Tactics and Strategies for Team, Social, and Executive Selling


Kris Rudeegraap outlines the best strategies in team, social and executive selling. He shares his experiences from working at Sendoso and offers suggestions for success.  


Kris Rudeegraap is the CEO and co-founder of Sendoso, the leading Sending Platform that helps companies stand out by giving them new ways to engage with customers throughout the buyer’s journey.  



Billy Bateman 0:01   

All right, everyone. Welcome to the show today. I’m your host, Billy Bateman. And today I am joined by the one and only Chris Rudeegraap. Chris, how are you doing? 

Kris Rudeegraap  0:10   

Thank you so much for having me, Billy. I’m doing really well today. 

Billy Bateman 0:13   

Yeah, imagine so. So, Chris is the CEO and co-founder of Sendoso. And you have an interesting background. You guys do really cool things at Sendoso. So for anyone that doesn’t know about you, or Sendoso Like, tell us a little bit about it. 

Kris Rudeegraap  0:30   

Yeah, so Sendoso is a sending platform that helps other companies send out direct mail, corporate gifts, swag, you name it, we can help you send it. And it’s a mix of integrations into your tech stack, your CRM, your marketing tools, a, you know platform where we can track analytics and see all the results as well as a marketplace of all the different gifts under one single software, and then fulfillment and logistics behind the scenes to get everything delivered. 

Billy Bateman 0:57   

Awesome. Awesome. How’d you guys get started with Sendoso? What was genesis? 

Getting Started with Sendoso

Kris Rudeegraap  1:02   

Yeah, so I was in sales for about 10 years prior to starting the company. I found myself trying to get more creative in breaking through that kind of noisy inbox. And I started sending out handwritten notes, I grabbed swag from the swag closet, I’d go find quirky gifts off Amazon. And it all worked really well. It was just super time consuming. You know, my boss would always be like, what are these weird expense reports from Amazon, or, you know, it was, but it worked well. I had this epiphany, like, why can’t I just click a button in Salesforce and send something out?  

And that was kind of the aha moment. When I did some research and saw that it, you know, already there were hundreds of billions being spent. It was just kind of offline siloed manual spreadsheets. So, I realized that there should be some modern software. And you know, here we are a handful of years later. And we’re, you know, about 500 employees, we just announced 100 million Series C last week. So, we’ve seen some awesome momentum and progress over the last couple years. 

Billy Bateman 2:03   

Awesome. Awesome. You guys are doing great work. I love what you guys do. And I think I think you got to get out of the noise of just the inbox. I mean, I get 20-30 cold emails a day and 99% of them. It’s just like, delete, delete, delete, maybe that one’s really spammy market is junk. But when people send something, I’m like, yeah, like, let’s at least look at what they’re selling. 

Kris Rudeegraap  2:30   

Exactly. At least grab your attention. And I think that’s the big thing is how do you grab attention? And how do you get creative? You know, I think with automation, you know, it makes it easy for a lot of sales reps to just be lazy, or marketers. And so, with that suggestion we kind of drive that creativity, and then help you stand out for that way, too. 

Billy Bateman 2:50   

I love it, man, for sure. So let me let’s get into it. That’s what we want to talk about. 

Kris Rudeegraap  2:54   

Yeah, yeah.  

Billy Bateman 2:55   

So, one of the things that you brought up, like, I really want to talk about a few different things. But let’s start with just team selling. And get your thoughts on Team selling and how that’s best done and where that’s going. 

Team Selling

Kris Rudeegraap  3:09   

Yeah, so I break up team selling into a couple different categories. So, I’d say there’s the exact selling where how does you get your executives involved to sell? How do you get your advisors and investors involved to help sell with you? And then really, how do you get your partners to sell with you? And I think the fourth one kind of customer selling, which I’d kind of bucket into like referral programs and advocacy.  

So, I think there’s something there too, but focusing on those first three, something that was near and dear to my heart being that I was in sales before Windows, so then I’ve always kind of been sales driven. And so, I’ve always thought, how do you? How do you do more with your network and social selling? And so those three categories are the three areas that we’ve really invested in? I’m happy to get into the weeds.  

Billy Bateman 3:58   

Let’s do it, man. How do you get investors involved in selling? 

Getting Investors Involved in Selling

Kris Rudeegraap  4:02   

Yeah, so Well, let’s start with start with investors and advisors selling. So, we use this tool called Kabbalat, getcabal.com cable was actually part of my inspiration the founders took in terms of how we activated our advisor investors. So, I think a lot of people have advisors and investors, and they’re kind of you know, on the outside, maybe you get maybe updated once a quarter or something.  

And so, we’ve purposely, well, I’ll reach out and do updates monthly, but I’ll also use this software to essentially ask for introductions into target accounts, or existing customer accounts that we want to expand. And so, I would say probably every other day I’m making an introduction from one of our advisors or investors. So, it is real. It’s a process now it’s tracked through Salesforce, so You know, at any given month, there’s, you know, 20 or more advisor or investor introductions happening. 

And so, it’s been a, it’s been a great process that we’ve operationalized, through Salesforce through this other software, we’ve done training and enablement on it. And so now, as part of the sales process, once you get an opportunity from typically stage two to stage three, there’s kind of a flag to say, hey, let’s get advisors and investors involved if we can. 

Billy Bateman 5:28   

Awesome, awesome. I love it, man. And then what about executives? 

Getting Executives Involved in Selling

Kris Rudeegraap  5:32   

Yeah, so executives are another one where we are actively trying to empower our executives to really make introductions and see how they can help. And so, I think there’s two things on the introduction side, it’s really, how do you how did the sales team get good at, you know, tracking, you know, shared connections, checking with the team, creating a program. So, it’s rinse and repeat. And so, it’s not awkward for, you know, a, you know, or to go to ask our CTO for an introduction, it’s normal, and it’s happening every day. 

So, it becomes part of their process. I think that’s the first part is really again, training and enabling it. So, it doesn’t feel awkward. I think if you don’t enable and train on it, and you just let salespeople be salespeople, they tend to not want to bug, you know, a CMO or CTO, but we encourage them to bug those people we say, the more you do that, the better. And in fact, in some cases, you have to do that to progress, an opportunity through its stages.  

So, I’d say that’s we’re overly emphasizing the importance of that. I think the other part on that is bringing executives into sales calls to help close bigger deals to whether it’s, you know, a product leader to talk about product vision, whether it’s, you know, our CTO to talk about security, whether it’s, you know, our CMO to talk to a peer, whether it’s me to talk about kind of the category and executive vision.  

So, we make ourselves very available, and again, encourage the team to go and put calls on our calendar to talk with later stage deals for this. And so, it’s not awkward, it’s encouraged. We’ve seen a lot of success, kind of building executive relationships by way of bringing in more people than just, you know, the sales leaders. 

Billy Bateman 7:30   

Yeah. So let me dig in just a little bit. Are you guys bringing them in? Like, once they’re at a certain stage in an existing opportunity? Or are you helping them source new ops? Or is it a little bit of both? 

Kris Rudeegraap  7:44   

A little bit of both. So, there’s kind of two programs? One is really how do you from an exec selling perspective? How do you leverage their network to get new introductions? And so, I think that is across the board being done both by SDRs and AES, as well as how do you get more executive coverage? In an account or more people on a buying committee? So even if we break into an opportunity, do we know someone that’s the boss’s boss, or?  

And so and so how do we network our way through team selling into that account? So that’s done, I would say opportunity, pre opportunity and opportunity stage, you know, one, one or two, kind of in the discovery call stage, once it’s in kind of negotiation, you know, it’s going to final eval stage, maybe even to contract, Pricing Proposal stage. That’s where we’ll more get the executives involved to talk about more of the product vision, the roadmap, the security, the how Sendoso uses Sendoso. So, from an executive standpoint, and really get them bought in on what’s next. Almost all kinds of future selling them, selectively closing them, so to speak. 

Billy Bateman 8:54   

Yeah, yeah. I love it, man. I love it. So, when you guys are selling to executives, and you’re bringing in other executives, what are some of the strategies, you know, you’ve talked about future selling, assuming anything else you guys are doing around that? 


Kris Rudeegraap  9:08   

um, you know, we do a fair amount of Sendosoing sewing to those people. So, we get them as excited. So that’s been working well for us as we get them through that. You know, there’s other, you know, executive kind of field events that we’re kicking off again, we did virtual ones, but now we’re kind of bringing back some in person ones as we can in certain areas. So, I think that’s a good way for us to bring some of these executives back into the meetings as well, too.  

Billy Bateman 9:37   

Yeah. So, are you guys doing physical events then again? 

Kris Rudeegraap  9:40   

Yeah, we are. We’re actually at a trade show right now for Sastre. Yeah, there’s some kind of happy hour and other events surrounding that. We had dinner a couple of weeks back. I think we’re doing some golf outing stuff. So, trying to bring it back where appropriate. 

Billy Bateman 9:59   

Awesome. Man, awesome. We’re excited to get back. We’re doing a silicon slopes tech summit next month. Oh, cool, excited to be at a physical event again. 

Kris Rudeegraap  10:08   

Yeah. You know, I was going to say the, the, the last area that we’ve focused on for team selling is really our partner selling, you know, our partners are an extension of our team in my eyes, because, you know, they are ultimately, you know, have skin in the game, they partner with us for a reason. So how do we get more out of them? And how do we return that favor?  

We’ve used tools, like crossbeam, and cosell.io. And these tools are helping with finding overlaps through our CRM data. So, we can see, hey, this, this is a customer to us, you know, a lead for you, or vice versa. So, it allows us to be much more data driven in terms of our partner selling motion.  

And so you know, in a can go into a conversation with a much more data driven approach, saying, Hey, here’s, you know, a couple con couple people we need to introduce, introduce this account that we know as a customer, versus maybe years and years ago, before those software’s existed, you’d kind of just have those calls, or it’s like, hey, let’s, you know, download your CRM, and then he was kind of, or like, hey, who can you introduce me to, and it’s like, oh, we already worried customers with them. So, it reduces some of the back and forth gets right down to business.  

And then with that the sales reps are, you know, doing co selling their jumping on the calls with our partners. We’re also having more workforce, our work sorry, workflow management, so we can see who we reach out to who we haven’t, has partner been involved. So again, our ultimate goal is how do we rinse and repeat. And so, for all those different areas, we, we’ve kind of enabled the team to rinse and repeat and all of these, and I personally think it’s helped us tremendously, it’s, you know, we’re not selling alone anymore. He, you know, has, you know, a handful of different ways that they can now, you know, get that deal across the finish line. 

Billy Bateman 12:05   

Ya know, what I love about your team selling, everything you’re laying out is, you know, we all know the buyers, they got more information than ever, like, manage, and they usually have, it depends on the, you know, the size of the deal and the size of the company. But it’s usually not just one person making the calls.  

Like, you have a bunch of people that are making the call on the other side, you need to be more than just a single A, or SDR going after any of these deals, if they’re any size that’s worth, you know, really going after. So, I love it, man. So, let’s talk about social selling for you guys very active on social, you know, what are some of the tactics and strategies that that you guys are using? 

Social Selling

Kris Rudeegraap  12:51   

Yeah. So, you know, we some of this, I’d say there’s two different ways. One is how do we drive followership and awareness of our brand through social and I think that comes with trying to think about brand awareness and investing in that, which also entails investing in content, and, you know, creating fun videos, creating, you know, not just using stock images, but we have, you know, photographers on our team that are creating quirky pictures and stuff that we’re posting, so feels more real and authentic.  

And so, going above and beyond, from a content perspective helps us get better content out there, which then performs better. I think we are with our social selling approach, also trying to figure out ways where we can make sure that we empower our SDRs and AES and even CSMs to spend some of their day engaging on social, you know, we’ve got a couple of days that I find posting a couple times a week, really thoughtful posts, and I’ll shout them out saying, Hey, good job there.  

So, I think it’s, you know, can you time block a half hour to do you know, social activity, which might sound counterintuitive to some people, but we really promote that as a way to get our brand out there. And then, you know, there’s you know, I was at the sastra event yesterday and I time and time again I was hearing Hey, I saw you post about this event, you’re or this podcast you’re on or I saw you know post about this and that and so while it might not be as trackable in some cases to leads instantly it it’s that extra awareness that’s going to give you that organic inbound that, you know, is much needed as you scale the company. 

Billy Bateman 14:36   

I love it, man. I love it. So besides, you know, shouting people out trying to give them some time. You know, what’s the secret to getting your team like really excited about doing social because we all have a few people on everything. They’re just going to do it no matter what. And there’s some that just aren’t. But there’s this big group in the middle that is given the right incentive. The right nudge, they’ll get, they’ll get involved. 

Kris Rudeegraap  15:03   

Yeah, so we’ve, in some cases, we’ll have kind of like a contest raffle where it’s like, hey, post to social, and we’ll pick someone to give 250 bucks kind of thing. We do that from time to time to kind of train for good behavior and get people incentivized to doing it. So that works. And I think, again, it goes back to creating authentic content or interesting announcements.  

I mean, you know, we had a ton of people share, you know, our 100 million fundraise round, which is just like, an obvious thing to share with, there’s other campaigns where we highlighted a, remember, we did like a dog day campaign, and people are sharing that like crazy. So, I think it’s just not authentic content that you can create. And then make sure that you create a process where you’re sharing that back.  

We have a Slack channel in all teams, where we’re dropping in, you know, posts saying, Hey, here’s an interesting post of the week. So, getting people to realize the visibility and not expecting everyone just to be always following us on Twitter or LinkedIn every day. But to bring that content to where they are to, we are also internal, you know, emails and newsletters also are sharing that intra employees so that they can find those little tidbits of content to share too. 

Billy Bateman 16:21   

Oh, dude, I like it, you guys are hitting them hitting your own employees as hard as the rest of us. Yeah. So, I like it, man. Let’s talk about selling to executives, we hit a little bit, but you know, when you guys are selling to executives, you know, so it’s not like $99 a month. Yoou know, usually somebody is going to have to approve a little bit of the budget, what have you guys found, especially in the last year and a half, where like, you’re not going to be able to fly in necessarily and, and meet with anybody face to face? How do you guys handle that? 

Selling to Executives

Kris Rudeegraap  16:55   

Yeah, so I think it’s, um, you know, a mix of one being able to really demonstrate value and really make good discoveries, prior to, you know, even bringing in other executives into the call. So, we really have trained up on how to, you know, really understand, the business drivers for our customers. I think it then goes to showing a ROI proof case, we’ve got lots of customer case studies and testimonial videos and sharing stuff like that.  

And, you know, being running a diligent process, I think it’s, you know, where every process, every sales cycle is going to have, hey, here’s, you know, executives, I will Cosa with you, partners, advisors, are you checking those check boxes, so really, creating a strong enablement team and ops team that can make sure that we’re running this process. So, I think, you know, the best sales reps are doing things to engage exact, so they’re, you know, using Sendoso or there, you know, thoughtful with discovery, but how do we train and make sure that all the reps are doing that I think is important. 

Billy Bateman 18:09   

Yeah, I think it’s important, especially on a bigger deal, like, I encourage our sales team to I’m like, Dude, you got somebody, like, I’ll sit down with them, you know, here’s the, you know, here’s the benchmark. And as soon as we’re there, like, I’m there.  

Kris Rudeegraap  18:24   


Billy Bateman 18:26   

But yeah, incentivizing the executives that everybody’s on board with selling, and then having the process in place. You know, you guys are a lot bigger. You guys are 500 employees. We’re much smaller than that at the moment. But yeah, just getting that process in place, I think, goes a long way. 

Kris Rudeegraap  18:43   

And I think it’s important to have that in your DNA in the beginning. So, we really early on, I was, you know, our first salesperson, and always helping, and then when we continue to grow, we really wanted to ensure that we didn’t lose that kind of exact touch. So, we continue to focus on making sure that, you know, as part of, you know, new sales, training and new hires and everything, they know that we’re approachable, and I probably get slapped, you know, 10 times a day by the sales team.  

I’m happy about that, you know. And it’s, it’s actually hard to, to really influence that kind of level of activity is I think a lot of other companies steer away from bringing their CEO in, or the CEO doesn’t want that level of involvement. So, it’s hard to change behavior. Sometimes trays that have, you know, been told not to do that place. 

Billy Bateman 19:36   

Yeah, no, for sure. Like at certain places. It’s just not an option for them. So, they’re not used to it. Exactly. Okay, so I want to hit one more thing before we break, and that is marketing to marketers. Yeah, we I mean, we sell to marketers, mostly a little bit to sales. You guys sell a lot to you know, marketing and sales I’ve seen Both use and Dosa. How do you guys get the marketers’ attention? What are you guys doing? 

Marketing to Marketers

Kris Rudeegraap  20:06   

Yeah, so, um, let’s see some things that come to mind. Top of Mind. One is, I’d say peer to peer storytelling, like getting marketers to tell their story and how they’re using Sendoso. I think we’ve got like six or 700 reviews on LinkedIn are on Jeetu. And we have something like 60 or 70 case studies. So, I think a lot of those marketers want to hear what other marketers are doing. And so, we can capture that and make it easy to tell those stories. I think that’s important.  

On that topic, too, we’ve really, we know we’ve got a handful of different communities, we’ve got our own community, we’ve got and then we participate in communities like pavilion, which used to be called revenue collective, there’s peak, there’s rev genius, there’s women in revenue. And so, these different communities we try to be active in, which is again, another area where marketers are talking to marketers, yeah.  

You know, even your own dog food, or I guess it’s what I like to call it drinking our own champagne. But you know, really, showcasing how we use Sendoso is important. So, our marketing team is kind of has webinars and shares content monthly on the different ways that they’re using the tool. And I think again, it kind of validates the use case and validates that for other marketers. 

Billy Bateman 21:31   

I love it, man. I think like drinking your own champagne, we, we believe in the same thing as chat funnels center of all of our sales and marketing. If we ever find, like, it’s not part of a campaign that it can be like, I’m the first one to be like, okay, like when you do either adapt this campaign, or change something in product to make it work for it. Because if we’re not using it, nobody’s going to use it. Yeah. I love it, man. So, I appreciate the time, Chris, thanks. Once again, if people want to get in touch with you and continue the conversation, what is the best way for them to reach out? 

Kris Rudeegraap  22:06   

Yeah, so if they’re curious about Sendoso, you can go to Sendoso.com if you want to contact me directly. I’m kris@sendoso.com Or add me on LinkedIn. Happy to chat there too. 

Billy Bateman 22:18   

Okay. Thanks, Chris. And we’ll chat later.  

Thanks, Billy.