Ascent Podcast Ep. 8 - Kris Rudeegraap, CEO & Co-Founder @ Sendoso - Ascent Conference Ascent Podcast Ep. 8 - Kris Rudeegraap, CEO & Co-Founder @ Sendoso - Ascent Conference

Ascent Podcast Ep. 8 – Kris Rudeegraap, CEO & Co-Founder @ Sendoso





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Turning Pain into Pleasure

This week on the ascent podcast, Andrew interviews Kris Rudeegraap, co-founder and CEO at Sendoso. With more than a decade of sales experience this executive in his prime, has built a successful company from the ground up. Kris has made a name for himself in the industry by quite literally finding pain points and coming up with solutions to them.

Started From the Bottom Now He’s Here

If you’ve every worked in sales or you’e an entrepreneur then you know how much work goes into marketing, getting access to the right clients, and how difficult it can be to overcome adversity. In the cut-throat world of sales, only the fittest survive. This is what Kris was going through in his years in sales, and was able to identify areas where improvement was needed. He then proceeded to develop an idea or concept that solved the problem, and then turned that idea into a reality. Sendoso is the worlds first Sending Platform, which allows businesses to send the marketing tools they want to clients and personalize it at scale.

Being a founder and CEO, viewers learn the process that it took to build a company from an idea. He explains his entrepreneurial beginnings and gives insight into his early formative years and how that’s translated into what he’s doing now in a very down to earth manner and with a refreshing amount of self awareness. They also take you through the transition from employee to employer and provides insider access to the ins-and-outs of a day to day in a company like Sendoso. In this episode you’ll learn of the importance of having humility and how that can influence networking positively, giving first-hand proof that actions have consequences.

Good Culture is Good Business

Seondoso’s work culture has been so effective and positive that the company is featured on the Forbes list for best start up employers in 2020, and Kris is also a member of Forbes Councils. In this episode you’ll learn the methods the company has come up with and applied to create a remote work environment that can still accurately provide employees a great space to work and feel like a unified team.

Tune in and go into the mind of a tried and true entrepreneur and obtain an understanding of key factors that have led to his success. Whether you’re an entrepreneur, you’re in the marketing industry, you’re thinking of or are in the process of creating a startup, or you’re interested in learning cutting edge methods that have proven results, you simply have to watch or tune in!

Time Stamps

00:01= Intro/ Welcome
02:32= Rapid fire questions
8:00= Early experiences with entrepreneurship, and college experience. Learning while growing
10:28= Birth of Sendoso/ Starting out/ Source of inspiration/ Developing an idea
14:42= Transitioning from employee to employer
16:30= life as the head of a startup/ Starting a startup
19:40= Remote culture/ Making virtual traditions
21:58= Do you enjoy what you do?
24:10= Pleasure Points/ adrenaline rushes in the workplace
25:36= Work pet peeves
27: 06= meeting with customers/ value in feedback
28:45= Read that Review!
31:48= Adapting to a virtual environment/ high growth SATHS in 2021
33:01= Strategy decisions/ steering the ship
36:15= things to watch out for in the future/areas of future concern
37:50= Morning routine
39:55= Outro

Transcription

Andrew Tarvin [00:00:00] Hello, hello, hello, everyone. This is another episode of the Ascent podcast, a live video conversation where we get to know the human being behind some of the top leaders in tech. My name is Andrew Tarvin, your host and emcee. And I’m excited because today we’re going to be talking to Kris Rudeegraap, the CEO and co-founder of Sendoso. But first, a few quick announcements. If you are joining us live. We are streaming out to LinkedIn and Facebook and YouTube as well, and LinkedIn kind of coming up in the future. But as we’re chatting, feel free to make comments in the chat, share any ideas that resonate with you, thoughts that you’re like this is something that I want to take away with me and of course, feel free to share any questions that you have. And we may do a audience Q&A section a little bit later. If you are listening to this as a traditional podcast, well, then all you have to do is sit back and enjoy the wonderful sounds coming to your ears. I’m particularly excited for today’s guest because not only is he the CEO of a fantastic company, but also really fascinating person, at least based on the research that I’ve been doing so far. So I’m excited to get to know him as a human being. Our guest today is Chris Ruediger, who is a CEO and co-founder of Sendoso, which is the leading Sinding platform. Kris has more than a decade of sales experience and has spent time at top desk apps don’t and Pechora. He has a California native and CSU Chico alum currently residing in the Bay Area. And according to his LinkedIn profile, back in his university days, he played intramural soccer and football. So, of course, you’re going to find out what positions. But please welcome to your eyes and ears. Kris Rudeegraap. Kris,thank you for joining us.

Kris Rudeegraap [00:01:46] Thank you so much for having me. Excited to be here.

Andrew Tarvin [00:01:50] Well, so I’ve got to start for intramural soccer and football. What positions did you play?

Kris Rudeegraap [00:01:55] Yeah. So for soccer, I was a forward trying to get those goals and for football it was more of a wide receiver going to play a position.

Andrew Tarvin [00:02:05] So, OK, so you like the idea of like you like being the one that gets to score to gain the point playing forward in soccer, wide receiver football.

Kris Rudeegraap [00:02:13] Exactly.

Andrew Tarvin [00:02:14] I love it. And so we are certainly going to talk about the work that you are up to at Sendoso. But before we do that, we do like to get to know the person behind the leader. And so we’re going to start with a rapid fire round where you can give answers to in one or two words. Are you ready for rapid fire start?

Kris Rudeegraap [00:02:31] Bring it on.

Andrew Tarvin [00:02:33] All right. Excellent. First question is morning person or night owl?

Kris Rudeegraap [00:02:38] Night owl.

Andrew Tarvin [00:02:39] OK, so what time is bedtime normally?

Kris Rudeegraap [00:02:43] Probably one a.m..

Andrew Tarvin [00:02:45] OK, all right. That’s certainly on the later side. Not one of those like nine pm and you’re certainly going down like it. Apple or Android. Apple. OK, introvert or extrovert.

Kris Rudeegraap [00:02:58] Extrovert.

Andrew Tarvin [00:02:59] OK, when you were a kid, what did you want to grow up to become.

Kris Rudeegraap [00:03:05] Good question. I’d say secretly an entrepreneur because I was selling mistletoe or doing a little side hustle as a kid. But honestly, I didn’t know what I wanted to be when I grew up really was something I figured out through high school and college.

Andrew Tarvin [00:03:19] OK, so you didn’t quite know what? What do you mean selling mistletoe? What At Christmas time you would sell some mistletoe?

Kris Rudeegraap [00:03:25] That would be like selling mistletoe at Christmas or setting up lemonade stands or doing yard work at the neighbors or watching their animals when they went out of town, things like that.

Andrew Tarvin [00:03:37] OK, I’ve heard of most of those things. Right, pet sitting you maybe do and chores or lemonade stand. But where does mistletoe come in? Like, I don’t understand the selling process of this. Is this like you go up to couples that are like near each other some mistletoe so they kiss or what?

Kris Rudeegraap [00:03:53] Good context. I live maybe two minutes from a Christmas tree farm. And so for the month of November or December, I would just set up a little table with a sign that said, mistletoe, five bucks. People would just stop by little bunches. And, you know, I wrapped up the dough.

Andrew Tarvin [00:04:10] I love it. Was this in coordination with the Christmas tree shopper? You’re just like, listen, they’ve already got the audience foot traffic coming in. We’re just going to take advantage of that.

Kris Rudeegraap [00:04:18] Exactly. More of the latter.

Andrew Tarvin [00:04:20] I love it. That is the entrepreneurial spirit really early on. I love it. What is a current favorite hobby?

Kris Rudeegraap [00:04:27] Golf.

Andrew Tarvin [00:04:29] OK, how is your golf game getting better?

Kris Rudeegraap [00:04:33] I think it’s a fun sport that you are never perfect at it. I’d say I’m about a fifteen handicap and I play maybe every other week or every week if I can.

Andrew Tarvin [00:04:44] OK, I mean the fact that you have a handicap and no it means you’re already better than I am. I played golf early on and I’ve always had a beautiful looking swing, but it’s never translated to hitting it. Well, that’s what other people tell me. They’re like when I see you on the driving range taking. Swings, it looks good, but then you step up to the ball and it’s it’s terrible. Do you have a good looking swing?

Kris Rudeegraap [00:05:05] I’d say I’m a good looking swing and it actually goes the distance.

Andrew Tarvin [00:05:10] Ok. Alright. So it’s certainly better better than me. What is a TV series or book that you are currently watching or reading or recently finished?

Kris Rudeegraap [00:05:20] Recently finished a TV series called All American.

Andrew Tarvin [00:05:30] OK.

Kris Rudeegraap [00:05:31] Is the random show about some high schoolers playing football? Ultimately I just got recommended through Netflix and Jim got me.

Andrew Tarvin [00:05:42] It’s impressive how well they actually do that. They’re like, we’ve seen enough of your history to know that you’re going to love this and you may not even tell your friends about it, but we know you better than they do. I love it. Who is someone you admire?

Kris Rudeegraap [00:05:57] I admire some of these amazing entrepreneurs like Elon Musk and Jeff Bezos. Obviously, they’re kind of the trendsetters. And then there’s some other CEOs like my previous one. Djogo forgot to ask some of the other ones I’ve worked with that I just admire. They’ve scaled their companies, which is a little bit more in reach, a little out of reach for me.

Andrew Tarvin [00:06:22] Yeah. I mean I guess if you want to become the richest person in the world, that’s maybe a mindset they kind of follow. But yeah, we might only one person can have that title at a time, so I like it. So last kind of get to know you question, which you can certainly answer in more than one word. But I think a fascinating question that we’re curious about for different groups is what’s the story of your name? Are you named after someone? Does it come from somewhere? Any story behind Kris Rudeegraap?

Kris Rudeegraap [00:06:50] So Kris part’s pretty basic, but the Rudeegraap, I think, is more unique. My mom’s last name’s Rudy and my dad’s last name’s Graap. And when they got married, they combined it into a newer no hyphen, just new words. So me and my two sisters and my parents are the only ones minus one sister who’s already got. So the Rudeegraap legacy is small, but I’m going to carry it on that.

Andrew Tarvin [00:07:17] That is amazing. I love that as an idea. How did they do you know how they decided on this spelling? Because it’s also not just like Rudy plus like it.

Kris Rudeegraap [00:07:27] So happened that one of them had a double e and double a and they’ve just combined it the name. So their names before.

Andrew Tarvin [00:07:36] How? Wow, that is fascinating. That’s the first time I’ve heard of that, that combination name. I don’t think it would work with me and my wife because it would be way too many syllables long for our kids. But I love it as a strategy. You don’t have to to explore that. I think it’s fantastic. So we we talk a lot of the listeners that we have on our entrepreneurs or at least have the entrepreneurial spirit. And so I am curious about that entrepreneurial journey. And it sounds like it started pretty early for you with, like you said, a lemonade stand, et cetera. So then going into school, was that the intent, like, hey, I’m going to do a job for a little bit, but I know the end result is that I’m going to start my own company eventually. Or was it like was kind of a dream. You went this way and then you happened to come back into it.

Kris Rudeegraap [00:08:23] So I would say in college specifically, I was really interested in entrepreneurship, so much so that I started a couple of companies while in college. First one failed. The second one, we’re actually through university able to raise a little bit of funding from the Center for Entrepreneurship and took that into where I was able to exit that company into a solid into a company as I moved to San Francisco. So I’d say definitely really enjoyed the startup vibe and being from the Bay Area really got to see some of the dotcom that I missed out on and really saw that astronomical growth numbers. And then after college inside the company that I realized that I didn’t know enough, I think, to really do it again. And so I really wanted to learn from other entrepreneurs while in the industry, while being in other startups, seeing other companies. So it’s been about eight years and various sales roles and a learning while helping companies grow and then ultimately looking for that next big pain point, the big idea that I wanted to start my own company on.

Andrew Tarvin [00:09:31] Yeah, well, I love that recognition that, hey, there’s is this skill set that I need a little bit more of. And rather than going back and getting an MBA or taking online classes or whatever, I was like, let me just get a job in that area that’s going to kind of force me to learn and maybe make some money and also network. So I love that as a mind that it’s very much the the Mark Cuban get paid to learn type thing.

Kris Rudeegraap [00:09:55] Exactly. And the network part is pretty huge to some of the first hires. It’s the. So her ex colleagues at other companies, so that’s an also a big takeaway besides learning and growing your network so that when you do recruiting and is one of the most important parts of my job early on and still is. And so having a bigger network was helpful.

Andrew Tarvin [00:10:15] Now, that’s that’s great advice for people that are kind of thinking about that, that it’s not it’s not like, oh, this is a bad thing to go and get a job if you want to be an entrepreneur, but you can be strategic about it. That is going to help you a little bit later. And so I know you shared in the past that Santoso kind of came from this idea. Like you said, it was a pain point that you were experiencing in sales yourself. And I think that would be a great source of inspiration for an idea. But how to walk us through a little bit, just how did that actually go from I have this pain point myself to there should be a service that does this, too. I’m going to build that service at to I’ve built that service like what is kind of an initial flow. How long did that kind of process take?

Kris Rudeegraap [00:11:01] Yeah. So as well as that, my last company talked desk that a couple of things happened. One is I was in sales. So as an account executive I was mostly sending out emails as I was going to be the tool of choice that we had access to. And it was really becoming more of a spammy outreach. And I was getting less responses and I really needed to diversify and get a little bit more creative targeting some of these named accounts I was going after. So I started to do a little bit of writing handwritten notes. I go to Starbucks and sit down some Starbucks cards. We had a swag closet that I grab stuff from. It was all super manual, but it was working. Also, marketing would try to do some direct mail campaigns, but it was really marketing saying I felt this Google spreadsheet copy and paste data in Salesforce and then we’ll get to it and it would take three or four weeks at times. And so it’s kind of a really broken process. And I really thought to myself, why can’t I just click a button and send something? And so that was kind of the pain. I talked to a bunch of friends and other colleagues who said they would use a tool that allows you to click and send other stuff out, like different gifts or mailers. And so my first step, though, was I don’t know how to build logistics and infrastructure and warehouse supply chain stuff. So version one was ultimately a company called Coffee Center, which was sending digital Starbucks cards through a Buckenham Salesforce that had some coffee. And so that was kind of the one where I really understood if people would send other things, paid money to send this and build it into their sales process. And over the course of maybe six months, there was like almost three hundred thousand dollars in copies being sent. And it was enough so that I was like, OK, this kind of validates my thinking a little bit more. Let me and I had a co-founder that came in and was really another actually account executive chairman, co-founder that was super stoked on the concept and was really like, hey, let’s turn this into something real. And then we really did a lot more brainstorming and said, hey, we need this physical component and let’s launch Santoso and come back to the drawing boards and then figure out the logistics infrastructure along with the software, and spent about nine months working behind the scenes and then launched it.

Andrew Tarvin [00:13:22] Wow. And so a couple of questions about that experience was, was coffee. Sándor, did you intend that as like this is going to be my my MVP, my minimum viable product, or was this more of like, I’m just going to start here and it just happened to prove out that this is something that would work?

Kris Rudeegraap [00:13:36] It was it was kind of a combination of both. I would say that, you know, you’ve got to start somewhere. And so it was like, hey, let me just get something done. And, you know, at first it was a little bit of beer money trickling in. And then it was really just dawned on me that this once I kind of got traction, that there was something more to it than that. And then that’s really where I was like, OK, this is a good version one. Let’s really double down on it on a bigger picture. But I wasn’t really trying to think about it too long term. It was more just can I solve of any pain point? And just like lock and tackle versus like building a business plan and spending months planning day, just like let me build this and figure it out and get users.

Andrew Tarvin [00:14:18] Yeah. Which I think is a great mindset can sometimes feel overwhelming if you’re like, nope, this was the whole thing. And I think sometimes entrepreneurs and new entrepreneurs or people who are thinking about it, they’re like, no, I have to have every plan, part of it mapped out completely versus start small. You start with that kind of evolution. And so for you, when did you when did you make the decision to leave the sales job at top desk? When did you know, like, OK, this is actually now worth me taking a step. Was it early on? Was it late in the process or was it like did you just have a moment where you flipped over a table and stormed out? Was it more of a gradual thing? Was is that part like.

Kris Rudeegraap [00:14:56] Well, it was really the realization that. Copy sender was validated and in order to build so I needed to be full time, I could copy center was nice because there was self-service, no infrastructure was really just a digital gift card. So it was really something that like a night weekend a couple of times a week. I could support it if I was going to make a big bet on myself and on Sido. So I needed to spend as many hours as I could full time on this. And so I really talked it over with my co-founder and wife and just decided to pull the plug and go for it. It was happened to be in sales to transitioning from sales to it’s really like there’s never a good time. Sometimes the sales always got pipelining. Boys got the next day. So it was really like the end of quarter cut off. And I just said, this is the last quarter I told my boss and told the CEO and the rest is destroyed. My CEO was pretty receptive for it, too. He’s now an adviser, has been super helpful, too. So he kind of it was nice to see his support for me wanting to be an entrepreneur.

Andrew Tarvin [00:16:04] Well, like you said, that’s the value of partially building that that network like that. You had that support system when you did leave. Some of that could become an advisor or mentor or that kind of thing, which I think is fantastic. And so I did a similar thing when I left Prague to start my thing. It was like I ended at the end of the fiscal year. There’s something nice about that kind of cut off versus like just one random day I. I left. And so I am curious because you mentioned, like, I needed to be able to put in those hours also managing kind of family and stuff. What was it like at the very beginning? Is it the like was it the story of one hundred and twenty hour work weeks out of one hundred sixty eight, or was it more manageable at eighty or was it like. Nope, I kept the nine to five. What was that those early stages like in terms of that actual quote unquote work life balance.

Kris Rudeegraap [00:16:55] Yeah. So I would say was a little bit of the nine to five of we had an engineering team over in Pakistan, so it was more of like a, you know, a night like maybe like an eight or nine to four or five and then like eleven to one and when and because the time zone difference. But it was not it was maybe 50 hours a week, nothing like working 80 hour. We still want it to be thoughtful of a good work life balance. I didn’t want to burn myself out. I want my wife to still feel like I was being a part of the day to day of having dinner, things like that. And I think that some people will tend to vote on the work 80 hours a week and you got to work really long. I was more like, let me work really smart and then still make time to play golf or to go on a trip and know that this is a marathon. And I’m four years into what will be a multi decade marathon. And if I was if I got burnt out too early or the four burned out my wife or my friends like that. So really that was my mindset at least.

Andrew Tarvin [00:18:09] I think that’s very refreshing because I do think that sometimes we we reach certain providers or we and again, we always see people’s highlight reels. So it’s easy to like take them for whatever it is that they’ve said and not necessarily know what they actually do in those unsign hours. But to to be able to say, no, this was a conscious choice, that it doesn’t have to be one of those things. You can still be successful without saying, oh, it’s got to be every single waking moment to that point that it is something that you can sustain much, much longer.

Kris Rudeegraap [00:18:37] And so I’m just going to say, as an entrepreneur in the early stages, there’s an infinite to do list. And so I can become overwhelming and give you anxiety or also maybe make bad choices of like scrambling to finish things because there’s infinite things to do. So I think that it’s a pretty strong ability to manage your tasks and to kind block and live and work life balance. And I think a lot of entrepreneurs slightly differently at times.

Andrew Tarvin [00:19:07] So, yeah, well, and I love that approach. And that’s what I mean. It’s a great Segway because you’re on Forbes Executive Council. There’s a recent blog post that came out that you’re quoted in on how to build a strong culture remotely. And one of the things that you said there around this idea of culture was using collaboration tools to still be able to stay connected, but also to maintain your culture by encouraging virtual traditions for your employees to participate in. And giving an example, what is a virtual tradition that you’re kind of keeping up despite everything else going on?

Kris Rudeegraap [00:19:45] Yeah, so, I mean, there’s things like we do these like virtual like wine tasting and happy hours where we’re sending out people can act like the physical wine or booze. And then so a lot of the things that we we had fun with. The water cooler moments that go in to get drinks after work, we really try to figure out how do we incorporate that into our our remote culture during covid. So that was key for me, too. It was. How do I have this ask Chris anything concept where I randomly get connected to like five or ten different employees every week for just, you know, no agenda, random conversation. Sometimes we’re talking about dogs and golf. Sometimes it’s talking about an interesting innovation idea. But I also purposefully spurs that spontaneous conversation that you get in the office that may be remotely at your house. You don’t get. And then we also have been really cognizant about trying to purposely build these little kind of tiger teams to really keep that cross compartmental collaboration going, which might be been more accessible in the office remotely. Sometimes you get stuck and doing your own thing. And so just kind of not forcing, but just make sure that we think about some of these things at the office and doing them remotely.

Andrew Tarvin [00:21:09] Well, and I love the intentionality behind and that’s certainly one of the things that we we receive. So human that works company that I run. We teach organizations how to use humor to be more effective. And I think it’s a big thing that people have recognized in person. They maybe had some of this happen anyway, like you said, the hallway conversations or the spontaneous chats that happen because you pass and the lunch room or whatever, but you don’t have those moments in a virtual area. It’s so easy to just be on for the Xoom call or WebEx or Google meet or whatever just for that time to be out of like, no, we’re going to take a dedicated time to to focus on. I love that intention. And so kind of along those lines, certainly around your work life balance and other things, would you say that you enjoy what you do or that you love what you do?

Kris Rudeegraap [00:21:57] Absolutely. I love it better than anything. This is the best I could ever ask for.

Andrew Tarvin [00:22:03] Which is amazing and so I’m curious, do you think that that’s an important do you do you wish that for your employees? You think that that is a requirement in terms of the people who work for you, that there’s some type of benefit to enjoying what you do at work?

Kris Rudeegraap [00:22:16] One hundred percent. I think you’ve got to be passionate about what you do, otherwise you’ve got to do something else. Life’s too short to hate your job. And so we’re we do a lot of performance reviews or one on ones just to really make sure employees are loving what they’re doing. And we’ve also done a good amount of cross departmental movement where maybe a strong customer support person is not one of our top product managers and one of our stars is now in our our partnerships team. So I think that while some people might have an idea of what they want to do, if they’re really smart and strong and great work worker, then we can really help them with their career progression, too. But yeah, I think that really loving what you do and loving your boss and the team around you not only makes you more productive, but makes it easier for you to just like, have a good life and balance your work life so that you don’t feel like you’re working. I I’ve never had like that. Whatever the Somebody Skerries or the Monday Skerries or whatever they’re called, I like sometimes look forward more or less to Sunday night to I can get up and work my team on Monday, so.

Andrew Tarvin [00:23:28] Yeah, I mean, to work in a job where you don’t have a feeling of this case of the Mondays, I think is is the ideal. And what’s crazy to me is just how few people realize that that is a possibility. There’s so often people are surprised. They get to an organization, I imagine, like Scinto. So if they’ve maybe been at other places, like, wait, I didn’t know I could look forward to working with my team, which I think is exciting. And my background is in computer science and engineering. So I’ve always like there’s that balance of like, well, of course people should enjoy what they do, but do they actually have to? And so it is an interesting question, but I love that that response and that dedication to it, like you said, of of finding what’s going to be of value or of interest to people and making sure that they’re enjoying enjoying their work. And so what’s something for you that gets you? Geeks are excited about the workday or something when this happens in the office or virtual office in this setting that you’re like, yes, like high five.

Kris Rudeegraap [00:24:22] I mean, besides getting the the closed one deal, when your customers get signed on or new customers renew or expand, I mean, that’s probably the number one adrenaline for me. They go to my sales roots, but I got a shout out to channel on CELAC that we’ve had since day one. And I love seeing the peer to peer recognition or just seeing someone get recognized for something. I had no idea what they did or could be small, could be huge. But, you know, I love seeing the peer to peer recognition. And outside of that, I think I still work across almost all the different teams meeting with tons of different people. And I’m still just jazzed about my meetings and meeting and talking to the team and what they’re what they’re building or what they’re selling or or what they’re solving and all the different things in between.

Andrew Tarvin [00:25:11] That is that’s great, and you touched on recognition piece, I think is so key, it’s oftentimes the thing that people feel is missing in their workplace. So what a great call out for early entrepreneurs or people who are just now starting to build that team. How how it doesn’t even have to be something big and grandiose, but something like a channel dedicated to that, to shout outs and stuff can be a great way to to great that that recognition. So I love that as an idea. I’m curious about the flip side, though. Do you have any work, pet peeves, anything that just drives me crazy?

Kris Rudeegraap [00:25:42] Um. I mean, one of them that comes up here and there are people that schedule over my meetings like probably once or twice a week, I have like, you know, you could look at my calendar like the schedule in between. So I hate when people schedule over. And I’m curious if they did that on purpose or if they just weren’t looking. So that’s probably one of my pet peeves. But honestly, I don’t think I’m a pet peeve type of personality. Not too many things annoy me, but that one kind of irks me because then I’ve got to figure out what to do and put it in a weird spot.

Andrew Tarvin [00:26:18] Right. And then you had to make that choice. And to your point, it’s like they’re in the system. Why did not you saw this happening? It’s not a surprise some on board that I think it’s OK to have that for sure. I my my pet peeve is I don’t know why this is a case, but I’m annoyed by people who are reaching out to me, who want to meet with me, and then they send me their calendar link like they’re like, oh, click on this calendar to the time for. And it’s like, listen, I’m happy to meet with you, but shouldn’t you be the one that’s like doing the work to, like, find a time that works for us? I don’t know. Mean, maybe maybe I’m less nice of a person than you are, but I love it. And and so it seems like you’re a pretty positive person, at least from our conversation. So I’m curious, do you read the reviews of Sentosa? Do you go on to two or other places and kind of check in on what what people are saying?

Kris Rudeegraap [00:27:12] Yeah, I mean, I think both from a new perspective of what our customers are saying. I’ve also last year met with about one hundred and forty of our customers through a virtual roadshow, which was a lot more than the previous year, which was all in person, and it was maybe a couple dozen. So that was a benefit of virtual is that I can way more customers. So getting a little bit more in the weeds about maybe some feedback and then I could dove in deeper in person. But I think customer feedback is critical at any stage of your company to continue to drive your roadmap to continue to ensure your platform success. So I’m a big believer in due to interest radius and other similar feedback site meeting customers as much as I can. I’ve got an advisory group of customers that I can spend more time with as well as some non customers. So I get another perspective. Maybe if someone is not using our platform, but still might be a CMO or a VP, and then the other obvious one is just Glassdoor and really caring about employee reviews or using Latisse to look at peer to peer, one on one feedback and reviews. So I think reviews across the board.

Andrew Tarvin [00:28:30] Yeah, I love it. You’re like, yeah, give it, give it to me all. Like I, I don’t know, I have a love hate with it because I have a stock that’s done relatively well, but because of that it’s on YouTube with a bunch of comment. And I’m so I’m curious. My question is going to be like how you handle this, because some of the comments are very positive. Some of them are just like this dude’s not funny at all. And so, like, how do you so am I going to actually put you to the test? Because we’ll sometimes do a segment here of basically instead of reading mean tweets, we read mean reviews to you. So this is a review, to be fair. It’s from three years ago, almost three years ago. This line to it’s one of the very few one ratings, one star rating. There’s not many at all. It’s hard to find. But the review, among other things, it says the primary thing, that their primary complaint is no benefits over off Amazon.com myself and sending via FedEx UPS. How do you feel when someone just kind of like there’s no benefit to this? I could do this all on Amazon?

Kris Rudeegraap [00:29:28] Yeah. I mean, I feel like that we did a disservice to them. We should have provided more value. And where did we drop the ball? And was it you know, they they weren’t educated about how to use our product. And it was an enablement opportunity, whether was it something related to our customer support and customer success team where they just did get the service levels they desired. Was it truly something that was operational and logistics focused and maybe it was an actual issue or or maybe it was a bug, you know, but our lists across the board, I think anything like that, for example, I’m sure we followed up with years ago. I don’t remember the exact details, but I could have maybe followed up personally. I like to do that a lot to review so that I can at least try to put my best foot forward. Maybe that the trust is lost and so be it. But at least we’re leaving on a good foot and showing that we care so.

Andrew Tarvin [00:30:24] I love it. I’m not going to lie. I part of me that’s helped me like well that just that person is just an idiot. That’s that’s the reason why you’re a successful business owner that you’ve created this. Right. That you’re using that as as in some ways it’s as data. That type of feedback is data to say in this particular instance, we didn’t meet all those needs. So what we learn from this, I love that as.

Kris Rudeegraap [00:30:47] We’ve got on this ticket buyers to which I think are providing a B2B environment, positive or negative feedback with the limelight, that it took them effort. I do think in some like consumer B2C scenarios, you just get those negative trolls coming on and just talking smack for for no reason. But we don’t really have we don’t really like trolling like that.

Andrew Tarvin [00:31:12] OK. That’s not quite that same level as, say, a YouTube comment or someone talking back to someone in a restaurant or whatever. I feel like people are offered up to servers for some reason sometimes. So one of the things I want to chat a little bit about is, is you all have adapted pretty well to a virtual environment. In fact, I love your tagline on the site, make virtual more personal. And so starting to think about certainly for many people, 20, 20 was just more of a like. Let’s just get through it as you start to think about twenty, twenty one. I’m curious where your head is at. And so for you, what does as a fast company, what does high growth look like to you in twenty, twenty one.

Kris Rudeegraap [00:31:57] Yeah. So I mean for us it looked very similar to high growth in twenty twenty where we had one hundred percent year over year growth, we were maybe a bit more agile in terms of planning both from a product and R&D standpoint and our marketing execution when it hit. But I still think we it’s really how do you continue to double down on the R&D while the infrastructure and operations support the growth? And then how is your your sales and marketing and go to market engine just continuing to expand? And where is the growth levers and where is the the hiring and recruiting to support all of that? So yeah, I mean, aside from being in the office or out of the office, I’d say we are not much has changed in terms of what we wanted to accomplish last year. I am very happy with the results for the team. They hustled and worked hard through the hard times and we’ll see that again this year as we have some phenomenal growth projections.

Andrew Tarvin [00:32:57] I love it. And so then that process, I’m curious how how does it work for you personally? Is it like, hey, I’m going to take a bunch of inputs to make those types of strategy decisions? Is it like I’m going to get hired smart people? So I delegate that out to them and I just kind of make sure everyone’s on board as the kind of like person helping to really steer that ship. How does that how to how do you help to make those types of decisions?

Kris Rudeegraap [00:33:20] Yeah. So now that we’re three hundred plus employees, the process has obviously changed drastically from years ago. I think last year we added maybe two hundred ish employees. It was big growth year back and we’re fifty people. It was quite different. But now I have a really strong sea level team and VPs and directors and managers throughout. So typically we do like an annual planning process. We did that in December of going into twenty twenty one where we looked at what we’re kind of the the key things that we wanted to focus on. And what were the initiatives. I put some things in place that we’re kind of company wide. And then how did the different departments underneath them support those with their own initiatives and then how to really allow the executives that I hire that are smarter than me and their domains to run their own destinies and plan out their strategy for their boards and their teams. And then my goal is really the conduit. Can I sprinkle some of my vision? Can I help with collaboration? Can I share some ideas? But it’s really how do we do that all together and build a plan and then run with it? And that was really our our plan going into twenty twenty when that market with covid we had to scramble and really do that planning again and and really plan for the the weeks and months to come versus the whole year and kind of rejig how we think about things. But it was a similar process, just shorter time frames and like best worst case scenario, planning to then drive the outcome, especially when you’re in rapid growth. There’s a big headcount associated with it. If you’re not hitting your top line, then some of the headcount coming in can start to be costly. So you’ve got to be cognizant that the recruiting engine is aligned with the the go to market engine and then the operations. Therefore, it’s a lot of moving parts. But long story short, I’ve got an amazing, smart team that takes care of most all of this. And I’m there to just kind of add in where I see fit and help with the vision and help with the blocking and tackling.

Andrew Tarvin [00:35:35] Yeah. What do you think? It is a great articulation of that value, of that that vision and also knowing when to get out of the way as as well. And like you said, I imagine part of that is also the cultural component, right, and high growth companies, that’s a big thing. That is it’s a thing that changes can change very quickly as we were that start small, small, kind of scrappy feel. And now we’re at three hundred people. What is that culture and are we being intentional about what it is? I love that as a as an approach. So with smart people helping to take care of some additional things that you’re giving some insight on as of where we’re at in twenty twenty one, what’s the cliche question? What’s keeping you up at night? What’s the challenge that you’re kind of like really spending a lot of head space on?

Kris Rudeegraap [00:36:20] Yeah. So ultimately people is kind of my biggest area of focus. I think whether it’s how do we make sure our recruiting team and me being a part of that team is bringing the best of the best talent and in a way that continue to scale up so that we can hit our aggressive goals. How do we maintain that talent and create a fun culture that we talked about earlier on? And so that’s I think one of the big parts of being a CEO is just the people portion of that. Let’s say that’s more or less what I would say if there is anything keeping up is just making sure we continue there. But I’d go back to my work life balance and I try to work at work when I when I sign off on the computer at 5:00 or 6:00 pm or whatever I do, then I’m hanging out with my wife and I’m watching Netflix and I’m going to walk my dog. I’m not I’m not staying up late thinking about things. And then I purposefully don’t think about work and think about my family and my friends and other things and leave work time to work time.

Andrew Tarvin [00:37:21] Yeah. Which is which is great because there is the thing, it’s called Parkinson’s law, where work expands the amount of time allotted for it. And so in that sense that you’re giving this kind of hard cap, it makes it, like you said you did, become more strategic with your time and your focus as you as you go through. And so I am curious because one of the other segments that we like to do on the show is ask about your morning routine. So. Right. You how do you start your day, which are more morning routine in 60 seconds or less?

Kris Rudeegraap [00:37:52] Yeah, I would say I take about a 30 second cold shower and sometimes shorter, and then I will have some coffee, some vitamins. And typically either my wife will make an omelet or some overnight oats or some kind of item, and then I will do a little bit of reading on Feedly, like about a ton of different blogs I subscribe to just generally here, random topics and then go to work and things will change if it’s summertime. Trying to squeeze in a walk my dog in the morning if it’s sunny out. So I’d squeeze that in and then a couple of days of the week I’ll squeeze in like a and right in the morning or maybe a run if I have time. Otherwise I’ll plan for that at the end of the day.

Andrew Tarvin [00:38:43] No, I love it. And so what is you what you like to start with? Just something tough right away of like a thirty second cold shower. Is this the whim of my method or something like that. Is that what it is.

Kris Rudeegraap [00:38:54] I felt like it was really just the shower was more routine to wake me up and a warm shower was kind of doing the opposite of feeling relaxing and not waking me up. And so the cold shower, just like did the did the job better. Also going to have to wait for the water to get super hot, warm. It’s just like instant and I’m good to go. And then I also have no excuse for taking like fifteen minute showers and being late for anything. I can’t stand that cold shower for longer than a minute, otherwise you’re freezing. So I just started doing it maybe a year ago, six months ago and would just have loved it since.

Andrew Tarvin [00:39:32] So I love it. Well as as an engineer I’m like because I’m hearing it from a few more people, like it’s not the first time I’ve heard it. You’re the first person that I’ve heard is like that’s the first thing I wake up and do so. But I’m going have to try it and see. I’ll let you know the result. I imagine I’m probably in fact, I’m probably gonna curse your name when I feel like this is his fault, but I’ll let you know how it goes. Well, Kris, thank you so much for joining us for the conversation. Love hearing both perspectives in terms of who you are as a human, the Gulf side, the scoring touchdowns and scoring soccer goals back in university days, also to the the leadership, vision and perspective of growing a big company, larger company in and what is particularly challenging times for a lot of people, but doing very well with. And so so thank you so much for joining us on the Ascent podcast.

Kris Rudeegraap [00:40:23] Yeah. Thank you so much. And you had a great time.

Andrew Tarvin [00:40:25] Thank you all. So shout out again. Thanks to Kris. There’s has been another episode of the podcast brought to you by the ascent conference, which you can learn more about at ascent comp dot com, as well as by humor that works where we help organizations learn how to use humor to be more effective and things like employee engage. It’s stress management and beyond, you can learn more about that at humor that works dotcom. We’ve got a number of great other sessions and podcasts lined up. So you’re not going to want to miss those. If you are listening in the podcast app, make sure that you subscribe and go ahead and rate as well. Dropsonde, five stars on this wonderful interview right there. You all have been great. I’m Andrew Tarvin and until next time.

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