Rosalyn Santa Elena: Welcome to the revenue engine podcast. I'm your host, Rosalyn Santa Elena. And I am thrilled to bring you the most inspirational stories from revenue, generators, innovators, and disruptors revenue leaders in sales, in marketing. And of course, in operations together, we will unpack everything that optimizes and powers the revenue engine. Are you ready? Let's get to it.

When I first met Kris, back in 2019, we had just signed up as a Sendoso customer. He reached out to me and I thought how awesome it was at the CEO and co-founder of Sendoso was reaching out to welcome me little did I know that he actually came to my office to see if I was open to a possible role on his team?

I wasn't looking for a new role at the time, but we had a chance to get to know each other. And he asked if I'd be interested in joining Sendoso as an advisor to help from a go-to-market operations perspective. These were early days before many advisers were on board. And of course, knowing how amazing the offering was.

I jumped at the opportunity to be part of the journey. For those of you who don't know Sendoso is the world's leading sending platform. Sendoso allows businesses to cut through the noise and reach people in a more meaningful way. Not only is it a game changer for revenue teams, it's just a cool and fun product.

In our discussion. Kris shares his journey as an AE, turned co-founder and CEO and how a real life challenge turned into a high growth startup changing the way companies engage with prospects,customers and employees.So grateful to Kris for the opportunity to be part of the Sendoso journey and for his time here on the Revenue Engine Podcast, take a listen and be sure to catch Kris sharing his story about branding and always appearing bigger than you are.

Super excited to be here today with Kris Rudeegraap, the co-founder and CEO of Sendoso. Sendoso is the world's leading sending platform, enabling businesses to reach prospects and engage with customers in a more meaningful way throughout the buyer journey. Sendoso has raised over $54 million in funding with the most recent series B in early 2020.

So welcome Kris, and thank you so much for joining. Yeah.

Kris Rudeegraap: Thank you so much for having me. I'm excited to be here today.

Rosalyn Santa Elena: Thank you. So when I was asked to start the revenue engine podcast, there were a handful of inspirational leaders, right? That immediately came to mind, given my love for you and for Sendoso as both an advisor for the company, as well as the two time customer, you definitely were top of mind.

When we first met, you know, in early 2019, I was already, you know, fascinated by the offering. I'm like such a fan girl, but as a go to market operations leader, I quickly understood the value prop understood the type of game changer that Sendoso would be. Okay. Really in enabling the end-to-end revenue process.

So the idea for Sendoso originally originated with a real life challenge when you were in sales. Right. Can you share the story of sort of how and why you decided to start Sendoso like was there is a sort of aha moment and if there was one, you know, and how was that? And I guess maybe if you could share sort of how your vision for the company has evolved and changed over time.

Kris Rudeegraap: Yeah. Yeah. So, uh, I started some, those two about four years ago. And prior to that, I spent about 10 years in sales. Um, most recently as an account executive at a company called mock desk. And so I was, you know, in individual contributor in the day-to-day and seeing a couple of things, one is just the, um, you know, the tons of email people were getting.

And that was kind of my main channel at the time for outreach and engaging with prospects and building rapport, and I was a creative person. And so I started to test out sending out handwritten notes. I've paid a Starbucks to buy gift cards and send them out. I'd even try to steal swag from our swag closet.

Mark yell at me there, be in the office packing boxes. And it was just, it felt too much effort. And, um, but it was working really well, but it just felt broken. And so, you know, it really dawned on me as like, well, why isn't there a platform that makes it easy to send stuff out? Um, and you know, that was.

Really, um, as you know, ABM was also, uh, very early in its kind of heyday of coming out and people were starting to talk about it. I think when John Miller, um, and Engagio, it was really starting to kind of bring thought leadership around that topic. Um, and I think general to ABM for me as a salesperson, I always had like named accounts.

I was trying to get after and really build rapport with, to sell into. So, you know, having a sending platform just felt like the right idea. And I asked other sales folks that I knew colleagues and other friends, and they were like, yeah, if you built a platform that made it easy to send stuff, you know, cool I'd use it.

And so that was really the inspiration in the long haul that, Hey, this is a pain point. This is broken. Um, and you know, I should fix this. And so one day I was naive the next day I was founder. And that really kicked things off in my, my vision. You know, from day one has, has really been the same as really making it easy to send stuff out and send the right thing to the right person at the right time.

And so we we've done that by building, you know, part software that integrates into your tech stack. So kind of data in data out and workflow, um, really empowering the end-users, the SDRs, the VAs, the CSMs to kind of have their own budget and decide when they want to send things, which. Previously marketing would mostly make me do like batch and blast, which was like, Hey, you know, spelled the spreadsheet and put your name in, or put the name of the prospect in.

And then like a month later they'd send them be like, Ooh, that person's already a customer now don't do that. And it was always back and forth. So having something that you can real-time send and, you know, control your own destiny was big. And then really incorporating all the, you know, limitless possibilities of what you want to send.

You know, uh, I think that's really been a creative. Uh, part of our platform is just the, uh, the many, many options and things you can do. And, and then obviously behind the scenes, all of our fulfillment warehouses and fulfillment partners, um, have been huge in making it, you know, the dream of connecting the dots of software, plus the filming and.

Yeah, that's a since day one, we've, we've really continued to evolve with more things you can send and better, you know, user features and this and that. But the core goal of building a sending platform is, has still to this day, going to the value proposition.

Rosalyn Santa Elena: That's awesome. That is so exciting. It's funny how I think that oftentimes it starts with just a simple challenge or a problem, right?

You go out and try to fix it. So you mentioned about the sending platform. So obviously Sendoso is the world's first sending platform. You basically created a brand new market category where there was none. And when I try to describe, um, the space that Sendoso is in, it's just, it's so unique, right? You've touched on it's it's demand gen it's, ABM, it's sales, it's marketing.

It's. It's customer success, right? It's employee engagement. You know, I think we're seeing a lot more of that, especially given the year that 2020 was. And so this area is that, you know, it feels like the areas that it touches con you know, seems really only inhibited by what someone can think up or create, right.

Something you can dream up. I mean, Sendoso is really in its own category. Right. Is this, um, is this how you think about Sendoso? Like, how do you think about kind of send doses mission as it relates to defining that market category and how would you describe it?

Kris Rudeegraap: Yeah, so, you know, going into it, we knew there was going to be a lot of different use cases, um, from a very early customer interviews and just ways customers were using it.

No, when I first first started, it was really like, okay, I know this is going to be used by AEs and SDR's. And that was like who I was. And so I knew that I wanted this tool more than anyone. Um, it was obvious that marketing, uh, controlled some budgets and also, uh, did a lot of demand gen efforts that needed this and customer success was really a key part of, you know, engaging and expanding your customer relationships.

Um, and then, you know, the, the HR component, uh, was always, uh, something that I knew in the back of my mind. And we, so we started to see this last year in the year before, but this year obviously just went bonkers with people remote, um, and you know, along the entire pro the tire journey. One of the reasons why we wanted to keep a broad, kind of a category name of a sending platform isn't really, uh, allows us to be broad enough, but specific enough.

So we're able to touch on these different use cases, but you know, at the end of the day, when you hear sending platform, it helps you understand what it is. It's something that helps you send stuff. So in my eyes, you know, naming your category and putting a name to it really helped us. Build on that category.

And it's been cool. Seeing companies come to us with RFPs for a sending platform that was like a really proud moment. Um, we also see people on LinkedIn putting Sendoso as a scale or mentioning sending platforms. So that's another like milestone in at least my life is seeing that happen. And, you know, we, we really, uh, invested in our brand and the category early on with thought leadership with.

You know, content creation, um, and you know, uh, with all that too, I think we've seen, um, some competitors emerge to where they're also now coming into this category and it's, um, it's giving the category the more legs because. VCs are investing in it. Um, and you know, we're not the only ones singing this category song.

So, um, overall though, I think, you know, um, you've just got to continue your thought leadership and continue the brand awareness. And, um, you know, in my eyes, our biggest competitor for ourselves is really just us not executing. But, uh, you know, it, it's also, we, we need, we know that, you know, the, the category is going to get bigger.

So, um, I like seeing competitors pop in.

Rosalyn Santa Elena: Yeah, definitely. It gives them meaning and sort of confirmation right at the space. So Sonos has grown significantly right year over year consecutively since the start. And your customer is base is made up of hundreds of the most recognizable logos in the world.

You know, being a previous customer and also a current customer myself. I'm certainly familiar with the value of having a platform like San. So for our overall revenue process, So you touched on this a little bit already, Kris, but how has your product offering and differentiation really helped in helped in accelerating your revenue growth and an expanding your customer base?

Kris Rudeegraap: Yeah, so, you know, one of the cool things about our platform is we're always constantly looking at how do we evolve, what you can send and also the data around it so that you can really deliver the right gift at the right time to the right person. And so. You know, uh, especially this year, we've seen a, um, an increase in our mix of like our digital and physical offerings, um, on the digital side, in the beginning of the year, uh, when COVID hit, we, we quickly helped kind of, uh, talk about thought leadership of playbooks around.

What you could send as it relates to, you know, Uber eats or door dash gift cards or Headspace and Netflix. So, um, or we had these like family gift packs, so really helping our customers, uh, think about what they want to send and what was everyone experiencing at the time when COVID started, um, with that too, as COVID kind of continue to evolve, you know, we offered up, um, new and interesting sends, like we launched a celebrity cameo sand where you could send like, Videos, we've seen that explode.

I've had some really funny laughs of some of these, uh, cameos. Um, I think Mark McGrath from sugar Ray is my favorite one was he'll like write songs and part of his cameos and we've seen a ton of that. So I think it's evolved in terms of just fun things that you can do to build rapport and engage with these recipients you're sending to and even more so, you know, as.

You know, field marketing, um, went completely virtual. We, um, helped our customers continue to evolve and rolled out new kind of, uh, virtual experiences that you could stand like a virtual wine tasting where you could have wine tasting event. And we, you know, maybe a Somalia would join a zoom call, but we would send the wine.

So I think our goal is how do we adapt and be agile in terms of what we offer based on macro trends or based on how we see go to market, um, you know, revenue machines, uh, where do, where can we plug in and play. And, um, so that's been a big and kind of overall like experiences, I think has been a buzz word about how do you create these experiences for, um, you know, the end recipient, uh, during these times where everyone's kind of locked up in at home.

Rosalyn Santa Elena: Yeah, definitely. I've been, I've been on the receiving end of that wine package and it's definitely a lot of fun. I think we got on a call with maybe a dozen or so other ops leaders and, you know, just talked about operations, drank wine. They had some cheese. It is such an amazing experience. So you touched on COVID a little bit, right.

And sort of how we've all been impacted by it and how it's obviously turned sort of everybody's lives upside down the way you prospect. So I really appreciate sort of just sharing some of those ideas and sort of different ways that, um, you know, Sendoso is really helped their customers be successful and thinking about how to reach your prospects now that everybody is, you know, has been working from home, um, in terms of sort of.

COVID and the impact, like how, um, and we touched a little bit on it already and by the way, I love the cameo. Yeah. We, we share that constantly in different meetings at Clari and, um, you know, where I work in kind of talk about that and how we use them for outbounding. Um, If they're really funny too, like you said, there's a lot that are really funny.

Um, and really just really great, very creative ideas. Um, so with, with, COVID sort of impacting, um, some of your customers and, you know, obviously it's impacted, you know, everybody professionally, as well as personally, are there other ways that you've sort of seen the impact to your business and to your customers?

And I, was there anything that, um, You know, for other companies, you know, that are looking at 2021, are there any sort of lessons learned that you wanted to share or things that maybe you do differently for 2021?

Kris Rudeegraap: Um, you know, for, for us specifically, I would say we would do nothing differently as a company.

I mean, we crushed 2020, uh, we're doubling down at work. Um, it was a good year for us in terms of, I think we're. Uh, right place, right time. Um, you know, and some of the things I think we, we did well was really, um, you know, being agile in our marketing and our content creation, really thinking about it, you know, weekly instead of quarterly, um, as things were changing.

Um, you know, really getting our product team to, and product marketing team to think about, uh, what's happening in the market and what features we can build, um, to adapt to that. Um, and then, you know, really creating a company culture that embraced has changed in route and, and rallies kind of one team, one dream.

Um, and so that really helped us, you know, be agile and the whole company was expecting that.

Rosalyn Santa Elena: So I love that. Um, so one of the areas that, you know, talking about customers that you've really excelled at, I think Sendoso so has as well as you, as a leader is really being a true business partner, right? Your team works really hard to ensure customers are successful and they seem to always be coming up with, you know, unique and creative ways, right.

For us to help drive the business. What is your philosophy sort of around driving customer success and value, and how do you think that's also contributed to revenue acceleration?

Kris Rudeegraap: Yeah, so, you know, I would say that I'm extremely passionate and involved in our, in our customer conversations. Uh, you know, since day one, I have loved talking to customers.

Um, and it's been something that our entire company has put as part of our DNA, which is like, how do we, uh, talk to customers as much as possible? Um, it's I mean, last year I virtually, you know, virtually visited 120 customers. Uh, my goal was a hundred, so I'm happy that I had that many meetings the year before.

I think I did about 50 in-person, you know, which was a lot flying around the country. Um, But we have, you know, in addition to that, we have customer success. OKR. We have a pretty sizeable, uh, cab or a customer advisory board. Um, real customers are everything, our lifeblood. So we, uh, everything we do, we really try to think about them.

So, , it's just, uh, in our DNA as a company,

Rosalyn Santa Elena: I guess, aside from the product, we talked a little bit about the products we talked about, the customer focus, you know, Cynthia also has a great brand, right? As an advisor, I'm asked all the time, like, what's it like to be an advisor for Sendoso, you know, how did you become an advisor?

It's must be so cool. I didn't hear that all the time. And I was tell them, yes. It is very cool. It is very awesome. It's a fantastic team. Um, you know, then I, I love to share the story of just sort of how you and I met, you know, when I was working down in San Jose, um, you know, you came down to the South Bay to visit.

We literally, you know, met up, talked about all things ops, right. And decided to, to partner from there. And, you know, as you know, I'm a huge champion. I just love being involved with the team there. Um, Part of the brand is obviously the product. Right. And then, but culture, I think is also a big part of it, right?

Like I said, you have an amazing team, amazing culture, and it all really starts, you know, it's kind of cliche, but it really is true. It all starts from the top, you know, with you and with Braden and with Michelle. So. Can you tell me, um, a little bit about the culture that you've built at San DOSO and, you know, sort of that culture that you've built to really help your team be successful.

Um, and maybe along the same lines, are there some aspects of the culture that, you know, you're super proud of and that you think you've done really well?

Kris Rudeegraap: Yeah. So, I mean, even one of the things I'm really proud of is just our regrettable attrition. I'd say this year we've added, hired about 200, I think 220 people when I checked this year and.

You're a regrettable attrition. I mean, no one on the sales team, like no, the SDR's marketing, our go to market team. Like everyone loves it and stays. Um, and so that's helpful as we continue to grow our culture because we're not in this world where the person next to you or that your, your colleagues like leaving.

So we've, uh, even some of our, our first, you know, sales hires are now sales leadership. So we've done a great job of really making it, uh, a great place to, to join and a great place to stay forever. Um, and, and I think, cause some of those things is, you know, really leveling the playing field. I think me as a CEO, I've really tried to make it feel like everyone's on the same team, you know, like I'm not too cool for school.

Like I, I meet with randomly, I, you know, I'm meeting with. So I'm like, I love getting in the weeds with anybody and everybody, and I think that's, um, has been helpful because everyone feels like it's a very collaborative, open culture. Um, with that empowering people to make decisions. I think people are, you know, they're not scared to take chances or to go out and, you know, do innovative things, um, or try new innovative, you know, outbounding techniques.

It's like, everyone feels empowered and we do a ton of promoting within. You know, I think that, um, every week at the all hands, it feels like more people are getting promoted, which is awesome. And it's not just, you know, uh, same department promotions, like, you know, an SDR becoming an E, but it's. You know, in some cases we have SDRs going to partner teams or going into project management teams, or so we really, uh, we had, um, you know, one of our, our best product managers came from our customer support team.

So we're really thoughtful in that we're hiring smart people that want to be with us for years or decades. And, you know, if they have career aspiration changes, let's, let's help them in their journey instead of, you know, uh, you know, hiring and firing, so to speak. Um, and then I think overall, the biggest thing that I can say is just work-life balance.

I'm a huge believer in that we actually pre COVID and back in the day, we had a, what we call WFP work from beach mutual, pay people to take vacations. You know, I, uh, that was something that, uh, Was big for me. It's like some companies have unlimited PTO. We took it one step further back in the day and paid people, which was fun.

Um, and then all, I think, you know, uh, fun is, uh, the name of the game. If you can have fun while you're working, you're not really working, you're just having fun. And we've really tried to instill that. And I think we got kind of lucky in that our product, uh, what we, what we sell or we offer the market. You know, makes people smile and is fun.

When we see like someone sending a Kenyatta full of mini group or, uh, you know, a giant, you know, cut out face of somebody or all these creative things we send, like, uh, just inspire, people's kind of laughter and creativity. And that, you know, in turn we hear tons of success stories from our customers. Um, and then that is just built back into our culture.

And we, uh, we even highlight that in our website in terms of. You know, uh, Austin sends and so that's been helpful in our culture.

Rosalyn Santa Elena: That's awesome. So I guess for anybody who's listening, it is very cool to be part of it. Continue to continue to validate that. Um, all right. So as I think about, you know, the revenue engine, right in this podcast, I'm really hoping, um, you know, others will be able to learn how to accelerate revenue growth and really power their revenue engine.

Right. So from your perspective, cause are there some key elements that, you know, you would. Be willing to share that really contributed to the high growth that Sendoso has experienced. And I guess along with that is sort of, you know, what are some of the things that you, maybe you wish. Maybe you wish you knew earlier, or maybe things that you might do differently if you had to do it all over again.

Yeah.

Kris Rudeegraap: So for your first question on like early, you know, early growth, you know, one of the things I'd say is we built the sales engine, like day one. Um, and so that was also, uh, because me and my co-founder we're both, uh, sales account executives. Um, so we knew like day one, what, uh, uh, in Austin, you know, revenue engine was.

And so we invested in sales development very early. I mean, like, uh, SDRs were like on our first 10 hires, which I think in some cases is not as common. So we built our outbound sales engine really early, which then just, you know, every month, every quarter, every year compounded how successful that engine was.

Um, you know, I think some companies really wait to build their sales engine and it's kind of like a years into their growth. They're like, okay, let's finally figure out sales. Um, we figured out sales days, day one, um, we also focused on brand early on and really got the Sonos brand out there. And, you know, maybe, uh, did things like sponsor a conference when we were like a 10 person company that, you know, was a.

Probably not always what people did, you know, in the early days, but it helped us. And it was also kind of a hacky thing too. I remember, I think it was actually an early demand-based ADM conference where, uh, we had like 10 people at our booth. It was literally our entire company. It was like our designer and it was like payment.

Like our presence was like, Oh, wow. So those are those huge, they've got so many people at the booth. Um, and so I think we kind of have things together in the early days where it made it seem like, Oh, this is a big company, they've got 10 people, but it was like our entire company. So I think, um, did some, uh, hacky things there in terms of our product too, which is like early on, we want, we knew we wanted to integrate with like outreach and SalesLoft.

This was, you know, three and a half years ago before they had their app marketplaces. And even before they even have like, EPI's allowing for it. Who were you like built like a Google Chrome extension that overlaid a button like in their platform. So you could like click and send, um, and you know, they weren't, we were so small, you know, we were like people where they were like, Oh, what's this Sendoso thing.

And, um, but they started to get, you know, questioning it or they start to get their CSMs hearing about like, Oh, so this was really working as a step. Like, and all of that kind of compounded into them being like, Oh, we should build out like integrations and we should. And the whole thing was. For both of them, actually, we were on stage when they announced their partner ships.

And we were like one of the first partners alongside like LinkedIn. And so it was really cool to kind of get in early with like a kind of more hacky view on and then see it grow. And, and then last thing I'll say early one is I give kudos to you. And overall, in terms of our advisors strategy, they want, and we surround ourselves with super smart people that were wastewater than us in our.

Certain areas that we felt like, Hey, we can find advisors and we can learn from them, then we'll be 10 times better off. And you know, it was, uh, it's been paying off, uh, tenfold. And so, you know, thank you. And, um, that was part of our, I think our success too, is having really smart people that we can say, Hey, what do you think about this?

Um, but. Uh, so that was the first question. I think your second question was, you know, what, something about what it would do if you knew earlier or differently,

Rosalyn Santa Elena: Is there anything that, you know, you wish you knew earlier, maybe is there anything that you might do differently if you had to do it all over again?

Kris Rudeegraap: Yeah. Yeah. So, I mean, I'll answer this in two ways. One, I would say, uh, nothing in the sense of a very opp, uh, kind of optimistic leader. And I think that when things happen, we've learned from them and become better versus. Maybe a mentality of like, ah, this stucks, like let's, let's be negative or let's like, you know, so I'm, I'm a big, uh, you know, believer in being optimistic and learning from what happens and just knowing that that maybe happened for a reason.

So, you know, with that in mind though, I'd say certain hires I have hired sooner. Um, and you know, I'd probably be more thoughtful about org chart and key hires and really. Working with advisors of like, okay, what, what are, what was somebody that I could have hired when we're 200 people? And maybe we should hire them when we're 180 or so I think hiring the right people at the right times is key.

Um, so that would be maybe the one thing that I would, uh, think about of like figuring out org charts as companies scale more or less.

Rosalyn Santa Elena: Yep. That makes sense. Um, so thank you so much for joining me, but as we wrap up before I let you go, I'd love to know two things. One, what's the one thing about Kris that others would be surprised to learn?

And two, what is the one thing that you really want everyone to know about you?

Kris Rudeegraap: Okay, good question. I mean, I've already mentioned like I'm an ag turned CEO, which I didn't know that. I think that's interesting because there's maybe a salespeople out there that think that they can't do it or they can't start companies.

So I've, I've, uh, You know, busted that myth open, you know, salesperson cured CEO. Uh, but I think another interesting thing is, um, and this goes back to having fun. And the last five years of besides this year, obviously I've traveled to 30 countries. Um, really, you know, I value work life balance. Um, and you know, I think from a top down perspective for our team too, I promote that.

But, you know, sometimes you think of founders of being like locked in their office, you know, 20 hours a day. Um, and so, you know, I'm kind of the opposite. I say, travel have fun. You only live life once. And if you have that mentality, you can still start a company and be a, a huge, you know, unicorn because of that.

So the, uh, the other question on, uh, What is one thing you want everyone to know about you? I say like, uh, I'd probably say I'm an open door. Um, I invite anyone on this podcast listening to ping me if they want to chat. I love talking to people about startups, sales and DOSO anything. So add me on LinkedIn, email me I'm Kris with a K care assets.

The Sendoso. So, um, I love hearing for people that are like, I got this idea. What do you think I want to start this, but I don't know how so. Or like, Hey, I'm scaling up. Huge sales team. You know, what's your experience here? So, um, I love networking and connecting with others and I'll leave that as something that, you know, maybe some people aren't as open and, and I'm, uh, I'm an open door.

Rosalyn Santa Elena: That's awesome. And you're probably going to get thousands of emails wanting to join your team, wanting to become an advisor, and also hopefully wanting to buy the product, wanting to become a customer. So that's awesome. Thank you so much, Kris. I, I, you know, as always, it's a pleasure to chat with you. I'm so incredibly grateful for your time and really for sharing your story, which is amazing.

And just sharing your perspective with us. You bet.

Kris Rudeegraap: This was fun. Thank you. Thank you. Yeah.

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