Kris Rudeegraap: The Comeback of Direct Mail in the AI Era

Welcome to Go to Market, a podcast for RevOps, sales, and marketing leaders to dive deep into industry insights and best practices. Go to Market is sponsored by Fulcast and Silicon Slopes. I'm so excited to welcome Chris Rutegrop, co-CEO of Sendoso. Chris, how are you doing?

I'm doing great, Amy. Thanks for having me on the show today.

Thank you so much for coming on the show. I've been wanting to have you on the show for a long time. I've known one of your colleagues, Tanner, for a long time. I've used Sendoso. I've loved Sendoso. It's, it's just such a great solution for making the, the gifting and ABM part of marketing go so smoothly. So well done on your business. It's not easy. I know. Tell me a little bit, how did you get started? How did you get going into this type of business and at Sendoso in particular?

Yeah, so, you know, I started Sendoso a little over 9 years ago. Prior to that, it's been around a decade in sales and that decade, you know, in the mid-20-teens, like 2014, for example, in sales, like I was early to use mail merge, and I was like, wow, this is best. I could book meetings so easily and, you know, get 90% response rates from emails. But that like quickly saturated and a lot of email sequencing tools popped up on the scene. I remember the original ones like the YesWears and ToutApps, then quickly Outreach and Salesloft and all those came about. And so I had once built like a competitive advantage around being the best mail merger. To now seeing that it's like the easiest thing ever to do. And so I said, hey, what else could I do that could be my competitive advantage in sales? And so I started manually, you know, sending out gifts. I'd hear a dog bark on a call and send a dog toy after. I'd go steal swag from our marketing closet and like pack it up or write handwritten notes after demos. And all of it worked so well. It was just very manual, very time-consuming, had to expense report, had to click tracking links, had to use you know, Excel spreadsheets, but it works. So I'm like, I got to do more of it. And then I was top rep, so my VPs were always like, yeah, keep expense reporting, keep doing it. So that was when I had that kind of moment that why isn't there a platform to operationalize, organize, and outsource a lot of the heavy lifting? And so with that, I took on the journey of saying, hey, I'm going to start this. And fun journey to say the least. But there's lots of learnings across the way because of the the nature of, you know, global fulfillment centers and, you know, supply chains, and then all of the software and data layer too.

Absolutely. So I, I remember when you first started, Chris, and I thought, wow, what an innovative idea. Like, this is so cool. And I thought, you know, how well will this be received? And just in the last 9 years, as we've seen everything develop, said doso has never been more important, right? Because there's so much noise in the ecosystem. Everybody's tried to go digital so fast and like bringing back to what's really about relationships and making people feel special is really what it's all about.

100%. Yeah, I think it's ironic that a decade ago I thought that digital was being saturated and look where we are today. I will caveat saying like I do believe in the power of digital, but I believe in you can't have a digital-only strategy. And I think there's a fair amount of sales and marketing teams that grew up and we're able to, you know, run only email and ads and be effective. But now that's less effective. So I think you need email, you need ads, you need content, you need direct mail offline, you need, you know, field events, you need everything in order to grab the attention of your buyers or customers and then furthermore, to create that relationship and that rapport.

Absolutely right. So as everything has kind of been moving into the new AI sphere, what are a couple of your hot takes that you might have about go-to-market?

Yeah, so maybe one hot take is, you know, this evolution of this go-to-market engineer. And I think it actually is the most critical role for go-to-market teams right now. And I kind of see it slightly different than some other teams might, which might be kind of a hot take. So I think go-to-market engineering became a role that was kind of an evolution of RevOps a teeny bit. But it also became a role popularized, I think, by Clay for the most part. But when I see it now and what I see the biggest area for go-to-market engineers, really this like go-to-market AI engineer. So it's not someone who's just running like Clay outbound. It's not someone who's like granting new users access to Salesforce or not someone who's creating forecast reports for the CRM or who's doing, you know, MOPs campaigns in Marketo. I think it's truly someone who's obsessed over AI agents, agentic workflows, someone who wants to build out these AI frameworks, someone who's savvy with APIs, MCPs, data warehouses, you know, some of these advanced tools like Claude, Code, N8N, someone who almost wants to be like an AI architect and that can, you know, translate these human roles and tasks into specs that, you know, agents can then take advantage of. So I think the evolution of that role and the importance of it is, is often overlooked, but could be the most critical role over the next few years to, you know, totally pivot go-to-market teams from yesteryear into the future.

I really love that. And that is exactly what we're trying to do at Fulcast. So thank you for, thank you for emphasizing the importance of it. Oh, 100%. So let's say that somebody wants to really lean in and provide an ROI for their boss on the importance of gifting and the importance of ABM. Do you have any like recent either anecdotes or stats that could help us understand like why is it such a hot market right now?

Yeah, so I'll take a couple different approaches to this. One, I'll take the approach of we have like 50+ case studies, data stories on our website. If you wanna get in the specifics of like, you know, hey, this company Gong or this company Capital One or this company Cisco, how they spend money and what they did and where it went, you know, refer to those resources to get in depth. But I'll say the way that I look at ROI is a couple different things. One is, you know, savvy marketing and sales teams should look into, you know, dollar in, dollar out. And how do they look at, you know, $1 spent on Sendesto can generate, you know, X number of dollars out and compare that against other channels that you may be testing or using. And oftentimes that can showcase that gifting and direct mail is actually a better returning channel than like ads, for example. And so you can shift budgets where— so that's one ROI way. And I think, you know, another way that some companies are looking at ROI is just the cost of goods sold and the cost of execution and taking into account that, hey, it's expensive to do this yourself or it's expensive to use high quality or high caliber labor like a demand gen leader to pack boxes or upload spreadsheets. Whereas, you know, an outsourced provider like Sendoso can automate this all for you. And also with our hundreds of millions of economy scale can give you better pricing. So I think there's a, an ROI story about like the cost of goods sold to execute on these campaigns and like the underlying labor and COGS. Look, the last is I think the cost of just not doing more of it. I think that should be an analysis that most teams look at all different channels like, hey, what if you could do 10 times more direct mail? What if you could do 10 times more content? And how do you look at what you, what you're leaving on the table as an ROI? Strategy.

Yeah, absolutely. I know for myself that ABM is really important to me. And in fact, 87% of B2B marketers report that ABM delivers a higher ROI than any other marketing activity. So if anyone is not using you to optimize their ROI for ABM, we all absolutely should be. So that, I think that one's really interesting and it not only helps with ROI and marketing campaigns, but ABM can give you a bigger average deal size with some people seeing an increase as high as 171% in the deal size. So, you know, the proof points are already there, right? And now it's just a matter of saying like, everybody go get Sendoso to help.

Yeah, well, and I feel for you too. I'm seeing a lot more marketers too care about post-sales ABM too and thinking about the entire journey and how do you still market to that customer to, to drive the expansion dollars too, which is critical to drive high NRR. And so I think ABM can be adopted for organizations that are looking for more land and expand opportunities too.

Absolutely right. Yep. So, well, clearly, obviously, Chris, you've struck gold here and you are at the absolute top of your game. So what do you do to stay there?

Gosh, lots of things. I'd say from a news and like what's hot, I use an app called Feedly and, and I basically track 200+ blog or media outlets and I'm constantly scrolling through. So instead of maybe doomscrolling on Instagram, I'm doomscrolling through news articles that are, you know, relevant to me in the industry, in the category. Love listening to podcasts while I drive. I also have a unique network of about 100+ advisors that I go to from time to time. When I have challenges or when I want to think about a new product launch or just some new product marketing concepts. So that advisory group really helps me stay top of my game. Always love going to tech meetups. I think meeting people in person at different tech meetups is something that everyone should be doing. And then lately what I've been doing too is I've been interviewing my team on what they're doing just to get more connected to, you know, how our engineering team's using Cloud Code or you know, what tools are our SDR team and how, what's booking them the most meetings. And so I think, you know, as companies grow and get bigger, it's easy to have things in your mind that you remember from years ago. But for me, it's like, how do I re-interview my team to figure out what are the ways that are working for them that I can then take that knowledge and run with it?

Absolutely right. Well, that's wonderful. And we should all do that. And I'm going to have to look at Feedly. That's really exciting. Well, thank you so much, Chris, for coming on the show. It is such a pleasure to be able to have someone, a real industry insider, leading the charge in something that's giving marketing teams the most ROI. Thank you. I really appreciate your time.

Yeah, thanks for having me on, Amy.

This was a fun chat.