Direct Mail for Sales Outreach: Kris Rudeegraap of Sendoso Speaks with Mailshake’s Sujan Patel

Sujan Patel is the founder of Mailshake, a sales engagement software used by 38,000 sales and marketing professionals. He has over 15 years of marketing experience and has led the digital marketing strategy for companies like Salesforce, Mint, Intuit and many other Fortune 500 caliber companies.
  • August 4, 2021

Sendoso is one of the top names in direct mail. But how exactly do you use direct mail and personalized gifting as part of your sales outreach? Sendoso’s Co-Founder & CEO, Kris Rudeegraap (also a former AE) shares his thoughts on how to incorporate direct mail into your sales strategy.

Video Transcript

Sujan Patel (00:01):

I’m Sujan Patel from Mailshake. I’ve got Kris Rudeegraap, from Sendoso. Kris, welcome aboard. Thank you for joining.

Kris Rudeegraap (00:06):

Yeah. Thanks for having me here today.

Sujan Patel (00:09):

Well, I’m pumped to talk to you about Sendoso. My team has advocated for direct mail for such a long time, but for those people who don’t know who you are, and Sendoso, would you mind just giving a quick intro?

Kris Rudeegraap (00:21):

Yeah, for sure. So I’m Kris Rudeegraap, I’m the CEO and co-founder of Sendoso. I started Sendoso about five years ago, prior to that spent about 10 years in sales, myself. And Sendoso, we’re a sending platform, which makes it easy for sales teams, marketing teams, to send out direct mail and personalized gifts.

Sujan Patel (00:39):

Love it, love it. I know my agency has used direct mail as a part of an account-based marketing campaign to send books, swag, cupcakes, personalized cupcakes. I don’t know where that idea came from, we tried it. But anyways, we’ve had some good success in direct mail in general. People these days, turns out they’re not used to getting mail that they may want to receive. All right. Well, so how’d you go from being an AE to starting a company?

Kris Rudeegraap (01:12):

Yeah. So, I really saw this opportunity when I was an AE, and kind of had that pain of trying to pack boxes myself, write handwritten notes, go find things to send out from our marketing closet. And so it really dawned on me, I had this epiphany. I was like, “Why isn’t there a button that I can just click and send stuff out?” And so that was really the starting point for starting Sendoso.

Sujan Patel (01:36):

Nice. I love it. Yeah. So kind of scratching your own itch, slash-

Kris Rudeegraap (01:39):

Scratching your own itch. Exactly.

Sujan Patel (01:41):

Like, “Jeez, how can it not be this painful?” Right? I hear you. All right. So in general, how do you… I guess, how does direct mail fit into sales engagement, outbound sales, in your mind?

Kris Rudeegraap (01:56):

Yeah. So I think you can look at it a couple different ways. One, you can look at it from more of a demand gen, air cover perspective, and how are you driving inbound leads from a marketing perspective? So, running these campaigns that are kind of hitting more of the masses. I then think, the big breakthrough that Sendoso had, and why I wanted to start the company, was taking the whole power of direct mail and gifting away from just marketing, and giving it in the hands of salespeople so they could real-time send stuff out. And so I think that’s where SDRs and AEs can use this in their outbound mix, as a way to break into an account and get a meeting, or as a way of accelerating and closing deals faster.

Sujan Patel (02:36):

Love it, love it. And I guess, where do you see, I guess… Sales reps already doing sales, where would you put this? Where do you put direct mail as a part of the cadence? Is that at the very beginning, or is it at hard closing, or where do you think it fits best?

Kris Rudeegraap (02:57):

Yeah. So, I think you have to take a step back and really think about the entire sales journey, and how you would want to integrate in direct mail and gifting. And I think that one thing to think about is really creativity as a differentiator, because with direct mail and gifting, you really get the ability to be creative almost three different times. With the gift itself, with the handwritten note or message that goes along with it, and even the packaging. So it really is, in my eyes, a differentiator for reps. And so to that point, it’s really thinking about, okay, this could go…

Kris Rudeegraap (03:29):

This could be the first thing you do to try to break into the account, and then you have a follow-up that references their direct mail or gift that just landed on their desk. Or it could be lower in the sequences or steps, and could come in in the middle, or the end. There is an associated cost with direct mail and gifting. So I think some companies don’t do it as many times as you’d do email or phone, given the costs. But then, that is also to the advantage of the people that are doing it, because most recipients are not inundated with a million different gifts because of the cost associated with it. So, long story short, I think it can go in the top, like the first few steps, the middle, or the end, but it’s more important to think about the entire journey, and how you’re mixing in email and phone calls with the gifts, so that it feels like a better experience.

Sujan Patel (04:22):

Love it. That makes sense. So it’s really not the location in the actual funnel where it goes in the sales model, it’s more so how things kind of work together. Where it’s, if you have a… You’re sending a cupcake and you’re like, no reference to anything at all, you’re just kind of going about your sales campaign, that doesn’t work. Right?

Kris Rudeegraap (04:42):

Exactly. That’s exactly how you got to think about it is, what’s the thing that’s going to come next in the sequence? So…

Sujan Patel (04:49):

I love it. That makes sense. It’s like, to me, direct mail is this… And I think to a lot of viewers, it’s this, “Oh, my God. Got to shift something? That’s weird. That’s different.”

Kris Rudeegraap (05:02):


Sujan Patel (05:02):

But it’s no different than any other touch point, LinkedIn, Twitter, phone call. Obviously, you spend time on crafting the message, and figuring out where it fit, maybe even testing it, you do the same thing for direct mail. That’s great to do.

Kris Rudeegraap (05:19):

Exactly. Yeah. And I think that that’s where… I think a lot of salespeople want to do it more, but the effort to pack a box, or to go find something, was harder to do. And so that was one of the inspirations for starting the company, is that we took away that extra effort of having to pack boxes, or come up with sourcing the item, storing the item. And so, you spend that extra time being creative to think what it is you want to send, the messaging associated with it, the steps that you want to integrate in. And so then, it becomes just as easy as a LinkedIn message or an email.

Sujan Patel (05:52):

Love it, love it. So, it’s crazy that gifting has become more and more popular. What do you… So I guess, from your platform, or from folks you know, or even your own company, what’s the most unique, or any memorable experiences when you see sales reps using gifting?

Kris Rudeegraap (06:10):

Yeah. So I’d break it down in a couple different categories, I think. I’d say one is, we have a really cool Amazon integration where you can go into Amazon, and there’s a new Sendoso Buy button. So an STR, or an AE can click that, it then uses their pre-allowed budget so they don’t have to put in a credit card or anything. They select that item they want to send, and then it sends to our warehouses first. We un-box it, re-box it, put in a handwritten note, and ship it out. And so the benefit of that is, you could be really creative with Alma Mater sports teams, maybe they tweeted about something, maybe they saw something in a Zoom background. And so you can really have an endless assortment from Amazon, but it looks like you’ve actually packed the box and wrote in a handwritten note. So the recipient unboxing experience is really heightened. So I’d say that’s one way to get really creative.

Kris Rudeegraap (06:57):

We do have a marketplace of thousands of gifts with a lot of unique items. So you could always do your searching through that. We also find that marketing at times, will say, “Hey, sales team, here’s a short list of 5 to 10 things that you can send, that have some kind of relation to the brand.” For example, I remember Gong was sending these little mini-gongs out. And so it was creative with the whole aspect of what that company did, and played on their brand well, which was unique to that. I’ve seen a lot of thought leadership books being sent out. Recently I saw a bottle of wine that had a combo code lock on it, with a pun in a handwritten note, where you couldn’t get into the wine unless you took a meeting and then you got the combo code lock. So I think you can really get creative with it.

Kris Rudeegraap (07:48):

And again, I think it goes back to… Back when I was an AE, five, eight years ago, you really had to spend a lot of your time on the lead enrichment, on the remembering the email, and create your own sequences in your mind. But now there’s awesome tools that take care of the lead enrichment, that take care of the email sequences, so you can spend more time with some of the creativity and the content writing. And so I think that’s where you can really think about, how do you spend time on gifting? I mean, I think five years ago, putting a time block to be creative on your calendar to come up with ideas-

Sujan Patel (08:23):


Kris Rudeegraap (08:24):

… would have been a waste of time, or you wouldn’t have had enough time.

Sujan Patel (08:28):


Kris Rudeegraap (08:28):

Now I think that reps are using it as a differentiated skillset.

Sujan Patel (08:33):

I love it. Yeah. I mean, I just want to harp on this for a second. So, with all the tools to help automate stuff, you’ve saved time.

Kris Rudeegraap (08:41):


Sujan Patel (08:42):

That time doesn’t go back in your pocket to go twiddle your thumbs, spend the time on the creativity, on improving the campaigns, what you said, all that stuff. That’s going to… Time on the creativity and the strategy, on the tactics, on the testing.

Kris Rudeegraap (08:56):


Sujan Patel (08:57):

I love that. I think it’s so easily forgotten that like, “Oh, yeah. I can just send it automation. I’m going to go do this. And I’m going to go find more leads.” It’s like, wait, hold on. The leads you’ve got, just come up with one test, come up with one better idea, try something new. And that is, I would say, because of how much better life is with all the automation, it’s like this forgotten art.

Kris Rudeegraap (09:20):


Sujan Patel (09:20):

Although it’s the most obvious thing, between you and… The sales rep and the potential customer.

Kris Rudeegraap (09:28):

Totally. And I think too, when you think about, you’re going into a competitive deal and you’ve got another company that is… How else do you break through it? You might have similar-ish products, but if you create a better buying experience, and you’re being more creative and thoughtful, they’re buying from you, the person, you, the sales rep. Not necessarily you, the product, if in their eyes, it’s pretty similar apples to apples, so.

Sujan Patel (09:51):

Love it. That makes complete sense. Kris, thank you so much for joining. I’m going to go talk to my sales team and figure out what type of gifts, and they’ll give them a budget. I love that send on Amazon, send from Sendoso on Amazon. It’s like the magic, that unboxing, that experience. Even if you send something small, that experience, that emotional reaction, it’s unparalleled. You don’t get that anywhere else, right?

Kris Rudeegraap (10:21):


Sujan Patel (10:22):

Yeah. So, so cool. I’m going to go figure out some ways to go play with that. So thanks so much for joining, and in the links below, we’ll have links there where you can check out more about Kris, and Sendoso, and whatnot. So, thanks again.

Kris Rudeegraap (10:35):

Thank you. Appreciate it.

Start Using Direct Mail & Personalized Gifting with Sendoso

If you’re a sales rep wanting to incorporate direct mail and personalized gifting into your outreach cadences, Sendoso can help. Here’s how to start sending in minutes with Sendoso.

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