Episode: 492 |
Krysten Conner:
Enterprise Account Executive :


Krysten Conner

Enterprise Account Executive

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  1. Krysten Conner


Krysten Conner, Will Bachman


Will Bachman  00:01

Hello, and welcome to Unleashed the show that explores how to thrive as an independent professional. I’m your host will Bachman and I’m here today with Kristen Conner, who has been an enterprise sales rep at three unicorns. And she also coaches sales reps. Kristen, welcome to the show.


Krysten Conner  00:21

Hey, thanks so much. I’m excited to talk with you.


Will Bachman  00:25

Now, Chris, and I got became aware of the work you’re doing from one of your posts on LinkedIn, which someone else had shared or liked and commented on. And it was quite well done very engaging posts, and you’re really crushing it with your LinkedIn content strategy. And when I kind of scrolled back over your posts back in time, you know, earlier ones, we’re getting a more modest, you know, 10 or 1520 likes and a few comments. But today, you’re getting 350 400 likes, you’re getting 6070 100 Plus comments, really quite extraordinary, particularly compared to like the size of your following which you have something like I don’t know, 15,000 followers. So you’re really getting excellent engagement, and love to hear a bit first, just about your content strategy for LinkedIn.


Krysten Conner  01:19

Yeah, thanks for the question. It’s definitely something that has evolved. And it’s also something that I’ve spent a lot of time and, and some money on the, like I said, I’ve taken three. Actually, I think I’ve taken four different courses on like, utilizing like finding your voice on LinkedIn, and then really a content strategy and then like how to be a better like writer or copywriter Justin Welsh has two different amazing courses. One is basically like finding your voice on LinkedIn. The second one is basically like, content strategy. Austin, belt ballsack, or belcheck. Did a free like LinkedIn masterclass, he has a million followers, just crazy. And then, and then the last one that actually I just wrapped up doing recently, is really just how to, like how to be a good digital writer, and write like for engagement? And it definitely took off during that time. And that is the ship 30? course they do. And they have a ton of free resources online too. So if you want to, if people want to check them out, and kind of get an idea of what they’re about before they pay for it, that’s that’s definitely what I did.


Will Bachman  02:38

What are some of your key lessons learned from this investment? You’ve made in your own skills as a writer? What are some of the key principles of digital writing?


Krysten Conner  02:48

Yeah, I’d say, like, find your niche. And you’ll, you’re gonna have to experiment with it. Right? Sometimes you’re gonna have to find what doesn’t work before you find what does work. And I would say understand all of the courses that I took really talk about, like how to make your writing punchy, and, and with, into right for how people read it. Yeah, it’s, it’s also like kind of the side benefit of that is it helps me as I’m, as I still am a rep, it helps me in demos and conversations with customers to be more succinct. And to think it helps me I think writing helps you think more clearly. And so it kind of helps you everywhere.


Will Bachman  03:36

What I’ve noticed about yours is, at least the ones now they seem to follow a similar kind of layout or design where you you typically will start out with this one kind of punchy, attention grabbing headline, like, I was an AE at three unicorns. And here’s, you know, a mistake that I used to make, or here’s three things The To Do When You’re or here’s three things they don’t teach you at the big firms. It’s, it’s always kind of like this attention, getting headline to try to grab people and talk talking about how you play with those, refine those get to those, you know, do you test out a bunch of ideas or walk me through how you came up with that. That kind of design and approach?


Krysten Conner  04:19

Yeah. So yeah, I mean, when you take LinkedIn courses, that’s one of the first things that they’ll talk to you about is like making sure that every sentence is an advertisement for the next sentence. And that when people read things online, they read quickly. And what you are asking them to do is trade a part of their time for you know, they’re spending part of their time with your content. So every line has to kind of lead them to the next line. And one of the things that they talked about in this in this last class that I took that I think made the biggest difference there’s like two things first is that you you have to You basically state your credibility. And I think the first thing that I wrote wrote that went really viral. That was whenever I started by saying, you know, for four years as an enterprise rep, you know, five years in tech sales are, you know, and three unicorns and here’s, you know, and, you know, here’s x, y, or z. And that’s it just took off. And that’s where I realized, I think the difference between what how I was positioning it is I wasn’t giving, I wasn’t telling people upfront, like why they should listen to what came next. Because and then the other thing that I realized after watching kind of the theme of what people responding to is, sales. People want to be taught and taught in specifics, not taught in concepts, sales, people get a ton of training around just like general concepts, you should multithread, you should run good discovery, you should get to the decision maker, but they are very rarely given examples of how to precisely go about doing that in the roles they have.


Will Bachman  06:15

So after a bunch of testing and refining, in these courses, what now would you say is your target audience who you’re writing for? And what are the topics that you’re writing about?


Krysten Conner  06:28

Yeah, I would say the the art the audience is really early stage account execs. And then a lot of times it’s SDRs, or BD RS that want to be a someday. And they’re, it’s mostly coming from, like smaller companies, where they don’t get a lot of training. And even some larger companies where it’s just like a reinforcement of the good practice, like the best practices they already know, like, to me in sales, so much of it is one on one, but it’s just remembering all of the one on ones like all of the time. And so some for those reps that are at Big or really good organization, sometimes it’s just a reminder of the things they already know, that they should be doing.


Will Bachman  07:16

And for those who aren’t necessarily familiar with those acronyms, or even spelled out exactly those roles do, what’s the difference between an account exec and an SDR, which I guess is sales development representative and a BDR? Which I guess is business development? Or what are those different roles? Do?


Krysten Conner  07:37

Yeah, thanks for that. clarification on the vocabulary I get I’m in SAS sales. So people I forget pillows, no. So yeah, so an SDR BDR role is, is generally like the first person that is going to reach out to the customer. So if you think about a salesperson, like cold calling, you know, email, doing a lot of email prospecting, like that is what people do in those roles. And then many times, and then once somebody agrees to take a demo, or agrees to like, have a, like a, like a first conversation, then that gets handed off to an account executive who is then responsible for helping kind of educate, and create kind of demand and then run the deal all the way to a closed deal.


Will Bachman  08:26

Okay, got it. Talk to me about some of the, you know, areas of content that you’re speaking to the audience about. So you mentioned that sort of, in general, they want to be taught but like, what do you have sort of three or four or five or seven different kind of content areas that you’re focusing on?


Krysten Conner  08:49

What are you what’s like been what’s gotten the most like response? And interest is, its first discovery calls, like that’s your first call with an organization. And it is so hard to do that? Well, where you’re asking good business questions, good, open ended questions. And you are helping them think, not just like show show up and throw up where you just show up and tell them a bunch of information about your product, but you’re really getting them to think about what might be better in their own organization. And it’s just, I don’t think reps are really sales reps are really taught that very well. They’re taught to ask a bunch of product related questions versus like business questions. And that’s, that’s actually the second kind of piece of content that people really respond to is like the training that I was very lucky to get on, like how to have a conversation with an executive. These are the business problems executives care about. Most of the training that reps get is around the product, it is not around. How does this apply to someone to the VP Apple who was going to sign your deal?


Will Bachman  10:05

Talk to me about your advice around getting that discovery conversation about sort of identifying potential decision makers, and then ways to approach that person.


Krysten Conner  10:20

Yeah, so the best way that I have found is to kind of back into it. So, you know, in sales, you’re, you’re always thinking about, like, these are the three main things that, you know, my, my product solves. And so then coming at it from then going, like the finding the 10 impacts of each of not solving each problem. And then understanding who who does that impact effect? Does it affect a manager does it affected director does it affect a VP. And so as you have different calls with people at different levels of the organization, they are going to feel that the impact of that problem differently, so a manager is going to care about how their team is performing, they’re really not. their day to day problems are not risk and market share. But when you talk to a VP, they are not thinking about how their west coast, small business sales team is performing, what they care about is risk and market share, and, and their accountability to investors. And so just understanding who you have on the call and how that conversation sounds different based on who you have on the call.


Will Bachman  11:44

What are some advice that you have on reaching out to that decision maker once you’ve identified those people? That’s one of the hardest things and so many who are getting bombarded now by you know, cold outreach on LinkedIn, by email, what are some of the tips that you have to break through that noise and get someone interested to get on the phone?


Krysten Conner  12:07

The overarching principle is, is it is never about us. It is always about them. If we are starting an email with AI, or we or our company does, that is the wrong way to start it. People don’t care, they don’t know you. And so it is always about them. And because people are bombarded, the first thing that you have to do is stand out. And one way that you can do that is by personalizing things and personalizing it by in showing them that you have actually done the research about them personally, you mentioned, if they’re an executive, sometimes they will have been on a podcast, something sometimes they will have written an article, sometimes they will have published something on LinkedIn, sometimes they volunteer for an organization. And if people spend their time to volunteer somewhere, they must care about that. And then taking the time to mention to notice something about that and then to then tie it back to the reason that you are reaching out or the other way that you think that it can help them. Also, most of the time, people are looking at emails on their phones. And so if someone has to scroll to read everything you wrote, like you are doing it wrong, and you will lose them. And no, and the last thing is, is that the phone is the least noisy channel. If you think about just in your day to day life, how many emails you get versus how many texts you get versus how many voicemails you get, you might get one or two voicemails a day people get dozens of texts and emails, if not, if not hundreds of emails, depending on your position, like the phone is the least convenient. It is the hardest, it is the most intimidating. And it is the least noisy channel to get someone’s attention.


Will Bachman  14:07

Will talk to me about that about your advice of just calling someone’s phone. And we’re just kind of intimidated do a lot of us wouldn’t want to get calls inbound calls. So do you recommend people just call someone’s phone directly with no kind of free, you know, vetting or permission to talk to me about that?


Krysten Conner  14:30

Well, I mean, if you are I mean, if you are in sales, like your job is to get ahold of someone and pique their interest in your product. And yes, you are like interrupting their day that is part of the job but also like most people, most of the time, you’re not going to pick up because they don’t recognize your number. You might and you should be ready for that. But most of the time, they’re not going to pick up up because they don’t recognize your number. And so you should have a very tight, scripted message that you leave. And I’d say Josh Braun has some great cold calling, or, you know, cold calling scripts, where he basically says, like, you know, hey, well, I saw, this is the kind of business you’re in, I’ve got two ideas on how you might improve X, Y, or Z. Hey, this is in this is Kristen Connor, this is my cell number, and no need to call me back, I’ll send you an email with more detail. So like, the voicemail is an advertisement for the email to go, that goes into more depth and asking them to call you back. So probably not going to go into anyway. But it’s just a way to stand out. And calling and like leaving LinkedIn. voice message is also like kind of unusual people, people might, you know, send you a message on LinkedIn. But it’s not often like a voice message or video message. So that’s definitely a way to stand out as well. And I can’t remember who said it, but basically, somebody might have been Zig Ziglar I, but I can’t remember. But they were saying, if you sell something that you believe in, and you really believe it can help people and solve their problems, you have a moral obligation to tell them about it. And, and I also, I believe that people aren’t aware of everything that’s out there, I’m helping them be aware, my stuff is not for everyone, but I owe it to them to tell them and I think it’s easier to make those calls if you really believe in, in what you’re selling.


Will Bachman  16:39

And so where would people you know, get those get that contact information, do zoom info, or one another resource such as that.


Krysten Conner  16:49

So definitely a lot of data providers out there, if you you connect with folks on LinkedIn, if you’re a first degree connection, you can leave someone like a voice message. And that’s really probably the easiest way to go about it. Because people’s lots of times, same info and other data providers have old information, that’s not correct. And so you might be paying for bad information. But if you spend the time to personalize an email, or personalized connection requests on LinkedIn, and you’re adding value, if you if you like and comments on something that someone posts and you’re genuine about it a couple of times before you send them a connection request, they’re probably going to respond and then you can connect and call them and leave voicemail, you know, or whatever. Right, right from LinkedIn. That’s, that’s definitely the easiest way I found lately where you know, after COVID, nobody’s in nobody’s in the office anymore.


Will Bachman  17:47

Tell me about your work coaching, sales development reps, business development reps and account executives.


Krysten Conner  17:55

Yeah, it’s kind of came about started really organically where I was just kind of mentoring people in, in the organizations, I’ve been a part of that were, you know, you know, that were new. And I was because I was very lucky to have people that were willing to do that for me. And so just kind of I can’t pay those people back that I can pay it forward. And then as I as I could have gotten more traction and more kind of visibility, writing on LinkedIn, people would reach out to me. So yeah, I’ve been coaching people for a number of years. And it’s really it’s not, I don’t have a, I don’t have a course I don’t have a curriculum, it’s really like we get together when they on their schedule, whether it’s once a month or once a week, and we just go over like, Hey, this is the problem I’m having, I haven’t gotten any product training, or I’ve asked my boss for help. And they haven’t helped me with how to prospect in my territory. And so it’s just, we just go over, you know, the things that they’re needing help with, and I make some suggestions, and I send along I suggest like resources, books, podcasts and stuff that have helped me and just try to help them. I get a little further along, I think I think most people in sales think that their manager is going to do a lot of coaching for them. And that is rarely the case.


Will Bachman  19:19

What are some of your tips on you know, when you’re coaching people about how when to reach out? Is there a good time of day to do that? Maybe it depends on the method should you try to, you know, call people’s cell phone or send them a LinkedIn Voice Memo at a certain time of day or day of the week.


Krysten Conner  19:41

I like sending people things at times where they are not likely to be as busy or where they’re where my message is not in competition with a lot of other things. So and that part of that comes from whenever I was working on that outreach, which is a tech company that has a lot of data around when the best times to reach out are. And as I looked at the data executives were responding to and reading and responding to emails in the evenings. And like on Sunday afternoons, and so I started then scheduling my emails and messages to I would never, I would never call someone I would never like call someone cell phone that I didn’t know didn’t have a relationship with on the on the weekend for sure. But as far as like written communication, email messages, LinkedIn messages, I like to send those like, after, like 7pm during the week, and then like Sunday, like early Sunday afternoon, because that’s when executives are sitting down to plan their week, and they’re not rushing from meeting to meeting like they are Monday through Friday.


Will Bachman  20:54

What about your LinkedIn posts, you’ve clearly experiment quite a bit and found a winning formula. Is there a day or time during the week that you find has gotten the best responses?


Krysten Conner  21:07

There’s lots of different kind of like schools of thought about that. And yeah, definitely done a lot of experimenting with it. I post mine in people that I am like that connect with myself, generally, it’s pretty like early in the morning during the weekday, and I will. And then also a lot of times, like on Saturday, so I post during the week, like, like three days a week and early morning, I don’t find much engagement on LinkedIn on a Friday, Monday is hit or miss. So I usually do Tuesday through Friday, Tuesday through Thursday mornings on LinkedIn, and sometimes one on Saturday. And on Saturday, it’s amazing how many people are are right there again, because they’re not in their work, email, but maybe they’re like trying to they’re looking for content, they’re trying to find something that’s going to help them, you know, in their job during the week.


Will Bachman  22:01

And what have you learned about the importance of engaging with their engagement? So if someone comments about replying or commenting on their comment.


Krysten Conner  22:13

Yeah, that’s one of the one of the first things they’ll teach you in any course any good course that you take on LinkedIn, which is the algorithm is picking up engagement. So as soon as someone comments, you want to immediately engage and reply to their comment and to and ideally, do so in a way that that creates, like further engagement further discussion where you, you know, they comment and they, you know, say something, then you can ask well, okay, you know, thanks for, you know, Thanks for the kind words about, you know, what I just posted, like, what would you add, because people love to give advice, and people are really smart, and they’ve picked up, you know, a nugget or two that they can share. And so, you know, asking a question that invites them to go a little further or is, is definitely going to get your, your stuff your content out there more and more, because I think it’s pretty well known that the LinkedIn algorithm definitely definitely favors engagement, the more engagement your content gets, the more people there, LinkedIn is gonna put it in front of because that that keeps eyeballs on their platform. Right? It’s that’s what serves their business model.


Will Bachman  23:30

And what have you learned about the importance of kind of focusing in on a sort of given topic area, versus kind of posting randomly on all the different topics? Did you find that you, you’re posting on a given topic area and narrowed in on that, that you started to go deeper and get that consistent? Repeated engagement from a dedicated audience?


Krysten Conner  23:54

Yeah, I think, yes, exactly. That I think you have to start, you’re gonna start by doing a lot of experimentation. And you’re gonna start by going pretty wide a lot of times, and then, and then you kind of let the engagement data speak to you. And it’ll be pretty clear. Like, if you get no engagement, like people are low engaged, like people are not, you know, interested in that topic, or they’re not, you know, didn’t find value in the way that I presented it versus, you know, obviously, something takes off be like, Oh, this is, this is a big pain point. So there are there’s definitely there’s a couple of tools out there also that I mean, you can kind of eyeball it, you know, but there’s some that go a little more specifically into like, which if you post a lot like which posts get the most engagement, but yeah, you just have to, it’ll be pretty clear like from just from the engagement numbers, what what people are interested in hearing about and talking about and then also frequently if people are kind enough to, to message me directly and say what helps them I will also ask them like this, you know, so nice, thank you for doing that. What other things would you be interested Did in in seeing would love your advice. And again, people love to get good advice. And a lot of times early career people are are really hungry for anything that can help them and they have. I’ve gotten people send me like six paragraphs like here’s, here’s all the things I want help with.


Will Bachman  25:17

Tell us about those tools that you mentioned to help monitor engagement.


Krysten Conner  25:23

So there’s, there is a company called shield analytics that is specifically for LinkedIn that will slice and dice your engagement data. It’s a subscription. And it will, it will definitely help you really pick up on on trends. And I found it super helpful. And then in the ships 30 course they have a product called timeshare, which lets you create like a content library so that you can go back to it. And that’s one of the hard things actually about if you’re writing on LinkedIn or Twitter, it’s really hard to have a concise or one central place where all of your content lives. And so type texture has been very helpful for that and timeshare will measure your engagement metrics, not on LinkedIn, unfortunately, but it will do it for Twitter. And so if you’re writing on Twitter and you want to measure engagement, it that’s one of the tools that will measure it, there may be others. That’s that’s just one I’m aware of.


Will Bachman  26:30

Kristin, if listeners wanted to contact you and find out more about your work, where would you point them online?


Krysten Conner  26:39

Yeah, they can get on my LinkedIn profile and it also links to the website for my coaching practice but the the website for my coaching practices Cross cuts.io Cross cuts is a is an old word for shortcuts. And so I like to think that I’m helping people and giving giving them the shortcuts that I wish I’d had are very early on in my sales career.


Will Bachman  27:05

Fantastic. Listeners, if we will include those links in the show notes, so check their follow up with Kristen if you want to learn more about her work. And if you are so inclined to give this show a five star review on iTunes. It does help others discover the show. Kristen, it’s been fabulous speaking with you congrats on all the success you’ve had building up a really amazing audience and producing excellent content.


Krysten Conner  27:31

Thanks so much for the opportunity to talk with you. It’s been really fun

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