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Hey gang, we re running a four-part series starting today featuring Chris Rudogrop from Sendoso.
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The first episode, we re going to cut into two pieces, but don t miss either one.
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In this first episode, we hear his founder s story while talking about what he calls the next normal for sales professionals.
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We ll talk about Chicago and the dreaded night I spent on the beach, the concrete beach that is, and how you can join the world s largest sales lunch.
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Welcome, everybody, back to the Advanced Selling Podcast, the longest running sales training podcast in podcast history.
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My name is Brian Neal.
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I m Bill Kasky.
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Go to our LinkedIn group.
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The thing is firing up or pushing 13,000 members right now.
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We re going to start putting lots of new content, lots of conversation, and also some fun things for you to learn.
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So just go to the Advanced Selling Podcast group on LinkedIn and check that out, if you would, please.
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Bill, I was in Chicago for the weekend for my game.
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By the way, just to, and I know we ve got a lot of listeners that love Chicago.
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The juice isn t worth the squeeze for me, Chicago.
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I sat in traffic, it s 120 miles from Indy, from where we live, and it took me like three hours and 45 minutes to get home.
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And then you still have a winter, I just don t get it.
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And I have so many great friends, my friends love Chicago.
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I just don t know.
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I think a lot of it goes back to how old you are when you fell in love with it, too.
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Because I was in my 20s, party time, trade shows, Omni Hotel.
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I mean, I was all over Chicago, and it was all over me, all the way up until I slept on the concrete beach that night.
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Whoopsie daisy.
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Dreaded night in 1985.
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I woke up with a seagull pecking on your arm.
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Had to go do a trade show the next day.
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Hey everybody, good to see you.
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How was your evening?
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Oh, it was very nice.
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Great night, yeah.
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Slept on the beach.
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Yeah, close to nature.
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That s the day, so.
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But I was watching my hotel room meet the press, and there was a guy from the Wall Street Journal.
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I just, I wonder where fashion is going.
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because I m getting older and I m starting to lose, I ve never had any fashion at all, but you know, you start to- Be conscious of it, yeah.
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This young guy from the Wall Street Journal had on a really nice blazer, button-down shirt, and he had this, like, basically like if you ripped the fabric from the back of the blazer and wrapped it around your head at a wedding when you re drunk and tied it on, that s what it looked like to me.
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And I m thinking, I guarantee this is fashion forward, like this guy has got great style, and I m just not there yet, but I didn t know if you or any of our listeners saw that.
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That might be worth a Google.
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to see the Wall Street Journal reporter on Meet the Press this weekend.
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Or maybe it was on one of the new... Are you sure it was Wall Street Journal and not like Rolling Stone or something?
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You know, it was Wall Street.
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I kept looking at it, like, for that reason.
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Because I was thinking, is this guy from the... Seems off-brand for the Wall Street Journal.
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Well, I don t know.
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But maybe it s not.
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That s what I m saying.
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Maybe not.
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Yeah, maybe not.
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Maybe we re the ones that are off-brand these days.
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Well, I...
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Interestingly enough, I sat in on a webinar the other day, and I won t say whose it was, but it was three 30-somethings, and they were literally raising the roof after every point that one of them made.
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They would go, wow, yes, yes, that s amazing.
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And I m like, oh my god, society has passed me by.
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I m not into raising the roof.
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I thought that was out 10 years ago.
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Nope, not for these people.
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Woo-hoo.
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We re hay boomers.
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Anyway.
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Uh, okay.
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Great.
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Uh, we re in, we re in good company today.
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Aren t we Bill?
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We are very, very quiet, special guests so far.
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He s waiting to talk.
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He s waiting to be introduced, but he s very, very patient.
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We re going to have, uh, our next guest on for a couple of episodes cause he s got so much cool stuff to share.
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He s got a great story of a great sales story.
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He s got a really cool company.
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That s really, really helpful to salespeople.
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We thought listeners need to have,
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Lots of information here.
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So Bill you want to see I m afraid to say his last name.
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Well, I ll give it a stab and we re gonna talk about that He can correct us which he probably will love it Yeah, the point of this is that we are in the interest of serving our audience We re always looking for things that work outside of maybe things that we re doing that Brian and I are doing for our clients And so we want a little hunt
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for, well, what s new in the world of marketing, in the world of customer experience?
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And we came across a company called Sendoso.
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Chris Rudegrop joins us, and he is the founder of Sendoso.
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And we wanted to bring him on because not only has he got a great experience, like you said, Brian, in sales, but also he s got some really good ideas for how we can all get better at customer experience.
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So Chris, welcome to the show.
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Thank you, Bill, and thank you, Brian, for having me today.
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Yeah, let s do the last name thing, man.
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First, we got to pronounce it properly, and then tell us the origin of your name.
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It s Rudy Grop.
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I saw, Bill, you did a two-take on that.
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You started once, you did it again.
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I did.
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I saw the extra B in there.
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Yeah, you second-guessed yourself.
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But yeah, the origin, it s actually Rudy s my mom s last name.
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It s Polish and Dutch, my dad s last name, Grop.
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They got married, they got creative, and they merged them together.
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That is awesome.
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That s fantastic.
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A made-up last name.
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There s got to be no rudographs anywhere.
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There s me, my wife, one of my sisters, my other sister lost her last name already, so it s just a small group of us.
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That is fantastic.
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That s a great story.
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Why don t more of us do that?
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Yeah, really.
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Make up your own last name.
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Yeah, exactly.
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Fantastic.
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And your parents, first generation Americans?
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No, no.
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Okay, got it.
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Yeah, that s just the heritage.
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Crazy last name and the heritage.
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Well, that was worth it right there.
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Made up last name, man with a made up last name.
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Well, that should be the trend in married names.
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Instead of somebody taking your name, I take yours, you take mine.
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We don t take either.
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We keep it the same.
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And then what do the kids do?
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And this makes it really easy, Chris.
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Then you just combine it.
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I mean, I think I got lucky in that they re both short and combined.
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So two long names might be harder.
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Yeah.
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You know, if anything, maybe Rudy Groff and the next person, your daughter marries.
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Yeah.
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Maybe just shave off a couple of letters here, a couple of letters there.
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And you know, sure.
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Bill and I got married.
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It would, it could be a Neilsky.
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Yeah, there you go.
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We ll remember that.
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If your daughter marries like a Hechtenstein or something, then it s Rudolph Hechtenstein.
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A little bit of a mouthful.
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All right.
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So first, Chris, we re really interested.
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You ve got such a cool story.
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We re going to talk a little bit just about the state of selling and that sort of thing.
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Tell us a little bit about your sales history, your sales life.
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Yeah, so for context, I started Sendosa about five years ago.
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And prior to that, I spent about 10 years in software sales in San Francisco, mostly at venture-backed startups where I was typically an account executive or senior account executive role.
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And I was doing that, crushing it for about 10 years.
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What part of that, did you get your first job out of college?
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Uh, so actually in college, I had a startup that, um, I started and ended up selling to another company.
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So I had my first taste of entrepreneurship in college.
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Um, but when they acquired my company, I then moved into a sales role from there.
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So I guess you could say my first job out of college is sales, but a little atypical in terms of going in through an acquisition versus going in through like an SDR.
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Yeah.
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Yeah.
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Right.
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And what did you, um, I m always curious to know what people,
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Because all of us remember our first sales jobs, our first sales calls.
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And I ll speak for myself.
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There was part of the sales function that I really loved and part of the sales function that I loathed.
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And I d be curious to know if you think back and even today, if you think back of your own personal experience in selling, what did you love?
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What do you love about it?
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What do you not like about it as much?
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Specifically for that first job, we were selling to apartment managers and property managers.
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I didn t necessarily love the receptiveness of the audience.
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I was selling online rent payments and they were like,
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kind of thing.
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So I think sometimes as a salesperson, you don t, you ve got to really understand who you re, when you re joining the company, who s the end buyer.
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Because you can, you know, if you re stuck in a conference with these people, you got to really love them.
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And so, you know, now I sell into sales and marketing leaders and customer success leaders.
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Those are like the best people on earth, in my opinion.
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And so I would like, I want to go to a conference to meet you because you re so interesting and fun to talk with.
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I d say the ICP that you sell into, I think as a younger salesperson, you need to make sure you love that audience.
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Wasn t it kind of weird selling the company and then going back to work?
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It s fascinating.
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Was it kind of weird?
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Well, I would say it was kind of weird because my day-to-day was vastly different.
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But I think my goal was I didn t know what I didn t know.
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I think the company only grew to about 15 people and then had an opportunity to sell.
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And so it was a good jumping off point to move to San Francisco and then to learn from other entrepreneurs and to see companies truly scale.
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like an opportunity back, like downgrading my path.
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Yeah.
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So then fast forward to five years ago?
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Yeah.
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When you started Sendoso.
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Yep.
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Tell us first off, what is Sendoso?
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And then the origin of the idea, because you obviously got a lot of entrepreneurial chops in you and a lot of DNA that s just creative.
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So how did you come up with it?
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And what exactly do you guys do?
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Yeah, so Sendoso, we re a sending platform.
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We help other sales teams, marketing teams,
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gifts, handwritten notes, personal gifts, you name it, we can send it.
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It s a mix of software where you can have users and teams and budgets and analytics and integrations.
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It s a marketplace of everything you could want to send all in one platform, and then the logistics and fulfillment behind the scenes to make that happen.
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So that s what Sendoso is in a nutshell.
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And ultimately, say about six years ago when I had a company called Talkdesk and I was a senior account executive there, I found myself just kind of spraying and praying, sending out a ton of emails and feeling like that was lackluster, that it was kind of diminishing response rates.
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I was like, hey, how do I get more creative?
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How do I be a better salesperson and break through the noise?
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I started stealing swag from our swag closet and boxing it up.
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I remember marketing would always yell at me.
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Or I d go find quirky gifts off of Amazon based on the prospect s conversation or maybe their backdrop on a meeting.
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I d go send them a Starbucks gift card.
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And so all those things started working really well and it was just a better way to build a relationship, a better way to get in touch with them.
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And so I ultimately tried to figure out how could I scale that a little bit more because it was painfully manual.
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And I d always get my expense reports declined because they re like,
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Come on, I just bought a cool gift for this prospect.
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And so that was kind of the first epiphany of like, well, why isn t there a platform that I can click a button in Salesforce and send something out?
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I love that.
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I love the fact that great companies are just built on what s needed.
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What s needed in the market and what do I struggle with and how can I take what I struggle with and assume that everybody else struggles with because they do.
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And I also think there s, I like that idea, you brought up the word relationship.
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Relationship s one of those words that, oh my God, everybody talks about it, we gotta go build a relationship.
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And yet, so little creativity really goes into it generally.
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Not at your company, of course, your clients, but it s amazing how little creativity we, or how little time we spend on, how do we really bond and create a relationship versus just flying out to see somebody.
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And that s what you guys have kind of mastered here.
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Exactly.
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I think creativity is the new secret weapon.
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Historically, when I was in sales, I actually remember eight years ago before the outreaches and sales lofts, and even before YesWares and these SDR automation platforms.
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It was like I got good at figuring out how to mail merge really well, and that was like a secret weapon 10 years ago, 8 years ago.
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But with all the software out there to automate so many things, now creativity is one of those areas that if you re good at that, you can really be a better salesperson.
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Yeah, and I think, and Bill and I, you know, we grew up in a time, and we used to sort of, in a funny way, sell against this idea.
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So this is pre, let s go back to pre-SDR, pre-SAS, where most salespeople were out and about going door-to-door to, you know, not door-to-door, like houses, door-to-door, even businesses, B2B outside selling.
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We still have lots of listeners who are in that boat.
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And we had, when Bill and I first, this is like forever ago, older sales, like older, like tenured salespeople, their number one strategy was bringing a box of donuts in.
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That was their big strategy.
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And they thought, oh, this is great.
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And we used to sell against that.
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Like you got to do more than that.
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And I want to make sure that we re differentiating between what we re doing here.
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And you tell me if I m getting this right.
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To me, this is a thoughtful, almost customized,
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send to somebody.
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So if I m talking to Chris and Chris says, I m a big 49ers fan, and I send him a little mini 49ers helmet, that s very different than just randomly dropping off a box of Krispy Kreme donuts at the front desk and saying, hey, put these in the break room for everybody.
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I would say that we do it all, to be honest.
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We have some people that are really good at the 49ers football, and we have some people that really leverage the DIY make-donut-kit send, which actually performed really well during COVID because you get a box making your own donuts and you re like,
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And so it was actually a semi-decent send that was creative enough to drive results for a lot of companies because just the interactivity and knowing that people are at home with their kids.
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So I think we specialize in one-to-one, one-to-few, and then one-to-many.
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And there s different scenarios where you d want to do those different things
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Yeah.
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So that was one of my questions, Chris, is if I m listening to this, I m saying, OK, I got it.
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I love his story.
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I like the idea of sending a three-dimensional hard something tangible.
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Where do most of your clients use this?
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Where does it apply?
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Is it more in the prospecting mode, or is it more just client satisfaction, and we just need to keep our clients close to us, and we want to be generous with our gifts?
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I know it s probably everywhere, but generally where do you start?
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Honestly, it s everywhere.
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We typically will start in one place where it s where there s the biggest pain point or where they re maybe already trying to do this manually and it s operationally cumbersome.
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top of funnel for SDRs or even demand gen marketing teams trying to help set meetings.
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How do we grab their attention enough to want to talk to us?
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And then even maybe that first meeting, it s sending a little Starbucks e-gift card saying,
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Maybe there s a thank you afterwards and some marketing collateral and maybe a gift comes in that first thank you.
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And then now the AE has the deal and now they ve got three months to close it and they re checking in.
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They re maybe sending some stuff here and there and then the deal closes.
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There s maybe a welcome customer kit and then there s different gifts throughout the customer lifecycle.
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related to the customer personally.
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Like, our customer just had a kid and I want to send them a little onesie to the 49ers.
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Or whether it s just something related to ongoing campaigns or driving people to virtual events or in-person events.
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Ultimately, I think wherever you would have normally had some communication via email, you could figure out how do you get creative and send them something instead.
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Yeah.
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You mentioned the welcome or the onboarding kit.
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That s a lost art right there.
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Amen.
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I think a lot of companies miss the most important opportunity is I just cut the check, or I just signed the order, or whatever.
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I m in business with you.
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And there s that, what s it called, not cognitive dissonance, buyer s remorse or whatever, that buyer caution.
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Man, if you get them right on board, get a really nice, high-quality welcome kit, they will say to themselves, we made the right decision.
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Do you find that welcome kits are one of your...
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big ones, or is it still kind of a lost art?
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No, welcome kits are worse.
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We re seeing that pickup as a trend a lot more than it used to be.
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And I think to your point, it s you get them right at the best time where they re most excited about your product.
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So it s really impactful.
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You can also use that time to have a more personal introduction to their new CSM.
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So we see people having like a picture of their CSM with like a handwritten note.
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So now you feel like you re more genuinely interested.
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We see people have these little mini booklets of best practice guide to get set up fast.
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So now you re having some collateral, like, I m so excited about using this new software.
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Let me look at a couple tips and tricks.
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And we even see something where people have, I ve seen some creative multi-step.
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We re looking really, we re looking forward to growing with us and part of the welcome kits, like a pack of seedlings and a little planter.
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And then like a month later, they send them a little watering can.
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And it s like, you know, you can get creative with it in terms of like anticipation, or we ve seen like a little passport send that has to get sending over some stickers over the course of the customer lifecycle.
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So, you know, it s all about just having fun with your customers, I think at times.
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Yeah, that s so and then Brian, I ll yield to you here.
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I m, I m asking a lot of questions.
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I think this is a great, it s a great topic.
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And you know what, it s something that every salesperson listening can do.
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You don t need to go to your marketing department, you don t need to get a million dollar budget.
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Any one of you listening can execute this in some way to
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help grow your business, and that s what we re all about here at the Advanced Selling Podcast.
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I love the idea of a picture of the person who you may not have met yet.
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If I m the prospect or I m now the client, and I get a welcome kit, and I have a picture of Brian Neal here, it s like, oh, I didn t know Brian s going to be my CSM.
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And it s that idea of human touch, even though Brian s not
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should we say in the box there, but he might be in the bag, but he s not in the box now.
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He s in the bag.
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But I love that idea.
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It s like you could introduce your, just the team, not the whole company, but the team who s going to be surrounding and walking alongside the client.
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That s a great idea.
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It s really great.
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It humanizes the deal.
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And even picturing that, you know, we re in the,
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I m going to say it, Bill, because we haven t said it in a while.
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I m going to say it.
2
SPEAKER_01
You ready?
2
SPEAKER_01
I think I know.
2
SPEAKER_00
New normal.
2
SPEAKER_01
New normal.
2
SPEAKER_00
I m kidding.
2
SPEAKER_00
The new normal.
2
SPEAKER_01
We hate that word.
2
SPEAKER_00
I call it the next normal.
2
SPEAKER_01
The next normal.
2
SPEAKER_01
That s what I ve been hearing lately.
2
SPEAKER_01
Bravo to that.
2
SPEAKER_01
Yeah.
2
SPEAKER_01
So, you know, where we are living remotely and doing business remotely.
2
SPEAKER_01
So anything that humanizes is a bonus as a part of the experience.
2
SPEAKER_01
Okay.
2
SPEAKER_01
So here s a question for both of you.
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SPEAKER_01
Um, I m trying to be the listener.
2
SPEAKER_01
I m channeling our listeners.
2
SPEAKER_01
They re driving or they re working out and listening to us and they re going to, you solve to the two biggest problems here.
2
SPEAKER_01
We hear all the time.
2
SPEAKER_01
I hear this all the time.
2
SPEAKER_01
I m not creative.
2
SPEAKER_01
People say this all the time.
2
SPEAKER_01
I m not creative.
2
SPEAKER_01
Um,
2
SPEAKER_01
I don t have any good ideas.
2
SPEAKER_01
I m not creative.
2
SPEAKER_01
They think creative means that they can draw or come up with fancy colors.
2
SPEAKER_01
Out of nothing.
2
SPEAKER_01
Yeah.
2
SPEAKER_01
From out of nothing.
2
SPEAKER_01
Yes.
2
SPEAKER_01
And so can you talk about the, uh, a salesperson s kind of maybe fear or anxiety around this?
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SPEAKER_01
Like, Oh my gosh, this all sounds great, but I wouldn t even know where to start.
2
SPEAKER_00
Yeah, I ll chime in on that one first, Bill.
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SPEAKER_00
I d answer that in two parts.
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SPEAKER_00
One, I would say, I actually find surprisingly a lot of salespeople are creative.
2
SPEAKER_00
They just don t know how to execute on their intercreativity because they don t have the tools in front of them or they feel overwhelmed by the actual act of being creative to execute on that.
2
SPEAKER_00
Part one would be, you re wrong, Brian.
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SPEAKER_00
There s actually a lot of creative people in sales and they just don t have the avenue to really execute on their creativity, which I think is what we ve helped on.
2
SPEAKER_00
That would be my first answer, to say the majority of people are creative by nature and probably want to be more creative.
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SPEAKER_00
are saying, hey, that s not me.
2
SPEAKER_00
F off, Chris.
2
SPEAKER_00
I would say for those people, I think the inspiration is we provide a lot of different ways that you can come in and see examples.
2
SPEAKER_00
And we have the ability for marketing teams to set things up so that it s kind of like putting on a little silver platter for the sales team to just click and send.
2
SPEAKER_00
And even more so, we have what we call send curators, who their full-time job is to be creative on behalf of our customers.
2
SPEAKER_00
And so all they do 24-7 is come up with ideas and help get those sourced ideas into the platform so that you can be the creative superhero
2
SPEAKER_01
A lot of edibles in that group.
2
SPEAKER_00
Yeah, really.
2
SPEAKER_02
Get them rolling.
2
SPEAKER_02
Do they create, do they document what they create?
2
SPEAKER_02
Like if they create something for a client and the client doesn t use it, does it go into a database somewhere so they re not constantly, they can go back and reference old creations?
2
SPEAKER_00
A little bit, but for the most part it s really on demand for that customer because it s really like, at the time, what s the goal?
2
SPEAKER_00
What s the recipient s ICP?
2
SPEAKER_00
So there s a lot of things that go into that to make it that creative.
2
SPEAKER_00
The other thing to remember, I think, with sending gifts, too, is that outside of just what the item is, you can get creative on what the message is.
2
SPEAKER_00
So if you re good at copywriting or if you re a good salesperson that thinks you re kind of witty with your emails, that translates really well into gifting because you can use that in the handwritten note or the printed note and use some of that
2
SPEAKER_00
writing creativity to your advantage as well.
2
SPEAKER_00
And so you might feel like, oh, I can send maybe a less creative gift with a more creative handwritten note, and boom, that is a recipe for success too.
2
SPEAKER_02
I was gonna say, as we close up this episode today, I d like to hear from you on, okay, so again, I m listening, I like the idea, what s the first step?
2
SPEAKER_02
And you also have an event coming up too that might be a good entry point for people as well, is that right?
2
SPEAKER_00
Yes, thank you.
2
SPEAKER_00
On Wednesday, in a couple of days here, we have our Connected annual conference.
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SPEAKER_00
There ll be a ton of speakers.
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SPEAKER_00
We ve got an awesome headliner, Trevor Noah.
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SPEAKER_00
I m going to be interviewing him, which will be fun.
2
SPEAKER_00
There ll be a sales track, a marketing track, a user track where you can listen in to best practices, hear ideas on creativity, get inspired.
2
SPEAKER_00
you know, we should, maybe I should throw out a little bonus for the audience here since we re a gifting company.
2
SPEAKER_00
Sure.
2
SPEAKER_01
I would love this.
2
SPEAKER_00
And this is what I think it is.
2
SPEAKER_01
I m not kidding about the Guinness Book of World Records thing.
2
SPEAKER_01
But go and tell them what it is, and then we ll see if we can call the Guinness people and see if it s a world record.
2
SPEAKER_00
Yeah, so let s get the first 500 listeners here today a little special promo that we ll give them free lunch so they can enjoy this conference on the list.
2
SPEAKER_01
Yep.
2
SPEAKER_01
That s the world s largest sales lunch.
2
SPEAKER_01
You know, there s a quote called never eat lunch alone.
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SPEAKER_01
So not ever don t eat lunch alone.
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SPEAKER_01
You should eat lunch with at least 500 of your fellow ASP listeners at the Sendoso Connected event.
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SPEAKER_01
That s what I m saying.
2
SPEAKER_01
That s a cool thing.
2
SPEAKER_01
We ve got to look that up.
2
SPEAKER_01
I ve got to see the largest business lunch ever.
2
SPEAKER_01
That d be a good little sticky thing to do, wouldn t it?
2
SPEAKER_00
That would be.
2
SPEAKER_00
That would be really cool.
2
SPEAKER_02
It breaks our record of three here at the Advanced Selling Podcast, because we had breakfast once with a client, I think, that came in town.
2
SPEAKER_02
We did.
2
SPEAKER_02
One time that came in town.
2
SPEAKER_02
Yeah.
2
SPEAKER_02
Don t get any ideas, because we do not.
2
SPEAKER_02
We had to buy.
2
SPEAKER_02
Yeah, we bought.
2
SPEAKER_02
Yeah, we split it, Bill.
2
SPEAKER_02
We went to Pattitude.
2
SPEAKER_02
That s fantastic.
2
SPEAKER_02
OK, so we ll put in the show notes the link to get on that.
2
SPEAKER_02
That would help.
2
SPEAKER_02
That way, if people are driving, they don t have to stop.
2
SPEAKER_02
So we ll put in the show notes.
2
SPEAKER_02
And then the other side of it is, if people are listening to this after the event, how does somebody start with you?
2
SPEAKER_02
What would be a step one?
2
SPEAKER_00
Yeah, so I d say step one, you can go to Sendoso.com and check out our website.
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SPEAKER_00
You can get inspiration from our resources page.
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SPEAKER_00
We ve got Sendoso videos on everything and anything you d want to know about Sendoso.
2
SPEAKER_00
And then you can click on the sign up and request demo and learn more about the product.
2
SPEAKER_00
Or if you have specific questions for me too, I always love talking to people that are interested.
2
SPEAKER_00
So you can email me as well, which is Chris, K-R-I-S at Sendoso.com.
2
SPEAKER_02
Thank you, Chris.
2
SPEAKER_02
It s a dose and also dot com.
2
SPEAKER_02
OK, got your last name.
2
SPEAKER_01
Yeah, thank you for that.
2
SPEAKER_01
Very smart move, man.
2
SPEAKER_01
That was a gift right there.
2
SPEAKER_01
That was a gift.
2
SPEAKER_01
Yeah, well, we ll have Chris come back to a future episode also and talk about I would talk a little bit about experience and just overall.
2
SPEAKER_01
Yeah.
2
SPEAKER_02
Kind of customer experience, how important it is, why it s so important.
2
SPEAKER_02
All those things.
2
SPEAKER_02
All right.
2
SPEAKER_02
Thanks, Chris.
2
SPEAKER_02
Appreciate it.
2
SPEAKER_02
Thank you.