Sales Hustle is now Sales Transformation
May 28, 2021

Episode #103 Make Your Team a Revenue-Driving Machine with Krysten Conner

Collin Mitchell welcomes Krysten Conner in this episode of the Sales Hustle Podcast. Let’s hear from Krysten as she retells her beginnings as a middle school teacher who shifted into a sales specializing SaaS Enterprise. She shares how Outreach helps you increase revenue.

Krysten Conner is a Large Enterprise Specialist at Outreach. Outreach, the leading B2B sales engagement platform, accelerates revenue growth by optimizing every interaction throughout the customer lifecycle. The platform manages all prospect and customer interactions across email, voice, and social and leverages machine learning to guide reps to take the right actions.

Krysten is a Founding Member of RevGenius. She is also a member of the Revenue Collective, and - Mentoring, coaching, and speaking on how to land your dream job in sales. And how to succeed once you get there.

Find out more and connect with Krysten Conner on LinkedIn at

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Episode 103 - Krysten Conner

Welcome to the sales hustle. The only no BS podcast, where we bring you the real raw uncut experiences from sales change makers across various industries. The only place where you can get what you're looking for too. Uh, your sales game today's episode is brought to you by sales cast sales cast helps sales professionals transform the relationship building process and win their dream clients.

[00:00:30] I'm your host, Colin Mitchell. What is happening in sales hustlers. Welcome to another episode today. I've got a special guest for you. I'm going to be talking with Kristen Connor, who is an enterprise, a, uh, at outreach, and she's a middle school history teacher turned into SAS sales enterprise, um, a E so Kristen, thanks so much for coming on the show today.

[00:00:52] Hey, great to be here. So just give us the short version before we jump into the topics we planned out for today. Like what's your sales story. Yeah, absolutely. Thanks for the question. Yeah, so I had a great, um, high school history teacher who convinced me that my life would be better if I, uh, was a history teacher and can mold young minds.

[00:01:11] And I did that for three and a half years and realized how freaking hard it was to. Do that. And I love the kids, but the parents were even tougher than the kids. So I decided I would volunteer with kids. And if I was going to work that hard, I really needed to make more money. Um, and so my, uh, I went to work in our family business for a while and.

[00:01:34] Thought I was going to end up buying that business and then decided after running it for several years, it was not for me, but I was always the one, um, pushing tech, like I was always going, how can we work smarter, not harder. How can we use existing tech to, um, to make our lives easier? And just throughout my career, I've always, always pushed for that.

[00:01:54] And then realize that that's probably where I needed to be since I was always pushing for that. And I wanted to get into it and I had done, um, Sales roles in my family business for a while. And those were the ones that I always enjoyed. I felt like I was helping people. And my teaching background definitely came into play there because with any sale, you're doing some form of education.

[00:02:17] And so I decided I want to get back into, I want to do sales full time and I wanted to do tech because that's what I was interested in. And I feel like you always sell things. Better. If you're interested in them, right? You have to be interested in them. For me, I have to feel like I'm making a difference to helping people.

[00:02:33] And so, but I needed, I needed a good segue into that. And so luckily for me, I mean, I was living in Kansas city at the time and there was a tech startup there that sold, um, SAS solutions to education. And so I came in knowing that vocabulary, understanding the issues in the industry. And that's how I got my start.

[00:02:50] Um, you know, 10 plus years into my career, pivoted to tech. Mm. Awesome. So what a great place to start with your background to kind of get into sales, right. And so I'm just curious. I, you know, a lot of people would be really nervous and, and not know how to sell themselves into sales, coming from a, you know, a teacher background.

[00:03:16] What would you tell those folks? Like what suggestions do you have? What really worked for you to kind of break into that? Yeah, I didn't, I didn't get that job by just submitting my resume and crossing my fingers. Right? Like you have to, if you are coming from a non-traditional background, you're asking somebody to take a chance on you.

[00:03:34] You have to strategize and think, how do I show that I'm a good fit for this? And people are. Interested in, in people, they know people like them. And so I had been a part of networking groups in Kansas city for a while, and I found a couple of folks that were connected with the organization that I was targeting.

[00:03:55] And one of them, um, I found out later had actually been the VP of sales at that company. And, um, so I, and he had a, a SAS like training company at the time. So I just reached out to him and I said, I'm interested in getting some training from you. Let me know, like, And I pointed out some things on his website that I was like, If you're going to asking you, asking people for, to trust you with training, you might want to revamp your website a little bit.

[00:04:20] So we met and he thought that was hilarious that I kind of called him out on that. So I gave him some suggestions for that. And, um, and then we just started talking and, you know, he. You know, understood the value prop that I had for the organization. And so he, um, contacted their current VP of sales and he said, Hey, you know, I have kind of a candidate, that's a little outside the box for you, but I think, you know, she would knock it out of the park.

[00:04:44] And so I got referred in from a prior VP of sales to a current VP of sales and that got the ball rolling. I wouldn't have gotten in without that. That's so different than what a lot of people are doing. Um, how, how much time, like researching and like putting, putting the pieces of the puzzle together, did it take you to, you know, figure out that you had that connection and then I love how you leveraged it to, as you led with some value in some real honest feedback, um, to show that like, you know, you were just going to be.

[00:05:18] More human and be yourself rather than just like tell people what they want to hear to try to get them to do what you want, which is a more typical path. Yeah. I'm, I've learned that you don't get anywhere not being yourself. And also if you get somewhere not being yourself, you're probably not going to like it when you get there.

[00:05:38] Cause I've done that. I've done that too. But to your question of how long did it take? It took a long time months of trying to figure out and chasing down dead ends. Like. Trying to get an angle in the organization and having stuff fall through. It took a long time. Um, But one of the things that I did, some of the best money I've ever spent is I found a, uh, again, a person that I was connected with through a networking group and networking group always had really solid people.

[00:06:04] And it was, I hired an executive coach and I said, this is where I want to end up, help me get there. And she had been involved in tech in Kansas city and had a very nice exit. And so she kind of knew the landscape. And so w w while what I paid her was a lot of money for me at the time. It absolutely leapfrogged my career because she knew people I didn't know.

[00:06:26] And so, um, and I, so I would encourage you. I don't know who says it. A lot of people probably say it, but your network is your net worth. And if you don't have, if you don't have those connections, there are find someone there there's all sorts of sales, coaches and sales trainers. Right. And if they're connected with the organization, you want to be a part of.

[00:06:45] Or there's a former executive or former even individual contributor. That was a part of the organization. You want to be a part of start, start there, start figuring out how you're connected to your target organization. Yeah. And, and, and just to add to that, right. I love that. And I'm a firm believer that your network equals your net worth, but you also got to nurture those relationships for sure.

[00:07:08] Right. You can't just. Give somebody a call or reach out every time you need something, right? Know who, you know, those key relationships are and put in the time to an effort to nurture them and to add value in a way so that when you do ask for something, whenever that will be, you don't know that they're more than willing to help you.

[00:07:30] Oh, yeah. I'm a huge proponent of, um, of adding value every time, every time you reach out, um, whether that is sending someone, an article that you thought that they in their role might be interested in sending them news about their company or their competitor noticing what school they went to. Um, You know, I mean, and that is in that research involves like looking them up on, you know, Twitter Googling, doing a basic Google search and understanding if they have an open Twitter profile and they're always talking about their college team, like you should probably mention that, you know, I mean, it is a lot of work to hunt it down, but that's what you're going to be doing in sales.

[00:08:09] Anyway, if you're doing especially enterprise sales, you're going to be understanding the people you're working with. And this is just like selling yourself into an organization is just like any other sale. Yeah. Yeah. I love that example. And you clearly were committed to this place. I mean, two months of, you know, looking for connections and hitting dead ends and, and the determination, I think a lot of people would have given up at some point, like, you know, move on to the next opportunity where you simultaneously looking at other places, or were you just all in on trying to get that job and sell yourself to that particular company?

[00:08:45] Yeah, there were other organizations that I was looking at. They were like online education. It was all stuff to do with education. So you never want to be single-threaded in any deal, including when you're trying to get into an organization. And so, yeah, I was definitely looking at multiple. Organizations that had to do with education and hunting down, um, all different kinds, all different types of leads and connections there.

[00:09:10] Um, because even though I had my favorite and that's the one I, even that I eventually got into, um, whenever that person or that company gives you an offer, you don't want that to be the only offer you have you. I don't. I have no, I don't play poker. I don't bluff. Well, if I am telling someone I have multiple offers, it's because I have multiple offers and I want to be in that position whenever we're negotiating.

[00:09:33] Um, so, and so I want to kind of just, um, go forward here a little bit too. So in the interview, actually negotiating, right? These are some skills that I think a lot of sellers that are maybe looking for a new place or trying to get into SAS. Don't have the skills to get the best possible comp plan or whatever the case is.

[00:09:56] So where did you get those skills? And you know, what tactical things, can you break down for people that are, you know, looking for that next place that they could utilize in their next, you know? Yep. So I think it. Sometimes in sales, like the one-on-one things are the things that we forget or Passover. Um, so I mean, obviously looking on glass door, what are the salaries that people are paying for the role that you are looking at?

[00:10:26] What are people saying about the roles, you know, that they either had, or that they're leaving? Um, there's another, there's another, um, website that's particular to sales called rep view, R E T V E. That it's mostly larger. Larger companies with larger sales orgs, but you can get a very good feel for who's making their number.

[00:10:47] What, what, what are they paying? How happy are people like those are things that you want to know going in. And as far as tactics, um, my favorite book, um, and audio book, I have both is never split the difference with Chris Voss, uh, which you know, is mentioned by people in sales. All the time. Um, and it's, it's an entertaining book to read as well.

[00:11:09] Cause he was an FBI hostage negotiator, and he has a masterclass as well, which I took, um, those. I mean, his negotiation skills are, you know, proven and the FBI. And I use them on everything from interviews to negotiating deals, structure, to talking about bedtime with my eight year old. Um, it's, it's very handy.

[00:11:31] Yeah. Yeah. I think that bedtime for the eight year old is probably the most difficult, absolutely 100%. She's a skilled negotiator. I hate to go, come up against her. Yeah, I've got, I've got a six, five and two and a half, and what's interesting is kids start to pick up things really quickly. So those negotiation skills that you start to use on them, they observe and start to use on you when they want something from you.

[00:12:00] For sure. And I take it a step further than that because my daughter yeah. Is very, um, She's a very intuitive personality, but when she wants something, she instinctively negotiates and I will point out to her, like, you're negotiating, you're asking me for what you want. If you ask me this way, I'll be much more likely to give it to you because that's going to skill that she's going to need her whole life.

[00:12:20] And so I try to be super intentional about that. Yeah. Yeah, no, I love that. Get them started early. Yeah. Sales is going to be in her blood whether she wants it or not. Yeah. Her dad and I are both in sales, so she's ruined. Oh yeah. Yeah. Um, all right. So now let's, let's shift gears a little bit because, and these things apply.

[00:12:41] I love the connection here. Right? So selling yourself and putting in the work and the research and prospecting for our job into negotiating into the role now. In the role, a lot of those skills that you use to get the role. If you're, if you're following this, this path apply in the role as well. Yep. So how does in something we said we're going to talk about is prospecting like a human.

[00:13:06] And a lot of people are talking about this these days, like be more human and how does a human be more human? Right. It's a funny concept, but let's talk about it. I think we all grew up watching movies where people were in business talked. A certain way, which means they said things that no one everyone says and no one really understands what they mean.

[00:13:28] It's just these generic words that fall out of their mouth. And like, like I said about adding value, like, I don't want to send something I wouldn't want to read. And so, um, and so like the human brain is visual. I try to send a lot of things that are visual, whether that is. Um, you know, a Venn diagram to under, to help understand a concept or a gift that's, you know, just funny and make someone laugh about something that's related.

[00:13:56] Um, but yeah, if I wouldn't say it to my neighbor or my best friend in that, in, uh, in that way, I try not to say it. Um, I try not to say it to other people because it's just, it's just a turnip. And I think that. The thing that machines can't do as well yet is, um, is personalized, right? Like connect all of the dots, figure out, you know, um, people on there on LinkedIn or other social profiles that they have will mention things that they are interested in.

[00:14:26] And if you can tie that together with your value proposition, it shows you did your homework. It shows you're not just spamming out, you know, 300 people at a time. And if you can show that you have some sort of. You know, insight or so, or that at least that you tried to add value. I think people will be much more, I have found people will be much more generous with their time.

[00:14:47] Um, if you are showing that you did your homework first. Yeah, absolutely. And I think that where a lot of people struggle is personalizing and then also tying it in. To their value proposition. So what, what, what advice do you have for those people? Because a lot of people find things and mention it and then just go right into the value prop, but there's no, there's no link.

[00:15:15] And so I think that's where a lot of people struggle because it's actually. I mean it's better than not personalizing. Yes. But it's almost annoying that they said they found something, mentioned it and then just, you know, through one sentence that has no relevance with what they're trying to do. So what tips do you have in tying it in?

[00:15:38] Or maybe you have an example. Yeah. Yeah. I have an example. And I would say in the example proves the point. Like don't be afraid to sit and think about it. For a minute, because I think what w because of how we are measured in sales, we feel like if I push out 50 prospecting emails that I got, I've gotten more done than sending out one good one.

[00:16:02] But if you push out 50 and you don't get any responses, versus if you take that same time and do one really good one, and you get a meeting like. Tell me, like, I think it speaks for itself, like what the best use of time is. Um, so like a quick example of, of when I sent out, I, um, was prospecting into this company that sells that is a publishing company.

[00:16:26] And I noticed that this guy that I wanted to talk to had worked at, um, B Dalton and Barnes and noble, which for, you know, millennials may not even remember B Dalton. I was a little kid whenever my mom would take me in there and I'm a nerd I love to read. And so I was like, Hey, I noticed that, you know, you and I put just like, um, Kristin and John Smith, B Dalton fans in the subject line.

[00:16:50] And I was like, you know, my best memories as a kid were going to be doll. And then, then, and then whenever I had kids, myself taking them into Barnes and noble and, you know, I mean, we've read Dr. Seuss and just really powerful memories. And I said, you know, The, the messaging I was going to send them about though, is the way sales have changed.

[00:17:07] And so I said, you've seen over the course of your career, how things have really changed in your industry. You know, you went from physical bookstores to now a digital publishing company and. You know, sales doesn't stop changing. So, and then I went into, you know, our value prop for what he was going to do, but I mean, it, it took me, um, you know, 15 minutes to sit and think about how can I tie that into what we're doing.

[00:17:32] Um, but it makes way more sense than just sending out something that has no value at all for him. Yeah. Yeah, no, that that's, that's pretty clever. And so I think what you're saying is a lot of people tend to want to rush it or not spend the time that's required to really tie it in. Or, you know, it's a little bit of just being lazy, like, okay, I got the personalization check that box.

[00:17:54] Here's the template ID piece that goes under that, you know, send it off. Um, and so what you're saying is don't be scared to spend a little bit more time in a creative, you know, Headspace to figure out what's going to have more impact and what's going to drive more meetings, even if it means, you know, Bringing down the volume a little bit.

[00:18:14] It's definitely a quality over quantity, for sure. Right. And I, I encourage you. I've always been in addition to always being a tech person, I've always been a data person. I track your data, right. Look at, spend one week doing it one way, spend another week doing it the other way and just see what you, you know, run that, do that a couple of times, you know, and you've, you've got a month's worth of prospecting that should give you some pretty good data to figure out maybe in your, you know, You'll figure out what works or should have a better idea.

[00:18:44] Anyway. Yeah. Now I know you mentioned using Venn diagrams and gifts. Uh, what about video? Yeah, I've started doing that a lot more during COVID. Um, because that's the other way of baking something super personal, right. Is, is showing, you know, this is personalized just for you and yeah, and I don't do generic, um, video as well.

[00:19:09] And I've had people send me LinkedIn videos to connect or to make a request. And I'll tell you the. Two times that that's happened, where somebody had a connection request and they wanted to ask my advice about something that they did it via video, and it was clearly personalized. And they'd clearly read about me.

[00:19:23] I was like, yeah, absolutely. Of course. Yeah. Yeah. People don't use video in, in LinkedIn nearly as much as you'd think. Right. Yeah, exactly. I found that to be true as well. It definitely stands out. I mean, people don't even use voice DMS as much as I think they should. Yeah. Yeah. So, all right. Um, and so tell me a little bit about the Venn diagrams.

[00:19:48] Like, what are you doing there? What are you creating? How are you using that to, you know, personalize and tie in, you know, with the value prop, give us an example. Yeah. So we all probably work in spaces where we have competitors, right. And there are some things that are the same and some things that are different.

[00:20:06] And so, um, you know, we were, you know, if you remember the Venn diagram from school, you have the, you know, the two circles and then the overlapping. So I've used that in the past to show like, here's what this space of our competitors and here's this other space of our competitors. And then here is. You know where we sit that's different.

[00:20:23] Now that, I mean, just like that it was that same, like a picture's worth a thousand words. Right. You can get in the, in an image in one second, um, the value prop and understand what I'm saying far better and far quicker than if I sent you a four to 12 paragraph email about all the differentiation, which you were never going to read anyway.

[00:20:44] Hmm. And are you just sending that as an image or you. Kind of talking through that on a video. Um, I have sent it as an image as like, as a conversation starter as a way to like, introduce the fact that, um, I want to have a conver, you know, are they interested in having a conversation around that? And if they're open to it, if they open that email, then I might, then I might follow up with a video after that.

[00:21:12] Um, I'm trying to think. There was another, um, other images that I use. Um, I will use images of logos of their competitors, that we are working with people, always, everyone is curious. Everyone wants to know what everybody else is doing. And so I will just send our logo slide and I'll superimpose images of their competitors be like, Here's some people that we're working with, people generally want to know what other people are doing.

[00:21:41] Can't tell you specifics, but if you'd like to know generally the problems we're helping them solve their X, Y, and Z. Is that interesting enough to have a conversation? Yeah. That's enough to pique some interest. Yep. Yeah, no. Awesome. Thank you so much for, uh, today. Really appreciate kind of you breaking down, like how to break into a role in, in the level of dedication that it takes to get the role that you really want.

[00:22:06] Um, also appreciate kind of talking through, you know, uh, how some of those same things apply into prospecting and some great examples of how to personalize and tie in. Any final thoughts or anything that you want to let folks know before we wrap things up here? I would say that like, I've come from a non-traditional background and I have used non-traditional methods to get things done, whether it's getting myself hired, getting a deal done.

[00:22:35] And so I would say to people, I think I, for a long time was afraid to like, be myself, be an introvert in sales, um, make, you know, book, uh, you know, Intellectual like humor, nerdy, you know, quotes or whatever. Um, but the more you're yourself and the more you apply yourself to that, to that process, and the more you show up, that's the most human thing that you can do.

[00:22:58] Right? And so when you do that, whether it's to get a job and you have to be polished about it, but just, don't be afraid to stand out because of the different things that you bring. And no matter what, yeah. If you make, um, whether it's an interview or whether it's, um, a sale, if you make it about the value that the other person is going to get from it, and it's going to go well, Yeah, absolutely.

[00:23:20] And, and just, just own who you are and how you're different and yep. And I think that's the best way for it, but then tying it in how that's going to bring value for the prospect or the employer. I love that. Yup. Yup. Chris, thanks so much for coming on today. If you enjoyed today's episode, please write us a review, share the show with your friends, and we're always listening for your feedback.

[00:23:41] Hey, thanks so much. I hope it helps somebody. Thank you for tuning in to this episode of sales hustle. Are you a sales professional looking to take your sales career to the next level? If the answer is yes, then I want you to go over to sales, check us out. And if you feel that you are ready, set up a time to talk with me and my co-founder Chris, I'm your host collum Mitchell.

[00:24:07] And if you enjoyed this episode, feel free to leave us a review. And share the podcast with your friends.