The Transaction

TT - 043 - Krysten Conner
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[00:00:00]

Intro
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Krysten Conner: It has never been harder to bring on new technology in an organization.

taking a call with us does not make someone a champion. It makes them a contact.

We have to develop champions and we can figure out whether people are receptive to that or not, but we don't have to wait.

We have to teach buyers how to buy, buyers are experts in how to do their jobs.

They are not experts in how to buy our thing.

Craig Rosenberg: Let's see, how late was I? Five minutes? Four minutes? Did you, by the way, Sam, did you catch the other day when Matt goes, I forget what he said, he's, it was like, maybe Christmas gifts, you're like, Matt goes, I'm gonna get Craig an alarm clock, cause I was 35 minutes late to the recording.

​[00:01:00]

Craig Rosenberg: so Kristen, I gotta tell you, you know, when we, we had, uh, Orlob on the show, we found him twice, but at one point, uh, There was a, he had come on and there was a LinkedIn post about the multi threading and we're like, Hey, can you tell me about multi threading? He's like, no, you got to talk to Kristen Conner about that one.

Cause she created that stuff. And that's when I first, uh, started to really dig into your stuff. And so, uh, and now I'm just like a big fan. So I'm so excited to, to, to bring you on. Yeah. And, um, so just so everyone knows today's guest is, uh, is a sales expert and I'd call you coach trainer consultant, right?

Um, that is modern. That's key for Matt, Sam and I, Chris, and just so you know, [00:02:00] because I mean, look, we've had, you know, we, we have old school guys cause they got a lot to say, but like selling SAS in today's world requires. a significant relook in the playbook and you're one of those people that talks about the right things, um, speaks about the rights about the right things.

And so yeah, you know, you had years of selling experience and and now you're sort of, you've taken that and you've become a a thought leader in the sales execution space. Um, it sounds, you know, you do training. So with Chris on P club, you have your own business, right? Um, people can go to kristenconner.

com for that and people can just follow you to get a feel for, I mean, hopefully the podcast will help them sort of see the beauty of what you do, but also your, uh, you know, the stuff that you're putting out there or through, you know, if they, Uh, if they, you know, happen to see you through any of the other sort of channels by which you deliver some of your [00:03:00] insights, but it's a real honor to have you on the show, Kristen.

And, um, we've been excited about it. It's a new year. So like, uh, we've, we haven't had a sales specific person on in like a month and that's rare for us. So like, uh, it's great to have you as that person to break the 2025 ice. So welcome. to the show.

Krysten Conner: Well, thanks so much for having me and thanks for the very kind words. Yeah, Orlob's been Super fun to collaborate with. We've done two, um, courses with them now. And yeah, to your point about sales being different now, it is. And it's a matter of, you know, how do we, and I think a lot of it is for the better, right?

It's more, uh, I think it's,

The "Let Me Help You Get this Car" Story
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Krysten Conner: Hopefully more transparent, hopefully more conversational, hopefully more buyer centric versus like, let me come alongside and help you versus like, what do I need to say to get you in this car today? Type of a type of emotion.

Craig Rosenberg: [00:04:00] Yeah, by the way, you guys, I have a funny story on. Let me help you get this car. So I, we had a buddy growing up. Um, it's, there's a sad part to it. It is important context, but like, he was like, he was like, uh, it's just a great friend of ours. He got in a bike accident. We're in fourth or fifth and he was actually in a coma for a week or two, but it really rattled him.

So it changed. And like, it was hard, like he wasn't hanging with the crew, you know, like, and we kept. And, uh, we weren't as close to him. We liked him, but like, we just weren't as close to him. Um, and, uh, you know, we had gotten out of high school. So we're like 19 and like, he didn't go to college. He sort of stayed around here.

And, um, Someone said, Hey, he's working at the car dealership. And so I'm like, dude, that's awesome. Like, you know, like, if you think about it, what a comeback story. And you know, he's like, screw it. You know, I'm just going to go sell stuff, right. And build my business career. And he's, and [00:05:00] so I was like, I'm going to go visit him and just say, hi.

You know, it's like, I feel terrible. Like we hadn't hung out throughout our childhood, whatever. So we go in there and he's so professional. Back then, man, those dudes were all buttoned up. Like, You know, he was probably, he was probably drinking Sanka coffee and whatever, he had his thing. And I'm like, Hey man, how you doing?

Like whatever. And he's like, Oh my God, it's so great to see you. And I'm like, cool. So what's going on? We're sort of in mid conversation. He's like, well, Craig, let me ask you this. What are you doing for a car these days? And I'm like, I'm not kidding. And he's like, well, let me show you this car and let's see if this is not a car that you don't want to drive off the lot today.

I'm not kidding. So like, it was this, I got this thing where I'm like, Oh my God, it's so great to see him. And then he just drops that bomb on me. And I'm like, right, man, I cannot, like, I am not buying a car. I mean, I was just out of college. I was like a teacher. I was like, no, there's no chance. But anyway, yeah, he was going to see if I couldn't drive that [00:06:00] car off the lot today.

So anyway, um, so, um, it again. At least he went with the discovery question, except he didn't ask me. liked and didn't like about my car. He just asked if I had one, you know, so, um,

Krysten Conner: like that was a transition question. I don't feel like we could really say that was a discovery

Craig Rosenberg: yeah, that was a deep discovery. By the way, second fun fact I meant to mention in the, um, the, uh, intro was that we've had a couple ex SalesLoft people on and they're, they went viral for us, so it's really great to have an ex, um, outreach person on, like, just to even cause a glow. Um, yeah. And, um, And so now we're, just so everyone knows, we're evening things out.

All right, so we got two things to start the show.

Matt Amundson: Sam has something to share.

Sam Guertin: I was going to say, you mentioned Cosiglo as a former outreach guy. Uh, no love for Scott Barker. [00:07:00] What's up with

Craig Rosenberg: Oh, well, he hasn't

Matt Amundson: His episode hasn't gone live yet.

Craig Rosenberg: Yeah. Thank you, Matt. There we go. All right. Good, good. Um, so, uh, so there's, uh, two ways we start the show. I, one, I didn't warn you about, so if I, if I, if I put you on the spot here, I apologize, but it's because it's a new feature wrinkle that was introduced by Matt, it's been really amazing.

Uh, just if.

Krysten's Embarrassing Sales Story
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Craig Rosenberg: We want to start the show with a story from you on anything over the, you know, you've must have seen lots, it could be funny, it could be heroic sales story, go to market story, anything like in your, in your travels around helping sales teams that would, uh, be a sort of, uh, fun or interesting or heroic story that you saw last year.

Matt Amundson: Yeah, it can be an old elementary school friend of yours who's trying to sell you a Chevrolet Grand Caprice.

Craig Rosenberg: I kind of preemptively said, uh, yeah, yeah.

Krysten Conner: my gosh. [00:08:00] Yeah. So I wouldn't say last year, but over the years I'll, I will say I have done so many, like, there've been so many embarrassing moments in my sales career. And so what I've learned is like, there is very little that you can't recover from. Like your buddy's question about like, how do I get you in this car?

That might be true. be something that would be hard to recover from. Um, but like, for example, one of my, one of my first, um, bosses in one of my first sales roles, I was selling like large commercial insurance. And, um, so like an insurance to con to like very large contractors. And so we were going to meet them on site and my boss, um, his pet peeve was being late.

He hated to be late. And he had, like, there was like this rumor that he had actually left part of the team, like, when they did not, like, come down to the lobby and, like, meet him on time. So, I mean, it was like, you were on time. So he had gone down to bring his car around, you know, white Lexus. [00:09:00] Three of us out there at the building lobby waiting for his white Lexus to pull up.

See the white Lexus pull up. The three of us each go pull a door of the white Lexus. Only to realize this is not his white Lexus. And the

Craig Rosenberg: No way.

Krysten Conner: Excuse me? Because every door of her car has just been opened.

And we were like, because we were like so focused on get in that car so you don't get left. And so we were like, oh my gosh, I'm so sorry.

And so then we all, you know, we're all like, oh my gosh, we close the door quickly. And they're like, maybe. You know, maybe he, you know, our boss was far enough that he didn't see that, right? That he didn't, he's two cars behind and he guys, he's like, he was not a nice man. And he's like, you are such bozos.

You don't even know what car you're in. And we're just like, Oh my God. Yeah, yeah. So that was, yeah. So that's one. Um, I've asked whenever I was traveling, like more than 80 percent of the time I joined [00:10:00] a, uh, I joined a team meeting on a zoom call, which I did frequently because I was always traveling and I had forgotten to turn the camera off first.

And I was like, literally in the middle, like I have a hair appointment. And one of my peers was like, WHOA! I was like,

Craig Rosenberg: Zoom fail. I love

Krysten Conner: Yeah, oh, I mean, this was before 2020, right? So like, there was, it was somewhat excusable. You know, after 2020 we should all know how to use Zoom. Um, and then there was one time in the, like, I think this was 2019 that I accidentally did what I never do, which is put my laptop in the back, in like the seat back flap on an airplane. And forgot it on the airplane and then, and was like down the tunnel runway and then turned around, which I didn't realize is a huge, like, no, no, you are not allowed to like reboard. I was nearly tackled by like a TSA agent that this airport would have to be hilarious. So all that to say, like, I've done those, all of those things and many [00:11:00] more, and you can still go on and have a great sales career.

And you'll

Craig Rosenberg: are great. Those.

Krysten Conner: of

Craig Rosenberg: Yeah, those are Road Warrior stories. I love that. Um. Those are actually our fir I think that's our fir No, we had some other similar road work. I'm so glad you went with the embarrassing moments too, because like, those are great. It's like, that's full opening with authenticity at its finest, so.

Krysten Conner: You have to laugh or you cry, right? And also like, everyone, once you start, everyone has them. Like, everyone has them.

Craig Rosenberg: Yeah. Totally. Totally. Um, alright, cool. So that's perfect. So Matt, once again, your 2. 1 feature enhancement worked swimmingly here. I love it. And actually, Sam, I think we should not tell people about the story thing in advance too, because it's awesome to watch them come up and be able to riff on the stories.

I think it's great. Okay, but this is one that we were prepared for. So the, the, the, uh, [00:12:00] The, um, the way we kick off the show, um, it just, for context, we just, you know, it's how we started, how I was talking about you, one of the reasons we want you on the show is because Matt and I were working together at Scale Venture Partners and we just kept going, my God, like the playbook has changed, right?

I mean, and it was funny because we were watching and they, like some of the companies we're working with would bring in this person that's got all these years of experience and even had. Let's say a five year run of doing something great in marketing sales CS, Matt, and it would flop because a lot had changed and you had to make adjustments with the time.

So for us, we actually started the show with this idea that could we go meet people like you and understand The changes to, to, and what you need to think about and what you need to do in the new playbook. So the first question is, like, what's something or some things, could be multiple, um, that the market thinks they're doing right.

It could be [00:13:00] methodology, approach, tactics, anything. Um, and they're actually wrong and they should be thinking about it differently. And, you know, what are, what is that thing or those things and what should they be doing? Um, and so we start with that and we'll let you go and we take it from there.

Krysten Conner: Yeah, I saw that prep come over and it's a really smart thing. Question, right? Like I was like,

Develop a Champion, Don't Wait for Them to Show Themselves
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Krysten Conner: this is a, this, and it's a different take. Like there's so many sales podcasts, but that that's a different take. Um, so the thing I immediately came to my mind was a mindset that I think many reps have. I certainly had it early in my career, which is, uh, wait for a champion to show themselves.

Like we have to, we have to kind of wait or it's almost a, it's almost a reactive, it's like a reactive mindset in a sales cycle where you're just like, we have to, I just have to see, we have to be in, you know, we have to be mid cycle before we know, um, if they're really [00:14:00] a champion. Now that kind of also speaks to my experience doing mostly new logo.

Um, so I, every, everywhere I was, I came in as a, as a hunter primarily. So if you, you're, if you're an AM and you're managing a book of customers where you already know people, sometimes you'll have to develop new champions, but a new logo where you're just like, you're talking to these people for the, you know, you're trying to introduce them.

your brand, your company, and you're trying to do this deal, you don't know, like, who's who in the zoo, right? Like, you're still figuring it out, but there is this feeling, this tendency that's like, well, I just have to kind of sit back and wait for it to figure out who's going to be my champion versus, um, I don't, versus being proactive about it.

And there's this phrase of, like, champion testing. I don't really like that phrase because it's Is like puts the rep in like this position [00:15:00] of like this, like what the checkbox like, are you good enough? And that's not what it, that's not it at all. But it's, it's really developing a champion. Like we have to develop champions and we can figure out whether people are receptive to that or not, but we don't have to wait.

There are things that we can do proactively. even after one of the very early calls.

Matt Amundson: Let's, let's get into this. Let, let, I

am, I love this.

Craig Rosenberg: That was provocative. I like it.

Matt Amundson: Yes.

Yeah. Let's get into

Krysten Conner: Yeah, you mentioned pclub of my course with them. This is actually part of my um, second course with them, which is keeping momentum in a sale because we're very rarely taught about that in sales either. You know what it feels like when a deal has momentum, but you, but, and sales leaders will hound you about like, why are we losing momentum here?

But they, there's very little like instruction about like, How do you keep momentum versus just getting blasted for [00:16:00] not having it? And so how do we kind of start that momentum and get it, get things rolling really well, and then keep that up at the, starting at the beginning. And I would say three ways that we can proactively think about how do we know if we have a champion or potential champion.

Number one is. Do they do work asynchronous of meeting with us? Number two is, do they bring other people to follow up meetings? And number three is, do they have a point of view on next steps? Like if you say, Hey, typically, you know, we get, typically we work with CFOs, but also usually a COO has to come in here and then IT as well.

You know, I don't know how that is in your org. Maybe it's a bit different. They should go be able to go off and running from that and be like, no, no, no. In our org, we have to start here, and then this, and they may not have the exact right answer, but they should have a point [00:17:00] of view on how things get done in their organization.

Like, instead of, oh, you know what, before we go to the COO, we really need to get the, talk to the chief of staff, because this isn't going anywhere, unless they bless it. You'll never know that by looking at our org chart. But we'll have to talk to them first. They should have a point of view.

Craig Rosenberg: okay. So, but, but, these are the things we look for, or these are the things we also can cultivate in them? Like, yeah. Tell.

Krysten Conner: Yeah, so do they have a point of view in Next Steps? If they don't have it, that can mean they're new to this org and they've never bought anything here. Right? So it's not necessarily like a red flag if they don't have it, but that's actually an area where we can come alongside them And, uh, I also kind of in the theme of being proactive, I'm of the opinion that we have to teach buyers how to buy, uh, because buyers are experts in how to do their jobs.

They are [00:18:00] not experts in how to buy our thing. And so like, think about, and we've experienced this, uh, personally, if you've had a good realtor, right? Like a realtor kind of should, a good one should teach you how to buy a house. Right? Like, well, first you have to get it inspected and then we should do this and you should probably have a structural engineer take a look at it, right?

Like they're selling it to you. They're gonna make some commission, but they should be teaching you how to do this, right? So it's like we can do that in a, in a B2, uh, in a B2B capacity, not just B2C. Um, so a simple kind of way of trying to develop a champion and seeing if they're willing to do this.

Examples of Asynchronous Work that Champions will Do
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Krysten Conner: So examples of, Asynchronous work that they can do. Will they collect some data that we need and, and bring that to the next meeting? Will they have an internal conversation with a peer of theirs that's going to help inform our next meeting? [00:19:00] Will they ask somebody internally to do a relevant. Task on their behalf.

If they're a VP, will they ask a manager or an IT director, Hey, can you, can you pull this data from me? Right? Will they ask somebody to do something? Will they, you know, will they have someone come on the next call with them? Will they forward, will they forward an email when we ask them to do it? Like it's not hard things.

Like it's just these very simple, um, You know, like, very simple, like, relationship things where we figure out how, how willing are you to, to be a partner on this with me? And we start slow, right? Like, you don't, just like we don't ask somebody to get married on the first date, right? Like we ask, what restaurant do you want to go to next?

Right. It's like, it's simple. It's baby steps.

Matt Amundson: So let me ask you a tactical question because I'd love a little clarity here. So would you say, like, let's say you have a discovery call, you're having an [00:20:00] early stage phone call. If there's multiple people on the call, are you saying like, Hey, you know, as a next step, we're going to need to see a data set that looks like this.

And then are you watching for who brings that data set back and then identifying Them as a champion, or are you thinking about like, Hey, I'm gonna assign of the four of us on this call, I'm gonna assign Craig that work and see if he brings it back.

Krysten Conner: Yeah, so ideally what happens is when we say, hey, to do, to do this next, to do the next thing, we're going to need a data set. Ideally, if we have leaders on that call, what leaders do is delegate, right? And so ideally we have a leader say, hey, Martin, I'm going to have you do this, or I'm going to get my EA involved.

And this person is going to go get, go run this down for us. Right? So hopefully they're being, when we say that, hopefully they're being proactive. If not, then yeah, then we can ask, like, Hey Matt, would you be the right person to, to run this down for us? Or do we need [00:21:00] to, do we need to bring somebody in? And their reaction to that will tell us.

a lot, right? Um, and then also like after that, after that call, we need to be individually following up with the people on that call.

And because we don't, I, because like an army of champions is better than just one, right? And it's not just, and incidentally, It's not just better for us. It's better for them to have multiple executives saying to a CFO, we want this thing, right?

Because then when, when they buy this thing, it's not just one executive's name who is attached to that, who is, who has the risk then of, if this fails, my name is attached to it. Versus If we have five people, 12 department heads saying we want this, like, only is it better for us? It's not a selfish ask.

It's actually better for [00:22:00] them too.

Matt Amundson: Mm-hmm . Mm-hmm . Mm-hmm

Craig Rosenberg: That's amazing. Wait, you guys, I hate to do this. I forgot the second one.

Matt Amundson: Oh geez. It's, do they bring other people?

Craig Rosenberg: Oh, so those two things kind of go together. Right?

Krysten Conner: So, so will they do work asynchronous of meeting with us? Do they bring other, yeah, do they bring other people to the next meetings? And then the third one was like, do they have a point of view on what comes next?

Craig Rosenberg: That's awesome.

Krysten Conner: on the prep, it mentioned like, you know, like a lead behind, I actually have those two things, like the, like two slides that I'll, that I can, if whoever's just send me the best email and I'll send it to you so people can see it.

Sam Guertin: Awesome. and Sam, what are we gonna do with those?

Link them in the show notes and probably put an image right here.

Craig Rosenberg: Yeah, we should put, we'll do an image on her video cuts.

Right? Or is that

Sam Guertin: Yeah, and in the full episode.

Craig Rosenberg: Yeah, a little.

Sam Guertin: we'll link them in the show notes.

Craig Rosenberg: Look at that. Look at the [00:23:00] synergies. I love this. Okay, so I think, I think this is actually, it's amazing because there's so many things in sales where you kind of. listen and you're like, God, that makes sense.

And you never thought of it. Like, so like it, that was a remarkable, uh, start to the show. The, um, what do you, but what, so you think today you would describe how we cultivate, we don't cultivate champions. We hope they raise their hand as one. Is that kind of, yeah, that's one. Uh, the second is I think, uh, salespeople assume that the first person they do a call with is their champion.

Is that

Krysten Conner: Oh my god, that's such a pet peeve of mine. Like,

Craig Rosenberg: right. I got one. Right. taking a call with us does not make someone a champion. It makes them a contact. We have no idea. We have no idea whether they will be a champion or not. I have had people take calls with [00:24:00] us because they favor a different solution and they want to see our demo so they know how to set up the evaluation process.

Krysten Conner: So they know what they're up against in the

evaluation, right? I've had people take calls with us. So because they have to, because of regulation or internal policy, they have to do due diligence and have three things, and they already know which one they want, but they have to do due diligence and go find out information.

That's what we call column fodder, right? You've just become information to get plugged in, plugged in in their column to show they do. Due diligence. Taking a meeting with us does not make someone a champion. It makes them a contact.

Matt Amundson: Mm-hmm . Mm-hmm

Craig Rosenberg: Okay. Oh, that, that, that's great. So if you, um, if we were going to, uh, help someone think about this. So, you know, the asynchronous works. So basically we want to set sales up with this idea of, Like, what is that, uh, asynchronous work? We could ask each of the [00:25:00] potential call, you know, potential champions that were on the call, um, to go bring something to whatever next step is in someone's sales process.

So, so we would enable against, uh, something like that. The second part would be like, we're. Is that more of like, uh, uh, just like, uh, a thing of, uh, a set of things that you would do in the closing moments of a sales call to try to ask them about bringing other people or do we test them and set up the next call and see if they bring other people?

Uh, that was my, I'm going to give you all my questions in a sec. And then, um, I actually got the last one, the last one we sort of dug in on, but on the other two, like in terms of helping sales go execute against those top two, like, uh, Those would be my questions, like how do we put those in play?

Krysten Conner: All right, are we talking about asynchronous work or bringing other people or

Craig Rosenberg: I would do, we could, uh, both, but let's start with two, cause we haven't dug in on that.

Champions will Bring More People to Follow Up Sales Calls
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Krysten Conner: So when we think about bringing [00:26:00] other people to the meeting, um, I am of the opinion, especially in enterprise, that we should be teaching buyers how to buy. And so when we get on that call, especially in enterprise, I should say, You know, we've gone, we've gone through the discovery call and been like, Hey, Matt, I appreciate you joining today.

It sounds like you're seeing some value and there's a, there's potential that we could be solving this problem for you. Lots of legwork yet to do to, to really prove that out. Typically, typically is a magic word and we can talk about that in a second, but typically is a magic word. Typically what happens next is One of three things.

We either do an in depth demo, you and I, and maybe some folks in your department, so you have a real solid idea of what we do. Second is, there are usually three departments involved in buying my thing. it's [00:27:00] it's operations, it's HR, and it's IT. And so in looking at your org, I would imagine Sarah, your VP of IT.

And Chris, your seat, you know, your VP of operations. I would imagine that's probably who needs to be involved or whose team needs to be involved. Every org is different. Is there a different next step that you think would be better? Right? Because I am like, I used to be, I heard you say you used to be a teacher.

I used to be a teacher. Uh, no one likes essay questions. Everybody likes multiple choice, right? Like I want to, I'm offering you a choice and saying like, and I use the magic word typically, why typically is magic is because We are, the psychology of sales is like what I love about it and why it never gets old.

As, as human beings, we are herd mammals. We feel safe when we do what other people are doing, right? Herd theory. So think of, and from [00:28:00] a B2C capacity, that's why Amazon tells you, or every other shopping website tells you, people who looked at this also looked at this. People who looked at this ultimately bought this.

Or they show you three, um, you know, good, better, best, and they say most common or most often purchased, right? That's typically in a, in a B2C capacity because we want to know what everyone else is doing. And it feels less risky, right? Like, oh, I'm making the choice that other people made. Got it.

Craig Rosenberg: Yeah,

Matt Amundson: At least if I'm wrong, we're all wrong together.

Krysten Conner: Right. It's, it's less risky because other people have done it this way. And if I don't know how to do it, and you're telling me most people do it, but I'm also leaving it on notice. I also left it open ended and allowed for the fact that it may be very different. in your organization. And if you [00:29:00] are a savvy buyer who just brought on new technology for a different thing three months ago, you probably know the better path in your org.

You may know that there's somebody in procurement that we have to bring in right away. Um, I dealt with two VPs, um, at a large cybersecurity company. They both wanted it, uh, what we were selling. And they both said, before we show this to anyone else, we have to bring in. This IT executive, because if he doesn't, if he can't fit this on the roadmap, or if he believes that this will mess up our integrations, this will go nowhere.

And that was fantastic because like they knew how their organization worked.

Matt Amundson: Yeah, so this is the number one problem that I see with early stage, uh, I guess startup companies that are selling either disruptive technology or a novel technology. No one knows how to buy their product. No one. Right? [00:30:00] And they oftentimes end calls the same way, right? Like a very, uh, sort of inexperienced account executive will end the call by saying, so what do you want to do next?

Krysten Conner: What do next? I was like, I almost let, I almost asked you to let me predict what that phrase was. Yeah. Where should we go from here?

Matt Amundson: Exactly. And they don't know because they've never bought it. Well, I have no idea. Right? So the thing that I've always said to people is like, suggest something based upon what most people do. But I like your take on typically because most almost feels like, Oh, well, everyone does this. But if your organization is different or if there's a different process or whatever, it feels like very exclusionary.

So I like the phrase. I like the word typically there.

Krysten Conner: Right. Yeah. Like phrases matter, small things matter. And I would say if you, to your point about startups or like disruptive technology or like new technology, people don't know what it is or, and or any organization that has brand new salespeople, like new. [00:31:00] org. Um, I have never ever been enabled as a new seller coming into an organization with any sort of like Spreadsheet of like, here is the technical, like part of the evaluation, like from start to finish, here is what happens in our sale.

And so what that now I am a self starter, you don't need to hold my hand. And so I will go find your top sellers and make them tell me. What is I'll listen to their, you know, call recordings and watch what they say. And then I'll ask them, okay, this is what I think the sales process is. This is what I think happens on the second call.

This is what I think I should be suggesting and have them tell me. Organizations should be taking that knowledge from between people's ears, whether it's the founder, who's done the first million dollars worth of sales. or the other salespeople there, and writing down. This is what typically happens after the first call, but it could be these two [00:32:00] things.

This is what typically happens after the second call. It could be these two things. You will speed up your sales cycle, um, immeasurably when you just tell people how to guide that process, because if no one knows what to do next, That goes nowhere.

Like it is hard to buy something. It's hard to buy something because it's change management.

It's hard to change. And if you, if so much about sales is like, our job as salespeople is like understanding what's in it for them, what's in it for me, for everyone involved, and friction reduction, making it easy for them to do the next thing.

Craig Details how he Landed his First Girlfriend
---

Craig Rosenberg: By the way, I, if, if you guys don't mind me interjecting a fun fact, is that

Matt Amundson: Please, Please,

Yes.

Craig Rosenberg: my first girlfriend in middle school, I wrote, I ripped off a piece of binder paper and wrote, will you go study with me? And I drew the box, yes, and the box, no. I gave her

a multiple Choice. Yeah,[00:33:00]

Matt Amundson: Well, we're all here with bated breath, man. What happened?

Craig Rosenberg: well, I did say my first

I said my first girlfriend, uh,

but the

answer was yes, the answer

was yes, but not from the note.

I didn't get the note back. I, we talked after and she said yes. So,

Krysten Conner: She was a smart negotiator and understands that all the best negotiations happen in person and

not like

Matt Amundson: Did she do any work? Did you have her do any work asynchronously for you just to determine whether or not she was a champion for the relationship?

Craig Rosenberg: Yeah. Okay. The, the, let's go. Yeah. That, that, by the way, that was really helpful. Um, and then number one though,

Who Should be Doing Asynchronous Work Within The Buying Committee
---

Craig Rosenberg: on the asynchronous work. So let's say, um, this is new to, this would be new, I'm sure to a lot of your. The people you work with. So am I developing, I'm assuming I'm looking at the sales process.

I'm thinking about what the next step is normally. And then I'm thinking about what things can I ask them to go do and bring to [00:34:00] the table. It could be number two, by the way, like it could be bringing people, you know, bringing people, but like the, um, do we codify this? Like, is this, this is something that we would, I'm assuming, as you said, we'd go write this down.

Uh, like what do we do? So we're looking at the next step and we're saying what things could we ask them to go do, or how should we approach that and implement, um, number one into our sales process.

Sam Guertin: Oh,

Craig Rosenberg: I

Matt Amundson: is, no one, no one's ever

Craig Rosenberg: to do that.

Matt Amundson: No one's ever done it. I love

it.

Craig Rosenberg: I had

a thought. I was like, and I got a real, I actually, while you were on, I got a really weird message on my screen from someone, you know, someone separate. So I was like, anyway, all right, what do we got? So, uh,

this

is

Krysten Conner: to do with that information. I

Craig Rosenberg: It's all discovery data.

Yeah, this is great.

Krysten Conner: mean, and these are, so this way, [00:35:00] we're not, we're not asking, uh, we're not asking people to do the same thing, right? Like, because one department is probably going to have the data that we need. And if we have leaders on the call, the somebody else that they're probably going to bring, that we probably want them to bring to the next call is, um, like a manager or a director from their team that is going to do the heavy lifting.

or the end user that's going to do the heavy lifting of the evaluation, right? Because leaders look at something and decide, is this something we're even, that's even aligned with our goals or is going to, you know, help us de risk something? Are we going to move forward on this? And then they send what I call like the scouting party.

Right? Like leaders come in at the, if we have leaders involved at the beginning, they're involved at the beginning and then they dip out while other people do the more technical evaluation. So then, and you know, that should be ideally, they're going to go talk to [00:36:00] that person on their own. But that's definitely something we can suggest.

Like, Hey, at this point, I'd usually ask, I'd usually say, we need an IT manager. Take a look at this just to, they're going to want to know if your integrations, if we're going to mess up your integration. So we might as well take a look at that now so we can answer all those questions.

Sam Guertin: so, so what Kristen, uh, just did, if I can interject, uh, for any of the audio listeners, uh, is, um, She shared her screen, uh, and it's part of a wonderful, uh, leave behind that we will have linked in the show notes, uh, with some examples of asynchronous work for your champion.

Craig Rosenberg: Okay. Well, flow flow has now been disrupted. I mean, Sam, that was a good interlude. I know, but like the moment of silence after we're not, we're just ready. So the, what I was going to say, you just brought up, I just want to, uh, either reemphasize or double [00:37:00] click, which is in most cases, our sales reps are starting lower

Matt Amundson: go. Mm. Mm hmm.

Mm hmm. Mm hmm.

Craig Rosenberg: and they're, and so, because the exam, I get the, um, you know, if we get the executives, which we've sort of.

Uh, you know, I'm brought up here. Obviously, I think, you know, that's, you know, that's great. And they're, you know, looping other folks, but in most use cases, in particular, if demand is being generated,

uh, you know, marketing or whatever, yeah, it's going to be bottom up. And so is the asynchronous work to bring in their executive or is the asynchronous work to build the use case or what do you see most often there?

Krysten Conner: Yeah, it could be, could be either. Um, so a lot of times for, and, and. And it is more typical that we would start lower than leaders. Um, it's much faster if we can start at the top that that, but we have an [00:38:00] S-D-R-X-X-D-R motion where they're making calls. It's just much easier to get like a manager or director on the phone, right.

Than it is a, a VP or COL. So it's not unusual. And so, yeah. So they like a manager or a director. Someone who cannot sign something, like they can't sign a purchase order. So in my view, they cannot be a champion, but they can be a coach. A champion is someone who has power, who has

the power to sign something, right?

But, we don't need just champions, we need coaches as well, who are gonna teach us, like, how to navigate the Orc, who can be an advocate. For us who understand, um, how, what we do benefits them and the teams they lead. Um, we, and you know, sometimes sales reps are told like, you know, get high in the organization, get to leaders.

That's important. Multi threading, especially in enterprise. We have to be present at three levels in the [00:39:00] organization. Like we have to be working with people who are end users. We have to be working with people who are managers of end users. And then we have to be working with executives. They all care about different things.

Um, and we have to be able to speak that language, but yes, to your point of, if we are starting lower than that, the manager director level, then the asynchronous work is to have them. Bring in, have them loop in a leader,

right? And, and again, with like teaching them how to buy. So if I have a, if I have a manager or a director and they really, they really like what they've seen in the demo, what I want to do as far as teaching them how to buy, so I don't waste my time or theirs is say, Hey Matt, it seems like you've seen some value seems like this.

You think this might be a way. I gotta tell you, in the last two years, it has never been harder [00:40:00] to bring on new technology in an organization. And what I have found in dealing with many other customers is, if this does not align with an executive priority, it will not go anywhere. And so, like, from your experience and your knowledge of the organization, like, what is the executive priority that we best align with?

Right? If they don't know, that's it. It doesn't mean they still can't be helpful, but that's a different conversation, right? If they do know, okay, then who's responsible for that priority? And here's some, here's some ways typically that we would, you know, start to work with them, right? Um, so we have to, the way that we teach people to buy is different based on their level in the organization as well. So they might, they may not bring a leader yet. That may not be a bad thing. They may bring a peer, right? Because if we have 12 managers or directors going to a [00:41:00] VP and saying, we need this thing, that's a very different thing than just one, right? So just because they're not bringing their boss doesn't Fairly mean it's a bad thing.

It's just, the test is will they bring someone else, right?

Like, will Yeah, us navigate the org?

Matt Amundson: And let

me ask you this, like, once they bring someone, do you feel like they are sort of a magnet for other people? Is that like a signifier that, hey, look, like maybe we run a long sales cycle. I do my first call with this person, by the next call they've brought one or two additional people. Do, have they sort of broken the the dam so to speak and now you can ask them like hey like it was great that you brought you know sam and craig on the call next time do you think you could also bring like uh susan and and and tom

Krysten Conner: Yeah. So that's, that's another thing we could ask.

Um,

Does Your Buyer have a Point of View of the Next Steps
---

Krysten Conner: something else that we can ask is, Hey, uh, we have, we, on that call because we're [00:42:00] good salespeople, we didn't leave without next steps. And the next step is this meeting. It's just, you know, it's a deeper leaving, deeper level meeting with Susan and Tom. I want to make sure that you look good.

Because you are the one who got, bring me into this conversation. I have the deck that I'm going to run through in that, you know, in that presentation. Will you look it over to make sure that we're on the right track? Or, you know, or will you get me the data that we need to inform? That next movie, but then looking over, just asking them to look over a slide deck so that make sure that, you know, because if they brought you in, they should care about how that next conversation goes because they don't want to look like idiots.

And so it's like, you know, so it's like, do you, do you want to look at this deck asynchronously? Or do you want to, do you want to schedule 15 minutes and go through this to make sure that you can tell me like, don't use this slide. Don't say that. He hates that word. This is the buzzword. [00:43:00] Like, when they start telling you, um, how, you know, how to speak to the organization, that's a very, you know, that's a very good sign that they're going to be like a champion or a coach.

We can also, another thing that we can ask them for, that's again, a very low, like, light touch, but will they share it with us? Important initiatives in the business always have a name. There's always like a code phrase, a catch name. It's 25 million in 2025, right? It's um, project pipeline. Like I've seen it called so many things.

It always has a name. And so if you say, Hey, generally, if this initiative is important, there's some, there's something people call it internally. What are people calling this? They tell you that. You can reference that in every email, in every presentation, because you want that presentation to look like theirs.

You want the communication to look like theirs. And the more [00:44:00] you, like speaking the same language makes People, one of us, not one of them, right? Like language shows we are, we are one of you. And so like if they give you that internal language, so if I was, so for example, if I'm selling to an insurance agency, they don't call their sellers, salespeople, they call them producers.

Or they call them brokers. I should never call them account executives. I should never, uh, I should never call them sellers. I should refer to them as producers. And if I, as the, um, as the salesperson don't know that my champion or my coach would be like, Hey, just so you know, it can be like, that can be like the little, that can be coaching, right?

Like, it's just like, Hey, you say sellers, but with us, like, we don't call it that. Like we call it producers. If you say that it's, we should replace that in the deck. Like that's how we should say it.

Craig Rosenberg: That was pretty cool. The uh, can I add, Yeah,

Mass Email Does Not Count as Multi-Threading
---

Craig Rosenberg: one thing I want to ask, I hope to not fully divert us, but you triggered me on something that Chris [00:45:00] mentioned is, you know, when we were talking about multi threading and you said in this call You said and you want to follow up Individually with each person on the call so you totally trick cuz that So, uh, specific.

It's so smart. So, and I remember this, so I had read, this is actually the story of how you got here because I had read this where you, it was something about how sales people say they're multi threading because they had 10 people on a call and then they send, uh, Reply, you know, a reply all thank you and you're and you at the time.

I credit Chris. He made sure you got the credit. Don't worry, but I he said no, like, because I had said that is a brilliant insight, which is after that call. You want to follow up with everyone personally, and then you add it in this call, like, in the case of champion [00:46:00] development, we might ask other people to do specific asynchronous things as well.

I just wanted to dive in on that. Cause I think that's a, it's an amazing insight. It's something everyone can do. So, uh, I don't know if I described it perfectly, but like, if

Krysten Conner: Yeah, I know exactly talking about. And it kind of falls on the line in that same vein of like, what do I think people get wrong? Um, when, when we send an email, mass email to 10 people, that, is like sometimes what we feel passes for multi threading. That is not multi threading. Multi that's mass emailing.

Um, well, true multi threading is establishing single lines of communication with anyone who influences a deal. And the little phrase that, um, I, that rung, rings in my head whenever, [00:47:00] uh, when I'm sending actually any email, if it's no one's baby, it's an orphan. Like, think about how you look at email. If it has five people's name at the top, most people are like, archive, not my responsibility.

There's five people's name at the top of that, right? Just like human psychology versus if it is directly to you, it's clear. I'm asking you for this. Like we are talking about this. Um, and the, the other reason that it has to be, there's a, well, there's multiple reasons it has to be, uh, single lines of communication.

One is yet to even to make it their baby. because it's their email. Um, the second is that every, like I talked about, like what the, what's in it for me, like the win of, of acquiring, like my product is different for every different level of the organization. If you're an end [00:48:00] user, all you care about is does this technology make my day easier or harder?

That's it. If you're a manager of an end user, what you care about is, does this thing make Help my team on a metric I am measured on. Does it help increase revenue? Does it help our efficiency? Does it mean we are free? We can spend more hours on a different product or a different project. Like, that's all managers of end users care about.

Then executives care about, does this help us in the future? Accomplish our initiatives, um, deal with risk, capture market share, like those level of things. If I email an executive about a feature function, I've lost them. If I email an end user about like how this will help their, uh, mitigate business risk over the next three months.

I've lost them. They don't care. So we have to be single threaded with those people because we have to essentially speak, and this is again an enterprise, like three different [00:49:00] languages. If you're not doing enterprise or if your, if your sales cycle is not as long or like not as involved, um, it still is usually two, right?

It's different, two different levels in an organization. Um, so we have to, we have to, you multi thread. By single threading.

Craig Rosenberg: that is a headline. Okay, cool. Um, sorry. You just, I just thought of it on the, and, and I think about, so it's interesting is like, uh, uh, well, both things on this call just help bring both things, uh, together. together for me. By the way, you know, the, the one I always used to tell sales guys is the 9 1 1 rule, right?

Which is like when you're training, um, in, uh, first aid, it's like, you never say call 9 1 1, you say, Matt, call 9 1 1. And you like, otherwise nobody will call 9 1 1. And like, uh, you know, it's a very similar thing, which is like, well, you can send this big email and then that, that ball is just going to sit.

Like it's [00:50:00] not, um, and you're asking very specific Things of folks. The, um, so sorry, I I'm just recapping through some of the things. So the second thing you said, I thought was important on the champion. So the champion has to be able to effectuate the transaction since it's the show. Uh, but like when we're looking at, is there anything, so we got the three attributes, but they also, it sounds like they have to be people that could actually.

Uh, sign, uh, or initiate a buying process. Uh, and then it made, so I wrote that down. Is there anything else we need to think about on the champion in terms of. Uh, would we add to the, you know, outside of the four that we just discussed on the call today?

Krysten Conner: What do you mean? The four that we

Craig Rosenberg: Well, we had, will they do asynchronous work? Do they bring people to the call? Um, and then, um, do they have, uh, Uh, you know, uh, uh, a narrative on how things get [00:51:00] bought there. And then we said, well, they also have to be an executive and be, well, have to be able to, to buy. Is there anything else you would add to that?

Krysten Conner: yeah, so, so if you think about it,

Who a Champion is and What They Will Do in The Buying Cycle
---

Krysten Conner: like one set of criteria is. what someone is and another set of criteria is what someone will do, right? So if we think about what someone is to be a champion, they have to, um, they have to have power. They have to want to believe that our solution is the best solution to that problem and actively work behind the scenes to sell when we are not in the room.

That's who, that's like who a champion is. When we think about what they do, they don't get there overnight, right? So like, unless, unless they were, unless they bought this before and like, this is how they've had success in another organization. So they're going to bring it in. Like they don't, most champions are not just like delivered to your doorstep.

They're, you, they're, they're developed and you [00:52:00] develop them by. By seeing like what they will do. And the first thing like, or first thing is like early in the sales cycle is will they do this asynchronous, work right? And then, and then, you know, then it's like, and yeah, I mean, asynchronous work happens, you know, throughout the, throughout the cycle.

But yeah, there's, there's like characteristics of what someone is and then there's characteristics of like what they will do.

Craig Rosenberg: Got it. That's perfect. Okay. Well said that I got that.

Krysten Conner: Now, and like I said though, we don't need just champions. Like we, people, I feel sometimes it's salespeople. I've seen salespeople ignore people that are like quote below the line, like they're not executives. And you do that at your own peril

because no, because of how hard it is to buy something and how much consensus people want to have.

If the end. Users, and therefore like the managers of end users, don't believe our thing will work and don't [00:53:00] want it. There's very few executives that are going to buy that thing in the face of that. You can't ignore someone who's not, nor should you. Because like as a salespeople, like we should be helping the organization.

Like that's, and so like, if it's not going to help them, if it can't work, like, you know, we, we have to know that by working with people that are, you know, not just, not just champions, but also coaches. So people that will help us that, that essentially don't have any power to do, to sign anything, but they have like, uh, the term might, might be like soft power, right?

They

Matt Amundson: Yep.

Krysten Conner: in the org..

Matt Amundson: Yep.

Yep. Influence. They can help you navigate. Like, these are incredibly important peoples in a deal cycle. People in a deal cycle.

Craig Rosenberg: Peoples. I love

Matt Amundson: Yeah, people. My goodness. My goodness.

Craig Rosenberg: No, no, that, I mean, that was actually piggybacking, not, not making fun of. I was down

with that.

All right, cool. So that [00:54:00] was interesting. Like more, I got more than I bargained for. I love the tact you took here because that was stuff I wrote down that, um, we actually, I need to make sure that everyone's doing.

I thought that was, I'm so glad I didn't know because that was a really good. That was a really helpful, really specific, really interesting thing that you are correct. The market doesn't know that they're not handling right. So that's what we try to do here on the transaction, Kristen. So I thought that was an amazing call.

And yes, Sam, show notes are in play. Show notes are in play and other things.

Well, Kristen, thank you so much. It was great hanging out and like, uh, look forward to, uh, Uh, seeing more of your stuff out there in the wild and, uh, uh, it's been, uh, I've been learning from even before I met you. So it's been, I hopefully everyone, uh, that's listening to the show is going to get that value and want to hear [00:55:00] more from you as well.

So thanks.

Krysten Conner: Yeah. I appreciate the opportunity. Thanks for the kind words. It was, it was fun. These are like the best conversations.

Craig Rosenberg: Awesome. All right. Thanks guys. Uh, appreciate it.