Sales Seekers

009 - Becoming a Tech Sales Superstar with Krysten Conner
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[00:00:00] Intro
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Mike Bird: Hey, you're listening to Sales Seekers and this week's episode is a treat, because it features former teacher turned unicorn Account Executive, Krysten Connor. We'll get to her in just a moment.

Really quick, I'm Mike Bird. I'm a career coach who helps people break into and up through the B2B tech sales world. You can check out what I do at salesseekers.ca and tune into this podcast and its new episodes every other Monday morning.

Now back to Krysten. Krysten started her journey in sales, after working as a History teacher and then in a family business. After leaping over to pursue a path in tech sales, she quickly became an enterprise AE at companies including Tableau, Outreach and Salesforce. Not too shabby. Still wanting to scratch the itch of teaching and helping others, Krysten now coaches AEs in their journey to becoming top performers.

She's become one of the most well-recognized voices in the world of software sales and opens up on this episode, not only about how she got into tech sales, but also how her career in tech sales has impacted her life and what other folks should think about if they're looking to either start or continue a sales career.

She's a fantastic person, and I'm excited to share our conversation with you, so let's get into it.

[00:01:13] What you'll never catch Krysten doing
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Mike Bird: Hey Krysten, welcome to Sales Seekers. How's it going?

Krysten Conner: Hey, I'm great. Thanks so much. I'm excited to be here.

Mike Bird: Yeah. Glad we had the chance to collaborate here. I always want to start off the show by helping people understand that sales people are more than just sellers. So can you complete this sentence in one phrase or less? If you really know me, that I am blank.

Krysten Conner: Never doing a cold plunge ever.

Mike Bird: Yeah. Okay. Okay. Why you live in Texas? It's hot down there, right?

Krysten Conner: I hate the cold. I hate the cold so much. Like I will do all the other things. I will do the, an hour of exercise every day. I will do meditation. I will do journaling. I will do all the things, but the cold plunge, they can just miss me with that forever.

Mike Bird: Forever. Okay. Unsubscribe, never subscribe.

Krysten Conner: Right? If you see that you know that there's been some sort of body snatching incident because, yeah, I don't do that.

[00:02:07] How Krysten broke into tech sales
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Mike Bird: Totally fair. Okay. Can you break down your journey into tech sales into three big steps? You've got a pretty interesting one. What should people know?

Krysten Conner: So I would say I was obsessed with tech in the first two careers I had before tech. And when I decided to get into tech sales, which was very intentional on my part, I targeted companies based on the story that I could tell that would make sense on why they should hire me. So a story where I could connect the dots for them. And then I networked my way in and multi-threaded every interview process I was ever part of before I even knew what that word meant.

I just thought of it as covering the basis.

Mike Bird: Yeah. There's a lot there that you just summarized so neatly. So I'm curious to know a little more about. What kinds of stories did you tell the employers who were thinking about your candidature? Like why this person? Cause you originally were a teacher once and that's so neat. What were you able to communicate to folks to really get them to see you as a great candidate?

Krysten Conner: Yeah. So a lot had to do with the companies I chose really specifically the company that I chose to target, which was a company that sold to K-12 education. So EdTech. And I knew I could tell that story. And so once I got laser focused on that, then it just made sense where I looked at. So I went to their website and I looked at all the different products that they were selling to educators, right?

And I was like, okay, these folks are selling to superintendents, they're selling to curriculum and instruction leaders. They are selling to HR people solving this problem. And then I just came to those interviews with insights about their buyers and just said, and use that to inform the questions I asked.

So it was like, okay I've noticed you have this product that seems to be solving this. I'm guessing that you also solve these problems or the curriculum instruction people really like this. And so by asking questions it comes, they were genuine questions, but based on a point of view.

So really coming with the point of view. And in asking the questions, I didn't have to tell them, Hey, I've done my research. Hey, I know your buyer's world. Amy Volas has this line about like your questions show your level of expertise. So, it wasn't necessarily the stories I told them about myself. It was the stories I could tell them about their buyers.

Mike Bird: Yeah. I'm imagining all this research that you were doing and just how it demonstrated, like I'll often say, and other people will say, job searching is a sales process. And I think people don't always realize how literal and true that is. You were doing discovery on these folks in your interview, it sounded like.

Krysten Conner: Yeah. And well before, and well before. And I went in high, got executive alignment. My sales coach, just like my first sales coach I ever paid really, I guess before I even started in tech sales, he had been their former VP. I sent him my resume and had him send it to their existing VP of Sales, because without that, I don't think I would have ever gotten that interview.

So, you get an executive to delegate it down and be like, "this is something we're going to take a look at." Like it is a sales process from the start to finish.

[00:05:29] On taking charge of your own development
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Mike Bird: That's wild. All of the little edges that you can get, it makes total sense. Cool. What's one thing that you've learned since being in sales that before-sales you should have known before making the jump?

Krysten Conner: I don't know if there's any way to know until you do it, but salespeople almost more than any other career are in charge of their own development. Like I falsely assumed that I would get a lot of coaching and a lot of like really individualized instruction and help from sales managers. And I was definitely wrong about that.

Not because I didn't have great managers, but they're pressed for time and they, are pulled into a bunch of different directions. And I don't think any sales manager I've ever met would say they have as much time to coach as they would like. I think they all would like to do that, or most of them, but Jim Rohn has a quote that says formal education will make you a living and self-education will make you a fortune. That's never more true than in sales.

Mike Bird: Yeah. I know Chris Orlob talks about you being " skills away" from a life that you want, not years away. And sales being this pathway where the stronger your level of mastery of the ABCs or the blocking and tackling, however you want to frame it, can really translate into real life impact for you as a seller.

It sounds like sales and your ability to develop your skill set has had a really big impact on the rest of your life. As you became a better teacher, like when you were in that part of your career, did you feel like, " Hey, I'm a better teacher now than I was last year or two years ago, and I feel more fulfilled" or "my life feels like it's going in a direction that I really want it to." Did you have as much impact on the rest of your life when you were a teacher and working through that role?

Krysten Conner: Teaching is... there are some aspects to sales that are very similar, right? I taught middle school and high school. So salespeople and middle and high school teachers both have hostile audiences who do not care at all about what you want to tell them for the most part.

And just like there are a few champions who really want to talk to you, there are a few students you really want to know. So in some ways that was great preparation for being in sales and also like you have to be able to talk to someone and help them understand something that they didn't know they might not care to know, this is going to be helpful for them.

So to do that in a way that is accessible and doesn't feel condescending and feels engaging. And I want to go on this ride with you. There's things that are very similar.

And yeah, in teaching, you are in charge of your own development in some ways, but there are, like in America and I'm sure other places, there was like continuing ed and like in-service days where they, where the district or the private school, helps you on that journey.

And yeah, the longer I was in teaching, the more I could tell that I was better at it. But frankly, one of the reasons that one of the many reasons I left teaching is no matter how good you are, it doesn't have that much impact on your income. So like I saw these great teachers and it was my third year and I was looking around and I'm like, okay, the teachers that I really respect are still the ones putting in 50, 60 hour weeks. And these are people that have taught for 30 and 40 years,

and they're still putting in this level of effort and it shows. I just was very real with myself and I was like, if I'm going to put in this level of effort, I cannot do it for this level of income.

And so, I will find a way to volunteer and work with kids and still get, have that part of my life that's important to me. But I was, but that was like, there's lots of ways to work with kids that don't involve making no money. And but yeah, what they pay teachers in America is a whole different, it's a whole different conversation.

Mike Bird: Whole other podcast episode for another show. I appreciate you sharing that because I think that's not just true of teachers. I won't go too far down this rabbit hole, but the idea that you hit on really well there is that some careers can contribute into having a better life around the time that you put in to work and getting better at your career can really translate into more fulfillment.

And I also was in education and I saw teachers who were in the game for decades. And I just always wondered if they still felt as fulfilled putting in all that work and that they got something out of it. I think people should have that in their career. And that's one of the big reasons I advocate for people to try sales.

Krysten Conner: Mm hmm. Yeah. And I think, we talked about this before, but it bothers me, it really bothers me when people talk about salespeople being coin-operated or solely money motivated. And first of all, there's nothing wrong with wanting to make more money. When you make more money, like you can take your kids on better vacations and maybe you help your parents fix their house.

And maybe you contribute to your local like nonprofit. There's lots of things that people do with money that are great. So that in and of itself is not bad. For me, I've always wanted to sell things and really have only sold things that I felt like made a big difference in other people's lives.

And like I could see the difference it made in their career. They were getting promoted, they were making more money. They were happier more fulfilled at work. And when, and then when you change, when you help a person change the trajectory of their career. It changes the vacations they can take and this education they give their kids and and all those things.

I find for me, I was raised like very values-driven, very purpose-driven and I don't think you have to, I don't think that's incongruent with the sales career. I think you just think of it differently. And I think no matter who we are, we, I think are wired to want to make an impact and do something bigger than ourselves, and you can definitely do that in sales.

Mike Bird: Mic drop. I'm not going to say anything on that. That's fantastic. I totally agree.

[00:11:10] Strengths Krysten has leaned into as a salesperson
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Mike Bird: I'm curious, what strengths would you say you lean into the most that allow you to be an effective salesperson?

Krysten Conner: I'd say a lot of the things that I thought initially disqualified me from a sales career. My husband, I was selling like large commercial insurance, but it was much more farming, not as much hunting. And, and there were goals, but it wasn't the same as like having a quota. And so I was like, I'm an introvert. Like I like to focus, I like to research. I'm analytical. My stereotype of sales was the stereotypical like used car salesperson, or the door-to-door salespeople, or, like the telemarketers you get it dinner.

And I was like, "no, I'm not never, I would never do that."

" You don't understand. There's lots of ways to do this." And and so he was doing enterprise sales and was talking about it. And then as I got to know more people who did enterprise and strategic selling, I was like, "Oh, these are my people."

We do the same things. We think about things the same way. I just hadn't had exposure to that . So introversion, thinking, liking to hunker down and do deep work. I'm not an extrovert. I don't get energy from being around people.

I like being around people, but after a networking event, like I'm the person that like, I want to go back to the room and sit in quiet for an hour before I go to bed. But none of that makes you, not good at sales. And in fact, in enterprise and strategic sales, those are the people that I've seen that do well.

Mike Bird: Yeah. It's not like you grow up through schools and get this idea of, "Hey, the enterprise sales career. That's a really great option for a lot of you,. Whether you're, as you said an introvert, an extrovert, an ambivert, whatever vert. But yeah, just getting the exposure to it. It sounds like just having your life partner show you, "Hey, this is possible."

Was one of the things that eventually took you in that direction. Is that a fair guess?

Krysten Conner: Oh 100%, 100%.

There's so many careers, right? There are careers that exist now that didn't exist when I was in school. Didn't exist 10 years ago. Yes, it's hard to know. So I did the same thing.

There was a lady that was a friend of mine in Austin and she was pursuing a nursing career and she hated school and she had run her own business and I was like, I think you would be great at sales. And she was like, no, we have very similar personalities. I'm like, "I think I know what you're thinking. And let me tell you, let me take a guess."

Long story short, we like reworked her like résumé and had her do some certain like trainings and stuff, and now she's in inside sales for a pharmaceutical company and helps sell things that she like products that she was super interested in, just in her own life. So yeah, there's all sorts of, there's all sorts of ways to be in sales and all sorts of ways to be really good at it, no matter what your personality is.

Mike Bird: Yeah. Love by the way, how you started in her world, being able to understand and acknowledge what her thoughts were. And then, Oh, what do you know? People start to move after that. Love it. Sales: never stops sometimes.

[00:14:06] Know this before transitioning to sales
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Mike Bird: So I try and ask this of all the sales folk who will come on this show. What's the one thing that people who are considering a career in tech sales should know either about the transition itself

or about the actual work and the life of a salesperson. And you've already shared a bunch of things, I think, on both of these fronts, but what else is coming to mind on this?

Krysten Conner: Yeah. It was something else that I didn't know coming in, but I've heard a lot of people talk about since, which is sales is a very emotional career, right? Like I'm not sure if you're a dentist that you have the same, or an accountant, maybe, I don't know. But in sales, like you can have like worst day ever, best day ever.

Sometimes the same day, sometimes within five minutes. Depending on what's happening with that DocuSign. And so that's definitely something I didn't expect. And it just there can be huge emotional swings. And so learning to really manage yourself well is crucial.

Like I didn't expect sales to help me grow up or learn to manage my emotions or help me be a better version of myself. But I think the people that I know, the great sellers that I know are like a testament to the fact that sales will either grow you up or it will crush you. And usually. And usually one before the other, right? Like Kyle Norton, CRO at owner.com, he made one of my favorite things is: sales is a personal development exercise disguised as a career.

If you take it seriously and we all know salespeople that go the other way with it, that drink too much and just try to escape. Cause it's, it's a lot of pressure. You can either let that run over you or you can let it, mature you. And and like my backwards version of Kyle's saying is like "sales will either make you crazy or make you Zen." And usually both, in that order.

Mike Bird: Yeah. I feel like I'm riding that still in my life. Like I'm only about three and a half years into my sales career and somewhere on the journey towards Zen, but many days spent on feeling not so great. Can you share what, if anything has helped you become a little more Zen or to just sort of emotionally grow up in the way that you were talking about it?

Krysten Conner: Yeah. Some of it is just like living through those years and seeing things happen and realizing that very few times does that the worst thing actually happen. And even if it does, you can come through it better than you thought. And so there's an article that I actually, that is on my Todoist app that comes up every quarter or whatever, but it's like an article from Medium and it's this doctor who did this study of how many things that we worry about never happen.

And it's like 88 percent of the things that we worry about never happen. Then he goes a step further and he said of that 12 percent where something terrible did happen, the majority of people said they handled it better than they thought they did and it actually, in many times they found like a silver lining. And so he's like the people who had something terrible happen and didn't cope with it very well is 3%. So, some of it is just seeing that the floor can drop out and you can get fired and you can have a terrible quarter and be like, "Oh gosh, people must think I'm absolute rubbish at this."

And yeah, I think I'm absolutely rubbish at this and then realizing that things will change. Some of it is just like life experience. That's why old people are wise. In the meantime, the coping skills, journaling has definitely helped me, exercise just like working out that anxiety, how it builds up in your body and going to the gym, getting that out. And, meditation, I don't sit there for an hour. I wish I could. But even just five minutes just to reset, you know, spending time outside. Yeah.

there's been a lot of things that have layered in.

And as it turns out, almost anything that makes you good at sales will make you good at life. Being a good communicator, focusing on the other people, like critical listening. That's the other thing is sales kills two birds with one stone, right? If you get good at sales, you get good at life.

Mike Bird: To maybe just take that one step further, because before in preparation for this, you had talked about the fact that you have kids, you have a few kids and so you're a parent. Can I ask how has sales made you a better parent, if at all?

Krysten Conner: Yeah, I think it's definitely changed the way I communicate because as you think about doing like discovery and coming to a conversation with curiosity and asking the question and also just the techniques, like we talk about mirroring and repeating back has definitely made me a better listener, right?

That carries over. In a good sales call, the prospect should be talking more than we are and so you want to encourage them to talk and really understand where they're coming from. You can't help them solve their problem, unless you know where they're coming from and so that has carried over.

Really to any conversation, even conversations with kids. Caveat to that would be the older they get, I feel like the better it worked.

Mike Bird: Yeah. Enterprise sales doesn't necessarily apply to everybody, but yeah I can see the parallels and I think for people who are either in a journey where they are early on in a sales career, or they are maybe thinking about moving to sales in the middle of their life and maybe they have kids.

Just seeing like the myriad benefits beyond what happens in the time that you put into your work and the impact it could have on income, but the impact that it can have on so many other things too.

Krysten Conner: Yeah, for sure.

[00:19:28] It's never too early, or too late...
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Mike Bird: Krysten, this has been a lot of fun. I've certainly learned a lot from talking to you on this call. One last question before we go to wrap this up, is there any other word of wisdom that you would want to pass on to someone who is either considering a career in sales or is early on and is maybe asking themselves, "is this really for me? Do I want to keep going?"

Krysten Conner: If it's any help or encouragement, I was the the oldest AE in my first foray into tech. It was a small company and lots of really young, right out of college, and I had four kids at home.

So I was n ot the same age, but I don't feel like you're ever too old. I don't feel like especially sales. You're never too young to start. If you want to start, just start.

I started looking at people who started different careers in their thirties and forties. And Vera Wang was 40 when she went out on her own and started designing wedding dresses, like, and that's turned out pretty well.

Like Julia Child was, I think 40, a famous like chef, used to be on TV um, movie about her a while ago.

But there, and there was actually a study that I read a while ago that talked about like founders who were like middle aged founders, actually do way better than the typical kind of what we think about like young kid with a hoodie, whatever. But like in the real world, companies that actually make money a lot of times, like people that are not, right out of college or dropping out of college, also do really well.

When I was at Outreach there, especially at Outreach um, there were a number of like SDRs who were, I mean, had to be forties, fifties, at least. And they were great. Like fantastic because they just had enough life experience they could just have a conversation right and knew enough about business and that's the career they wanted. They didn't want to travel. They liked sales. They liked talking to people.

God. They were some of the best SDRs. You don't have to let what somebody else thinks or what you think they think, define what success looks like to you. And so like if you're 50 and you want to be an SDR, you should be an SDR, and you don't have to be an SDR manager and you don't have to want to be an AE.

I mean, like some of the best, like SDRs I've ever had have been people that are like, "this is what I want to do and I like doing it and I'm good at it." And I was like, yes, amazing. Anybody who ever disrespects that part of the job, like that, those people, those sellers has never done it because that's like some of the hardest part.

Like I can do cold calling. I have done it. I've opened deals that way. It's not my favorite. And I was never great at it. I was passable. But the other thing too, is, I was talking with a salesperson that I coached about this because she's kind of weighing " should I stay in sales or should I go into leadership?" And I was like, first of all, you are already in leadership.

Scott Ingram has a phrase where he calls like leading from the field. When you're showing people this is what's working for me, or this is something I'm trying, like you're already in leadership.

So you would need to change your language there and reframe that for yourself. But the other thing is I think it's very smart to, to take a hard look at what we actually want out of a sales career or any career and be like, when people start saying oh, aren't you going to go into "leadership" or don't you want to lead a sales team? And don't you want to be, you could be a VP, you could be an SVP.

I've had to do this, a sit down with myself a number of times, but, and be like, do I make that pivot into, you know, leading teams? And every time ego-wise, like those titles would be great. Like I've peers who, you know, my same age and tenure in sales that have had those, and I'm like, "yeah, that title sounds great."

And then I look at their calendar and I'm like, I don't want to sit on eight hour, like back-to- back Zoom calls. I'm too much of a control freak to like, not want to run my own deals. And. I don't want to manage a team of salespeople. As you mentioned, I already have children.

And so, that's been a hard like gut check, but again, like growing you up and being mature, like being real with myself. Because like life is too short and also days are too long to do something I don't like. And I would hate that. I just know I would hate sitting in. Meetings looking at forecast dashboards. It just kill me now.

So, it's not fun, but have the courage to sit down and really sit down with yourself and be like, do I like this? And does it make sense for me to move from an SDR to an AE if I don't think I will like it? Does it make sense for me to be a manager or go from being a manager to being a director, a VP, if I If I know myself and I know I wouldn't like it?

Why should we let what other people think dictate what success means? That's not a life I want. And I think in sales, especially in fast growing like tech companies, it's like, "well, if you aren't moving up, like does that, are you not really engaged?"

And you're like, "are you paying attention?" Look at all the other things I'm doing just because I don't wantto sit on an eight hour, eight hours of Zoom calls doesn't mean I'm not engaged or with the company. And I think good companies recognize that and don't view that as like a red flag that you don't want to move up.

It's like, thank God we have some stability on this team. But yeah, that's a, that's an interesting one for people that, as you talk about your sales career, don't let somebody else define what you can do or, or what success looks like for you. Cause it's not the same for everybody.

Mike Bird: Yeah, you're alluding to something that Kim Scott calls Rock Stars versus Superstars. Superstars are those high growth want to get promoted five times in, in six years or whatever. But then the Rock Stars who are very steady, usually individual contributors who have mastered their craft and the decades of contribution that they've maybe made to the company.

And she worked for Apple. And so imagine being someone who has made all of the iPhones, the impact that's had on everything, the company, the people who use the product. Yeah. You need those folks. So I appreciate that perspective you're sharing. We got to wrap this up. This has been a great call.

I've appreciated this conversation.

[00:25:08] Learn more about Krysten's work
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Mike Bird: Can you share a bit more about what you're up to and where people can go to check out what you're doing?

Krysten Conner: Yeah. No, this has been so great. It's I love talking about this stuff because in the hopes that it's helpful for anybody else. Cause everybody falls into sales, but very few people, you know, out the jump right at 5 years old, they're saying I want to be a salesperson. And if they are kudos to them, but definitely wasn't. So it's fun and hopefully it helps other people.

Yeah, you can find me on LinkedIn and so what I'm doing now in everything that I do is actually combining what I learned in sales with my teaching background to help salespeople take charge of their own development and walk through this is how we do best practice.

Because managers, a lot of times sales managers are great at telling us what to do. And even why to do it, right? We should multi-thread: it de-risks our deals. We should do, second and third level discovery. What is harder, I think for sales managers is, uh, because of time or personality or a lot of things, they don't always tell us how. This is how we should do it. This is what good looks like. These are the steps. What I do now full time is coach and teach AEs and do group training to help people actually do the things that we know we should be doing. But it's a matter of how, that's the biggest thing.

And that it's fun to have that teaching part come back around and be able to see the light. I always like seeing the light bulbs come on for people who are like, Oh, like this isn't that hard. It's Oh, it's not.

Mike Bird: Oh my gosh. Love that. Thank you so much again. I'm excited. Hope people go and check out what you're doing. I get your emails every Saturday. They are great. They give me something to think about. And what you're doing on LinkedIn too, typically also very helpful in terms of actually getting to the how, to your point earlier. There's lots of surface level stuff that people can talk about doing, but " How do we do it?"

I love it. Thank you again. It'll be fun to publish this.

Krysten Conner: Hey, thank you so much. This was really fun.

Mike Bird: Hey again. Thanks for tuning into my conversation with Krysten Conner.

If you're new to the Sales Secrets podcast and found this content helpful, then go ahead and hit that subscribe button.

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I appreciate your help. And we'll catch you again in a couple of weeks. Bye for now.