Kris Rudeegraap (00:02)
there's some psychological feeling when you unbox something, you're touching it. There's some emotional connection to that. especially if you're surprised by it and it's creative and interactive or it's different.
Benjamin Ard (00:38)
Welcome back to another episode of Content Amplified. Today I'm joined by Kris. Kris, welcome to the show.
Kris Rudeegraap (00:43)
Thanks, Ben. Thanks for having me. Excited to chat today.
Benjamin Ard (00:44)
Yeah, Kris, I'm excited. This is going to be a fun subject. I think it's going to kind of be a fresh break from all of the AI conversations we're having. Now, obviously, AI plays a role here. But I'm excited to have another conversation about building relationships, new and exciting ways. But Kris, before we dive in, let's get to know you. Let's get to know your work background, history, all that kind of fun stuff.
Kris Rudeegraap (01:08)
Yeah. So I started Sendoso about 10 years ago. Prior to that, it's been about a decade in sales and a lifelong entrepreneur was an entrepreneur in college knew I always wanted to start something. And so at my last company TalkDesk, while I was in sales, I saw firsthand this kind of pain of, you know, email being less effective and feeling spammy and saturated. And so then I felt even more pain trying to send out mailers and guests. would pack boxes in the evenings and go to the FedEx store and look at tracking links, hoping that they'd get delivered in time and just dreamed of a solution that did that all for me. And so that's where Sendoso came about where the world's leading direct mail and gifting automation platform. take all the heavy lifting of, you know, the orchestration of fulfillment and supply chain logistics and put it in a nice kind of software enabled platform. And had a lot of fun doing this. You can only imagine the creativity I see working with marketers and wanting to send out gifts. So it's a lot of fun.
Benjamin Ard (02:11)
100%. I'm also firsthand. I've had experience using the platform. It is amazing. I think I've sent out millions of dollars of gifts and it's a great way to do it. There's no way I could have managed it any other way. So I'm excited. So when, when Kris and I connected, I was excited to have him on. Now what's cool is we're going to talk about digital content, but really when and where and how it can be utilized offline. So you can do it print and mail it and all that kind of fun stuff. So we're going to dive into that. Kris, so let's kind of start at the beginning. How do you identify content that's digital content that has some legs to stand on that may be worth actually mailing to a prospect or someone that you're trying to get in front of? What does that process look like?
Kris Rudeegraap (02:59)
Yeah. mean, the beauty of the digital content is you have a treasure trove of data to shortlist what pieces are getting the most engagement digitally that can then perform best offline too. And so I think there's probably a few different systems that I would look at. One is your, whether it's a sales enablement or your content engagement platforms. These are like the Highspot, Seismic, Showpad, MindTickle, Guru of the world. A lot of those are repository that marketing sets up and then sales pulls from for or opens up these little digital sales rooms and content is shared. So within those, you can see clicks, can see views, you can see time spent. So you should get a short list there. You should also be able to see based on your website or blog or CMS web analytics, what content is being engaged with, downloaded the most. Viewed the most if you don't gate it and take that data into play and then lastly I do see a lot of marketers running Paid ads digital ads that have a call to action saying hey fill out this form download this white paper download this data study And so you can get data on which ads performing better And so amongst those three you should be able to triangulate What's some of your best performing content that could be mailed out to your prospects to grab their attention and drive results?
Benjamin Ard (04:18)
Okay, I love it. So we've gone through and we decided, okay, we want to have a physical mailer kind of physical sender approach. We go through all the data that we're collecting from all our other systems. We're finding the highest performing pieces. And then we decide, okay, we're going to go and send this. So what does that kind of look like? So I've found the piece. Obviously I can't just click print and then I'm off to the races. Like, what does that look like as far as launching a campaign? and actually using digital content in a physical mailer kind of a situation.
Kris Rudeegraap (04:49)
Yeah, so I'd say there's two paths. I'll try to put the path together of like, you're not using a platform likes in this or you are, so I can kind of bridge that gap. You know, I think first is, you know, one don't ever think it just picks one, you know, piece content and the target audience associated with that. You could even say, I'm only going to pick, you know, 20 target accounts that I'm going to try this piece out on if you want to go really small or 200, depending on your, your ICP and your ACV. And then you know, it's as easy as if you're doing it manually in-house. Hey, go, don't boil the ocean. Just go print them, put them in FedEx envelopes. you know, spend some time looking up the mailing addresses or buy some data. and, create some kind of offer or some reason for them to reply ideally. and ship it send it. so I think there's, you know, there's probably some tracking you'd want to do on the backend, whether you want to put a QR code or whether you want to put some other offer. to drive responses. Or if you want it to just be kind of more top of funnel and you want like an SDR to follow up with it after it's delivered. So I think that's one component to it. If you're using a platform like Sendoso, obviously all those steps would be automated and shrunk down to like load the content, click send, hey, we'll find the addresses for you. Hey, we'll write a note, a handwritten note associated with that message for you. We'll track it in your CRM or marketing for you. you know, we'll, do all of that behind the scenes, but you know, if you're not, if you don't have a platform that shouldn't prohibit you from, know, doing some, at least a test campaign.
Benjamin Ard (06:17)
I love it. Okay. So I found the contents. I'm either using a platform like Sendoso or I'm doing it the really difficult way and I'm printing all on myself and sending it and going through all those motions. And which is like, obviously a great route if you're just starting out and say, does this have any legs on before we kind of engage on a platform side? But I'm going through that process, right? When should I send the material? Like what part of the buyer's journey do you feel like physical mailers have like a good place and how do you make it also just not like noise? Like obviously you talked about seeing a need in email 10 years ago. My goodness. mean, the need is infinitely greater now to get away from that channel if possible. How do you make sure that you're not becoming noise in the physical mailer space as well?
Kris Rudeegraap (07:02)
Yeah, it's a great question. take that in two different approaches. One is, you can take that great piece of content and convert it into something that's more interesting. So you could, for example, maybe this great piece of content, you can then repurpose into like a custom Mad Libs book. We've done that for clients. So same content, just different form factor. Or like a scratch off insight card where there's some kind of interactive component or like a workbook. where instead of just reading it, you're actually trying to answer questions or fill in the blanks. Or it could be like more of a video mailer where you take that content, have like an executive or CEO reread some of that content in a video format and send a video mailer out as part of that. I can go on and on some of these creative mediums. You you've even seen somebody create some trading cards, some like a very high quality printed magazine that people are now subscribing to quarterly. So there's a lot of great ways to repurpose content into something more than just a printed eight and a half by 11 stapled PDF. So I think that's one piece is how do you rethink of that content? Then the second piece I think to that is, a lot of people have the opportunity to like reimagine their buyer's journey. depending on where in the buyer's journey, this might come. you know, top of funnel and then following it up by SDR saying, Hey, I shared this super personalized mailer with you about how X, Y, X, Y, Z wanted to follow up on that to see if you had a chance to read it, you know, or it could be farther down where maybe marketing automatically triggers one of these case studies off when a stage three hits, because you know that, you know, at stage three, they're, you know, in the evaluation, they're comparing you to competitors and maybe without even the AE having to do anything, marketing is providing air cover and getting these out as just another means to sit on your desk for that buyer that's gonna look at the case study as well. Or it could be a, we've seen some of our customers have these post sales, once the deal closes, they send out like a welcome onboarding kit and it's a printed booklet of everything to look forward to, including kind of the onboarding timeline. And a lot of times that is digitally formatted in like an onboarding deck, but repurpose that into a nice printout so that they have something that they can look through in anticipation of that onboarding. And I think it's all about rethinking that journey where you can interject physical into the digital journey, whether that's in the buyer or post sales.
Benjamin Ard (09:28)
I love that. So you've had a really cool experience where you get to see this firsthand. And I love all the examples. They're right there at the tip of the tongue. I mean, I'm sure you guys do so many cool things. I guess like down on like a relationship building level, like you started talking about that very early on. It's not just another cold email. What is a physical mailer like sending something actually in the mail? due to a relationship, how does it impact it? And you talked about, hey, it may be the top of the funnel, the awareness stage, or later on down the funnel, or even after they've become a customer. But how does that impact the relationship? As I'm looking at the customer journey, how does it actually build a relationship? Why is it different than digital?
Kris Rudeegraap (10:13)
Yeah. So I think there's a few things that come into play. One is there's some psychological feeling when you unbox something, you're touching it. There's some emotional connection to that. especially if you're surprised by it and it's creative and interactive or it's different. So I think there's one thing is just like the tangible psychology too. a lot of times it's a pattern disrupt. And so it's not like this, like another email, another email, another email, another email. It's like, like this is interesting. Let me see what this is. And that elicits some kind of like, you know, unique dopamine hit of like, what's in the package? And oh, it's like, this person put together a nice little note that accompanies this print, collateral piece. And it's personalized to me. And I only got one of them today, I didn't get 100 of them today, or 1000 of them today. And so I think that pattern is rough and uniqueness is hits home there. I think there's also a way for you to stand out. aside being a pattern disrupt, but if you're in a competitive deal cycle, somebody's sending you this nice physical piece and the other competitor's just doing pure digital, it stands out and it gives you a reason to pick something differently because they're doing that. I think we also see for some of these mailers, they'll attach like a QR code for a bonus gift alongside it. And that can be as simple as saying like, here's a recent data study that I thought you'd find interesting, maybe. By the way, scan this QR code and grab coffee on me or scan this QR code and grab lunch on me. And it's just a link to a digital gift card to Starbucks or DoorDash. And it's simple, not all of them get redeemed. So you're not like always out money. You're only paying if they do get redeemed. And it just creates that another piece of like give and get. You're not just like aggressively saying, here's this piece, you you owe me. It's like, hey, here you go. Enjoy some coffee while you're reading, which is just like something nice to say.
Benjamin Ard (12:03)
Yeah. And to that point, like this is a weird aside, but I can tell you from personal experience using a platform where you don't have to pay unless something is redeemed can save you a ton of money. I've done both systems where if you're doing an Amazon gift card, for example, as soon as you redeem that directly from Amazon, money's out of your bank account. Whereas if you're doing this at all in bulk and you're using a platform like Sendoso, It is very refreshing at the end of the month to be like, Hey, there is a certain percentage of your audience that didn't redeem this. So you don't owe all of this money. You get a portion of it back and all that kind of stuff. So that's kind of a pro tip if you do it in bulk. Yeah.
Kris Rudeegraap (12:37)
Exactly. Yeah, and you can take that to your advantage in print, like you said, and that can be, you know, a big differentiator for driving more conversions because you're only paying if someone's engaging.
Benjamin Ard (12:48)
Yeah, 100%. So I mentioned that it's kind of fun to get away from the subject, but I do have to bring this back to AI. With this new technology, what are you seeing in the physical mailer space that AI, how is it contributing, especially like, is it allowing you to write personalized digital content that you're printing? What is that kind of doing and how is that technology being utilized in the space?
Kris Rudeegraap (13:13)
Yeah, you nailed it on the personal side. So I think AI is really good at personalization, whether that's, you know, in depth data powered algorithm that selects like what's the right gift to send or personalizing down to like the content message being personalized, the individual, the persona, the segment, the company, print on demand. so it's printed just for this one person. so I think that's a big for AI. AI can also help draft the handwritten note message too that accompanies the e-mailer. So strongly recommend not just like sending out a case study, a data report, some printed collateral with nothing. you always want some, whether it's a post-it note, whether it's a handwritten card, printed card associated with it, but AI is really good at drafting a version of that. AI is good at, finding mailing address data. So, we have a feature called smart delivery where we can say, Hey, Kris, doesn't live close to the Phoenix office. He lives in San Francisco, probably works from home. Here's Kris's home address, send it to his home address. and so that data, accuracy is critical with AI. and then I think AI, whether you call this like a pure play AI or just like an agentic workflow, but you can come up with a lot of these automated workflows that trigger. you know, these, physical touch points with digital content versus maybe the historic click and send, or the worst case is like the one time print a bunch and mail all at once. And so I think that, you know, with AI or these automated workflows, you can have these like always on, you know, signal based or stage based or lead score based or intent based based on like intent score data, that will then trigger these off. And these are just like living and breathing. Yeah.
Benjamin Ard (14:54)
I love that. That's so cool. Okay, Kris, we've dove into a lot of different areas here. I think this has been a great masterclass about getting into physical mailers, turning your digital content into physical content. One final question, because we're almost out of time for anyone today who's listening and saying, you know what, we probably should do a better job here. We should at least experiment with this. How do they get started? Like what can they do this month? to actually start getting out there and sending digital content and physical mailers, like any tips or tricks to get started.
Kris Rudeegraap (15:26)
I'd say one, go look at some of your content data system, find the best performing asset the last quarter. Boom, now you have your piece. Go get it printed, print, you know, 50 of them. Boom, you got, now you have it. Go find 50 deals that these could influence. So use in pipeline deals, those are probably quicker to showcase or test 25 in pipeline, 25 target accounts that you haven't broken into. Write a little note associated with each. or tell your sales reps to do it and then send it. There's nothing stopping you from testing this. If it works for you, boom, automate it more, sign up for Sendoso. If it doesn't work for you, try it again until it works.
Benjamin Ard (16:04)
I love it. That's awesome. Kris, this has been great. For anyone listening to this episode who wants to reach out and connect with you online, how and where can they find you?
Kris Rudeegraap (16:12)
Yeah, love connected on LinkedIn. So add me on LinkedIn. Maybe you can add a link in the show notes. Find me at kris@sendoso.com if you want to connect with me directly, or if you're intrigued by some of the stuff we talked about today, check out sendoso.com.
Benjamin Ard (16:25)
love it. And we'll have all the links in the show notes below, regardless of what platform you're listening on. Scroll down, click on the link, connect with Kris. It'll be great. Kris, again, thank you so much for the time and insights today. It's been amazing.
Kris Rudeegraap (16:37)
Yeah, thanks for me on, Ben. It's been a pleasure.
