentally, you must get to the end of the year as an employee and think, yeah, we did a lot this year and we learned a lot from our user base this year.

Speaker 2: 22:53

I would say I hope so, but I do also. I mean, every company has values that get lived more in different pockets day to day, and I do think I mean we, like every company, have pros and cons. And we are very strong analytically, I would say, and our experimentation culture is strong, but what that also leads to is sometimes analysis paralysis of when you have so much data available, there's always more data to go mine, and so something I'm trying to encourage the teams to do more of is Striper Better, not Perfect. So, while it is one of our values, it is where, sometimes, even where it is one of our our values, it is where, sometimes, even even where it is one of your values, you may not live it every day, and so we have to, it has to be a mantra and we have to keep saying strive for better, not perfect, just ship it.

Speaker 1: 23:39

Yeah, yeah I love that. Um. Do you have any strategies or initiatives you implemented to improve diversity recruiting uh within engineer and data science teams at Viator?

Speaker 2: 23:51

So, like many tech companies, this is something that we struggle with, and so it is something we're trying to be a lot more intentional about than perhaps we have been in the past, and so the first thing we do is measure and just see how are we doing now? So then we have a baseline and that's everything from the very top of the funnel, all the way to how many candidates were interviewed, to, ultimately, what does our hiring profile look like. And so we're measuring and baselining how we're doing and we could definitely do better and we're, this year, really focusing on OK, what are those programs that we can implement to make everything from the top of the funnel to our hiring profiles just more diverse? And specifically, we're focused on female candidates this year, and that is one of my personal goals is how do we hire more female engineers and female data scientists and machine learning scientists?

Speaker 2: 24:44

And so a couple of the things we're doing is partnering with companies like yours and looking across Europe for which companies in each country. That we're doing is partnering with companies like yours and looking across Europe for who in what, which companies in each country that we're really trying to recruit heavily in, and for us, that's the UK, portugal and Poland, and who are those partners that we can partner with to to build the top of the funnel, to be more robust? And then something else we're doing is trying to focus on our junior talent pipeline. So we have both an internship program as well as a rotation program for both engineering and data science, to try to get more candidates in earlier in their career, before they're necessarily set and whether they're going to be in tech or not. We want to encourage more people early in the career to go into tech because it is is a great, great place to be.

Speaker 1: 25:34

Yes, yes, I couldn't agree more on that. I love the fact that you talked about measuring, um, what you're doing, because lots of companies, um, we have noticed here that some companies, they'll tick a diversity box and they'll say, you know, we, we partnered with an organization and that was it. They'll tick a diversity box and they'll say, you know, we, we partnered with an organization and that was it. And they tick a box, um, but actually measuring what you're doing, the impact of what you're doing, um, and and how that is making an impact within, uh, your business and also the products that are released, um, it's so important to be able to measure actually what you're doing instead of just thinking you know what, we'll just try everything and see if it works, and Vyator is such a such a big company that you know you would need to. I'm assuming you would need to measure things at different stages as you grow and grow, to see what is working and what isn't working.

Speaker 2: 26:28

I always find that's where you have to start, because you will will optimize your activity towards what isn't working. I always find that's where you have to start, because you will optimize your activity towards what you're measuring.

Speaker 1: 26:35

Yes, and you said that you're quite heavy on the data and analysis side and everything in your company, so why not obviously make sure that that is also in the diversity side of recruiting as well, to see what is working and what isn't? We are almost out of time and I could ask you several more questions if we had more time today, but I wanted to ask you finally, what is your advice that you would give to aspiring product managers or leaders who are looking to make an impact in the tech industry? Is there something that you wish somebody had told you in the tech industry.

Speaker 2: 27:11

Is there something that you wish somebody had told you? Sure, I think it's that product management is both a skill set and a mindset, and I think the skill set can be learned by reading books, taking courses. There's so many more resources available to people now than when they were when I started. I mean, just start by reading Marty Kagan's books. I mean that will tell it's Kagan's books. I mean that will tell it's good and that'll help give you some of the mindset. And I think that the mindset that's really important is around thinking about the customer and what are their pain points and opportunities and how do you help them, how do you understand their journey and how do you build solutions that help them solve their jobs to be done and so all of these things Jobs to be Done is another great book. None of these books existed 20 years ago when I was starting. So I would say, get the skill set and the vocabulary by reading books, taking courses, but it's really having that right mindset.

Speaker 2: 28:05

And part of how you can get that mindset is, in whatever role you're in, now that you're a subject matter expert, in, just start thinking about it from the customer perspective. Okay, what is the customer trying to achieve here. How do I understand from a data perspective, what are they trying to do? How successful are they in doing that thing? And then again the mindset you're halfway there doing that thing. And then you're again the mindset you're halfway there. And then if you can bring those ideas fully formed to a product management partner, then in partner with someone in product management to help get that solution to the finish line, then you are starting to build those skills, even when you're sitting in a different role. And then maybe for the next one you can say oh, actually I can do more of the discovery work myself. And so you can start to build more and more of those skills until you find yourself, like I did, where you just are a product manager all of a sudden Because you started doing the job kind of gradually over time.

Speaker 1: 29:00

Yeah, and a lot of students say that as well that when you're studying sometimes what you're studying doesn't always apply to real world problems and actually helping people and somewhere like Biotor, that's much easier to be able to think. You know what, as a customer, as somebody that has used these products, to always think of the customer first, what would I like, how would that help me? Well, you said, when you went on holiday yourself, you used the product holiday yourself, you use the product. So, um, to always be thinking customer first, then you're, you're in one of those roles.

Speaker 1: 29:35

That, that is, you know, you're making a real world impact, which is what a lot of students say they would, they would love to be in, they would. You know, they don't go into tech thinking I just want to write lots of lines of code. I would actually like to help people, I would like to make a difference in people's lives. Um, and somewhere like Viator, you can definitely uh see how, how that applies to making an impact on people's lives. Definitely. So you're right, I love that. That it's a, it's actually a mindset in product management, um, more than anything it is, and it's a fun one.

Speaker 2: 30:08

It's a fun mindset you get to use every day. Yeah, because you're and you're getting to help people. Exactly that is very, very rewarding wonderful.

Speaker 1: 30:17

Well, thank you so much. As I said, I could keep talking to you, um, for another uh series of questions if we had time, but we are already out of time. It's absolutely flown by. Thank you so much for coming on here and having a chat with us. It's been an absolute pleasure hearing all about your role in product management and being a leader at Vital. So thank you so much for joining us, thank you for having me and for everybody listening, as always. Thank you so much for joining us and we hope to see you again next time.