(888) 815-0802The Power of Personalized Gifting in Sales, with Kris Rudeegraap [Episode 1138]
This week, Alastair is joined by Kris Rudeegraap, CEO at Sendoso, to discuss innovative sales strategies with a focus on gifting and personalization. He emphasizes the importance of authentic and creative outreach, using data-driven insights to tailor gifts and messages to specific personas. The conversation also delves into shifting trends in sales behavior, the rise of mid-funnel engagement, and the growing role of customer success teams in driving revenue from existing customers.
Podcast Transcript:
00:00:00:07 – 00:00:19:06
Speaker
Most salespeople sell like the kids game of telephone. If I say something to you, then you say to somebody else, and then by the time it gets back to me it’s a completely different message. Right. Yes.
00:00:19:07 – 00:00:43:19
Speaker
Welcome back, everybody, to this week’s Sales Strategy & Enablement podcast. I’m Alastair Woolcock, Chief Strategy and Revenue Officer at Revenue.io. and I’m thrilled to have with me today the CEO of Sendoso, Kris Rudeegraap. Kris, it is really great to have you. Sendoso has been on a tear for the last couple years coming out of the pandemic. All of those things again is that it’s a shifting quick market.
00:00:43:19 – 00:01:13:19
Speaker
So I’m very keen to dive in with you today on what’s changing in terms of some of the sales behavior, customer behavior, marketing behavior, some be fantastic. So welcome. Thank you. Excited to be here. Excited chat. Now, Kris, we’d love to start off with our news of the week. And one thing that I was just reading about recently was the ad Week part just published an article called B2B Marketers Find Corporate Gifting Wildly Successful.
00:01:13:21 – 00:01:46:23
Speaker
But then they had a dash and it says when infused with data, do you think they reported that actually having over 80% of prospects reported that he saw up in the package on the rise of them? But there is some data correlation here that now occurs. I think people tend to think of gifting. I’ll defer to you here as the expert and kind of this simplistic while we just we just dropshipping stuff, stuff like the SPI, but it’s not that and is sophistication in usage of data when how and sales cycles is is hugely germane to this space.
00:01:46:23 – 00:02:09:18
Speaker
But what are you saying? Is that is Adweek right. What’s your thoughts when you hear the headline. Yeah, I think they’re absolutely right. And I think personalization leveraging data is is the equal and synonymous to kind of the evolution of email to I think, you know, as a channel there was lots of spray and pray generic messaging that didn’t work as well as when you personalize it.
00:02:09:20 – 00:02:26:04
Speaker
And I think for a while there people thought, hey, I could just like send a bunch of emails. People are going to reply just like people thought, Hey, I could just send a bunch packages. People are going to open them and magically call me. But in reality, you know, with anything, you really have to focus on the personalization and typically a personalization that requires data.
00:02:26:06 – 00:02:53:18
Speaker
Yeah, absolutely it does. I feel like we’ve come a long way and I’m going to date myself here, but there is there’s like aggressive gifting campaigns like, you know, the likes of NetApp and big OEM and Cisco and HP, IBM, everybody used to do it with Partners and Designs. Oh yeah, marketing development, fabs to drop shift. It’s one of the one of the old ones that it used to be was you’d send a remote control car really nice one out to people but so you get that you get the remote when you meet.
00:02:53:20 – 00:03:28:18
Speaker
So always you do it around Kristmastime. Well, that’ll be a good gift for my kid. All right, I’ll take the meeting just to get the stupid remote from you. Yeah, and but we’ve come a long ways. Like, that’s just generic big push. When you think of personalization, how you using data decide personalization? Yeah. So I think it can either be personalization, the gift itself, like knowing the recipient’s interests, their location even based on maybe more of like their persona, you might gift to seeing something differently than you’d gift, maybe like a marketing manager.
00:03:28:19 – 00:03:51:05
Speaker
So I think one that you get based on persona too. I think there’s how you are kind of personalizing and using data for the handwritten note or the message that goes along with that gift, which I think is equally important. And then how do you tie that together all in a very sync kind of sequence or outbound effort.
00:03:51:05 – 00:04:12:02
Speaker
So the message before the gift, the gift, the message after the gift for that email, our phone call all needs to come together so that you’re not just sending gift hoping for reply, you’re sending a gift calling up and saying, Hey, you get that remote, you know, or you know, and even using some more fun language to make it more of a personal approach.
00:04:12:04 – 00:04:43:20
Speaker
If you don’t mind, I’d love to just double click a little on language. We’re hit because an issue I often encounter. I saw this at Gartner, and even today, in our space of sales technologies, you know, there’s a lot of sequencing, there’s a lot of when to reach people. And those which is which is hugely important. Yeah. But the touch point and personalization to me is so much more than simply you use my name or you dropped in something you scraped from LinkedIn about where, how do you how do you articulate it?
00:04:43:21 – 00:05:12:15
Speaker
How do you guide people on personalization? Kris Like what? What’s, what’s ideal? Yeah, so I think you can personalize the gift with the value prop. Maybe you send like a locked bottle of wine with the code and the message is around, Hey, do you want to unlock more revenue? You know, use XYZ solution. So there’s a bit of a play on words in a sense that makes the, you know, the recipient when they read it, feel like, hey, this person actually put an effort, this is creative, this is interesting.
00:05:12:17 – 00:05:34:18
Speaker
So I think it’s the creativity there. Yeah. And then I think it’s the signal when you send to it’s similarly like when you send an email. You got to think about what you said to get to, whether it’s is there a third party signal based on a funding announcement or some maybe they went to your website and downloaded a white paper and you want to send them maybe a Starbucks e-gift card to enjoy while they’re reading it?
00:05:34:20 – 00:05:58:07
Speaker
It just comes across more human. And, you know, really, how do you build rapport as if you’re trying to build a friendship with that prospect? Let’s start conversion next. Let’s set this market in particular. You know, I think for a lot of our listeners right there in their sales leaders, their neighbors, is all of these things. One of the front and center things is how do you drive Pipeline, Right?
00:05:58:09 – 00:06:20:09
Speaker
Yeah, certainly during the pandemic, there is there is a heavy rise of virtual anything essentially. Right. And getting people there. But what have you seen coming out of the pandemic? What are you seeing now in terms of, you know, is this still a mechanism that is front and center for people like it was over the last 24, 36 months?
00:06:20:11 – 00:06:39:01
Speaker
Are you seeing a shift in dynamic of people wanting more of their say, what are you seeing in your ones? So I’d say the kind of two or three biggest trends that I’m seeing now. One is prior to the last year and a half, there was more focus on just really to be top of the funnel. Yeah, try to drive people into the funnel.
00:06:39:03 – 00:07:02:10
Speaker
We’re seeing getting used more lower in the funnel to try to drive more conversion. At the end of the day, you’re trying to drive revenue. Do you put more the top of the funnel or do you convert more? That’s already in the funnel. And so we’re seeing people really trying to focus in on converting stage two, three or four, shortening sales cycles or bringing in more buyers into the buying committee by way of using gifting.
00:07:02:10 – 00:07:17:15
Speaker
So I think that’s a trend we’re seeing and I think that coincides with some of the larger narrative of the headwinds of the economy and maybe having lower budgets to spend. And so do you go and do a bunch of more pipeline or pipeline? You already have to try to close more of that. So I think that’s one trend we’re seeing.
00:07:17:17 – 00:07:44:09
Speaker
The other we’re seeing is for us the use case of the 16, whether that and mostly the account management team, they’re starting to pick up and get licenses themselves and using us as more of a land and expand play where previously we had a ton of demand. Gen SDR, you know, full cycle years, we’ve seen a influx of customer success and account management teams wanting to use this as a way to instill better retention or lean and expand.
00:07:44:09 – 00:08:05:17
Speaker
And I think that’s a trend to how do you drive more revenue from your existing customers and what tools can you use to do. So let’s expand on both of those so you don’t mind like the first one, what I think I heard you say there is you’re seeing a lot of almost mid funnel development, right? Stage two or three for progression and that that isn’t surprising to me.
00:08:05:17 – 00:08:29:20
Speaker
But what I really like is this concept of Multi-threading. Yeah. So how by opening or proactively engaging with somebody that is in going to be a part of the adjacent buying group, or maybe not my direct buyer, but a supporting cast member in the game just to drop a Gartner number on here. Buying groups sit on average around nine people on most deals.
00:08:29:21 – 00:08:51:21
Speaker
He is large 13 but it sits around nine. Yeah and what we always saw was and certainly the recent data on it is the groups have actually grown coming out of the pandemic. So when I think the pandemic actually buying, we’ve shrunk slightly, not a lot but the little they went down on average seven because there was just so much pressure to go, go, go, like just get change done, right?
00:08:51:21 – 00:09:23:09
Speaker
Yeah, but coming back out and in this economy, people are very risk adverse. So when there’s more risk, you have more oversight. More oversight expands the buying. So now using a mechanism to engage those additional resources or at least drive awareness is is is massive because most people in companies, most salespeople and go to market teams, they sell like the kids game of telephone.
00:09:23:11 – 00:09:40:14
Speaker
And Kris said you know and you think of the game of telephone I if I see something new that you say to somebody else and then somebody says, Dave, our producer on this line, by the time he gets back to me, is a completely different message, right? And sales reps tend to sell with I have my one or two champions on my account.
00:09:40:16 – 00:09:59:03
Speaker
I told them the message, they understand the value, they’re guiding the process. Yeah, but that poor person is the buyer. They got to go convince nine other people. Precisely. And by the time that game and telephone goes all the way through, it’s all wrong. It’s the values on something is broken there. And you think a stage two three development.
00:09:59:03 – 00:10:28:09
Speaker
I love the idea of using that language tied to gifting and engagement and sequencing that invites adjacent buyers to the table exactly like it invites them to hear the narrative of the conversation that they need to am I thinking, read in the right way? You know, one of the things you mentioned, too, and I think some sellers get this wrong, is that you know, that large, you know, call it nine, ten people, a lot of sellers say, hey, I need to meet with every one of them right now.
00:10:28:09 – 00:10:44:02
Speaker
And I need And so they they really are trying to engage with the call to action of let’s meet for 15 minutes 30 minutes when in reality one of the things you mention is the awareness factor and the right information for that awareness. And so I think that’s an interesting angle where maybe that other VP, you don’t necessarily need to be with them.
00:10:44:02 – 00:11:02:05
Speaker
You just want to make sure they have the right information and they’re aware of the solution that your champion is trying to buy. And so that’s where you can send a gift or a printed collateral or, you know, maybe it’s, Hey, have lunch on me while you read this bridge collateral. By the way, I’m talking to your colleague X, Y, Z already about this.
00:11:02:09 – 00:11:20:04
Speaker
Wanted to keep you in the loop. There’s no CTA but it’s paying it forward saying, Hey, here’s a DoorDash gift card. Here’s some content that they’re going to probably quickly flip through. But now when that champion buyer goes to ask that boss or that other person on an adjacent team, hey, what do you think about, you know, X, Y, Z?
00:11:20:08 – 00:11:38:20
Speaker
You’re like, Oh, yeah, I already know a bit about it. Like, let’s go, let’s do this. Yeah, yeah. So I think, how do you build awareness in a friendly way and gifting kind of warms up that buying committee awareness. I love a warming the committee. Yes, right. That that is that is such a great way of describing it.
00:11:38:20 – 00:12:08:00
Speaker
Right. Because endearment or that feeling that okay, you gave me something therefore I should reciprocate you know that it’s a psychological technique that works very well, right. Forced reciprocation or at least in that way. So quite fortunate in inviting the person to reciprocate. I think it’s really, really powerful. I want to be personally picky here. Yeah. On this I get sense from vendors times here and they’re like, Oh, here’s take a meeting with me.
00:12:08:03 – 00:12:25:00
Speaker
Is 25 bucks for Starbucks or to use a gift card to thank you so much. And if I’m honest, I never even click on the things like, look, I don’t have the time and I’m not going to go through this for 25 bucks. Now, I’m not a prima donna. My wife might argue, but I don’t think I’m too much of that.
00:12:25:02 – 00:12:43:18
Speaker
But when you look at the touring of the personas, are you seeing different things work better for different personas and any advice as you think about it, the context should be to be like, is there bias transactional to see? Is there more progression or stuff like what’s a way to drive engagement by the persona as well? Any thoughts there?
00:12:43:18 – 00:13:08:20
Speaker
Yeah, I think you definitely have to segment what you’re going to send based on personas and also the tactic and call to action. So I think there’s historically gifting use cases where I’ve seen, Hey, you take a meeting with me, I’ll give you $25 to Starbucks that almost feels like you’re trading value. The Italian for a gift card, which it doesn’t really feel as as human or you’re not even explaining the value of the service.
00:13:08:20 – 00:13:40:13
Speaker
You’re trying to You’re just saying, I want your time and here’s a gift card. So I think that tactic doesn’t work as well as really trying to go and try to solve the potential buyers problem. Hey, what is the pain point you’re trying to solve? And can you trickle in gift card as part of that? So you might start with the value proposition, start with, you know, try to do a little bit of a pain discovery and then maybe even second piece, by the way, you know, here’s a gift on me or pay it forward or, you know, even sending them something first and then trying to really deliver a value.
00:13:40:13 – 00:14:11:07
Speaker
So for our suggestions, it’s really how do you still do what you should be doing in sales, which is discovery, figuring out pain and try to solve that pain and using gifting as a attention grabber or a way to build rapport with that prospect too. And I think I’d add on there the importance of personal note. Yes, I that is made a real resurgence because it’s unique, this physical book, there is something that goes with it, and I think we took the effort to actually literally write my name.
00:14:11:09 – 00:14:39:02
Speaker
Yeah, write something. Okay. Again, doesn’t guarantee you I’m going to jump up and down. Yeah, but I do notice that that is much more than not right. And I think and in our domain. Right. You know, we’re using generative now to create personalized, automated email follow up and do other actions inside there like that that will resurgence around genuine, authentic personalization.
00:14:39:04 – 00:14:58:19
Speaker
Yeah, I think that’s what people are looking for. No, in the why did kids a lot of ways Polaroid made a resurgence Polaroid cameras they didn’t with debt ten years ago and now is front and center back because you have an entire generation of people, you know, teenagers at this point largely to go that all I’ve grown up with is digital.
00:14:59:00 – 00:15:20:22
Speaker
And I actually the physical is is finite. I can lose it. Ache. It’s gone. It’s a moment. It’s a picture I took. That’s it. And when it’s gone is gone. Yep. There’s no no sharing recovery. I had to be there in that moment as a and I think if people embrace that personalization with digital, yep that is how we’re going to drive better pipeline and conversion.
00:15:20:22 – 00:15:37:19
Speaker
Yeah and I think the two of the things there to hit on, but just human psychology and human behavior is what is curiosity. So I think the Spark Twins interest, they see a handwritten note or they see a box. They’re curious what’s in it. They’re curious what this note says. So there’s a bit of curiosity. And as humans, we’re curious.
00:15:37:19 – 00:16:01:23
Speaker
And so we want to continue to read or continue to open and explore. And then the other is creativity. I think humans in general enjoy creativity. And so if you can break those patterns with creativity and creativity, being in the note and the message or that the digitally written email, all those things are just going to break up patterns that you see day in and day out, and that creativity will draw your attention in to want to got to read what says, Yeah, 100%.
00:16:01:23 – 00:16:21:22
Speaker
So now I have to ask as well because just on the spirit of curiosity here, what shouldn’t people do? Yeah I think that’s a good question that equally is what you should do is what you shouldn’t do. And I think we kind of talked to one already in terms of gifting, which is just that, hey, I’ll give you 25 boxes if you take a meeting and really use that as a transactional key.
00:16:22:03 – 00:16:50:19
Speaker
I think while I do think that can work in advertisements, I’ve seen time and time again where there’s like take a demo, get a get AirPods, and if you see that on an ad and you’re willing to spend your time, I think that transaction works well. And we see swag and gifts work well in advertisement incentives. But from a human to human interaction where you’re trying to build rapport with a prospect, you want to do more human related, you know, messaging and not transactional type.
00:16:50:19 – 00:17:10:08
Speaker
So I think that’s important. You don’t want to, you know, pray and pray and not follow up. So I think that we see time and time again, we’re like, Hey, I’m just going to send out, you know, $1,005 Starbucks gift cards and I expect, you know, 500 replies like around like, you know, you’ve got to be thoughtful and you’ve got to put time into it.
00:17:10:08 – 00:17:38:00
Speaker
And I think those are the other ones that popped to my mind. So it doesn’t sound like an email to get away with this for my Kristmas shopping any time soon or to send it off to all my loved ones. Yeah. Hey, there it is, Kris. We are going to run out a little bit of time here, so I’m going to shift to song just ever so slightly and maybe you’re going to have a part two as well as I really want to get into some of the data pieces and you know, how do we drive the additional personas which today we just taught top of the funnel largely.
00:17:38:06 – 00:17:59:16
Speaker
Yes. I want to hit all that second piece that is so key. Expansion. Yeah. Customer success followed through because in these markets over 80% of growth for most companies is coming from the existing base. So I would love to have you back and dive into that topic next. Yeah, would be a fun session. Just focusing on that now.
00:17:59:16 – 00:18:20:03
Speaker
We always love to close off a little bit of trivia here instead of acting in the market right now as well about. So I’m going to ask you a question. You give me three choices about what’s going on here. And and this is and forgive the Gardner reference yet again, I feel like overdue step four today by is latest sales enablement study.
00:18:20:03 – 00:18:46:11
Speaker
And this is actually just released about 90 days ago now. It talks about the increase in budgets now through 2027. So when you think of enablement, enablement is expanding into the up space, you know, there is there’s a lot that’s going on there, right? It isn’t just training, coaching anymore. It’s it’s literally customer enablement all the way through to the CSA function as well, which we should hit on on our next discussion.
00:18:46:16 – 00:19:24:03
Speaker
Ed But now maybe three budget numbers. How much is it going up by? A 40%, B, over 50%, C, over a whopping very big 60%. How about C, It is close is just over 50% increase. That’s good. Nonetheless, that is a phenomenal jump. That’s great. And for those in our our neighbor when misters. Yeah like be proactive put together a plan but don’t just ask for more money start to thinking about well how’s this money tying into how I am going to go train my sellers to enable the buying groups?
00:19:24:03 – 00:19:53:12
Speaker
I think, Kris, we you said earlier there is so key there. There’s many steps, one of which is personalization and showing somebody that I actually care and know something about you as an individual at that. I didn’t say that’s a huge, huge opportunity for these teams. And there are a final question for you moment. What some moments that you laugh about, a moment you regretted, life’s a moment you could redo.
00:19:53:14 – 00:20:16:05
Speaker
I mean, I loved love that I started to know. So maybe I would have started it sooner than maybe, you know, taking the jump from being individual contributor or, you know, employee at another company to starting a company. I think that, you know, I would redo it. I’d become an entrepreneur and a founder even sooner. Why? I could not even think of a better sentiment than that.
00:20:16:07 – 00:20:37:15
Speaker
I’ve always maintained a life that if you got a bug and you know how to build something, build it, because that’s what creates jobs. Exactly. Kris You generated hundreds and hundreds of jobs. So thank you for doing that. And let’s continue to hold that up and encourage everybody with an idea. It’s hard. It’s risky, is daunting. Yeah. Is sleepless nights.
00:20:37:17 – 00:20:59:11
Speaker
It’s all of the bad stuff. But when you can turn around and see a group of employees that are there and their families livelihood and they’re building a working towards accommodation, there’s no greater reward than that. So thank you for doing that. How, how awesome. Kris, thank you for the time today. It has been brilliant. Yeah, we will have you back.
00:20:59:13 – 00:21:23:00
Speaker
We’re going to dive in further into the, you know, the post-sale side of this Zinnia is a fascinating conversation. But again, Kris CEO send us so thank you so much. Really having you on. Thanks for having me on. It’s been great. And everybody else, thank you for listening. And today’s Ad Sales Strategy Enabled podcast. Please remember to like and subscribe and fold in email.
00:21:23:00 – 00:21:30:02
Speaker
Send your questions to Howard and I. We will do our best to get to them on a future episode. Thanks for listening and we’ll see you next Thursday.
