Kris is a former tenured sales professional turned founder and CEO while also acting as an advisor to several growth-stage companies. His company Sendoso helps companies stand out by giving them new ways to engage with customers throughout the buyer's journey.
Kris is a former tenured sales professional turned founder and CEO while also acting as an advisor to several growth-stage companies. His company Sendoso helps companies stand out by giving them new ways to engage with customers throughout the buyer's journey.
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Hatchet Ventures website: https://www.hatchetventures.com
Hatchet Ventures LinkedIn: https://www.linkedin.com/company/hatchet-ventures/
Chet Lovegren’s LinkedIn: https://www.linkedin.com/in/chetlovegren/
Kris Rudeegraap’s LinkedIn: https://www.linkedin.com/in/rudeegraap/
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Narrator: 1, 2, 3, 4. Are you a founder, co-founder, aspiring entrepreneur, or just someone who loves to hear about how companies are built? Then join us as we talk with founders and CEOs who have been there and done that. Welcome to The Founder's Formula Podcast. Sponsored by Hatchet Ventures. And now your host Chet Lovegren.
Chet: Hello and one welcome all to The Founder's Formula Podcast. The show that's designed to bring you the latest and greatest stories and insights from founders worldwide, who have been there and done that. My guest today is a former tenured sales professional turned founder and CEO, while also acting as an advisor to several growth stage companies, his company Sendoso helps B2B businesses stand out by giving them new ways to engage with customers throughout the buyer's journey. Please welcome. Co-founder and CEO of Sendoso Kris Rudeegraap. Kris, welcome to the show.
Kris: Yeah, thanks for having me, Chet, excited to be here.
Chet: Likewise. And for those that don't know I jacked up the first intro, so he's really nice he, let me go a second time. Hey Kris, we're really excited to have you, and I know everyone wants to hear about Sendoso how it came to be. But first, really what I want to dig into is tell us a little bit about your background up to the point of founding Sendoso and some of your experience prior to that venture, tell us a story.
Kris: Yeah. Born and raised in Northern California, went to college at a place called Chico State University. Found my way into entrepreneurship and startups in college. Actually I was pretty intrigued about how startups come about. Took some classes on it. Ended up actually starting a company in college that I was able to sell to a company in San Francisco right after college.
Very small though, like a handful of people, but it gave me the itch. But then I really knew that I didn't know enough. And I wanted to learn more. And so I found myself in various sales roles for the course of the next kind of eight or nine years at a couple different companies. Mostly in kind of account executive roles or early first salesperson at a startup roles.
And really learned a lot of how companies really grow and start through those experiences.
Chet: That's awesome. And I know for some people that are probably living on Mars and aren't aware of what Sendoso is could you tell us a little bit about. Sendoso what it is, how it works, who your ICP is.
And then we definitely love to dig into really the story about how you came to, to be a founder of Sendoso and how you created this amazing product and company that you have.
Kris: Yeah. Sendoso we're a sending platform that helps other companies send out direct mail, corporate gifts handwritten notes, swag, you name it.
We can help send it with a mix of SaasS software. A marketplace of all the different things that you could send and then the fulfillment and logistics behind the scenes. We are, I started the company thinking that this was gonna be used purely by sales. We've since seen that, marketers love it, sales, SDR leaders customer success, customer support, client service, HR.
The list goes on across a myriad of different industries from high tech to finance, to hospitality, sports teams, et cetera. So it's a pretty wide use case of different ICPs that can benefit from sending stuff to, prospects customers or employees.
Chet: That's awesome. And how did you come about creating this concept of Sendoso? Like, how did you think okay, Hey, direct mail, that's a thing again, or like, how did you break into that? Cause, like even now I feel like direct mail is making an even bigger comeback, but like at a gifting level, like where did this concept come in?
Where does it play into the sales process primarily when you were getting acclimated with it?
Kris: Yeah. Like I mentioned, I spent about a decade in software sales prior to starting the company. So I was in the trenches as an AE, booking meetings, closing prospects, et cetera.
And I saw the evolution of email through those years. And, a decade ago you could send, ten emails and get nine responses and it was, email was like the obvious way to, to prospect and reach out to people. But, there's just been diminishing returns with the, trillions of emails that are sent every year.
And so I saw that first hand about six years ago while I was working at my last company Talkdesk. And I said, Hey, it's so easy to send a gazillion emails. What else can I do? And I found myself writing handwritten notes. I found myself grabbing swag from the swag closet and boxing it up or I'd go, see that a prospect, tweeted about playing golf and I'd send 'em some golf balls.
But all these things were, packing boxes, writing notes, running a little mini post office at the office worked really well, but I was like, Hey, why isn't there software to make this way easier. And so I did some Google searches and there really wasn't anything out there to meet my needs.
And so I said, shoot, this is gonna be a huge opportunity today, but even bigger in the future. And let me see what I can do. And so I said I dove in decided, Hey, I, I can do this myself. I can, I know what kind of software is that I need to build because, I am the end user.
And so I decided, Hey, let me just draw up what I want on paper, convert that into some screen kind of mockups found in an external agency to help build it. But it all actually started with a concept called coffeesender.com a Salesforce app called CoffeeSender. So Sendoso was version kind of 2.0, I would say.
And kind of the first iteration was, Hey, can I build a Salesforce app and a simple gift card sending company to see if people will actually like pay to send stuff before I go into the whole logistics functionality side of things.
Chet: Yeah. And as someone who uses Sendo. So I know that your logistics operation is pretty intense, so I'm sure it's almost like y'all are in the logistics business these days.
That's you got warehouses all over the country, right?
Kris: Totally. Yeah, it's definitely a big behind the scenes. We try to make it as simple as possible for someone who just click and send, but behind the scenes there's software and a lot of moving parts from warehouses and supply chains to get something from point a to point b.
Chet: Yeah. And I want to dig into V1 of, as you say, Sendoos is kind of V2. So CoffeeSender. So you basically created this whole thing and were using like the thing that you had built before you started trying to offer that to customers. Like you were, you built this whole thing just to solve your problem as an AE, and that's when you were like, let's go and do it like for other companies.
Kris: Exactly. So one of the things I was doing aside from sending swag and packing and boxes is I'd grab Starbucks cards and I'd send 'em out to prospects. And that was working great. And so I was like what's like the simplest version that I could create day one. And that's really where I landed on CoffeeSender, which is, Hey, can I make it easy to send Starbucks gift cards out to people?
And that was something that I said, Hey, I can bite, bite this off. I can put some money into it and I could build this for myself first, test it out. Use it. And then actually that's how I met my co-founder Braden in that he saw CoffeeSender liked it was another salesperson using. And was like, I could sell the heck out of this.
Let me join forces, and his company was actually going through an acquisition. So it was like perfect timing for him to come in. And he saw the greater vision of Sendoso right away too. And we pivoted off of CoffeeSender into Sendoso after about nine months of of CoffeeSender being in existence.
Chet: That's awesome. And yeah how did that work? Were you still, cause I know a lot of people they do as much in similar situations do as much building as they can, before they go see a nine to five. And pursue this thing. How did that work was Braden the first one to jump fully into it? Were you the first one to jump fully into it were both you doing behind the scenes and then nine months later you jumped fully into it? What did that look like for you?
Kris: So I was doing some of the behind the scenes kind of product engineering, operations, like more of the stuff that doesn't need the nine to five customer facing interactions. And then Braden actually jumped ship about six months before I did to jump into CoffeeSender full time and basically just run demos, support and customer success all day, every day.
And so at that point he was having so much demand that I said, Hey, I need to jump into this full time too. So I jumped in and then we spent about a three months winding down CoffeeSender while building out Sendoso, and then another three months building out Sendoso and then launching it.
So it was a perfect transition period because we. A bit of confidence and proofpoint that we had something. So it wasn't just cold turkey starting day zero.
Chet: Yeah. Yeah. That's really cool. And fortunate too, right? That you didn't have those facing roles where you could It was very fortunate to have 'em and then I think that there is a decent amount of stuff you could do in your nights and.
Kris: And so it's, instead of going to a bar, getting drinks with a buddy, I was staring at my computer screen trying to fix bugs or, draw out user flows and stuff.
Chet: Still as equally exciting in my mind. Now before starting Sendo so I noticed you had a lot of senior and enterprise sales experience.
How do you think that experience helped guide you on this journey of being a co-founder and CEO so far? What are some things that you've drawn from that experience? As you started Sendoso that you think were applicable?
Kris: Yeah. So I'd say probably the three biggest takeaways for me there - one is, day one going after customers right away.
I think Braden myself, both being sales backgrounds, we're not scared to cold call to reach out, to start building pipeline like day zero. I think oftentimes there's certain kind of product and engineering founders that want to perfect the best features and make it the prettiest, and don't want to talk to customers for, years and years.
And so we did the opposite, which is we talked to customers like day zero. We actually had contracts signed with slide deck and screenshots before the product was even launched. So it was a good testament to like building like product market fit while you're building the product. I think that's the first thing is just like going and selling this.
Now the second thing as it relates to really venture funding. So we've raised about 155 million in funding over the course of a seed, an a, a B, and a C round. And so each of those is like a sales cycle in itself. You're going out, you're pitching, you're running through a demo. You're getting a bunch of no's you're getting one yes, you move 'em through the pipeline.
So I just thought fundraising was just like another sale. I'm just like closing, million dollar or a hundred million dollar deals. And so that's how I position it in my head. Again, I think some founders might feel like, ah, this VC said no to you.
They might take that personally. And I was like, I don't care in sales, you get lots of no's and you move through it. So I think that's important. And then the last is really recruiting, which especially in the very early years, when you're 5, 10, 15 people, recruiting is crucial. And again, you're selling people the dream that they should quit their, maybe higher paying job to go out with something that's a bit more risky hopefully more upside. And so there's a bit of sales involved in terms of just like recruiting in the early days too.
Chet: Yeah, the sale is never done, even if like, you know - I think there's this vision for a lot of people that they're like, once I become the CEO, once I found my own company, I'm done.
Sam Jacobs at Pavilion always told me, he's you don't think I have bosses to answer to, I got a whole board. I got investors. It never stops, man.
Kris: You're always selling. Even today I'm constantly talking to customers. Talking to new prospects, et cetera. So I think it's, it also helps our go to market team, seeing a CEO that's very out there on, I just did a road show.
I met with part virtually part in person about 120 customers. And so I think that also goes back to my love of just one on one FaceTime with people and from my sales days.
Chet: Yeah that's so cool, man. And I'm curious so you have this, co-founder the two of you are working on this together. Tell, tell us a bit more about that relationship, especially what interests me is because - you were both from the AE the sales world. Yeah. What skills do you feel that both of you have that compliment each other and like, how do you find that working relationship? And, especially it's interesting to me cuz you're both sales people, right?
Yeah. So like in that like sales people pretty much have some inherently similar core skills. What do you feel is different between the two of you and how does that work out?
Kris: Yeah. So if I were to look back, if like I were to look on paper at this, it'd be like, wow, they're doomed to fail. Two AEs starting this company, same skillset. I think the thing that made it work for us is, I, stepped up, stepped out and started focusing on product and what needed to be built because we were building for sales people.
So it's kinda like I knew what we needed to build. And I took the leap to learn a little bit more about product and engineering while Braden stayed focused on sales. And so I think that helped divide and conquer in the very early days. But, you pretty quickly about, I think maybe fifth or eighth employee, we brought on a really seasoned COO and she was instrumental still with us today in terms of the auto alot of the other areas like legal and finance and HR and operations and some of these other areas that didn't have a lot of expertise in either.
And so I think we quickly hired around ourselves and found people that were experts in you know, engineering and product and operations. And I I think as a CEO, your job is to delegate and just hire people that are smarter than you.
Chet: Yeah. And I'm curious, you just hit on something interesting. So you covered those bases on the operations side, the finance, the legal, that stuff very early on , but what's really interesting to me and I know that the Sendoso that I'm using today is not the Sendo so that you built originally. So obviously you've had a lot of engineers and product and people working in coding, but like in the earlier days, even with the base product that you initially the initial concept, even if we're going back CoffeeSender. Not being an incredibly technical person. It sounds like you taught yourself a lot of those skills on the product side to make it work the way you had to make it work for the time being, is that correct?
Kris: Yeah. So by no means, am I like doing code reviews and like load balancing servers, but I could understand enough where I could be in a conversation with somebody who could actually do it.
So I think that was helpful. Just the confidence of what's possible and then making sure people are actually doing that. And then I built a good advisor program where I had other, engineering leader advisors in the early days that would spot check or do other things that I wasn't doing.
And I had some strong trust in an early engineering leader that we found through this outsource agency that worked because I, we didn't have a technical co-founder. I didn't wanna not build this idea because I didn't have an engineering background. Went out and hired an agency to help with it.
And then that agency ended up years later we ended up bringing them on as like full-time engineering employees. So that was helpful there, but I think it was a mix of, knowing what needed to be done and having enough level of confidence that I could have conversations around the technical side and then surrounding myself with some advisors who could actually, get into the weeds a bit more than I could.
Chet: Yeah. And that's really interesting. I'm seeing, it no longer, is it the days of the, I always say it's like the Mark Zuckerbergs and stuff where it's, the very technical person who then doesn't have the people social or sales skills to be able to take it to the next level, and they have to bring in someone else.
We're seeing the reverse of that. We're seeing a ton of sales people and go to market leaders and advisors are like, I'm gonna solve for this problem that I have. I'm gonna scratch my own itch. And then they're like, exactly, I'll go find the people to do the product and the engineering and make that work.
And it sounds like you went through a lot of self education as well. So you could understand what to look for in those conversations and make sure you balanced all your known unknowns. Exactly. Yeah. And I think that's why we're seeing more of a surge of the sales tech MarTech space too, is because exactly the phenomenon you just explained.
Yeah. You were talking about the skill of sales in your presentations and in your acquisition of rounds of funding, right? You've had multiple rounds of funding. I'm curious to hear which one did you find the most challenging? Was it that first round? Was it the most recent round? Was it one in between, out of all the rounds of funding you've raised which one did you find most challenging and why?
Kris: Yeah. So one of the middle rounds. So our seed round, which was 2 million we were able to semi-bootstrap a bit in the early days. And so we were able to get some traction enough. So what, we had a half a million in ARR when we went to raise a seed round, which you know, and a lot of companies today, are raising money off of ideas or pitch decks and having no traction.
So we had a good amount of traction going into that. It was also a warm introduction from a previous CEO who was wildly successful. And so it was like a successful CEO introducing another founder to the VC firm that backed him. So that was helpful in terms of a warm intro plus traction made the seed round easy enough.
I think the A and the B rounds were the harder ones because that's where, 10 million and 40 million were invested. And, there was a or 12 million and 40 million, but there was a more proof of traction, more proof that this was a category. I think in the early years, people are like, oh cool gifting, will people use it?
Or is that like a de facto category? I think by the C round, we proved that for sure. And that round of a hundred million from SoftBank was more obvious than ever in that, Hey, we've got tens of millions in revenue, hundreds of millions of gifts being spent, millions of gifts being delivered.
And so it was like the proof is obvious, but we had to convince investors in probably the, A round, which was maybe the hardest that this was a true category that we had the team to build it, that, we were ready to go into growth mode.
Chet: That's really cool. And I know that a lot of the listeners like we have people that are current founders looking for new insights and best practices. We have first time founders and also obviously a lot of aspiring entrepreneurs. Yeah. For more the latter two, the first time founders and aspiring entrepreneurs in those rooms when they're pitching their idea, or maybe they already have a product with some traction.
What are what are some tips that you would give them as they're going through that whole process of trying to secure around of funding in that very early growth stage? What kind of things can you say, recommend this don't recommend that what's some advice you would give.
Kris: Yeah. So I'd say one. Don't be scared to get out there and start talking to VCs. A, VC's not gonna steal your idea. So pitch as much as you can make a pitch list, like thinking about it as prospect and like here's the 20 VCs I want to talk to. Maybe there's five VCs that you don't really want to take money from, but you could go pitch them first so that you can get the kinks out.
So I'd say put together your ideal prospect list. I'd say, share your slide deck with other CEOs. Like I oftentimes get reached out to and say Hey, raising a seed round would love your eyes on this deck. You think, blah, blah, blah. And I'm like, sure, like interesting. I'm happy to, pay it forward and look at it.
So I'd say get others to look at your deck. You might, there might be a blind spot. I think there's a lot of people willing to help out there. So I'd say third advice is like find some advisors that could be CEOs, could be other area, other experts that have maybe been there, done that and, ask 'em for advice.
And I think that a lot of people out there and myself in the early days and still today, I have a big network of advisors that I ask for a myriad of different things. So I think, don't be scared to ask people for help.
Chet: Yeah. Community is everything. And I think a recurring theme on the podcast is that just cuz you're the CEO or the founder or co-founder doesn't mean you have to have all the answers.
In fact, it's probably good if you don't have some answers because you don't want to be a necessarily a Jack of every trait. You gotta be able to delegate something at some point have that trust in that process. Kris we're coming up on time here, but I would love for you to tell the listeners any parting words of wisdom, especially with, all the what I've been saying unknown unknowns that we're headed for, even though we know what they are, we're just waiting for us. We're just waiting to get through 'em. What kind of words of wisdom would you give to any founders or CEOs out there right now? And what are some parting words of wisdom you'd have for them?
Kris: Sure. So I'd say for folks that are, that haven't started or have an idea, or that are working full time and, deciding on what to do. I said, go do it, go find, go find some engineers off of Upwork, go find an agency, go figure it out. And what's the worst that could happen if you fail or you'll lose some money a little bit, go back you could go back to your other job.
So I'd say for the people that are not entrepreneurs yet, or that are in the weeds, too scared to to try stuff, go try stuff on the weekends, figure it out. For you know, other entrepreneurs, successful entrepreneurs, people that are later stage, one of the, one of, my secret powers is building a community of advisors and I'd say, get out there and do that for yourself, and that will pay off dividends.
And that's my advice for folks that maybe only have, a handful of advisors where I've, a hundred ish plus advisors, and it's been a kind of an amazing kind of hack for me in terms of just having my, a community of people that I can ask advice for.
Chet: That's awesome. And I've been a happy customer at multiple companies, so you're doing a great job. You guys gotta keep it up. We could obviously sit here all day and talk about all the additional things Sendoso does we probably didn't get to cuz I got at my last company, I got a great look at what you're able to do on the customer success side as well. I've always thought of it from a sales point of view.
That's how I've always used it. But as something, even as simple as using it as a gift box for year one renewal, Totally. That's, there's another thing it's just so incredible. The opportunity that Sendoso provides to do what other companies won't do so you can accomplish what they can, right?
Kris: Yeah, exactly. The creativity that it inspires is just amazing to see. And it's just a really nice tool in your tool belt that you can go out there and engage with customers and prospects and ways that you could never do before.
Yeah, I love it, Kris. Thanks for the time today. If people wanna engage with you, obviously you're busy, so don't look 'em up on LinkedIn and send 'em a bunch of sales emails, right?
Let's give Kris his time, but if people are interested in connecting with you or with Sendoso what's the best way to find you.
Yeah. If you're intrigued about Sendoso go to Sendoso.com Sendoso.com. You could email me. It's Kris. K R I S at Sendoso.com. Always happy to connect with other entrepreneurs on LinkedIn too.
So just look me up there. It's Kris Rudeegraap. And like I mentioned, I love chatting with other entrepreneurs and founders. Or people that are, wanna be a founder, and a salesperson that has a good idea that wants to know a little bit more in the weeds on how I did it. So hit me up and happy to take it offline.
Chet: And another example of why, if you're a salesperson and the person you're trying to talk to has been on a podcast, go listen to the whole podcast. Cause you never know what kind of contact information they might drop the end. That's like the that's the What is it? That's like the reward, right?
The reward for the people that got all the way through the podcast. And we'll make sure to put all that information on Sendoso's website, as well as a link to Kris' LinkedIn.
In the show notes below, if you're interested in interacting any further with Hatchet Ventures the sponsor of this episode, we will have their information in the show notes below, and you can also connect with me on LinkedIn and The Founder's Formula Podcast.
And we will see everybody on the next one. Thank you, Kris.
Kris: See you, Chet.