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Success Story Podcast

Kris Rudeegraap, Founder & CEO of Sendoso | How to Fuel Revenue & Drive Modern Sales

By January 9, 2022February 28th, 2022No Comments

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About The Guest

Kris Rudeegraap is the co-founder and CEO of Sendoso, the leading Sending Platform. Kris has more than a decade of sales experience and has spent time at Talkdesk, Yapstone, and Piqora. During that time, he discovered that creating meaningful engagements through direct mail and gifting was an effective way to drive demand and increase sales — which helped inspire the idea for Sendoso.

Talking Points

  • 2:00 – Why Kris jumped back into entrepreneurship after quitting once.
  • 3:25 – How Sendoso was started.
  • 6:45 – At what point did Kris quit his job and commit to Sendoso full-time
  • 10:41 – Some tips and lessons regarding MVP’s.
  • 13:45– How Sendoso was first sold to the market.
  • 15:20 – At what point in a company should you migrate the sales function from the founder to a sales team.
  • 16:30 – Sales lessons learned and experienced at Sendoso.
  • 21:40– Lessons on co-selling.
  • 26:37 – The decision-making process for future growth at Sendoso.
  • 27:37 – How Sendoso managed and coped with Covid-19.
  • 29:04 – Thoughts on future trends in sales.

Show Links

Podcast & Newsletter Sponsors

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  4. Hubspot Podcast Network – podcastnetwork

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What is the Success Story Podcast?

On this podcast, you’ll find interviews, Q&A, keynote presentations & conversations on sales, marketing, business, startups and entrepreneurship.

The podcast is hosted by entrepreneur, business executive, author, educator & speaker, Scott D. Clary.

Scott will discuss some of the lessons he’s learned over his own career, as well as have candid interviews with execs, celebrities, notable figures and politicians. All who have achieved success through both wins and losses, to learn more about their life, their ideas and insights.

He sits down with leaders and mentors and unpacks their story to help pass those lessons onto others through both experiences and tactical strategy for business professionals, entrepreneurs and everyone in between.








Machine Generated Transcript


sales, hubspot, customers, sentosa, company, build, salesforce, athletic greens, people, success, sdr, roi, entrepreneur, important, today, mvp, ae, quit, platform, Kris


Kris Rudeegraap, Scott D Clary


Scott D Clary  00:00

Welcome to success story the most useful podcast in the world. I’m your host Scott D. Clary. This success story podcast is brought to you by the HubSpot Podcast Network. The HubSpot Podcast Network has incredible podcasts like the gain grow retain podcast the podcast is hosted by Jeff Bruns, Bach and J Nathan. Now gain grow and retain is built to inspire SAS and technology leaders who are facing the day to day challenges of scaling hosts, Jeff and Jay share conversations about growing and scaling subscription businesses with a customer first approach. If any of these topics sound interesting to you, you’re gonna like the podcast creating more brand advocates SAS as a predominant model for business, customer success at scale, or the challenges of integrating new tools with CSM some of these topics pique your interest, you’re gonna love the podcast, you’re gonna love gain grow, retain, go check it out wherever you get your podcast, remember, gain grow retain on the HubSpot Podcast Network. Today, my guest is Kris Rudeegraap. He is the co founder and CEO of sin dosa, the leading sending platform Kris has more than a decade of sales experience and spent time at talkdesk, yapstone and pakora. During that time, he discovered that creating meaningful engagements through direct mail and gifting was an effective way to drive demand and increase sales which helped inspire the idea for sin Dosso. So what did Chris and myself speak about what we spoke about his origin story how we started Sindo. So why he jumped into entrepreneurship after he quit the game once? At what point did Kris decide to move from working for a company into going full time entrepreneur, we spoke about some tips and ideas and lessons for launching MVPs. We spoke about how he tooks and also to market and how he got his first customers. We spoke about which point should a founder migrate from the sales function to focusing on higher level vision for a company. We also spoke about some sales lessons that Chris has figured out through his career that he implements us and Dosso and what he means by CO selling. And then lastly, the vision that Chris has for us and also and why every entrepreneur has to have a vision and how Kris basically define his vision for the company. And then lastly, the decision making process that Chris goes through when deciding what new initiatives to take on and why his decision making process has been so integral to the success and the growth of his company. So let’s jump right into this. This is Kris Rudeegraap, the founder and CEO of Sentosa.


Kris Rudeegraap  02:54

So to give you a little context, I’m Kris Rudeegraap, CEO and co founder of Sindo. So I started Sindo. So about five years ago, prior to that spent about 10 years in software sales. I got my entrepreneur bug in college, actually. So I started a company called all student rentals in college, made it easy for students to find housing, pay their rent online and find roommates ended up selling that into a company in San Francisco and then work my way through a handful of different startups in mostly account executive roles. To where at my last company prior to starting was a company called talkdesk. And it was there where I was an AE. And you know, I found myself sending out a gazillion emails but wanting to figure out how I could be a little bit more creative and add some new touch points to my outreach. So I started to write handwritten notes I grab swag from our swag closet and ship it out. I’d even go on Amazon to find quirky gifts to ship to me then I ship it back out to the prospect and all worked really well but was just in tensely, time consuming and just kind of hard to do. And so I just dreamed up one day like why isn’t there a platform allows me to click Content something and here we are today. So Sydow so for those of you don’t know we are sending platform makes it easy for other companies to send out, you know, direct mail, corporate gifts, handwritten notes, you name it, send anything out part software, part fulfillment centers, and you know, you can send it out through HubSpot or other tech stack tools. He


Scott D Clary  04:24

is very cool, man. Okay, so this is like your second iteration of entrepreneurships. He had one successful venture exit, then you just jumped into corporate AE. And now back to send Oh, so why jump back into entrepreneurship after one exit was yeah, something that you’ve always wanted to


Kris Rudeegraap  04:42

do? Yes. And so I’d say that first exit was mildly successful, like I wasn’t able to buy a yacht or an island or anything. So it was it was a nice taste of success and made me feel good. But you know, it wasn’t, you know, monumental wealth creation. It was also, you know, we were doing about 15 employees when we exited. So rather small. And I really felt like I didn’t know enough to do it again. I wanted to learn from other entrepreneurs, see how their companies scaled, and being kind of a part of that, but not being the sole purpose responsible for that. So I was kind of a secret entrepreneur in training, so to speak, watching other entrepreneurs and seeing what to do, what not to do. And then, kind of in the back of my mind, I was always kind of thinking about what’s the big pain point problem that I can solve? And I remember one of the things I used to do, I had this email address, it was 365 And I would, you know, try to train myself to be like, what is the what is the nasty pain that I’m experiencing today? Trying to get in that habit of figuring out what’s the biggest next thing that I could start? But, you know, took me eight years per se, to land on Sentosa. And that kind of just happened.


Scott D Clary  06:00

So yeah, but what So walk me through what what just happened means? Because I think everybody, I think a lot of people are in roles. A lot of people who listen to this podcast, probably in like SDR AE roles. And they’re like, Wow, I wish I could start a company to solve the pain point in my job that I’m already experiencing. But it’s not even it’s not even easy to pinpoint that. So what do you what do you mean by just happened? Was this a side hustle? Did you go get a tech to like a technical fun? Are you a developer? I have no idea how you started Sindo. So So


Kris Rudeegraap  06:28

yeah, yeah. So, you know, I think that the point of the 365 ideas mentioned is that I tried to train myself to think about pain points. And I think that’s something that’s hard enough to do. You know, you go through your day to day and you might feel it’s hard to pinpoint problems that you could solve. So, I think, you know, Scenario One is, how do you get better at problem identification, and then also sleeping on it and not like, you know, one hour after you find a problem, like, quit your job, it’s like, Hey, I would, you know, email myself these ideas and check back in like, months later and be like, That was dumb. That was dumb. That was dumb. And, you know, so there’s a bit of that, I think, is step zero, which is how do you get better at pain point identification, some people just land on it, because they’re in a certain industry. And this is, you know, basically, I just got started as I felt the pain of packing boxes, mixing that with, like, hey, this could be easier. And then the kind of the aha moment came off on and then that’s when I had to go into, okay, how do I start a company mode. And for me, I have a sales background, you know, graduated with a business degree in marketing. And but I did know that there’s sites and tools out there that can kind of get you to the next step. So actually, my first iteration was just drawing things, drawing my idea for the software to send stuff in on paper than transferring them online through some mock up tool. And the original version was actually called Coffee So that was like, MVP, version, one of Sentosa. And it was really a Salesforce app that I could click a button in Salesforce and send a Starbucks coffee. And there was a digital gift. And so that was like, I think mentally entrepreneurs are like, oh, I want to solve this problem. Like, oh, this is too big of a problem. I have no idea where to start. Like, I’m just gonna not start because it’s overwhelming. So for me, it was like, what’s the least overwhelming thing that I can actually do and conceptualize? And so coffee sender was that and, you know, drip the mockups, found someone on Upwork for five grand, and he found an engineer that could build it for me. And so cost me five grand, I got a Salesforce app, a website. And now I’ve got coffee center going and for $6, you can buy a credit to send a $5 stuff, Starbucks coffee gift card, that was kind of the model. And just told my friends about it, I started using it colleagues used it. And pretty quickly there was 10s of 1000s of people using it, including, you know, my current co founder now Braden, who was using it and was another AE, and was like, This is awesome. We I knew him from college, he ended up just kind of using it by by way of hearing about it. And then we were drinking beers one day and like we should send more stuff. And then I ended up quitting my job at talkdesk to say, Okay, I’m going to figure out warehousing and logistics and build that.


Scott D Clary  09:21

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Kris Rudeegraap  11:48

Yeah, so it worked out? Well, where my co founder Braden, so probably had coffee Senator going as like a night weekend?


Scott D Clary  11:56

By the way, that’s a really cool ended of itself. That’s that’s such a useful tool for a sales rep.


Kris Rudeegraap  12:01

Yes. So that was pretty cool. It was a you know, ping, you know, beer money, and then some. So that was kind of the original goal is just like, Can I pay my beer and rent from this. And it was doing hundreds of 1000s of dollars in maybe the course of like six ish months. Braden, my co founder was at a scenario was at a kind of a crossroads at his at his last job that he could quit. And they were already kind of being sold off. So it’s like good timing. So we actually quit his job about three months prior to me. So he was working on coffee center full time. While I was like, nah, this is not a, you know, a billion dollar idea. I can’t quit my job and making you know, 250 and as a sales rep, like, be crazy to quit. And then it just started to snowball. And I started to see more success with it. And I said, Hey, this is my chance. My wife got behind me and said, Hey, if you go and create a platform, you know, at the time, we didn’t know the name was to know so but if you can go build that, like let’s try it, what’s the worst that could happen? In my eyes, I was, you know, a rockstar, a AE, I could always go back to being an AE I, you know, I I could sell anything in my opinion. I think I had the confidence there. And so I basically just was like, waited till one of the quarters ends. I think sales quitting and sales is tough because there’s always like, I got another deal. That’s illegal, like, what could I quit? So I just put a date in the sand instead. All right, you know, it was end of q3 2016. And I said, I’m gonna quit today. I’m going to quit that day. And I’m gonna work backwards. And, you know, my CEO at my last company was was also open to that, and he’s an advisor now and quit that day. Then it got back to square zero where I had no money really coming in. We decided to kill coffee center. And then I had to go back to figuring out okay, let me sketch up what Sentosa is going to look like. And I spent probably nine months being, you know, Product Engineering person, building the infrastructure and new software.


Scott D Clary  13:55

Okay, so nine months, so So what was the what was the day when you actually took Sindo? So to market? How, what was the MVP of Sentosa? Like you actually had like a pre MVP? So what was the the first launch ascendo? So


Kris Rudeegraap  14:08

yeah, so that was about the summer of 2017. And we had a platform where you could log in, create a user set a user up with some budget, we had a, you know, a myriad of different things that you could send on demand. We had all the gift cards, so not just Starbucks, but any gift card. And then we had our first warehouse was in Chinatown in Las Vegas. And so we had this little warehouse, probably the size of a bedroom. And we turned the lights on and said, Hey, anyone can sign up, you know, we’ll source stuff for you. We have some stuff available on demand and or you can send us swag that you have in your office to our warehouse. We’ll organize it put it online for you so you can virtually see what inventory you have left. And then you can click About in Salesforce and HubSpot. We had Marketo we had a couple other integrations. And you can you know I think sales often outreach we He had kind of hacky integrations with them before they even knew what an integration was. So we were like their first integration partners, because we had built this like Chrome extension that put a button in their platform. And it overlaid it. And so they were getting like support and customer success. Questions about sit down. So and that ended up driving us to be one of the first launch partners on stage at both their conferences like two or two or so years ago.


Scott D Clary  15:28

That’s awesome. You built up you built basically forced them, you move that you force their hand to build out this.


Kris Rudeegraap  15:33

Yeah, exactly. Yeah. Okay.


Scott D Clary  15:36

Okay, so MVP. So what are some MVP lessons that you could you could talk to the audience about that you experienced? You had the first MVP, then you sort of had like another sendo? So MVP? Was it too early? It was too late? Was it just right? What are some things people to think about?


Kris Rudeegraap  15:52

Yeah, so what are the things that I did is I, there’s a ton of ideas that we got that I had, and the co founder had, that we started to get from customers. So we really wanted to like, what’s the what is the best product we can get out, that will work. And then let’s backlog all the other features and come back to them. And we constantly were like taking out things. So it’s like, What’s the best thing we could ever build? And then let’s take out everything that you know, is gonna take time and effort and delays from launching. So I think some entrepreneurs, well, kind of feature creep annatto million things and like, let’s just get something there that we can start getting customer feedback on. So I think that was important is just like, you know, drawing a line in the sand and going for it.


Scott D Clary  16:32

I think when you do that a lot, by the way. That’s, that’s smart.


Kris Rudeegraap  16:35

Yeah, very smart. So that was big. I think, you know, ultimately, we then need to figure out, you know, from an MVP perspective, you know, for us, we are in, you know, an outsourced model. In the beginning, were we so it was like, how do we how do we conceptually budget for this? And so we had kind of like, what’s the MVP? And then how are we going to start budgeting hours thereafter. So I know some co founders will have an engineer where there’s maybe not that hard cost. But if you find a outsource agency to help you, you know, we budgeting was an important part of the early days. So we didn’t go through all of our money because we were bootstrapped. We were using our own money and some of the money from the coffee Center Project. So I think budgeting in the early days for engineering specs. Yeah. So I think those are the the my lessons was really get something in the market. And then then you got to kind of test, you know, besides product market fit, like, what’s the pricing model? And how does that fit and start to build on that to then getting to a place where you can test to see if you could even like hire salespeople and have a sales, you know, CAC to LTV ratio, or, you know, can you hire SDRs? Do you have, you know, what’s your price point to afford that as part of your your CAC, so that it became less about focus on product market fit and more of like, go to market fit.


Scott D Clary  17:57

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Kris Rudeegraap  20:31

Yeah, so my co founder, I both being in sales just immediately started reaching out to prospects. So it was like, Okay, let’s build our target lists. Let’s enrich that list. And let’s outbound to that list. We, you know, did you typical multi touch outbound, and got meetings, demos, and closed customers. And so we, our pricing model was a, you know, a SAS annual subscription. In the very beginning, for the first couple of months, it was a month to month, we quickly realized that we needed to go annual, we also, you know, were able to kind of up our prices, after a few months to as we realized we were significantly under priced. We also had the benefit of hiring like a really awesome CEO early on, she was like one of our first first investors turned employee, so she was analyzing, like, Okay, you’re selling us way too cheap, you’re not gonna be able to afford, you know, to scale. And so once we kind of right sized pricing, and, you know, we realized that we could outbound and get meetings and close deals, we then said, Okay, let’s hire a couple ladies and a couple SDRs and see if we can have other people who are not the founders sell. And then that was like one of the challenge. Yeah, once that started working, then I think it was more like we knew we had something because then you can figure out formulas thereafter to pour fuel on the fire, which is ultimately, you know, raising venture capital. So then you can hire people ahead of, you know, profits and then scale out faster.


Scott D Clary  22:02

What what point do you think in a company, should you migrate the sales function from the founder to a sales team,


Kris Rudeegraap  22:11

I think as early as possible, to be honest, oh, well, I’d say at two parts. One is founder should always be selling. So I still sell today. But as soon as you can, in the early days, I think it’s important to realize that someone else you need to, in order to be successful, you need to figure out if another human can get in there and actually sell the product. And in a way that, you know, founders are overly passionate, they’ll do anything, you know, that you might not even getting paid as a as a founder, it’s so like, of course, you can get a customer for a cheap amount of money, and you’re not paying yourself and you know, that you’re talking to, you know, your ex colleagues, boss, like you hack together your first couple dozen customers. And it gets important to have those together. Because then you have customer feedback, you have maybe some case studies, you have some references. But as soon as you check box, all those things, it’s you need to immediately hire in my eyes, SDRs and AES to prove that you can have a sales model.


Scott D Clary  23:11

And and I just want to and I also want to understand, because we didn’t even really, we kind of touched on the pain point that Sindo sells. But I want to like double down on that. Because obviously, you having a lot of experience as an account executive. And and using basically manual manually sending out items as part of the sales process, you haven’t probably a fairly significant understanding of what’s broken in sales, and why people should even bother. I should have touched on this in the beginning. I apologize. why people should even bother using physical items as part of an outbound sales campaign, because not every team does. This is not like status quo. Yeah, it’s not that every team does this either. And I think that’s an important thing to chat about two. So let’s even talk about like, a couple a couple sales lessons that you that you learned that Sentosa solving for the you’ve probably implemented as an AE that you’re using, as you’re probably I’m assuming your own team is using to scale send Oh, so


Kris Rudeegraap  24:10

yeah, 100% we use invested more than anyone. So I think as a an AE, you know, some of the areas that are even true today was that, you know, you have to think about this kind of buyer experience and kind of multi touch ways to get in contact with somebody, you know, and that involves, you know, email, phone call SMS video, LinkedIn, you know, direct mail, Sentosa gifts, you know, everything that you can do to get in front of somebody, you know, is going to help you better your chances. And I think it’s a semi numbers game in that regards where it’s like, what are what’s the optimal way that you can get somebody to talk to you and break through the noise. And if you’re only doing email, then you’re missing out. If you’re only doing email and social, you’re missing out. So once you incorporate, you know, Santoso and it gives you just another shot on goal and sales. All about, you know, as many shots on goals as you can. That being said, I think the other thing that we’re seeing in sales is just the evolution and advancements of just tech in general and automation and everything else. And so one of the things that I believe suggested, does well as it helps reps be more creative, too. And I think creativity is one of those soft skills that doesn’t get talked about a lot. But, you know, can help differentiate you from another competitor with a similar product and that, can you build better rapport with that prospect? Can you send them something more unique, that is memorable, and you know, they choose you the person, not, you know, the company product. So I think that’s also becoming ever more true. And that, you know, maybe 10 years ago, when I was in sales, even before outreach and sales, I was one of the first like Yesware and tout app users. And like, that was like a secret weapon. For me. It was like, Oh, I can automate things like not no one else can.


Scott D Clary  26:00

And so now it’s over automated. Yeah.


Kris Rudeegraap  26:03

So now it’s like, okay, let’s take a step backwards. And like, how do we read, you know, humanize the sales process and personalize. And so that’s, that’s one of the inspirations for starting soon. So


Scott D Clary  26:15

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Kris Rudeegraap  28:16

Yeah, so I’d say one for specific like case studies and exact data points. We’ve got like 50 case studies on our website. So check it out there if you want to read it to the specific details. But at a high level, you know, you’re correct, like digital marketer, we kind of take that offline kind of blackbox what’s happening and turn it into more of like a digital marketing channel. So when whenever anything sent automatically checks back to, you know, HubSpot, Salesforce. So now there’s a paper trail, which previously really wasn’t there. You know, when I was back in the day pack my inbox, I wasn’t like logging tasks in Salesforce, it was another extra effort. So now, everything’s automatically tracked that data then can with attribution modeling, can see if it’s last touch or whatever, attribution you use weighted average attribution, you can start to see, okay, we sent them this, and then two days later, an opportunity was created. And so you can start putting the puzzle pieces together that way, and track ROI. There’s also ROI of like, if I’m doing this myself back when I was in sales, like, Okay, I’m gonna spend it two hours of my day doing this, should I be packing boxes and sourcing things? Or should I be selling and so there’s an ROI of like, the the time of that rep, which is, you know, super crucial time you can’t get back. And then you know, there’s other ROI that you know, we kind of have a Costco model in terms of we can buy a book and pass those costs along to our customers so we can buy things ship things way cheaper than you could individually. So there’s an overall ROI on just like the cost of goods and services.


Scott D Clary  29:46

Amazing. Okay. And a couple other things that I hear you speak about often that I thought would be good lessons to teach over. You speak about CO selling with CEOs. Walk me through that and what’s the what’s the strategy For that, if you’re trying to sell to, I guess, JMeter enterprise.


Kris Rudeegraap  30:03

Yeah, so given my sales background, I think I’ve never stopped selling. Even though you see SEO, you have to do a million things. I think whatever I can help our SDR a AE team, I am all about that. And so I’m really trying to empower my team to think about CO selling. And so that could be the AE working with me. And then I will then reach out and collaborate with executives at that prospect. I have a huge advisor network, there’s about 100 Plus advisors. And so, you know, our E, SDR or even our account management team can leverage me to then use one of our advisors to help break into account. So that’s useful. And so I think more than more than ever, I’m involved in dir deals, and especially of the enterprise ones,


Scott D Clary  30:51

you kind of just the theme that you keep coming back to is like the CEE should never stop being engaged or involved in the sales process.


Kris Rudeegraap  30:58

Yeah, with that, too, I mean, outside of just the sales process, I think you’re kind of always selling even to customers, or learning from customers, or expanding customers. And so, you know, earlier this year, I did a 95 customer virtual roadshow. Last year, I did about the same the year before I was in person, which I was only able to get to maybe 20 or 30. But this year, because it was virtual, I met with 95 of our customers for about a half hour each and learned a lot there and was, you know, learning and getting feedback, but also solid, you know, where’s the action opportunities, you know, where other areas that we can, can, you know, help our customers use our platform and grow more?


Scott D Clary  31:38

And how do you use? How do you use that feedback for your business, your sales, your sales process, your product?


Kris Rudeegraap  31:45

Yeah. So you know, basically, I’ll take ton notes, I’ll record the call and transcribe and take notes. And after each one, you know, put together things that I can then say, hey, this information is useful for our product design team, this information is useful for a product marketing team, this information is useful for our, you know, a team or expansion team. And so basically just trying to then action item it out, and so that we no different departments can learn from each customer interaction.


Scott D Clary  32:16

Is that Is that something that permeates your culture? Meaning does every executive on your team build a feedback loop into their particular business unit, I would say


Kris Rudeegraap  32:27

others join me or others are doing this more of the customer facing functions, like our books, maybe our CTO is not doing as many customer roadshows as I am. But I think like I have my unique background in wanting to talk to customers being in sales, you know, building the product puts me at a really perfect place for you know, talking product, talking, expansion, talking use case talking, you know, customer success, and then I can kind of distill that out.


Scott D Clary  32:55

Okay, and that’s obviously, you know, lead to some some measure of success. So, where is where’s lindowsos? Today, in terms of as a company? What are your you can talk figures, not specific revenue numbers? Like, what is your vision for the company, and how long it is going to take you to get there?


Kris Rudeegraap  33:11

Yeah, so just kind of sighs So we’ve about 40 to 50 employees, we’ve raised about 55 million in funding. Were, we’ll see this year, about 100 million spent on our platform, and will be in kind of the 20 30 million range in terms of ARR. So just gonna give you some points there. Yeah, we we see this being a huge, you know, built multi billion dollar public company one day, and so we’re just getting started.


Scott D Clary  33:44

That’s amazing, man. Great. First of all, congratulations. I didn’t realize you were that you were that large. It’s very, very impressive. Yeah. For you. I was gonna you know, just for you. This is like your first I not first this is like, well, it is it’s your first like very large entrepreneurial success, even though like you’ve been, you have like a year, you’re like a one like every single time that you come up to bat like you’re you’re killing it, like you never strike out with startup so far, which is actually not normal. So that’s, yeah,


Kris Rudeegraap  34:12

well, I I’ve definitely incubated different ideas in my brain that I just pulled yet on. So I think it’s that’s helped me in my efforts in that I just didn’t like jump into something just because it was my first idea.


Scott D Clary  34:27

Yeah, it’s actually I love that. That incubation idea and that 365 idea thing that you were doing, I think that’s very smart, because I think it just like qualifies out a ton of really shitty ideas. Yeah, that you would have had to have tried and failed and exact a lot of money and time. And for you, what is your strategy process? future growth, steering the ship decision making process as you grow? Sindo so do you have a specific framework that you follow? Is it mentorship is it what is what is it?


Kris Rudeegraap  34:59

I think it’s a mix of all other things, I think it’s one it’s, you know, a mix of, you know, having a vision that people can get behind, you know, OKRs and, you know, in ways that you can track the success of the company going forward. It’s, you know, you know, always thinking about company culture and making the best fun place to work. You know, always trying to hire and inspire and grow the team is kind of people are the foundation for everything. So, you know, and I think it’s hard work, but I think about it as like a marathon, not a sprint. So, we’ve also got to, you know, live life but you know, this is going to be a long, long game.


Scott D Clary  35:37

I just want to take a second and thank the sponsor of today’s episode, HubSpot. Now, you may have heard me speak about leveling up in the past how we can level up our careers or businesses or customer experience. I wanted to take a minute and focus on that last because when we level up our customers experiences, we transform our customers into evangelists and help our business and our careers grow like crazy with new features dedicated to helping your sales teams improve your customer experience, HubSpot is on a mission to help millions of companies grow better starting with yours. Conversation intelligence tools help your teams get real time insights into calls with automatic recording transcription and call analysis with more visibility into customer conversations, coaching and customer feedback becomes that much easier, easy share meeting links. Let customers see availability and book meetings for you all from the HubSpot platform. This cuts out endless cycles of scheduling email, learn more about how you can transform your customer experience with a HubSpot CRM And how have you managed How have you managed COVID? Were you already fully virtual before? Or was that something you had to figure out?


Kris Rudeegraap  36:46

So we weren’t fully virtual before. But we did have three offices, which, when we were a 50 person company, we were already having three different offices in three different locations. And so that already drove more collaboration than probably most companies when they’re 50 employees all in the same office. So we already had collaboration and you know, zoom and everything else in our blood. So when we then would as we scaled to I think we hit COVID, we were about 150 employees. So we’ve actually grown pretty substantially maybe added about 300 people since COVID. Started. But we already had, you know, remote collaboration in our blood. So it was not too hard for us to then just fully go remote, that we also have day one, our executive teams and investors kind of got put our heads together. And so for the first couple of weeks or month, there was more rigor around what the heck is this? How are we going to survive this. But then we saw some big tailwinds from it. And we are actually a solution that benefited from COVID. And in terms of like people remote, how do you send things to people, all these field sales reps are now inside? How do they build rapport with prospects? How do we do these field events that are now digital? How do we onboard new employees with swag? So, you know, we definitely quickly started creating content and thought leadership and features for our product that benefited from whatever one was facing.


Scott D Clary  38:11

And in terms of the the future, you know, question for future of the industry, future of sales? Are there any things that you see, that are interesting you and how we sell and how we communicate with customers that are going to trend in the next, say, five years, that are different than now?


Kris Rudeegraap  38:29

I’d say the biggest thing is just there’s just gonna be an onslaught of technology that salespeople will use. I think if you look back 10 years ago, it was like, Oh, I use Salesforce. That’s like the one tool I use, like, oh, maybe you use you, maybe you’re an early adopter, do you use it? Yes, we’re a tout app. Or maybe you use like a, you know, a zoom info or something like, you were maybe lucky to do that. And so now, I think there’ll be, you know, if you look into the next five years, there might be, you know, 50 tools a salesperson could use, and you really have to take that as a competitive advantage and figure out how are you as an SDR and as an am, like, good at using technology and learning it and, you know, mastering it. I think I was I tried to master Salesforce 10 years ago, and I could run reports and find leads that no one else was working. And like, that was some of my secret sauce, but like, now how to use all these other tools. So I think that’s one is just the onslaught of tools and being good at using them. And then I think, two is some of those soft skills that, you know, automation, you know, can’t you know, really control which like creativity and some of those areas of, you know, skills that you build as a salesperson will be ever more important.


Scott D Clary  39:42

And and I guess one I want to I want to do a rapid fire just to pull some career insights from you. But one last question that I wanted to ask one question that you would ask somebody who’s in your position now when you were starting out in sales


Kris Rudeegraap  40:01

I would probably ask like, maybe what your what, like, draw me Your Org Chart? What’s your, I think it’s really interesting to see, you know, from a company from zero people to now 450 How Your Org Chart grows, and one of all these different roles you need to hire for and when And that’s been something that’s been unique to learn. And so I think like, that would be a question that would be like, you know, really interesting to to understand.


Scott D Clary  40:32

And then also, Where would people reach out to you if they want to connect with us? And also, what’s your favorite social or email or website?


Kris Rudeegraap  40:39

Yeah, you can always find more information on Santos on, you can email me personally, Chris, it’s KR is at Sen. You find me on LinkedIn, and I’m happy to chat. I love talking with other entrepreneurs a ease, you know, happy to get pitched a news, you know, cool tech software that someone’s come up with love hearing about the newest things?


Scott D Clary  41:01

Awesome. Okay, um, what was the what was the biggest challenge that you overcame in your journey? And how did you overcome it?


Kris Rudeegraap  41:10

I probably the biggest thing, it was really just making that jump from having hundreds of 1000s of dollars going into my bank account to zero. And quitting my job. I think as an eight, there’s always There’s always more money to be had, like, the next week, the next deal close. And so I just had to say, eff it. I’m gonna, you know, make zero money and hopefully longer term I’ll make, you know, way more.


Scott D Clary  41:37

That’s it. That’s it. That’s what that’s like, psychologically, that’s tough. Yeah, it’s very tough. And, you know, I didn’t mention this before. But you know, whenever you leave a company, like you know, that there’s going to be like, a battle for Commission’s that are gonna be paid out, like in like six months, you know what I mean? So that’s alright, um, if you had one person, it’s probably been a few. But if you had one person who had a major impact on your life, who was it? And what did they teach you?


Kris Rudeegraap  42:02

Yeah, so I would say one of the most impactful things I remember, was an entrepreneur and Chico’s name was Chris friedlin, he started a company called Build, Build calm. And when I was had my startup at when I was in school at Chico State University, he was very inspirational and seeing his success, like talking to someone in a, you know, in his office at a company that was doing hundreds of millions in revenue, and was like, wow, I could be him kind of thing. And so I think that was an area that it wasn’t very inspiring me to then, you know, see that I could make do this one day.


Scott D Clary  42:41

Very good. Very good. If you could tell your 20 year old self one thing, what would it be?


Kris Rudeegraap  42:49

Buy Bitcoin? That’s my answer all the time. not working anymore. Yeah. No, I’d probably just say like, do what you’re doing. I feel like I back when I was 20. I still had the mindset of like, I want to become an entrepreneur, I want to go big, like, you know, startups are cool. Like, I’m gonna figure this out, and I’m gonna have fun. And so I think I wouldn’t change my mindset or anything. Okay, cool.


Scott D Clary  43:15

And then a source. It could be a book could be a podcast, you’d recommend people go check out that you’ve enjoyed.


Kris Rudeegraap  43:23

Yeah, I’ve got a couple podcasts. I love I love snacks daily. I love acquired how I built this because of my favorite ones.


Scott D Clary  43:33

Awesome. And then most important question last question rather than almost support but last question, what does success mean to you?


Kris Rudeegraap  43:40

I think success is happiness. You know, if you’re happy then you’re successful. And you know for me happiness comes with starting a company and and you know, being successful that way. But you know, for you know, an SDR listening, you might be hitting hitting your meeting goals for the week and that’s success. So, for me, happiness is what makes you happy. If you’re not happy hitting your goals, then you’re doing the wrong thing.


Scott D Clary  44:05

Yeah, very good, man. Very good. I love that. Okay, that’s it. That’s all I got cool.


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