Why Is Direct Mail Outperforming Email in Modern B2B Marketing with Kris Rudeegraap

Welcome to the B2B Growth Blueprint podcast, where we talk with entrepreneurs, founders, and leaders at B2B services, tech, and SaaS companies to learn the systems and processes they've used to create success for their business. We'll also learn from marketing and sales experts to provide insights to help you grow your business. I'm your host, Mark Osborne, and the podcast is brought to you by Modern Revenue Strategies and their 10x ROI B2B Growth Guarantee. Schedule a free diagnostic call to learn the fastest path to double your B2B revenues in just 90 days. Hello and welcome to another episode of the B2B Growth Blueprint Podcast. I'm your host, Mark Osborne, and And today I'm very excited to welcome my guest, Chris Rüdigraaff. Now, Chris is the co-founder and CEO of Sendoso, which is the leading sending platform that helps B2B companies break through the digital noise and create more human, memorable buying experiences. Chris started his career in sales where he saw firsthand how hard it was to stand out once inboxes became crowded and buyers became harder to reach. And that insight led him to co-found Sendoso, which pioneered programmatic sending and physical touchpoints as a core part of the modern go-to-market strategy. Under his leadership, Sendoso scaled from an early-stage startup to a category-defining platform used by hundreds of leading B2B companies, raising significant venture capital along the way, including a major investment during the peak of the growth-at-all-costs era. More importantly, Chris also led the company through the less talked about, Part of the journey, pivoting from hypergrowth to profitability as market conditions changed. Chris today is recognized as a thought leader in go-to-market strategy, pipeline creation, and the intersection of technology, data, and human connection. He speaks frequently about founder evolution, sustainable growth, and how AI is reshaping marketing and sales teams without replacing the fundamentals that actually drive revenue. Chris.

Wow, thank you, Mark. That introduction is the best one I've ever had. I appreciate that. That was really, really well written.

Oh, well, thank you. I appreciate that. So I'm super excited for this conversation. I've been looking forward to it. But before we jump in on some of the topics that we've been chatting about, why don't you give our audience a little bit of sort of your personal story? Like, you know, what did what I just read really look like in practice? Tell us the twists and turns of your career that brought you to where you are today.

Yeah, of course. So I went to college for marketing, but immediately out of college realized that sales was more my calling than marketing. I saw myself enabling the sales team and then the sales reps taking home the huge paychecks. So I said, hey, let me switch over from marketing to sales. That was early in my career, and I really loved sales. I really love building relationships with people, and I did sales for about a decade. And then in about 2015, 2016 at the time, I was at a SaaS software company and I saw myself wanting to get more creative. I think my marketing background kind of pulled me in to say, hey, how else can I engage with prospects and build that rapport? And so I started manually, like writing handwritten notes after calls and sending thank yous, or I'd hear a dog bark on a call and send over, you know, a dog toy from Amazon, or I'd go grab swag from our marketing closet and pack it up and send it out to a prospect that was ghosting me. All those things worked really, really well. It was just like running a mini mailroom. It was a nightmare operationally in the office, packing boxes. My wife's like, where are you? I'm like, I'm at FedEx. I'll be home soon for dinner. Sorry. It became almost like a bit of a nuance to where I was like, it worked, but it was just so hard to click tracking links, expense report, pack boxes, and I just dreamed of a better solution. Ironically, at the time I thought email was nearing, you know, its too spammy age, which was a decade ago.

Yeah, I was gonna say, I think, uh, I think it's only gotten worse.

I can attest to it got way worse. Um, but direct mail response rates are quite high. Um, we've even seen some stats where it's anywhere from 5 to 9 times higher than email. And so it works so well. And so that's where I dreamed up of Sendoso and said, hey, why isn't there a platform that's as easy to send an email as it is to send a mailer out, whether it's a bottle of wine, whether it's custom branded swag, whether it's thousands of postcards, or whether it's a super unique personalized item to the individual. And doing so, tracking it through CRM systems, you know, all the expense reporting and finance all on the back end. And that dream became a reality. And I quit my job as a sales rep, and the next day was the CEO and co-founder of Sendoso. And kind of the rest was history. I think I solved the problem that I deeply, deeply understood and deeply wanted solved for myself. Obviously lots of learnings along the way from scaling to hundreds of millions in spend on our platform. But the initial thesis that, you know, direct mail and gifting is gonna drive better relationships and better rapport and ultimately grab someone's attention, which I think in today's world, that's what marketers and sales reps are hoping for is how do I grab someone else's attention and tell the story on how your product or service can solve their pain?

Yeah, so such an interesting story there. And it's not often that the chance to chat with folks that have sort of been through that evolution of, you know, having an initial role and then, you know, having this market insight that then sort of leads them to create a category that they can be king of. I'm curious if you can share a little bit of, you know, what's it like as a company grows, you know, so quickly because you really found this opportunity in the marketplace to shift from being the founder that's got the ideas and that's running everything.

Yeah.

And it's really just sort of trying to create scale around something that you were doing that you knew would work to being a CEO who's instead sort of leading teams and guiding people on, you know, corporate initiatives and things like that. Talk to us a little bit about that, you know, both sort of personal as well as kind of operational shift that you've gone through there.

Yeah, so I think in the early years, the first kind of year or two, my sales background and sales acumen really helped with more than just sales. I think obviously getting our first customers was really easy and low-hanging fruit to me, but when it came to pitching and selling investors on raising money and the You know, 150 million plus we've raised over the last decade. That really boded well to my sales background and willing to go pitch, you know, 30 investors and get 29 nos until you get the first one. So I think my sales background there helped with fundraising, and then my sales background really helped with recruiting. And I think in the early years, recruiting is really challenging. You're saying, "Hey, quit your good job that is at a reputable company and go join us for." Who knows what is going to happen next? And you really have to sell the vision, the dream, the energy, the optimism. And so again, I think my early sales background there really helped in that. And I think those gave me some early, you know, tailwinds and momentum to say, okay, I'm a founder, but now I'm recruiting and leading a team. I'm building a finance organisation. I'm, you know, raising funds. I'm managing a lot more than just sales. And then That kind of snowballed me into becoming more of a focus on delegation, you know, and I think as a founder, you tend to try to solve problems yourself. As a CEO, you've got to delegate, you've got to trust in your employees and team. And I think being a really good delegator has led me to really let go of the areas that I didn't need to own anymore and help me focus on really other areas that the business needed me for. The other area that, you know, I think really good CEOs, you know, tend to do well at is storytelling and thought leadership. And I think in the early years that is, you know, translates well into early customers. But then how do you, how do you really continue to shape the narrative? Because the story day 1, month 1, year 1 needs to evolve. And how do you continue to tell interesting stories to the market as The market evolved. For us, that was interesting moments as it related to when COVID hit and how does that storytelling change because we were delivering mailers and gifts to people's offices and now everyone worked from home. Or how has the story changed in recent years where AI has accelerated the, the spammification of inboxes and, and how does, you know, ad prices going up and these other channels becoming saturated, how does our story come back and And tell a way that then, you know, really makes the market continue to want to demand our product and services. Yeah.

So you hit on something in there that I think is worth kind of tapping into, which is you talked about being a good delegator. And I know that's something that, you know, oftentimes CEOs, especially as they're early stage and founding, you know, really struggle with because they feel like, Well, no one can do it as well as me.

Yeah.

Sometimes that's true. Oftentimes it's not. It's just a perception. But talk to us a little bit about how you built that muscle. How did you become a good delegator? How did you, you know, learn to not only delegate, but then, you know, enable other folks to elevate, you know, what was happening with a particular function within the company?

Yeah. So tactically, there's a few things early on. I mean, one of the very, very early on things was I was obsessed with Upwork and still am to this day. And I think that's like low-hanging delegation where you're like you have a specific task that you want to delegate to someone else to do, whether it's a project, whether it's you know could be a myriad of things. But it's a great way to say, hey, there's things I need to do that I can't have time to do. So who else can do them? And in the very early years, then it became well, I have so many of these marketing related tasks. I need to hire a marketer to do these things. So I really got good at delegating from like a per task basis to then figuring out okay, I need to hire someone to own these. These tasks than to go above and beyond. So I think that tactically was an early delegation skill set I learned. The other thing that I did in terms of my management abilities is really set the stage when I hired people to say, "I work for you," and I'm going to be an idea guy. I think a lot of founders are, you know, have really good ideas. And so my my my theory was always, "Hey, here's some cool ideas that could help in marketing and product and finance." You take these ideas, you tell me if you're gonna— you tell me if you're gonna do them, you tell me if they suck, but you're the end decision maker on your own domain. And I think that broke the barrier down from being either one feeling like I was a micromanagement type of leader to being I was a collaborator and someone that wanted to win together. And that philosophy has really helped me in the years and years to come as we've grown and gotten bigger and bigger. I will say though that I know it was probably 3 or 4 years ago. I did have some whiplash from me being too in the weeds at times. And I think as a CEO, you need to know when new employees come in at certain stages, like when we are Series C, that they're not used to maybe a CEO getting in the weeds saying, hey, let me help you with this deal, or hey, I have this product feature, here's a screenshot, let me fix that. And so oftentimes I needed to step Set the stage with new employees, and one of the things I I did was hosted this weekly new hire from the founder kind of one-on-one and and or group session, kind of sharing my way of leadership and share and trying to you know break the barriers down to saying, "Hey, I'm not some scary CEO in a tower in a corner office. I'm just like you. I want to help. Let's win together," and that really helped. too, by making people feel comfortable kind of talking with the CEO when at certain stages of the companies that can be a little bit scary.

Yeah, well, I love that. And, you know, you, you didn't name it this, but, you know, it's this concept of sort of servant leadership of like, you're— you serve the— you serve the audience. And, you know, I've heard it said before, and, and I've always seen this to be true, is, you know, someone asked one time like, how do you motivate people? And the answer is Well, you hire motivated people and then you clear the path for them.

Yeah.

And many people are motivated, but they get demotivated by the work environment that they're in because someone's leaning over top of them trying to micromanage or not empowering them to own their domain, as you said. And so, I love that sort of setup, and it's no surprise that that's been successful for you. To pivot a little bit, I want to dig in on the specific problem Sendoso solves because I think it's really valuable You know, we spend a lot of time on this show and in the work that I do with clients talking about, you know, how do you break through in a, you know, sort of go-to-market strategy in motion? And the idea of, you know, sending lumpy mailers or sending customized things is something that really has gained a lot of traction. And as you say, especially as the digital world has become noisier, it's become even more valuable, but not everyone can kind of immediately envision, well, how would this fit into my business?

Yeah.

So, talk to us a little bit about how Sendoso really enables that and maybe some of the kind of unique plays that maybe it's worked for, you know, sort of boring businesses that don't think like, oh, I'm the type of person that sends out bottles of wine or, you know, things like that. There's, I'm sure there's some creative ways that people have used the platform To do things that really, you know, go beyond what's expected, but then help them break through with, you know, those, you know, decision makers that could really 10x their business and things like that.

100%. Yeah. So I can take this in a couple different directions, but I think the first thing to note is that like, why aren't— why isn't everyone doing it? And I think it comes down to, you know, doing direct mail, lumpy mail, physical gifts, etc. Tends to seem hard, and it is generally hard if you're not using like a platform to automate a lot of the heavy lifting. Because as you know, you alluded to there, and I alluded to earlier on when I started the business, I was you know manually going out and sourcing and buying things, and then packing boxes, and then writing notes, and then trying to log things in CRM and track expense reporting. And so all those things are like ah, I don't have enough time in my day. I'm just gonna like set. Another email because that's easy and it's a click of a button. And so the benefit though of that is that not everyone is doing direct mail, so you still have this ability to stand out. You still have— and because of that, there's a cost component of doing direct mail and gifting that people can't do unlimited clicking of emails or running insane numbers of ads everywhere because of just the ability to do so. And so it creates this like saturation prevention mechanism, which is why it delivers such higher returns than other channels. But once you get turned on and know that there's like a Sendoso that exists, the world kind of changes for you. And you can now say, okay, well, now I could use creativity to break through the noise and I can come up with different campaigns, whether it's a bottle of wine or whether it's, you know, could be, you know, a cool postcard campaign. It could be something clever as, you know, The world's your oyster, and marketers are like the most creative type that can come up with these campaigns. We also offer some really interesting Campaign Studio that will come up with ideas for you, or we have an AI product called Smart Send that will say, hey, Chris, we know Chris likes golf, we know Chris lives in San Francisco, we know Chris has a kid, here's some things Chris could like. And we have this like interest graph and we'll suggest the right thing to send. Additionally, you might be like, Hey, I don't want to do direct mail because I don't have people's mailing addresses. Well, we've solved that too by saying, hey, we've got a database and a smart delivery feature that will help you suggest to saying, hey, Chris works from the office and here's the office address, or hey, Chris actually prefers to confirm his address and he'll confirm his address for you and then you can mail it there. So we figured out what are all the pain points and solved for it, making direct mail and lumpy mail gifting as easy as sending an email. The other misconception I hear too, which is listeners like, I don't have money to send a bottle of wine. Well, the way that I look at it and the way that our most savvy customers look at it is what's dollar in, dollar out kind of math. If $1 in, you know, on an ad generates $2 in pipeline, but $1 in direct mail generates $12, well, like, where should you put more of your money? Um, and email is one where it's like $1 in generates like $1.10, and this is like the true all-in cost of like the human labor involved in it too. So doing some of that math makes you quickly realize that this is a very high-performing channel. Um, the other way I look at it too is grabbing attention is hard, as you alluded to, and if you could spend $50 on a mailer today that grabbed your prospect's attention and you booked a meeting you know, 2 months sooner than just like a 2-month email-only campaign, well, what's 2 months in revenue worth to you?

Yeah.

And so there's this like opportunity cost of not getting revenue sooner. And again, I'm not an anti-email person. I still love email, but I'm a multichannel, multi-strategy to grab people's attention. You know, it might be an email, it might be a phone call, it might be a direct mailer, it might be a social post. All those different things can then lead to somebody willing to listen to your pitch.

So you hit on so many things that are important there. And one of them is that, you know, a lot of the reason why, you know, the reason why everyone doesn't do it is they sort of fail to take the time to strategically think through who are the 10 clients that if we got, would really change the landscape for us. Instead, they treat everyone, you know, we just need more volume.

So true.

Just send out to 1,000, you know, and who knows the difference between them? And we don't have— we're not going to take the time to figure it out. And so, we're just sending out to everyone. Whereas if they strategically thought through their approach to the marketplace, those 10, they could afford to do something different with. Uh, and they could really understand the value that it has. And then also the strategic storytelling, as you've got, as you mentioned before, of what's the thing that I could send them, uh, that would resonate with them but also be relevant to me. And again, it comes back to they just don't have the strategy, uh, that underpins it, which is why so much marketing, you know, kind of falls flat.

Yeah.

Um, and, and the other thing that I find is You know, although it is more expensive than sending, you know, clicking yes on send another email, I find that, you know, creativity comes from those constraints.

Yeah.

It comes from saying, well, I can only afford to do this much in a direct mail. So now I got to be strategic about who I send it to and then creative about what I send and how I send it in such a way that that's what really allows things to break through.

And, and you hit on a great point too, where even if you are selling a solution to SMBs where you don't have the ability to even spend $50, we've seen some super creative, like, sub-$10 mailers where it's like someone sent some, uh, some prop money that was burned, uh, so it looked like burned money in an envelope. It says like, is your current solution burning money? Check out XYZ.

Yeah.

Um, somebody sent some fake aspirin pills in a little like Rx jar saying like, is your current solution giving you a headache? Talk about XYZ. There was even one that was pretty creative. It was like a fake milk box that said, like you know, reward if found, looking for solution X. And and so those things are like you know low cost, not not expensive. But the creativity is then going to grab that prospect's attention and being like, wow, you know, I actually am going to spend you know five minutes reading this, and now I have this top of mind. Versus, you know, the alternative.

So, well, and not only that, but what I see with when we do campaigns like this is that, you know, that little bottle of aspirin doesn't immediately get tossed.

Exactly.

Yeah. You know, the email that you sent immediately gets deleted. Even the ad that you serve immediately gets scrolled past. Yeah. But the little bottle of aspirin sits and there's the old adage in B2B that You know, 95, maybe it's even 97 percent of your market is not in market at any given time.

Exactly.

And so you want to be top of mind when they are in market. Well, if your little bottle of aspirin or whatever your you know sort of memorable mailer was is still sitting on their desk the day that they start thinking, you know, I'm going to prioritize solving this particular problem, and I know those guys. Do that, you're going to be one of the calls that they make. Whereas instead, you would be just sort of at the mercy of would they find you through other sources, would be one of the people they would even consider.

Yeah, I was having a fun conversation with a customer recently, and they were talking about top-of-mind time. And it was just, they had this kind of mindset where it's like, you know, for an email, you might have, you mean, less than a second of top-of-mind time. Even if you read it, you still might read a quick email, scan it, and it's You know, a couple seconds. But the top of mind time for opening up a box and a gift is like that could be six minutes of opening it up, looking at it, you know, reading the card, seeing what the gift is, unboxing that even further. And then if you take into account if that sits on your desk or sits in your cabinet or in your in your on your you know shelf behind you, now you have like hours or weeks or months of top of mind time compared to like the seconds. that you could have had before. So I think it's an interesting mindset to think about, you know, how much top-of-mind time do you have with your prospects or customers?

Well, and, you know, then even if they don't keep it on their desk, even if they just spend that time opening it and looking at it and thinking about it, all of that additional top-of-mind time means that 3 months down the road when they become in market for you, are they more likely to remember the person that sent them that or the, the email that maybe they even read and You know, thought about that email and said, one day I might, you know, find a solution like this. I want to remember these guys. Now delete the email versus spending the time thinking about that sort of physical, physical product.

Exactly. Where I've even heard a story from a recent customer that just said they got something from us months and months ago, then went on ChatGPT to say, what's the best gifting providers? We came up number one and they remembered that we sent them a gift. So it was like, again, that like, you know, you gotta be top of mind, but you also could be many months ago that you did something that then connects the dots being like, okay, wow, I remember that from many months ago and I see them here again. I gotta pick them. Yeah.

So you, you touched on something earlier that I thought was really interesting. I'm just curious to, to learn more about, which is you've built sort of an AI tool that, you know, sort of helps come, come up with creative ideas for what to send folks. And, you know, the usage of AI within, you know, within marketing and within business, you know, writ large is, you know, obviously a big topic today.

How—

talk to us a little bit about how you came up with that as an application of AI, and maybe what are some other places that you're seeing either clients that you're working with that you're hearing about how they're using AI and marketing in unique ways, or Other sort of interesting and relevant use cases.

Yeah. So our AI strategy really evolved from a lot of time talking to our customers on where they had bottlenecks in their gifting and direct mail strategies or where technology could drive more outcome for them. And so we kind of narrowed in on a few areas. One was, okay, what should I send to somebody? And that can be solved by either somebody spending 15 minutes looking through you know, social media posts and this and that, or it can be solved by AI. And we launched a Smart Send feature that really figured out based on huge datasets, what should I send to Mark? It was— we then said, hey, what's the message that we should send along to Mark? And that could, again, could be a 5-minute type-up by a marketer or a sales rep, or AI can come up and draft V1 based on the problem solution, based on maybe a pun from the mailer or gift you're sending, based on the recipient and what we know about them. And so we launched Smart Message that then made writing the note associated with the mailer easier. We then said, hey, well, now you gotta figure out where to send to. You either have to have your data in your CRM, that could be messy.

Yeah.

You could go and, you know, spend minutes like finding that address data elsewhere, or you could come to us and use our Smart Delivery feature. And we're gonna help triangulate saying, is this person in the office? Are they at home? What address are they at? And then have a fallback to ask for their address if, we're not 100% confident. And so that became really a popular AI feature. Again, big data and decision engines there. We're also rolling out some new features around Smart Signal to say when to send to somebody, pulling in on first-party data in your CRM. Like maybe you're working a specific account, you've engaged with one of the contacts in the buying committee, but 2 others haven't. Maybe, and we can suggest, hey, smart signal, send this person something, or a third-party signal like a job change alert, a promotion, funding news, or other things that are available through third-party datasets that we can say when to send. And this allows for hyper-personalization of like the right person, the right gift, the right message, the right delivery channel, the right time, ultimately leading to more scalable campaigns and mailers, and then ultimately better outcomes and results for our customers. And so We think the end goal is kind of this always-on, you know, gifting agents and mailer agents, similar to how you run ads, where it's like you kind of set up the parameters and it runs, removing all of the bottlenecks. It would be a nightmare if you thought about, hey, I want to run ads on, you know, New York Times, but every day I'm going to go there and I'm going to pick the ad, and every day I'm going to wait for the audience and I'm going to tell them that, you know, it'd be amazing. You know, it's all kind of Automated for you, and so we see a really cool AI future of you know mailers that are working while you know you're sleeping.

Yeah, that's interesting. So we've done some things like with Clay. Yeah, where when you know someone changes jobs, you've identified this person is an important person for you, and they just got a promotion. So they're now likely to you know be in market for the thing that you sell. You can create all these automations that flow. From this external signal that comes in and feeds an engine like that. So it sounds like you're setting up similar things, but with, you know, actually the physical products going out.

Correct. Yeah. And we strongly believe in like an integrated ecosystem. So integrations into Clay, integrations into your CRM, your marketing automation platforms, your sales sequencing engagement tools, all those, so that whether you want to trigger an automation through your existing systems, that is the best-case scenario. We still allow you to send in bulk or through triggers through our own system. But like in the Clay example or sending through HubSpot or through another tool, it always makes it easier if it's a part of your workflow and we just sit in those workflows. Especially as these systems have more AI-enabled automations, we want to just be another way to to help you engage with prospects and cut through the noise.

So interesting. So Chris, you're obviously an expert in a lot of really interesting topics and we could talk all day, but I've got to be mindful of your time. But before I let you go, like kind of give us the pitch, you know, pitch us Sendoso. Like what types of companies do you work with? How do you help them? And, you know, sort of give us that call to action. What's the best way to get engaged?

Yeah, I mean, really, we work with a myriad of companies across industries like B2B technology, financial services, professional services, even into sports and gaming, into hospitality. The end goal, it's, you know, are you a sales marketing or CX professional that wants to build better relationships with prospects and customers or partners? It's almost everybody, which is the benefit of how our platform works. And ultimately, we want to help you scale that out so that you can be the hero and build that relationship that then Converts into revenue, and my theory is that people buy from people and relationships drive revenue. And so if we can help you build those relationships, that's what we're here for. And always happy to help either directly by you know looking at a demo of Sendoso on our website sendoso.com, connecting with me on LinkedIn. I even love having one-on-one conversations with people that just want to talk shop about you know AI marketing tech whatever it may be. So. Maybe you could drop in my LinkedIn into the show notes and happy to connect one-on-one with listeners too.

Absolutely. Well, that's a very generous offer from you, Chris, because you bring a lot of expertise that people— I'm sure our audience has benefited from today and I always enjoy. So Chris, thank you so much for taking the time to join us today.

Yeah, thanks for having me on, Mark. Great conversation.

All right. Talk to you soon.

See ya.

Thank you for joining this episode of the B2B Growth Blueprint podcast. We hope you've gained insights to grow your business. If you enjoyed this discussion, please rate, comment, like on your favorite platform, and share to others who will find it useful. Do you know a CEO, founder, or leader at an early-stage B2B services, tech, or SaaS company who would like to be a guest and share their story? Send us a note. Let's schedule a conversation.