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All right, we're back. I'm Pouyan from Scratchpad, and riding shotgun again is Ross.
Ross (Corporate Bro) (00:20):
AKA Corp- AKA Corp Bro, to those who know me. Only Pouyan and my mom call me Ross, so what a treat.
I'm super excited for the conversation we've got lined up today with Kris Rudeegraap, CEO of Sendoso.
Kris Rudeegraap (00:33):
Thank you so much for having me, guys.
What an incredible story you have, though. From payment processing sales to selling marketing solutions to being an AE at Talkdesk, incredible company, and then a jump to founding a company. And not only that, a super successful company now doing incredible things. So, how do you go from AE to founder of a company?
Kris Rudeegraap (00:57):
I think the answer is lots of money with no money overnight, so that was the first thing. And really, just the pain of being an AE who isn't really trying to send stuff out spending my hours packing boxes versus closing deals. And you know, I decided, ‘Hey, I need to do something about this.’ Marketing would always yell at me for stealing swag from the swag closet, and I was like, maybe, I'd always try to, expense-
Ross (Corporate Bro) (01:22):
Of course they were, of course they were. I mean, that's the thing: the swag.
Kris Rudeegraap (01:26):
I decided like ‘Hey, if I created a software where I could click a button and use their money to send these gifts, then I'd be happy’. I'd close more deals and make more money. And so, that was like the whole starting factor, just the pain of kind of the marketing sales alignment.
Ross (Corporate Bro) (01:41):
Okay, so how long were you working on this like as a side project? Like, I think a lot of people, they assume you have to just jump.
Kris Rudeegraap (01:48):
Ross (Corporate Bro) (01:48):
Right? And usually there's a lot that goes on behind the scenes that kinda builds you up to the actual jump. Can you talk about that process? Was that while you're still working?
Kris Rudeegraap (01:55):
So, Sendoso version was actually called CopyCenter.com, and so the first version was five grand on Upwork to make a Salesforce app that you could click a button. It says ‘Send coffee’, and it sends someone a Starbucks E-gift card. It's kind of a simple model connected to Salesforce. And my ultimate goal is if I could get 10 or 20 of those a day, that's like two free beers when going out in the city. And so, if I could just do a lot of coffees being sent, that's a lot of free beer money. Uh-
Ross (Corporate Bro) (02:26):
That is how you should think about it-
Kris Rudeegraap (02:27):
Ross (Corporate Bro) (02:27):
How much beer is this worth?
Kris Rudeegraap (02:29):
Ross (Corporate Bro) (02:30):
That is the best unit.
Kris Rudeegraap (02:32):
Yes, who needs revenue? You just need beer units. And so it got to a point where I had more beer than I could drink, and so it was like, ‘Okay, there's something real here’. It also helped that my company-founder Braydan was also another AE, so two AEs starting a startup is kind of twice as unlikely to be successful, I guess you could say in some cases.
Okay, so, so we're gonna have Braydan on as one of the next guests, just to validate everything that Kris is saying.
Kris Rudeegraap (02:56):
Kris Rudeegraap (02:57):
He was crazier than me, and then he jumped ship. He left his last company about four months before me and started full-time selling coffee. And I was like, ‘You can't sell coffee full-time’. This is like a beer money company. But he proved me wrong and was just closing a ton of logos that wanted to just spend 10s of thousands sending coffee gift cards.
Is Bra- I, I mean, I'm speechless. What, what kind of beers were you drinking?
Kris Rudeegraap (03:24):
Yeah, it would be San Francisco draft beers, so those are like, you know, 10 bucks a beer.
Yeah, I was gonna ask, 'cause I was doing the math in my head. I was like ‘Wait a minute, I could probably make that money stretch a little bit farther, though, to more than two beers’. But let's go back to early, you know, young Kris coming up and just getting the first job. Like how do you end up in sales?
Kris Rudeegraap (03:45):
I was actually, kind of an entrepreneur, I'd say by birth. I was always hustling, like back in the day selling lemonade. I had a Christmas tree farm close to my parents' house, so I'd sell mistletoe near the holidays and just make a boatload of money that way. So, I think sales and entrepreneurship were in my blood. In college I had a startup that was an online rental listing company to find housing close to college campuses. So, I kinda was able to kind of learn by doing in terms of some software entrepreneurship in college. And I sold that to a company called Yapstone. And from there I went into marketing initially for probably about six months. I know you're probably gonna choke, uh-
Ross (Corporate Bro) (04:29):
Ew, well, sorry-
Kris Rudeegraap (04:30):
Sorry for saying that.
Ross (Corporate Bro) (04:31):
Is it a prerequisite to be at Chico state, then go into sales. I feel like you either went to Cal Poly or Chico state if you're in sales in the Bay Area.
Kris Rudeegraap (04:38):
Ross (Corporate Bro) (04:38):
Like it just is. It's over like 50 percent of all salespeople.
Kris Rudeegraap (04:41):
Exactly. Oh, they're very social institutions, so you, you learn to talk.
Ross (Corporate Bro) (04:48):
Kris Rudeegraap (04:48):
Ross (Corporate Bro) (04:48):
You learn to party, I believe is what you were gonna say.
Kris Rudeegraap (04:49):
You gotta talk to party.
You said at some point you learned sales as your calling. What called you?
Kris Rudeegraap (04:56):
I think probably money, to be honest-
Ross (Corporate Bro) (04:59):
Kris Rudeegraap (05:01):
... be real.
Ross (Corporate Bro) (05:01):
That's what's up.
Kris Rudeegraap (05:01):
Ross (Corporate Bro) (05:01):
Kris Rudeegraap (05:02):
Ross (Corporate Bro) (05:02):
Now we know he's telling the truth.
Kris Rudeegraap (05:03):
You know, there's a thrill and a rush of getting someone on the call or sending someone an email, getting them hooked, getting them on a demo, closing the deals. And then you just wanna do it again, and again, and again. So, I think it's, if you get good at sales, it's just like a drug where you just wanna keep doing it.
Ross (Corporate Bro) (05:18):
When you think back to the snapshot of your sales career, like what are some of the instant stories that you think of in your mind? Like any ridiculous, like wins or losses, or like experiences where you're just like, this one kinda just epitomizes my experience?
Kris Rudeegraap (05:34):
I mean, I, what I remember is I really loved to try to create happy ways to break into accounts or to get more meetings. So, I created a mail merge tool from - I'm big on Upwork. I've probably spent like 200 grand on Upwork, on like-
Ross (Corporate Bro) (05:51):
I love Upwork too. I use it all the time.
Kris Rudeegraap (05:53):
I just like to get people to make me these tools. I hacked together and made a sequencing tool through Upwork and some engineers that would pull lists from Salesforce and then email them and update fields. I built this other like ‘Where's Waldo’ tool, which would take the prospects' LinkedIn photo and overlay it on a Where's Waldo map, and then I'd use that image and drop it in the email and-
Ross (Corporate Bro) (06:12):
I did that with a milk carton! The missing person milk carton, and this woman - I did send it to a bunch of people to great success - but this one woman was so offended by me just like “there are real missing people out there”. And I was like, yeah, and I was concerned, okay?
What else was it that set you apart? 'Cause you, you're clearly successful in what you did.
Kris Rudeegraap (06:30):
Yeah- I was also great at Salesforce. I know it's kind of funny to say, but, uh-
Like did you practice on weekends or something?
Kris Rudeegraap (06:40):
Well, I was like, (laughs) I wouldn't say I was practicing, but I would either try to be like the Salesforce admin or I'd know how to run all the reports. Or I'd know where Marketo was losing leads in the system and I'd have that report and I'd have like 30 of these like backup accounts that were getting nurtured, and then I'd take them once they hit a score that no one else knew how to report on.
Ross (Corporate Bro) (07:02):
How is your mentality or thoughts around sales change, now that you're at the top?
Kris Rudeegraap (07:08):
I mean, I've always thought really highly of marketing.
Ross (Corporate Bro) (07:14):
Do you hate me? Like are you trying to hurt me right now?
Kris Rudeegraap (07:18):
I've always thought really highly of sales, so I think that sales teams might not be getting the best rap, or they’re like ‘Oh, sales is an easy job’. And so I was very, upfront that sales is like a super important job early on. We had SDRs. In our first kinda 10 people we had SDRs as the key hires early on. I really wanted to build this outbound engine that supported a model where we could have AEs that didn't have to fully focus all their efforts on outbounding, but they could focus on closing deals and build that engine.
Ross (Corporate Bro) (07:54):
Got it. Sounds like the dream. Every AE is listening to this is going to look for jobs at Sendoso right now, just like, ‘Where I don't have to prospect? Are you joking?’ But how do you think about now as a CEO, like at some point you're gonna do a seed.
Kris Rudeegraap (08:06):
Ross (Corporate Bro) (08:07):
And you're gonna try to scale even more aggressively.
Kris Rudeegraap (08:11):
Ross (Corporate Bro) (08:12):
How do you do that and think about that, and not totally just fucking over the sales team and scaling too fast, and trying to like hit outrageous numbers because you took on funding to like blow it.
Or let go of half the team?
Ross (Corporate Bro) (08:24):
Yeah, then let go of half the people, and then your favorites are gone too and everybody's mad.
Kris Rudeegraap (08:27):
Yeah, so we're methodical in that we kind of step stair and I'm not gonna let VCs push me around there either where this is my company to run.
Ross (Corporate Bro) (08:37):
Kris Rudeegraap (08:37):
(laughs) You know, not to talk good about marketing, so close your ears, but we wanna make sure that there's lead flow that's coming in, so we're not overflowing the sales team with headcount, but also not enough inbound to make up for that. So we have a really strong 50/50 amount outbound model right now. And if you look at the SDRs that are contributing, like the AEs right now, they were above quota capacity like at the end of last year where they were closing. Like we needed more butts in seats.
Ross (Corporate Bro) (09:10):
Don't you think sales development is sales? Why does it have to be marketing when the first word is sales?
Kris Rudeegraap (09:17):
Yeah, it's an interesting topic. I mean our sales team actually lives in marketing, so they report-
Ross (Corporate Bro) (09:25):
Why would you do that to them? They're people.
Kris Rudeegraap (09:29):
(laughs) I know. So marketing is enriching and putting in all of our accounts in Salesforce, because SDRs aren't going to find their own accounts. Like very early on, day zero, we enriched all of the accounts in Salesforce, so our first SDR wasn't spending time enriching data, or what lead they should go after. They had their target lists, so marketing's doing the target lists. Marketing is helping create some of the content like the product marketing talk tracks. There was a good synergy to have them next to each other. And ultimately driving demand in.
We have a lot of folks that are going to be listening to this that are probably where you were maybe at Talkdesk or a little bit before that, right? How do you go from being the rep with the quota to becoming the founder? How is it that the stuff you learned in sales not only helped you identify the problem, but tactically build the company in the early days? Or even say, ‘Hey, is this even worth building’?
Kris Rudeegraap (10:28):
You could either put on your Oculus and play some video games, or you could spend a couple hours mocking some stuff up on some software, dragging and dropping some arrows around and trying to use your time that way. You can get away with a working version for using resources like Upwork, and using some design tools online and put something together that's not crazy tough. I think I got an idea. What would it look like on the computer? Let me draw it up. Let me see if I could find an engineer that can let me put five grand into it. And each of those things are gonna kind of unlock new opportunities. Maybe you realize that this version is crap, but you learn that customer that you talked to wants this, and you take down another rabbit hole. So, you're really just creating opportunities for yourself, and opening new doors by kind of getting outside of your comfort zone. I'd say there are no excuses. Just get shit done and get out there and find some piece of paper that you have in your desk, draw something, and then turn that outline, and then post it on Upwork.
Ross (Corporate Bro) (11:29):
There's so much, there's, you said a lot there, and I think there's two pieces. And this is what I tell, people are always like ‘I wanna, you know, let me, let me come be one of your videos. Let me come like do, I don't know, whatever Corporate Bro shit I'm doing at the time’. And it's like, ‘Sure, Saturday morning, 7:00, 7:00 AM I'll be at the office here.
Kris Rudeegraap (11:44):
Ross (Corporate Bro) (11:45):
And I'll be shooting this thing. It's like, oh, shit, well, you know, I'm like going out Friday night, and so it's gonna be tough for me to get up. That's a choice you're making. Like there's so many choices that we could just make differently.
Kris Rudeegraap (11:56):
Ross (Corporate Bro) (11:56):
If we wanna go down that route, and also recognizing, I think, one of the things that gets underappreciated. It's just like the goddamn grind of when like nobody is around. Like when you don't have the product, when you're there on those nights and weekends trying to figure some shit out. And the gears are turning, but then also you talked about just having your antenna on at all times of like to the problem. One thing you did, you do this naturally is you're seeing the problems and recognizing ways. And maybe I can solve this problem versus just like, goddamn that's just an annoying problem that's there. Updating Salesforce. I can raise millions of dollars. Pouyan, if it, like-
Is that a thing?
Ross (Corporate Bro) (12:30):
... Salesforce sucks.
Ross (Corporate Bro) (12:31):
Shit, we should start that.
Ross (Corporate Bro) (12:33):
No, I got a 10 right here if you need some funding. What does that get me?
Kris Rudeegraap (12:39):
I was gonna say, you said one of the thing that I'll chime in on is that how did sales help me in my endeavors of being a CEO. A couple things that were really apparent was day zero I wasn't as afraid to talk to customers. We were selling the slide deck before the product was ready with a bunch of screenshots. I think my sales acumen has tremendously helped with prospecting into candidates and selling them the dream, and demoing them and getting them excited about Sendoso. So that I think is another thing. And then, shit, raising 55 million bucks in funding, I had to convince some investors with a nice little shiny -
Ross (Corporate Bro) (13:16):
A lot of beer.
Kris Rudeegraap (13:17):
It is a lot of beer.
You know, my last company, we went through Y Combinator, and then I would go back and talk for a lot of batches on, you know, the sales bootcamp. And I'd give this talk on how to do outbound because a lot of folks that are in my seat have the idea and building something, but then it's like ‘How do we actually get this to market?’ And I think what you said, if I could double click, triple click, quadruple click on it, is it’s never too early to start outbound.
Kris Rudeegraap (13:45):
In fact, that's what you should start with. In that process you learn so much about your market, your customers, why they're making the decision they make, how they purchase, um, what's important to them. I don't know about you, but for me, fundraising is a part of building a company I just dislike the most. It's a necessary evil, depending on the type of company you have to build, but it's just filled with lots of rejection.
Kris Rudeegraap (14:09):
And I feel like if you're in sales, guess what, you get to deal with a lot of rejection and you build up your resiliency, you know? Regardless of what type of company you're building, that resiliency is what matters.
Ross (Corporate Bro) (14:20):
Oh, I think that's likethe biggest thing is collecting signals, and the only way you're gonna do that is by actually getting out, right?
Kris Rudeegraap (14:25):
Ross (Corporate Bro) (14:25):
Like, period. Whatever those signals are, good or bad, that is all data.
Kris Rudeegraap (14:29):
I think the true test is can you build like an outbound engine and a go-to-market engine, and how soon can you build that to show success that you could repeatably take some cold leads and turn them into money. And as quick as you can learn that process for your product and the messaging that delivers that I think is crucial.
A lot of investors I've talked to will actually have that as a qualifier. If you go in and say, ‘Hey, look, we've got X number of customers’ and they’ll say, ‘Okay, how many of these are customers with zero connection?’
Kris Rudeegraap (14:57):
Yeah, that's great.
And one of the things we did is we actually set a bar for ourselves to start. We're not going to count anybody that we have a connection to and say, ‘Can we just fast forward and say can we get users or customers that we have no connection to whatsoever?’
Kris Rudeegraap (15:12):
'Cause if you can do that, even if you get one, you'll probably get two. And if you get two, you find your way to get there. And so, I think just pushing yourself outside of that comfort zone is so key.
Kris Rudeegraap (15:23):
Ross (Corporate Bro) (15:24):
We have like one very important question. Well, it's kind of like a two part important question. I'll let Pouyan ask it. It’s not gonna blow your mind by any means, but it's important for us.
So, what's your hype song?
Kris Rudeegraap (15:36):
My hype song?
You're going in to close that series C-
Kris Rudeegraap (15:39):
... and then the series D - what song just gets you going on that? And then what is your, well, let's just start with that.
Kris Rudeegraap (15:47):
Yeah, so it's ‘Count it up, count it up’. I don't know if you heard, you know that song? ‘Count it up.’ I don't know who sings it.
Ross (Corporate Bro) (15:54):
Oh, J. Cole?
Kris Rudeegraap (15:56):
J. Cole. (laughs)
Ross (Corporate Bro) (15:57):
Okay. That's a deep cut J. Cole song.
So the flip side to that, when you just get that terrible loss, that punch to the gut, they went with the competitor, they said no and they completely screwed you over, what's your recovery song?
Kris Rudeegraap (16:14):
I'd probably just like sulk in, in quietness, in silence.
Ross (Corporate Bro) (16:17):
That's the second time we've gotten this answer.
All right, Kris, this has been awesome, man.
Kris Rudeegraap (16:21):
Thank you so much. If anyone wants to get in touch with your or follow up on your end of this, how can someone get connected to you.
Kris Rudeegraap (16:30):
I love the kind of AEs wanting to make the jump, too, and wanting to kinda get into the weeds, so I’m happy to chat it up any time. You can reach me on LinkedIn, search me, ‘Kris Rudeegraap’, or send me an email. It's Kris with a K, firstname.lastname@example.org.
Ross (Corporate Bro) (16:44):
And don't come in there saying you're trying to make the jump and then start pitching some bullshit.
Kris Rudeegraap (16:47):
Ross (Corporate Bro) (16:47):
Kris Rudeegraap (16:48):
Ross (Corporate Bro) (16:48):
Miss me with that, right?
I'm in with a customer, seriously.
Ross (Corporate Bro) (16:51):
Don't connect with him on LinkedIn and then pitch him. That's some bullshit.
Kris Rudeegraap (16:54):
Ross (Corporate Bro) (16:55):
(laughs) Yeah, sales only, if they ask, strictly.
Awesome. Thanks, Kris.
Ross (Corporate Bro) (16:58):
All right, Kris, thanks, man.
Kris Rudeegraap (16:58):
All right, thanks, guys.