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In this episode, Jay interviews Kris Rudeegraap, Co-Founder and CEO of Sendoso, about using gifting and direct mail to stand out in sales and marketing. They discuss the power of sending physical gifts versus just relying on digital outreach, how Sendoso automates and scales gifting for companies of all sizes, creative ways to select meaningful gifts, and how gifting ultimately boosts sales by building stronger connections.

Main Discussion Points:

– Kris founded Sendoso 7 years ago after realizing physical gifts help sales reps stand out from constant email outreach. Sendoso handles sourcing, packing, shipping, and tracking to automate gifting at scale.

– Tangible gifts in the mail grab more attention than digital messages in our saturated world. The creativity and surprise of an unexpected gift can really engage prospects.

– Sendoso works for companies both big and small. Low cost gifts or offers can work if timed right and personalized based on the recipient’s interests.

– The key is using gifts to demonstrate understanding your customers and prospects as humans, not just targets. Sendoso can even automatically pull in interests from social media to suggest relevant gifts.

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Transcript
Jay Schwedelson:

Welcome to do this, not that, the podcast for marketers. You'll walk away from each episode with actionable tips you can test immediately.

You'll hear from the best minds in marketing who will share tactics, quick wins and pitfalls to avoid. Also dig into life, pop culture, and the chaos that is our everyday.

Jay Schwedelson:

I'm Jay Schwedelson.

Jay Schwedelson:

Let's do this, not that.

Jay Schwedelson:

This is going to be a blast. I'm super excited about this. Do this, not that. We have Chris Rudrap here. He is the co founder and CEO of Sendoso.

Before you tell you about Sandoso, Chris, I want to welcome you to the show.

Kris Rudeegraap:

Thank you, Jay. Excited to be here. Excited to chat today.

Jay Schwedelson:

Awesome. All right, so let me tell you my version of who Sendoso is and I'll let Chris tell the story.

So in my brain, Sandoso is the leader in direct marketing automation. But the real secret sauce of Sendoso is that they are the gifting platform. Gifting platform.

y're a beast. They started in:

They have hundreds of the most amazing companies around the planet using their platform all over the world and their incredible growth. And Chris is the engine behind a lot of that. So, Chris, I probably get that all wrong. So who are you? Who is Sendoso?

And then we'll get into the fun stuff.

Kris Rudeegraap:

Yeah, you nailed it. So I'm the founder and CEO of Sandozo. Started seven years ago.

Prior to that, spent about a decade in software sales myself and realized that there was an opportunity to engage with prospects and customers by way of sending out gifts, sending out direct mail, sending out swag, and doing so was super manual and time consuming. And I said, hey, why don't I automate this? And that's where we're born.

And so Sendoso is a one part software with integrations into your tech stack automations reporting, one part marketplace of literally anything you could ever want to gift or send. And then we have all the fulfillment and data behind the scenes.

Jay Schwedelson:

So let me go back with you a little bit.

So you were an ae, and I think a lot of people listening, maybe they're account executives themselves or they have a team of salespeople or whatnot, but you're an AE back in the day and you were sitting there like, I want to do something. I don't just want to keep sending emails to whoever I want to do more than that. And that's where this was born.

Like, what was the actual frustration that you were trying to overcome?

Kris Rudeegraap:

Yeah, so I was early in using some of these email automation tools like the Yesware, then ToutApp, then Salesloft and outreach, where it became so easy to send out a gazillion emails. And so I said, well, if everyone's sending out a gazillion emails, then what can I do to be different and break it through that noise?

And so I would write handwritten note and send it out. I'd go steal swag from our swag closet.

Marketing would yell at me or I'd hear a dog bark on a call and send over a dog toy through Amazon and I'd have to expense report Amazon to my VP of sales. And I was the top rep though. So they're like, whatever you do, just keep doing it.

But you know, being in the office at 9 o' clock at night packing boxes is not ideal.

And so I dreamed up of a solution that allowed me to really automate that and outsource the sourcing, the packing of boxes, the shipping, the tracking.

You know, I would remember I'd had spreadsheets full of tracking links for FedEx and every morning I'd go in and click to see which ones were delivered to then follow up with. I mean, I was running a little mini post office.

Jay Schwedelson:

Well, which I'm sure the USPS was thankful because they could use all the help they can get.

So what we're really talking about is gifting in a really sophisticated way and really bigger picture is in this world that we're in now, this idea of receiving something tangible in the mail allows you to stand out more. I mean, is that what you have found?

I mean, do you find that when someone receives something physical, it's a game changer in terms of their engagement?

Kris Rudeegraap:

It does, yeah.

And I think that in today's world, where you're bogged down with a gazillion different noises from your phone and your computer and everything else, salespeople, marketers, CX leaders need to be able to stand out and be unique. And I think when you have so many commoditized solutions out there, the buying experience can be a big differentiator.

And so if you are wowing a prospect with a gift through that process and your competitor's not, then the buyer has more momentum and reasons to go with you.

Jay Schwedelson:

So when you have a gifting platform or you want to start incorporating gifting into what you're doing. Number one, is this for all size marketers or is this only for, you know, enterprise people that have sophisticated account based marketing programs?

I mean can you be a solopreneur or a small company and use gifting as a way to drive business? Who is this for?

Kris Rudeegraap:

Thousand percent? I think we have everyone across the gambit where we have a five person company all the way up to, to some of the largest companies in the world.

And it also doesn't matter if you're selling a hundred thousand dollar like enterprise software or you're selling $50 products. There's a price point or a gift or a mailer that makes sense. And it's not always the most expensive thing wins.

A lot of times it's the creativity or just sending something out that can make the impact.

Jay Schwedelson:

And is it that people go on, they go I just had a really great phone call with so and so I want to get them out something or is it that it's more of an automated thing where oh, they just hit a pricing page on our website, they're automatically going to get this, this random thing. I mean is it both or is it one or the other?

Kris Rudeegraap:

It's both. We're seeing a surge right now in the ladder of automations.

So we're seeing a ton of marketers setting these automations up based on web traffic, based on lead scores. Someone downloads a white paper and you trigger something. People are putting GIFs or swag in ads to drive better ad conversion.

Someone integrates with their marketo or HubSpot or eloqua and triggers off of people attending webinars. It also can be integrated into your outreach or sales loft or SDR platforms.

So really the automations are probably the biggest thing that we're seeing right now and companies just setting it and forgetting it. But we still offer the click and send through a button and CRM or click and send through our platform.

Jay Schwedelson:

Meanwhile, I need to incorporate this into our webinar for the people that actually watch the entire webinar that they automatically get something because those, those people deserve an award.

Because as you know right now getting people to actually getting them to register is one thing, getting them to attend another and getting them to actually stay for the whole thing they deserve gift in this saturated order.

Kris Rudeegraap:

Throw a QR code up at the end of a webinar and then that drives to a landing page where you can claim your gift and it's completely automated, you don't have to do anything. And it's a great Way to drive attendance.

Jay Schwedelson:

So when I first heard about gifting platforms and Sendoso, I was like, who cares? I don't need another mouse pad. I don't need another pen. You know, that was my idea of gifting.

And then as I got deeper into, I'm like, what the hell are these people sending out? Like, give people the spectrum of the type of stuff that you guys are involved with sending.

Kris Rudeegraap:

Yeah. So if you know your prospects, a New York Yankees fan and just had a baby, you could send a New York Yankees onesie.

Or you could send out an engraved bottle of Casamigos with the person's name on it. Or a funny send that we saw a couple years ago. Someone came to a conference and was on crutches and broke their ribs in a snowmobile accident.

You could send them a rack of ribs in the mail from a barbecue joint. Like, it's more about the creativity and the fun.

Now you can send pens, you can send T shirts, you can send water bottles, you can send really anything you want.

But I think at the end of the day, we give you the ability to be creative and, and not have to deal with the back end, packing boxes, sourcing, finding what to send, shipping, all of that. It's just click and go.

Jay Schwedelson:

How do you source? I don't even understand. Like, do you have a meeting internally? Like, okay, guys, we need to expand our product portfolio of what people can gift.

We want to talk about gifting ribs.

Kris Rudeegraap:

We have a whole team dedicated to just expanding our marketplace. Whether it's items that are drop shipped from some of our partners around the world.

You can, you know, you could send someone macaroons from a bakery in France to a prospect that's in France. So we really try to find local, regional, or unique things that you can send out.

And then we also have a really unique custom integration with Amazon where you can use your Sendoso account balance. Go in there and there's a new buy button.

That's a Sendoso buy button across Amazon and it customizes it, syncs it back to HubSpot or Salesforce so you can track the results. And it sends it from Amazon's warehouse to our warehouse or the nearest warehouse.

We unbox it, put in a handwritten note, repack it up, maybe throw your logo on the box or on the handwritten note and then ship it out. And so the recipient's like, wow, this person actually sent me something super unique.

And really, you just searched for the hundreds of millions of products on Amazon.

Jay Schwedelson:

Dude, that is bananas. I love that first of all the best job in the country, I think is being on your sourcing team. That sounds like the best time ever.

Kris Rudeegraap:

They just rack up the credit card points because they're buying a bazillion things. They're getting wind and dine with all the vendors sending them samples. I'm like, hey, I'm the CEO. Send me samples.

I want to try that whiskey brand or I want to try really nice new AirPods.

Jay Schwedelson:

That's amazing. I mean, that is, that is a very, very cool job. So let me ask this. So what about different target audiences?

Like, it's one thing if you're sending somebody who's like, I don't know, the director of marketing somewhere, okay, you can send them anything you want. But if somebody's like, you know, C level executive, you can't move the dial with a 20 Starbucks card or something like that.

Like, like, is gifting different really depending on the level of seniority that you're marketing to?

Kris Rudeegraap:

I think you want to be creative and you want to segment, and it's based on the segment of who's buying. Like, if you, you have a product that sells to SMB and enterprise, then you could afford to spend more on enterprise.

And if you're selling something that you could get the executive CMO engaged versus the marketing manager, then you'd want to segment that. And so I think there is things that move the needle.

Like if you're going to send a CMO with a, with a generic note that might not hit, but if they just posted on Twitter that they're having a terrible day or they love this new pumpkin spice latte and you mentioned pumpkin spice latte and a $5 card, maybe that moves the needle. So I think it's not necessarily the value of the gift, but it's the message and the timing that goes along with it and the creativity.

But you know, Scotty Cameron Putter to a golfing CMO might bode better than just sending them a little, you know, nice pen or something.

Jay Schwedelson:

You may not be doing it on purpose, but in some ways you are upping the salesperson's ability to stay focused and pay attention to their prospects or clients. They really have to learn who they are, what their interests are, what they care about, and, and not just be pushing their product.

And I think that using a gifting platform kind of forces your hand to be a better salesperson in terms of getting to know your buyer, which is, it's just cool.

Kris Rudeegraap:

We have a service where we'll actually go out and scour the web automatically and add tags of their interests, their alma maters, and then provide suggested gift options based on the person's interests and history. And so you can also pull those in. Like you're on a gong call and someone mentions they play tennis, you can add that tag in.

And so it creates this personal graph of what this prospect soon customer is interested in.

So if you're an SCR having a call and then an ae and then, you know, six months later, the csm, you can share along that data set so that the CSM can be like, oh, I know Chris likes Casamingos tequila. He just, you know, got married. Maybe I'll send him over a bottle.

Jay Schwedelson:

And that is cool. That is actually. That is.

Kris Rudeegraap:

And everything I'm saying is true. So if you're listening, send me Casamigos. I like golf. Scotty Cameron putters.

Jay Schwedelson:

Very, very subtle. I like how it's so subtle. You know, it's like, this is what I want. Well, that brings us to the second segment of this thing.

So we have a segment on this podcast called since you didn't ask, which has nothing to do with anything, really. And so I have a question for you. Holidays are coming up. Yep.

Because of who you are and what you do, I would imagine everybody in your universe, your personal universe, thinks that you are the greatest gift giver of all time. I mean, you need to be. I mean, you can't. If I got a holiday gift from you, I would expect it to be the greatest thing I've ever received.

Like a miniature donkey that had my name on its forehead or something. Like, is this true? Are you an exceptional gift giver?

Kris Rudeegraap:

I think I am, yes. I love giving gifts. I love surprising people. I still write handwritten notes to people. So all those things are very true.

Jay Schwedelson:

Do you judge? Like, I almost would never want to give you a gift.

Like, so when you get gifts, are you like, well, this thing sucks and you know exactly probably what everything costs. Are you, like, judging people that give you gifts?

Kris Rudeegraap:

Yeah, but I'm also on the. On the positive side, I'm wowed. And I'm like, you know, every box I get, I can't wait to open it.

I'm like, oh, this is something that we should have in our marketplace if we don't already. Or, oh, this is incredibly unique. Or, oh, this is like, right, get rid of it.

Jay Schwedelson:

You want nothing to do with it. That's amazing. Every time you get something, you're like, this needs to be in our marketplace, like, immediately.

Kris Rudeegraap:

But I'm still like, the guy that goes to conferences and leaves with a backpack full of swag. Like a thousand pairs of socks. I think I have like two cupboards full of yetis.

It's almost like an art form for me to collect all these different swag items. I feel compelled and excited to see the new ones.

Jay Schwedelson:

I don't know if it's an art form or you potentially are a hoarder. I mean, we may have to have an intervention for you.

Kris Rudeegraap:

It's research and development. Okay.

Jay Schwedelson:

I mean, it is not a coincidence your favorite show is Hoarders. I mean, you know, this is what it is. You know, I get it. You know, it's all good. So. All right. So where. Where should the world find you?

I know you're over LinkedIn. Where should the world find Sendoso. I want everyone to be gifting each other. How do we do that?

Kris Rudeegraap:

Yeah, so you can find us@sendoso.com. we also have a free plan if you want to come in and try us out. So. So.com youm can email me directly if you want. Want to Talk Shop, Chris?

Krisindoso.com Add me on LinkedIn. Follow me. You know, gift me all those things.

Jay Schwedelson:

Buy tequila. What I've got out of this is Chris wants Casamigos Tequila. Probably reposado. Not like if you make Blanco. Blanco's weird. And I think I nailed that.

So, yeah. So Sendoso is awesome. Chris, thank you for being here and do this, not that. And happy holidays.

Kris Rudeegraap:

Happy holidays to you. Thanks, Chef.

Jay Schwedelson:

You did it. You made it to the end. Nice. But the party's not over.

Jay Schwedelson:

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Jay Schwedelson:

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