By Matt Heinz, President of Heinz Marketing

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We were thrilled this last time to talk to Kris Rudeegraap, CEO of Sendoso, a fast growing MarTech company that really helps create better customer experiences and is improving communication and getting attention from your target prospects.

This episode is entitled:  “Personal Touch at Scale: How to Make Your Marketing (and Sales) Irresistible”

Personalization at scale doesn’t mean you’re doing everything in an automated way. Sometimes it simply means you have a system and a process to allow you to more efficiently personalize what you’re doing, and it makes a difference. I think when you’ve got a set of target accounts, the question you need to ask isn’t how much does it cost. The question more is “what is it worth?”, “what is it worth to maybe not necessarily just spend more money, but also spend a little extra time creating something special?”. And I think that’s part of why I think creating a systematic way to really make a mark and stand out is so popular right now.

Sometimes it’s not just about getting the demo or getting you to come to our webinar. Sometimes it’s creating a unique experience that is memorable.

Matt:  Thank you for joining us on Sales Pipeline Radio today. Appreciate you all joining us. For those of you listening live on the Funnel Media Network, thank you for joining us during your work day. For those of you that are joining on the podcast, thank you so much. We are just inches away from the goal line of hitting 100,000 listeners, and very excited to see our continued growth. Thank you so much everyone who’s listening to us. And as always, you can find every episode of Sales Pipeline Radio, past, present, and future on Each week we are featuring some of the best and brightest minds in B2B sales and marketing. Today is absolutely no different. Very excited to have the CEO of Sendoso. He is Kris Rudeegraap. Kris, thanks so much for joining us today.

Kris:  Thank you, Matt. Excited to be here.

Matt:  Well, I appreciate you joining us today. So much we could talk about here. I mean, you’ve been in and around the tech startup community for a long time, and about three years ago started up Sendoso. Talk a little bit about the problems Sendoso is solving because you guys have really risen very quickly partly in the ABM, account-based marketing side, but also just in helping companies personalize the sales and marketing efforts and driving greater results. Talk a little bit about what that means and what Sendoso’s part has been for it.

Kris:  Yeah. For sure. So to give you a little context, I think I’ve got a unique backstory where I was an account executive, sales rep for about a decade in various tech startups for turning into a CEO. And so Sendoso was really born out of necessity where I was doing a lot of manually handwriting and sending out these little quirky gifts, following up with thank you notes, and swag. And it was working well, but I would be in the office unto the late evenings or I’d ask marketing if they would put it on the bottom of their to-do list. So I really conceptualized, “Hey, why isn’t there a platform that allows you to send out almost anything integrated into your text stack, allows you to operationalize and personalize all of these direct mail gifts and all these other offline activities that you want to do in a very easy to do manner?”

So about three years ago, and fast forward to today and we’ve got tens of thousands of senders, and we’ve just grown the company tremendously.

Matt:  Well, I mean, you really hit a nerve, right? I mean, I think we were talking to someone before this call about the idea of personalization at scale. And personalization at scale doesn’t mean you’re doing everything in an automated way. Sometimes it simply means you have a system and a process to allow you to more efficiently personalize what you’re doing, and it makes a difference. I think when you’ve got a set of target accounts, the question you need to ask isn’t how much does it cost. The question more is what is it worth, what is it worth to maybe not necessarily just spend more money, but also spend a little extra time creating something special. And I think that’s part of why I think creating a systematic way to really make a mark and stand out is so popular right now.

Kris:  Totally, and I think that you nailed it. It’s really the direct mail offline world, it does take extra work, and there’s labor intensive time to it. So if we can help scale that where you can put a little bit of extra effort into what you want to send, such as, for example, doing a little research on you. I could send you a University of Washington like mug through our platform that might rise above the noise from just a random email you get. Just that extra effort in being able to do that across all your target accounts can be super impactful.

Matt:  Well, I think one of the things that you guys have certainly done for me I’m staring at right now, and I think, Paul, you can’t see me here, but I’m holding this bacon button.

Kris:  Yeah.

Matt:  I think… I don’t remember was it you or was it not. It was a couple years ago I was joking with your team about the fact that we make a lot of bacon and I use bacon as part of my sort of shtick when I do presentations. I said, “It’d be fun to start to give away bacon to people that are prospects. It’d be awesome to have a bacon button right in CRM that we just tell you guys to like send out bacon for me.” I think the next time I saw something, they said, “I have a gift for you.” And literally, if you seen those easy buttons from Staples from their ads a couple years ago, your team sent me a button that says bacon on the front. And when you click it, it does this, “Give, give me bacon.” And it does that, and it has a few other. It has nothing to do with anything other than just it is memorable. I’ll tell you what, I mean, the reason I was able to pull that so quickly it’s on my desk. And every time I look at it, I think about you guys.

It could’ve came from you or it could’ve come from any other company trying to sell me something, but sometimes it’s not just about getting the demo or getting you to come to our webinar. Sometimes it’s creating a unique experience that is memorable.

Kris:  Exactly. And I think that we’re seeing a trend too where STRs and AEs are almost becoming mini-marketers in terms of just the creativity level that they’re incorporating into their outreach and leveraging a platform like Sendoso or giving gifting and direct mail is a very creative avenue to think outside the box, like that bacon button or I’ve got dozens of other stories that just make me smile. Similar things like that that we hear our customers doing to just kind of breakthrough that noise and provide another avenue to engage with prospects.

Matt:  So we’ve got so many directions we could take this conversation. Talking today with Chris Rudeegraap. He’s the CEO of Sendoso, a fast growing MarTech company that really helps create better customer experiences and sort of improving communication and getting attention from your target prospects. I feel like I see you guys all over the place now. I feel like you guys are really growing very quickly and getting a lot of customers.

It was less than three years ago, Kris, you were a successful account executive at another sales tech company, and you mentioned that that you had a career in sales and then found this opportunity. Talk a little bit about that transition. How do you make that transition so quickly, and in your case so successfully?

Kris:  Success didn’t happen overnight. There was probably about a three month period where I was basically just praying to the wife that I was going to start making money soon and things were going to pick up. And it really just clicked. It took a handful of time to build out the product, to really get to version going. I mean, we’ve got warehouse facilities around the world. So that was also an interesting beast to be able to set up warehouse fulfillment centers, printing facilities, and all of that and streamline the behind the scenes logistics. So there was a solid first, six-nine months where it was really how are we going to make this work.

And then once we went to market, it was like the flood gates opened. So it was unique that both myself and my other co-founder were both sales guys. So we had sales backgrounds. So our go to market strategy was impeccable. We were really move fast as I think a lot of companies have early product or engineering founder that might have a little more struggle on the sales side. So sales was just a natural way for us to get customers fast.

Matt:  Coming in from the sales perspective I think is a unique and good and really powerful opportunity. I think you see a lot of founders that don’t have sales and marketing experience that have maybe more of a build it and they will come mentality. I’ve got a great product. I’ve got a great market opportunity. So this totally is going to solve everyone’s problems. I don’t need to do sales and marketing. I could just release it and it’ll all work. I mean, coming from the sales perspective, you know that that’s not true. So I think you’ve got a better eye for what it’s going to take to take your product to market. What are some things you’ve learned where sales and marketing might be a blind spot for first time technical CEO? What are some things you’ve learned that you need to sort of backfill either with your experience or with your team to help grow Sendoso?

Kris:  Yeah. I mean, early on we just really invested in sales and success. So we were using marketing automation right off the gate, using Sales Loft right off the gate, and actually used Outreach too. But we were using both of those off the gate. So we were really investing in tools up front because we know we wanted to plan for the future, and we know we wanted to start building in those kind of core competencies of using all that day one. I know some CEOs or founders might be skeptical of software up front and wait to grow. But that was one of our things that we really invested in software early to build that muscle memory.

Matt:  Talking again today with the CEO and co-founder of Sendoso, and Kris, as you think about the growth of the market obviously, I think any company as well we don’t really have competitors probably doesn’t have a market. I know you have competitors in the marketplace. We see a lot of the same people at all the same conferences, and I’m sure you see some of them in deals as well. How do you think about competitive differentiation in the crowded market from a message standpoint, from a product standpoint? How do you sort of ride the wave of a market that has created competition yet sort of stay unique and different and at the top of the wave?

Kris:  Yeah. So, I mean, one of the starting with customers and we have a ton of raving fans. I think that’s why you keep hearing about us so much is because people talk about us and how we’ve been able to provide that customer experience, that fun product that people love to use, and the customer success and the team behind it. So I think we’ve really built a fun company culture that our customers kind of feel. So that has been a big win for us early on. It’s just we got tens of thousands of raving fans out there talking us up.

Outside of that, I think that staying very close to the customer and seeing features and helping product align with sales and marketing, customer success has been important. So I know that in terms of standing out from the competition, we’re really the only company that’s able to offer all these different sending options, whether it’s handwritten notes, whether it’s booze, whether it’s printed collateral on demand, whether it’s cupcakes or direct mail or postcards or custom boxes. We have the assortment of everything you could want to send and all the integrations you want to send it out of. That was really just built out of necessity from what I thought when I was a salesperson and in the B2B org what would I want is that perfect tool and how do we get there.

Matt:  Well, we’re going to have to take a quick break, pay some bills. We’re going to be more with Kris Rudeegraap from CEO of Sendoso. We’re going to be talking more about personalization at scale, talk about what it takes to continue to drive scale and maintain culture inside your own organization, and much more. We’ll be right back on Sales Pipeline Radio.


Matt:  Next week, we will be on the road again. I will be in Boston for the Ramp Conference from InsightSquared. So we’ll be on the road again. But some great guests coming up here the rest of June and July. We’ve got Lindsey Peterson, one of the nation’s foremost B2B branding experts. We’re going to talk about the impact and importance of brand in B2B and what that means and how you do that. Coming up after that, we’ve actually got the results of a unique content marketing survey that we recently completely with a partner. Some really interesting insights. Some of that we’ll be highlighting next week from the InsightSquared Conference as well. Some marketing automation satisfaction research that we’ll be launching. So more today thankfully with Kris Rudeegraap. He’s the CEO of Sendoso.

Speaking of the MarTech stack, Kris, Sendoso on its own is phenomenal, but it is one of, what? 7000 MarTech tools. We talked about sort of rising above the wave in a competitive set. But it seems like there is a little bit of MarTech fatigue by a lot of buyers, by a lot of B2B marketers today. Are you seeing that at all? How do you combat that as a member of that community?

Kris:  Yeah. So we’re not seeing that too much on our field. I think one of the things that we do is for a lot of companies, direct mail and gifting is not necessarily a brand new thing. People have been doing it for a while. So if someone is doing it, it’s a very manual, rigorous thing or maybe if they’re doing it through some legacy provider, it’s kind of a broken process. We’re really not some random shiny object that they’re not sure if it’s going to work or not. They know it’s working. They just want to kind of operationalize it and streamline it and provide more personalization at scale. So that’s one thing.

I think the other thing that’s interesting too for us is that we also play well with other departments. So the customer success org, the HR org, the sales org directly. So sometimes we get creative with pulling other buyers or other groups, which helps lighten the loan on just being another MarTech tool.

Matt:  Got it. And as you guys grow, and I mentioned before we left just some of the challenges of growing a company, especially a fast growing, early stage company. What are some keys for you as the CEO to maintaining quantity and quality of that growth?

Kris:  Yeah. So I interview almost every person that we bring into the org. So really it’s a goal of mine. I’m basically a recruiter now in terms of what I do. Staying close to the talent. We’ve got a couple different offices now across the U.S. and globally, so that’s been a challenge in terms of how do we keep everyone together but in separate offices. Then just investing in people. I think we have the benefit of what we do and what our customers are sending out as a very fun product. So we can have fun with our brand. To our benefit, that might if you’re selling something else, they might be a little tougher to align everyone internally.

Matt:  Yeah for sure. I think to have fun with that brand both internally and externally is certainly part of what you’ve done. I think as you scale, is your intent to continue to interview every candidate? Even if you can, what do you do to maintain level of quality and integrity of the people you’re looking for? How do you do that as you continue to scale and grow?

Kris:  I think hiring great leaders is important. We also have a whole sales and enablement, and we also have just a general learning and development team we’re investing in early to help make sure that our employees are up to speed on everything we do so there’s no frustrations. There’s no like lack of knowledge sharing. So a lot of those things I think is just building out the processes to scale the company and finding tools to help with that.

I also try to do as many one on ones as I possibly can. With everyone through the org, whether it’s an SCR or whether it’s our VP of sales or it’s our direct of engineering, I’m constantly talking to different people, which I think just helps show that I’m just another peer that they are working with. And I think that helps build good rapport throughout the couple.

Matt:  To finish up last few minutes with the CEO of Sendoso. I’m curious to hear your answer to this question. We ask a lot of our guests to talk a little bit about the people that have been influential to them along the way, professors, authors, former managers, people you want to recognize or people you might recommend to other people who are listening to go check out as well.

Kris:  I’ve got a laundry list of blogs that I follow. My favorite author is Malcolm Gladwell. I enjoy some of his books. I’ve got about 15,000 connections on LinkedIn, and I’m obsessed with just looking at LinkedIn like throughout the day. That’s kind of one of the things that I spend some of my good time on is just chiming in and spending effort and engaging the community on LinkedIn.

Matt:  Talk a little bit about sort of your own sort of content strategy. As you’ve gone, built a company, and you’re building a brand for yourself, how do you think about content strategy for you? And I’m not just thinking about Sendoso but also for you as an executive, whether you are trying to build the brand of the company, trying to build your name associated with that brand. Maybe depending on if you’re looking fundraising, how do you think about your own content and brand strategy?

Kris:  Yeah. So I think two part question. I think so as I speak at conferences and different events and we have a PR agency that’s getting me into these chambers and things like that. I think having a CEO on the face of a company helps put a face to a brand, and it’s something that I really enjoy doing, getting on stage and things like that. So I think from a personal standpoint, I think I’m doing a good job of executing on that.

From a company branding perspective, I think we are trying to create content. We’re relaunching a new website where we’re having Sendoso TV as part of the section. So had a lot of awesome video content from all of the cool projects that we doing, all the warehouse activities, all of our customer stories. So video is a big push for us in terms of content creation and content sharing. We actually have a videographer on our staff that’s doing more and more video for us.

And then something that a lot of people think is kind of an obvious thing to do but there’s still a lot of education and learning about how you scale it how or what used to be controlled by marketing and demand gen as a top of funnel, “Hey, let’s send 10,000 postcards.” And now is something that an SCR can send themselves. So there’s a bit of learning there. So we’re doing a lot of thought leadership content in terms of how do you like operationalize and personalize that scale and how do you bring all this down to every employee at the company who’s customer facing.

Matt:  So, Kris, I feel like I see you at a lot of the events, B2B events around the circuit. I know you travel a lot. I imagine that you are working just a ton as well. What are some of your keys though to sort of create balance? And I’m not going to say work/life balance, but I think we all have work that can keep us going 24 hours a day and not get it done. How do you focus? How do you triage and how do you find balance to keep yourself refreshed and energized and ready to keep going?

Kris:  Yeah. I mean, one of the things that I do travel quite a bit. But one of my things I like to do is I like to stick around cities or areas that I travel to for a bit and work remote. So that kind of at least alleviates me from the get in and get out mentality and rushing through things. So it allows me to explore and travel a bit, work remote. So I like that, and that kind of balancing things out. And then I’ve got a good routine. I’m more of a work smarter than harder kind of CEO. So I’ll put in a solid eight-nine hours a day, but you’re not going to see me putting in 15 hour days or anything. I think that can get burnt out by that, and I’d rather be laser focused and really smart in how I work. And I also like to do other things. Surfing, mountain biking, golfing. So I try to get out and have fun with customers or even employees and things like that too.

Matt:  So what I’m hearing is, if I can summarize, is to be intentional about what you focus on, have outside interests that draw you to them, and learn the discipline of being able to say no.

Kris:       Yeah.

So my follow-up question then is on that last piece. So I think this is a big challenge for a lot of people, not just that are in your position running a company but in any role where they want to be successful. In some cases, they want to make people happy. In some cases, they just want to take advantage of opportunities that may turn into something. How have you developed the discipline of saying no when needed?

Kris:  Yeah. So I think it really came that I’ve been in startups for the last decade, and I really seen putting an effort and seeing how different people work in different orgs. Looking at different CEOs, looking at different VPs, and really kind of copycatting what I liked and what I didn’t like and putting all that together and being a bit more thoughtful in how I put myself out there as the CEO. So I think along with that, I’ve got some good mentors and a good advisors that I keep in touch with who kind of keep me aligned when I’m thinking through some of my leadership mentalities or my work/life balance stuff.

Matt:  Awesome. Well, unfortunately, we are out of time. I’ve got to wrap up here, I promised we would cover a lot of ground today, but appreciate our guest today. Thank you so much, Kris from CEO of Sendoso. We’ll put a link to Sendoso in our podcast notes. If you want to share this conversation with others on your team, you’ll find it up on Sales Pipeline Radio here in a couple days, and make sure you check us out next Thursday and every Thursday for new episodes.

On behalf of my great producer, Paul, thank you so much for joining us again. This has been Sales Pipeline Radio.


Sales Pipeline Radio is sponsored and produced by Heinz Marketing on the Funnel Radio Channel.  I interview the best and brightest minds in sales and Marketing.  If you would like to be a guest on Sales Pipeline Radio send an email to Sheena.