Using Data to Increase Growth

with Ryan Whitney,

Chief Sales Officer, AnyRoad

In this episode, Pete is joined by Ryan Whitney, the Chief Sales Officer at AnyRoad, to discuss how data can help companies increase their growth rate. From biggest challenges to advice for aspiring leaders, there is much to take away from Ryan’s experience.
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Key topics in today’s conversation include:

  • Ryan’s background and career journey (0:38)
  • Where AnyRoad is at in its journey (8:20)
  • Challenges to mitigate the risk from (15:29)
  • Advice for aspiring leaders (23:30)


The SaaS(ramp) Podcast explores how tech leaders scale from product adoption to enterprise success. Learn more at


Pete Thornton 0:06
Hey everyone, welcome to The SaaS(ramp) Podcast. I’m your host podcast beat with me today Ryan Whitney, Chief Sales Officer at AnyRoad. Welcome, Ryan.

Ryan Whitney 0:15
Thanks, Pete. Good to be here. Appreciate the time.

Pete Thornton 0:18
Yeah, thanks so much for coming on. Then looking forward to having you on looking forward to speaking to any go-to-market leader of such a fast-growing organization like AnyRoad, always like to start kind of on the personal side, though. So love to know who you are, you know a little bit about yourself, how’d you get where you are today.

Ryan Whitney 0:36
Ya know how I’m happy to share. So I’ve been in the sales profession my entire career. So when I left college, I did a year of consulting and I always had a passion for sales. My father and mother were both in sales growing up. So I saw the dedication that they put in the hard work and then the success that paid off from that being one of four. So I always love to be around people, I always love to communicate and help solve problems and in sales was kind of just a natural progression for me, as I got into the work industry and thought, let’s, let’s go do it and take some of the learnings and some of the coaching I’ve had from other mentors and go that route. So I’ve been fortunate, I’ve worked with many, many great leaders and mentors over the years, many great companies that has led me to AnyRoad and lead in the global sales organization here.

Pete Thornton 1:35
Nice. Okay, so interesting. I saw a meme yesterday, or two days ago on LinkedIn, and somebody’s walking down a road, and this garage door is accidentally closing and it actually closes this person into it. And so and you see the security cam from the inside, and she’s just stuck, she has no idea how she got there. And she has no idea how to get out. And somebody’s like, this is everybody’s journey into sales. And so it was like a make fun, you know, but in your case, like, that’s very, like some people are from a family of medical, you were from a family of sales.

Ryan Whitney 2:05
Yeah, it’s, it’s interesting. You know, I have I had many friends growing up where their mothers and fathers were in the medical industry, or they were lawyers. And, and I always appreciated what, what they did. And whether you call it it was never smart enough in school to go go to all the years to get there. But also I just, you know, I was a big sports, contributor and player in when I was younger, and that team environment, the coaches I had, and then yeah, my both my parents in one form or fashion, we’re doing sales in different industries, their ability to, to have success, but also the work ethic that came with it. And it just kind of cascaded down to myself. And ironically, my younger brother is also in technology sales. And so I think we just kind of saw it from, from a parental perspective, and from a sports and teaming and winning perspective is what attracted me kind of to the to sales.

Pete Thornton 3:10
Okay, interesting. I was going to ask about siblings, like, did it? Did it take across the board? So to two out of four is not? It’s not? It’s not too shabby, actually.

Ryan Whitney 3:19
50%. The other two ones and fitness. So kind of, you know, doing coaching and mentoring and the other is actually in the mental health industry. So kind of a broad background.

Pete Thornton 3:30
Okay, great, great family. That’s very, very cool. One more thing, in that in that journey, and that’s the movement from maybe like consulting, I mean, everybody comes out of college, and you’re looking for a role, or something to get into sink your teeth into for your first job. But was there a, was there a dedicated path to software? Or did was there an opportunistic journey into software? Kind of how did it move across from consulting into SaaS?

Ryan Whitney 3:58
Yeah, I was a little bit opportunistic. I mean, when I moved out of consulting, I worked for a nonprofit, worked with universities, and worked with students, along with with the faculty in the universities around kind of West Coast. And I was fortunate enough that my first sales job in kind of technology was in medical. And I, he’s one of kind of my early mentors. The President, CEO of the company, which was based in Southern California brought me on to run kind of the western territory. So I started in medical, and it was a lot of travel and travel by car. And I had a family friend that was in the technology, software, space, and kind of brought me up to speed and educated me on the technology world outside the medical software hardware. And that then encouraged kind of my thinking and spurred me to think more in on the pure kind of software technology side. That was kind of the compelling reason to go went to a little bit of a different direction and focus more on the technology side software hardware. And then that led me to just you know, where I’m at today selling kind of pure SaaS solutions.

Pete Thornton 5:11
Right? Okay. Okay, that’s great. So your intention was that direction and then somebody said, you know, you can, you can hypothetically not be on the road quite so much like have that have that grind that it is a physically taxing I have an uncle that does the same, does extremely well. And it’s just, it’s a tough one when you have three, three kiddos, any kiddos, I suppose but that’s that situation.

Ryan Whitney 5:34
Yeah, and to put it in perspective, I was driving about 60,000 miles per year in a car. So I got to a point where I wanted to get off the road as much as I was, and but still stay in sales go really enjoyed what I was doing just wanted a different, a different flavor. And that led me into software.

Pete Thornton 5:55
Okay, okay, fantastic. I see the gain site experience, it looks like you made just a lot of headway there, like maybe had a lot of role changes really made a progression through Was that a formative company? Or was it just happened to be a lot of movement within that type software company?

Ryan Whitney 6:15
No, it was part of where our growth came from. I’ve been fortunate when I left the medical field to work for some really good companies. And two of the three that I worked for, were category creators. And they were early on in their maturity when I joined. And so it really gave me a nice perspective of early-stage growth companies, what it took to be successful, the opportunity to move within the company based on success, and just more responsibility. And Gainsight, when I took that role in 2013, was just that, I came in, you know, early on to work directly for the CEO, and the culture was all around really empowering employees to do more within the organization and find new ways to help grow them as individuals, personally and professionally. And so, you know, it was a, it was a great honor and a great experience for me to move in my career, do all the things I wanted to do from selling to managing to mentoring to coaching all of the teams that I had, and so I’m really forever, you know, keep them in high regards, and thankful for the opportunity I had there. That’s also led me to where I’m at today.

Pete Thornton 7:36
Yeah, that’s fantastic. And that really is kind of like why ask because like, what, when you start to join a company at that size, like there’s always a first time and there’s a slightly different type of Persona, who does it, there’s a little bit of an entrepreneurial mindset, or somebody who enjoys building a function as opposed to maybe continuance of a function or managing a function, certainly a different one. And then from my outside looking in at AnyRoad, it seems it seems to be in that in that same realm. So yeah, just maybe 30,000-foot tell us about AnyRoad. Where’s it at in its journey? What are we doing? Is it a category creator, as well love to know all about it?

Ryan Whitney 8:16
Yeah, absolutely. I’ll give a quick overview. So yeah, we are creating a category around experience, relationship management. And it’s all around kind of the experiential marketing space. And we have a technology that supports large brands, brands, on the retail brands, within automotive brands, with beverage, just other kind of just consumer product groups. And we really help them understand from a data perspective how their events and experiences are connecting to their consumer. And the spin on what we’re doing is not so much wanting to be a ticketing company, it’s really to be a data company, that decisions are made through the data and help influence a chief marketing officer or a VP of branded experiences, around how they need to invest, where they can optimize to get the biggest connection with the consumer, drive brand loyalty, and ultimately drive kind of lifetime value from their events and experiences. And the missing gap has always been how do you measure what success looks like? How do you measure what the ROI of these events experiences are back to the consumer, and we’re helping bridge that gap. And so what attracted me to your point earlier, I had been with you early stage companies, I love to build, I love to be early on and help kind of transform and the company and as they mature, find new ways to grow. And then when I looked at AnyRoad coming out of Gainsight, a lot of those things attracted me to the company, the market opportunity, the ability to have a real kind of positive impact with In the companies and brands and people that we are selling to, and stand behind kind of the data and metrics to help them do better in their job and help them do better connecting their value to consumers. And as someone that has always been to events and done experiences, personally, I know the power of community and the power of connection. And that’s one of the things that we help fuel. And so that attracted me to the company, along with a few others.

Pete Thornton 10:28
Okay, that’s, that’s fantastic. Yeah, that sounds like an amazing platform. And it does solve like, even outside looking in, I’m not in the marketing space whatsoever. But if you know anything about marketing, there’s always like, how do you measure the return? Like everybody knows, they like, what is that the famous thing that they always say is like, you’re gonna waste half of your marketing spend, you just don’t know which half? And so having some data actually drive that. Tremendous. Okay. And then and then on the builder side, so. So your, your journey. First of all, congratulations on A, Series B, looks like about six months ago, nice big series B led by some really reputable venture capital. That’s, I know, that’s a it’s an investment, but it’s a milestone in the journey of a hypergrowth. organization. So always big congratulations there. What, where would you say you are in the development, like, if you’re looking at the idea, like in product lead growth, they always put out these kinds of graphs, and they talk about, you know, in precede, or trying to establish an organization establish a product, and then you’re trying to drive a product market fit. You’re trying to establish like a go-to-market organization, and then scaling enterprise offering, it’s kind of this not everybody follows the same stair steps, but it is kind of a broad categorization. Where do you see yourself now? And where are you guys hoping to get to?

Ryan Whitney 11:53
Yeah, I mean, we’ve had some really early positive success at the stage of company that we’re at, that obviously led us down the fortunate series be late last year. So right now, you know, we’re focused on is predictable growth, along with high growth. And what comes with that is the ability to take a step back and say, Okay, where are we today? Where do we want to go tomorrow? And how do we all really align around the focus over the next 12 months of where we think we can have the biggest growth. And I think that alignment is super important, because when you’re early on, it’s easy to go after every opportunity, every industry, and say, We can do it all. And I think we have learned and others, companies that I’ve been a part of have learned that if you kind of focus, continue to really nail the product market fit, really understand your ICP, hire the right people. And from a business perspective, have everyone aligned to a common goal. And using data to help influence where you are on that journey, I think gets you to that high growth faster. And so I think that’s one of the things that we’re really looking at is how do we look at our success over the past three, four or five years and double down on where we know we have really strong product market fit, and focus our energy and investments in people there to continue to grow, continue to invest, and then be opportunistic at the same time, right. And I think as a young company, it’s always good to take calculated risks, because you learn, you might find something in that risk that allows you to open up a new channel, a new industry, a new use case, but I think you got to be careful in the balance of how much and that’s one thing we’re really focused on is predictable, sustainable growth, especially in today’s kind of landscape. And really just be smart with the money we have. And to grow in a methodical, high-growth way but be thoughtful and not just grow at all cost.

Pete Thornton 14:08
Yes. Okay. So what I’m hearing you say like that, you kind of unpacking it definitely leads into some of these mean these common questions with a company about this predictable growth, meaning, you know, it’s moving fast, but you’d like to be able to, you know, let everybody around you understand, like, what expectations can alignment towards common goals, like at least understanding what you’re moving towards as a company and being able to let each of the independent pieces and parts know and use of data to measure and that it kind of all fell into this realm of like just trying to get behind the strongest product market fit. And then line everybody up measure according to that kind of like work on what’s but it sounds like there’s because there’s this makes it sound like a science show like Oh, good. So you’re following steps A B and C but there’s things that you’re saying in there that like lean into the art of this the Like alkylated risks, there’s an intuition and a bit of a gut to that. So maybe the question actually is like, what challenges have you seen because of your, you know, in your career, like seeing these repeated patterns with, with sales teams, or even like companies at large? Like you’re kind of like, leading right now? What challenges do you see at this stage of growth that you’re trying to mitigate the risk from?

Ryan Whitney 15:28
Yeah, I think I think across the board, what I’ve seen and even early on it Gainsight. We looked at this, which is alignment, internal alignment to what we want to go after, and how we’re going to go after it. And the messaging that supports that alignment. And I think it’s important as a company, if I put my any Red Hat on, you know, we had to take a step back a couple months ago as a leadership team and say, Where do we all want to go? Where are we having the most success? Where do we want to continue to focus, knowing that we can’t do everything for everyone and be successful, to retain all those customers. And you know, when you have a finite set of resources, and you’re trying to build the repeatability and scalability, you have to really make some hard decisions around where you really are having the most success in the market and where your solution and product provides the biggest value. And I think that’s a key point in any growth of a company is that decision of do we want to be something for everyone, or you want to stay focused around what we know, we do really well, and really get and hone in on the right type of customer. So kind of within your ICP, making sure you do have good product-market fit, and not work can be that phrase can be thrown around quite a bit. So I think you have to really look at, you know, we looked at what are the use cases that we really know we can support? Well, based on where our product is today, our product is going to continue to evolve, every high-growth company is going to continue to evolve and invest. But where can you drive the most benefit today, that allows you to continue to retain and grow your customer base, as your product continues to mature. And as the market continues to mature, I think those two things, you know, have to somewhat work in concert, you can be way ahead of the market, which may be good, but you need the market to catch up, or you have to pull the market towards you. And I’ve seen that a couple of different companies. And it’s striking kind of that balance. And I think that can be really hard because from a go-to-market side, you know, we want to grow the company as fast as we can. But we also have to look at where we should focus the time, energy and resources we have, knowing that they aren’t an abundant amount of resource across the board to make sure we have the greatest success, short-term, and long-term, you know, for our customers and for the market. And I think that, in that the timing of that can become a struggle, because everyone comes out with a different point of view. And so I think that alignment that then cascades down to the to the teams, so everyone knows what you’re doing the direction you’re going and we can all rally behind the same is really, really important as you start to mature and pivot.

Pete Thornton 18:16
Yep. Okay, that sounds it sounds exceptionally similar, you know, like, like, postman organization that I work for today is in a similar, it, it’s in its series D 650. Employees. You know, since I’ve been there, it’s 100% year over year, almost like headcount growth as well as revenue growth. But these things, they just happen again, at the same, they just, there are levels to it, and it continues on. So it’s, again, like when you’re walking through some of these things, and we’ve heard them before. And it’s really interesting to see these things come through. The idea was one day, we’ll just codify this and it will be only a client, it’ll never happen. That’s a worthy goal. Yeah. Okay. So I mean, just constant assessment of what value providing for whom, at what timing, so that you can just take and focus from the leadership all the way back into the teams, and in an effort to align ultimately align on on the, I guess the, you know, even the tactical activities that a team is taking from day to day.

Ryan Whitney 19:14
Yeah, I think the last thing I would just say is keeping one eye ear, one ear to the market, and making sure that you’re also thinking and looking ahead, right, so you never get behind either where the industry is going, where you want to drive the market to what your customers need. And that’s another kind of, I would say element of balance is you have to focus on what you do well today, but always be thinking about what does the customer what does the market what are the industries need tomorrow and plan for that as well. You’re always relevant in you’re always thinking ahead, so you become highly valuable as they grow in scale.

Pete Thornton 19:53
Okay, that makes sense to dad does hear somebody recently say like, Hey, if you’re driving a car, it’s probably pretty important that you’re staring At about 30 yards ahead. And you know, it’s simplistic, but it’s just a good reminder as well. Yep. Okay. Helpful. Let me ask you just and you know, we’re kind of like, it’s a little bit of a past, present and future on this. And sometimes we like to dive way into the future. But sometimes it’s better just to like, you know, it’s a quarter at a time at certain elements. So maybe you’d like us a short snapshot of back and forward. Biggest challenge over the last six months. And again, you might have touched on it already. But just if there was one major challenge that was like, Oh, that was the toughest thing that’s happened in two quarters.

Ryan Whitney 20:36
Yeah, I think it’s, you know, for, and I’ve seen this just with folks that I have spoken with, in my role, and others, I mean, I think it’s been a challenge has been hiring, right? hiring talent over the past six months, has not been easy. And I think finding the right talent for the right stage of company, to help you get to the next. And so we’ve had some starts and stops. And that’s been a little bit of a challenge. And then, you know, for us, we have so many people that are new. And I think it’s when everyone comes in fairly new over the past six, eight, nine months, how do you get them all? aligned? How do you get them all enabled and trained? How do you get them all part of, of the culture you have? But also how do they bring more to your culture, to be additive in a direction, and a maturity of where you want to go? And I think for us, you know, as we’ve been, as we’ve been going out, and, and trying to raise, but also recruit, a lot of people don’t know, AnyRoad, right? So we’re having to build the brand, internally, externally, find the right types of folks based on the stage that we’re at, in the market was highly competitive, right. And so that became a challenge to scale as fast as you want to, or bring the right people into the organization of which you need, just based on the competitive nature. And I think based on, you know, there’s a lot of people that I think also that were doing, you know, well and having fun at their companies, they weren’t interested in moving. And so I think there was a higher bar to entry. So as I look back from kind of start of the year, that was one of the challenges we had was just keeping up with what how fast we wanted to grow the hiring, and then making sure that for the maturity and for the stage we were at we were hiring the right people that understood what it would take to build a company because we are instilling the building phase.

Pete Thornton 22:39
Yeah, absolutely. I would if we had the time, I would take that one all the way down. I’m enablement, it’s just it’s too much of that. It’s like everything you want to unpack out of that one. But given our time, because speaking of hiring, you may have to have another call to take. How about one last one, you are a chief sales officer, this is something that like a lot of people will aspire to be at a hypergrowth organization with great funding, great backing great people around it sounds like great culture and product set and Product Market Fit Tip for yourself, or maybe an introductory member of your team from 10 years ago, if you could tell yourself anything from a Ryan with a 10 years ago, what would that perhaps be?

Ryan Whitney 23:21
Yeah, I think it and I share this with some of the you know, our younger employees is come into each day with a plan and have an organized view of what you want to accomplish. Work with urgency, work with creativity, and always have a thirst for learning, and wanting to know more. And I would say the last piece of that is surround your is best that you can try to surround yourself with just good people, right? Try to find companies that really are building a culture of collaboration, you know, of winning, of learning. And I’ve been fortunate to be able to do that. And I have worked for many leaders and mentors that have helped guide me on that journey. from a sales perspective. I just heard this about 10, 15 years ago, which is stay hungry, work with urgency, and always put the customer first. Right and I think that has served me well over the years. I may not have always been the smartest person on the team. But I tried to always think about how can I out work? How can I build relationships? How can I work with extreme urgency for my customers and my prospects? And how do I just become a really good team member where I can support others growth and others journey and help them I’m along the way. And if I help them, I’m going to inevitably help myself because we’re all going to learn. And we’re all going to grow and mature together. And I think that combination has served me well. And I tried to I try to bring that to my teams and teams I’ve had before. And I think people appreciate that, right? honesty, transparency, working hard, all ends up with a positive result over time. And so I would just continue to share that with people be who you are, right? That’s probably the biggest learnings I had from Gainsight is, you know, bring your true self to work. Don’t try to be someone different. And I think that shows up. And I think you will have more fun, you’ll enjoy whatever role you’re in. And people enjoy being around you. And so those are things that I just share. And I’ve learned 10 years ago, and I’ve continued to learn them, you know, along the way.

Pete Thornton 25:57
Yeah, that’s tremendous. Oh, it kind of fires me up there coach, like, athletic background as well. And some of those things are just remember being like a five foot seven nothing and trying to make it and then eventually being able to play some college ball. And it was just, you know, they might, it might be an ankle biter, but eventually, you know, some of that commitment will turn into creativity and skill sets from the quantity and things outside of it.

Ryan Whitney 26:21
Absolutely. I think it gives you confidence. You have fun. And I think that’s what, in my, in my experience, working in a professional job, or any really any job, if you can have fun, be around the right people work hard. Challenge yourself, you’ll find a way to be successful in your own right. Success means different things to different people, but you’ll find it and it’ll make you feel good and give me confidence to go do more.

Pete Thornton 26:49
That’s great. That’s great. Well, thank you so much for the insights. We really appreciate that. Thanks on behalf of the SaaS(ramp) audience and best of luck moving forward with any rollover and find out the product.

Ryan Whitney 27:01
Yep, for sure you have any Pete really enjoyed it and best of luck to you as well.