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Outbound Squad

31 Aug 2026 · 1h 13m · 28 chapters

Episode artwork

Tackling new territories, multi-threading, and more with Krysten Conner

In short

How to hit the ground running in a new territory (enterprise/strategic AE focus) using “martini glass” pipeline thinking, account/exec research, warm entry paths, and outbound-led discovery. Also covers multi-threading and building POV/hypotheses.

Guest

Krysten Conner runs a coaching business (kristinconner.com) helping AEs win six- and seven-figure deals. She previously sold enterprise at Outreach and Tableau (and other major tech companies). Background includes teaching middle school history, then working in her family’s niche insurance agency (equine/race/show horse coverage), and later transitioning into tech sales after being a buyer herself.

Key claims

  • ICP must be based on who actually paid (CRM “where we win”), not marketing’s target.
  • New leaders (e.g., hired in last 3 months) are a top signal for openness to change.
  • Narrow by industry, employee count, company age/growth, and deal outliers; don’t start with an alphabetical list.
  • POV must match the right “altitude” (end user vs manager vs executive).

Notable examples

  • POV example for Samsara: earnings showed profit driven by >$100k deals; hypothesis tied to building enterprise teams and transformation-focused conversations.
  • Referral/intro tactic: send a short list (<10) with LinkedIn links; ghostwrite a first draft; don’t mention the product name.

Written by AI. May contain mistakes.

Chapters

1:30

Understanding Pipeline and Account Strategy

Discussion on effective account management and building a pipeline strategy.

“Really, we're all about helping you generate qualified pipeline.”
3:08

Kristen Conner's Sales Journey

Kristen shares her background in sales and how she transitioned from teaching to enterprise sales.

“but how to analyze your own ICP, look for account patterns, how to get introductions, how to create a POV or hypothesis, how to find the warmest path in.”
4:25

The Niche of Insurance and Sales Skills

Kristen discusses her experience in the niche insurance market and its impact on her sales skills.

“Our average client increases qualified pipeline created by 20 or more percent within 90 days.”
6:02

The Unique Perspective of a Former Buyer

Kristen talks about how her experience as a buyer influences her sales approach.

7:30

Challenges and Realities of Enterprise Sales

The discussion covers the unique challenges faced in enterprise sales compared to SMB sales.

“Did you develop a passion for sales during that time?”
9:04

Personality Fit in Sales Roles

Kristen explains the importance of aligning personality traits with sales roles, especially in enterprise.

11:50

Starting a Coaching Practice

Kristen discusses her transition into coaching and the frameworks she uses to help AEs.

“The project management skills, I think, of working in an enterprise deal, it's not for everyone.”
14:00

Understanding the Reality of Enterprise Sales

Learn about the emotional challenges in enterprise sales and the importance of self-awareness.

“Um, so I think people have to be really real with themselves about what they're, what fits their personality and how they want their days, how they, what they spent their days, how do they want to spend their months?”
14:43

The Journey to Coaching: How It All Started

Discover how Krysten Conner transitioned from sales to coaching and the importance of teaching.

“So before we get into that, how do you how did you land into like starting your coaching practice?”
17:48

Mindset for Tackling New Territories

Explore the mindset needed for account executives when starting in new territories.

“So let's talk about the first kind of big topic that you help account executives with and how to tackle a new territory.”
Show all 28 chapters
19:16

Identifying Ideal Customer Profiles

Learn how to analyze CRM data to find patterns and identify ideal customers.

“That is in my mind, the only criteria for what makes ICP.”
21:45

Exploring Company Characteristics and Sales Signals

Understand which company characteristics can influence sales strategies and opportunities.

“So one is number of employees, meaning like company size.”
24:27

Filtering for the Right Executives

Discover methods to identify the right executives for sales outreach and engagement.

“So I'm curious how your guidance might change with this because I'm sure there's kind of a range depending on how enterprise or strategic a rep might be.”
28:01

Identifying Executive Success Indicators

Learn how to evaluate leaders based on their previous achievements and connections.

“You know, you might have a new C-level leader that brings everybody over.”
30:00

Account Mapping Strategies

Discover effective techniques for mapping accounts and identifying key players.

“The people that are really going to care about making change.”
31:39

Building Warm Connections for Sales

Understand how to leverage connections and referrals for better sales outreach.

“What are some of the strategies that you typically recommended and have seen success with here?”
35:01

Effective Referral Requests

Learn how to ask for referrals in a way that feels natural and easy for others.

“So let's say that there's someone I'm connected with and I want to ask them to introduce me to someone.”
38:00

Crafting Point of View in Sales

Explore how to create compelling points of view for engaging with accounts.

“I'm going to, you know, this is not a referral or an introduction that you're going to be embarrassed about.”
39:22

Understanding Industry Trends for Sales

Learn to tie industry insights into your sales strategy for impactful conversations.

“Um, let's shift gears a bit and talk about POV and like hypothesis creation.”
42:05

Understanding Sales Team Dynamics

Discusses the importance of recognizing sales team dynamics for effective engagement.

“So usually we find that there are two or three tension buckets, problem buckets, that we have triggers that lead into those tension buckets and then trust statements below that.”
47:34

Outbound vs Inbound Discovery

Explores differences between outbound-led and inbound-led discovery processes.

“So like when you talk about like martini glass, like that funnel, right?”
50:42

The EMT Discovery Framework

Introduces the EMT framework for conducting effective discovery calls.

“So what are kind of the key parts to this?”
56:00

Excavating Pain and Matching Urgency

Learn how to effectively excavate pain points and match urgency during sales calls.

“This gets you hopefully there in the first couple minutes.”
1:05:36

Rapid Fire Questions with Krysten Conner

Engage with Krysten Conner as she shares how she leverages AI and her personal insights.

“And that is when we help buyers think through that, we are helping them make a good decision.”
1:09:06

Influential Insights on Buyer Psychology

Discover the importance of understanding buyer psychology and decision-making.

“but it probably changed the way I think about just psychology in general and influence in general.”
1:10:01

Reflecting on Family Dynamics

Exploring new perceptions of family gatherings through different lenses.

“And once you read that and see those things, you'll never like look at Thanksgiving or a family reunion ever again.”
1:10:46

The Importance of Coaching in Sales

Discussing the value of coaching for sales professionals to achieve success.

“Like when I got my first tech sales job, I hired a sales coach.”
1:11:58

Building Effective Sales Processes

Understanding the need for sales processes aligned with buyer behavior.

“next role and in their next company like having an actual process because the sales process that we're given is really more like forecasting process or like CRM process.”
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Transcript

Automatic transcript. May contain errors.

0:00Beginning of a quarter, or maybe it's the beginning of your fiscal year, and you're handed a new set of accounts. For some of you listening to this, that's going to be really exciting, right? You get to start over, you get to start from scratch. And for a lot of you, probably a lot more in our experience listening to this, is you might feel super overwhelmed, right? Especially if you're not an enterprise rep and you have dozens or hundreds of accounts, you might be thinking like, where to start? Where should I spend my time? And what most reps end up doing in our experience is they just work their account list from top to bottom in alphabetical order, or you just cherry pick some of the top accounts.

0:37And the reason why this is very ineffective, especially if you're trying to build pipeline, is that if we don't think of our pipeline like a martini glass, so we got to shrink that top of funnel so that we can go super deep on fewer opportunities. it's everywhere you look statistically it is harder to get a meeting and it takes more and more touches via email social and phone and it's also harder to sell win rates are actually slightly up right now according to the data but it is taking longer to close deals and the average deal small deal size rather has shrunk dramatically buyers are wanting to get started smaller more proof of concepts, pilots, et cetera.

1:18So today's episode, and we'll introduce the guest here in a second, is all about how to tackle new territories and really hit the ground running, especially if you're an account executive. But before we get to that, my name is Jason Bay. I'm CEO at Outbound Squad. Really, we're all about helping you generate qualified pipeline. So there are a couple of different types of folks that listen to this podcast. So one is, you know, you work for a a company like a Shopify, Zoom, Rippling, Gong, category leading company, and maybe you're leading a sales team, whether it be SDRs, AEs, where, hey, we've never really formalized a methodology or process with how we do outbound, right?

1:58And we need to create a common language. That's something that we talk a lot about on this podcast that we help a lot of great companies with. The other types of folks that listen to this podcast are maybe just getting started with outbound. And maybe you've been primarily inbound led and you haven't had to do a lot of outbound. So as an AE team, you're self-sourcing pipeline for the first time. As an SDR team, more of you are going outbound. Maybe you have account managers that really need to go more outbound, quote unquote, into your customer accounts. You're definitely in the right place as well.

2:26So everything that we talk about is pipeline generation related. So today's guest, we are talking to Kristen Conner. Kristen Conner is really great. I've known her for a long time now. She has her own coaching business at kristinconner.com where she helps AEs win six and seven figure deals. She was a previous enterprise account executive at Outreach, Tableau, a bunch of other really great companies. And she's someone that really just has a lot of experience as a practitioner of sales. Someone that has done a lot of enterprise sales at least. And that's sort of her specialty. So one of the first things that we talk about is how to tackle a new territory.

3:07Everything from analyzing your ICP, no, not the one that marketing or rev ops gave you, but how to analyze your own ICP, look for account patterns, how to get introductions, how to create a POV or hypothesis, how to find the warmest path in. A lot of what she talks about too is how to run that first conversation when it is outbound led. When someone comes inbound and they've already decided that they're at least open to getting help, that's a very different conversation from someone that you got a hold of over the phone or through maybe a referral who took this meeting and wasn't really feeling like a problem or maybe didn't have a project or an existing initiative to bring on a solution like yours.

3:45So we talked about that. We talked a little bit about multi-threading. We actually got a chance to catch up in Dallas when I was there in person a month or two ago. So this is really awesome. Two things before you listen to the episode. One, I have something free to give you. It is our outbound mastery, uh, masterclass rather that can be found at outbound squad.com slash masterclass. It's our very best content in course form. So I spent about six hours in a studio to produce two and a half hours, three hours of our best content, everything from, you know, some of the targeting and, uh, strategies that we're going to talk about today, a cold email, cold call, how to use the phone, email, social, et cetera, to secure meetings.

4:22All of that's there at outbound squad.com slash masterclass. Make sure to check that out. The other thing is if you listen to this episode or you've been a listener, you know, like, you know what, I really would like to talk about Jason and team to see how they could help our organization source more pipeline. Our average client increases qualified pipeline created by 20 or more percent within 90 days. And we've done that for Shopify, Zoom, Rippling, Gong, iHeartMedia recently. And we work with a lot of startups building out their first outbound motions and then everywhere in between, just send me an email directly.

4:55Jason at outbound squad.com would be happy to chat with you. All right, let's get to the episode.

5:06So I'm excited. This is our first time in person, which is crazy. So I know, right? I think we, last time we talked, we were like, how have we not met in person? Yeah. Yeah. It's crazy where you're like, have I met this person? I feel like I know them really well. So yeah, it's crazy that it is, but I'm glad we did this. Yeah. And I've been a big fan of your content for a long time too. Um, and I'm really excited to dig into it, but we have to go back a little bit. A lot of people get into sales on accident and I'm curious if that's the case for you or if it was something that you, you know, your parents did or something like that.

5:38No, I wish I would have realized it that early on that like, you know, I think it's a gift and people are like, this is what I'm going to do. But no, I thought, what I thought I was going to do was change the world. I was, I went, I was a teacher. And so I taught middle school history for three years and then burned out after three years, like a lot of new teachers do. And so then I was like, okay, well now what? Um, and I, my parents are both entrepreneurs and I had grown up working for, my dad ran an insurance agency and um and I'd worked for him since I was like 14 yeah in the summer and so at the time I was leaving teaching he was like hey we need somebody to come help kind of modernize everything would you come do that and I was like yeah but I don't know what I'm doing after this so sure and then he was like oh well this can be my succession plan like we can work so you can buy the company the agency and so I worked in all these different departments including sales and what i learned insurance super niche so my dad actually is uh retired now but large animal vet veterinarian and so we insured horses and horse farms so like race horses really fancy show horses especially where we're at right now in texas right right yeah yeah yeah all the yeah crazy it's like you know places you can go take riding lessons there's like there's like therapy that people do like equine assisted therapy with horses so anyway any place that does anything like that that's what we insured and so it's like super super duper niche there's not a lot of places that do that and so he like built a business doing that and and then because he was a vet he like would um he could also adjust the claims like if the horse died like making sure that the horse you know actually died accidentally and not that somebody was like i really need money i'm gonna kill off my two million dollar horse anyway yeah people do weird things this is not something that godfather right but yeah it's not something you hear about on career day but what i tell people that i learned most about running that agency for like six years is that i learned i did not want to run an insurance agency like i i did it but it was really scary to tell my dad like hey remember how this was our plan and this was my plan for my future and my family i don't want to do this and so then it was like okay for now like the second or third time in my life being like now what do I want to be when I grow up?

8:00Did you develop a passion for sales during that time? Yeah. Because when I started thinking about, okay, well now what do I do? Because obviously it was a transition. It wasn't just like one day I just left. And so I started thinking about, okay, well, what, what do I want to do? What do I like to do? And of the, all the different things that I liked, I really liked, um, sales and like helping our, cause it, it was a very collaborative say like you're you're helping like people that you know run horse farms like they're passionate about doing that they are not necessarily passionate about the business side so it was really a lot of education around like hey this is what you need so it was very helpful like very collaborative yeah and i really liked that piece of it and also kansas city has like a small this is where we were living has a small like tech hub and like so there's there was like there were some tech companies there and i just i followed startups just like recreation because i was interested it and so then as i started thinking about okay well what do i like to do how would this make sense i was like well i like sales and i like tech but i'm like who's going to give me a job in tech sales with a teaching insurance background but then there was a startup that i followed that sold to k-12 education and so i was like well yeah i've never used salesforce before true story um but like i know your buyer better than you do like i know i know what they think about i've been on the opposite side of the table and so like putting that narrative together like in a way that made sense is how I talked myself into that or talked myself into that role and talked to the leaders into giving me a role there so yeah so you're at Tableau and Salesforce yep and then you met you know Clara Johnson yeah through outreach outreach yep um and Clara was I was talking to her I was like so you know Kristen she's like yeah she was always like just top-notch enterprise seller we're always asking her for stuff and advice and stuff and um but where did you really develop like your specialty is like enterprise and strategic like deals like where did you really develop like the acumen for that like what was what was that process like yeah i think that that came pretty naturally to my personality which is um but i mean you certainly have to develop your skill at it but the reason i say it came pretty naturally to my personality because that was actually a reason i thought i shouldn't be in sales because in my my husband was actually like you should like you should be in sales and i was like yeah should i you know because i was you think of like used car salesman and like super high pressure and i'm like and he's like you already are but i didn't think of it in the insurance world i was like well i'm helping he was like are you not selling them stuff and i was like oh i guess i am yeah um but but the teaching part of it too is like when you teach something you have to break it all down into the parts right and like to build a curriculum over a year you have to be like okay well we're starting here we're ending here how do i reverse engineer nine months of a school year so that everybody gets what they need yeah right and so that part of it was just um having an analytical personality and so i love to tell people that they're like well i'm not an extrovert it's like well if you want to do enterprise and strategic sales fantastic that's gonna that's gonna work better for you because you need to be able to like sit quietly and think versus being you know the more like small town, you know, you know, guy that runs the only car lot in your town who needs to be super friendly and love everybody.

11:20Right. So yeah, very, very differently. But also because I came from a teaching background, also because I had worked in our agency, I had been the buyer. Yeah. And so I think that gave me a really unique perspective. So I didn't know, cause I didn't grow up in tech sales. I didn't know like the way we always do it. I just knew how it felt bad habits or anything. yeah um and well also it also was like i came in yeah it was like you know that was the silver lining of not having the bad habits but also like i was scared spitless my first sales job because i never used salesforce i had never like forecasted i was like how do i forecast a deal like it's coming in or not right well right but it's what now and i know that now but like i was terrified at, you know, at the, at the beginning, but yeah, it, it, um, but having been the buyer, I was just like, so many things about the way we do sales didn't make sense.

12:13I was like, why, why would we do that? Why would we ask a question like that? Why would we say it that way? Uh, and I think that was, and not being afraid to just use common sense and just psychology to be like well this seems like a better way to do this so yeah so it sounds like a big part of it was you got into enterprise sales and it was more of a natural fit for your personality yeah which i think is important not to gloss over because you know people always talk about like enterprise and strategic sales and like hey if you're if smb fits your personality more like you it's okay yes like Do the SMB thing.

12:55The project management skills, I think, of working in an enterprise deal, it's not for everyone. It is not. You've got to be hyper-organized, and you've got to work really independently. That's okay if that's not your strength. A hundred percent. I think it can be such an ego thing. In fact, that's why I went after enterprise to begin with. I'm super driven. I got into sales, and I was like, oh, enterprise is like these are the top dogs. Sign me up. That's where I'm headed. but not realizing how different those deals were and really having culture shock that this is not just like a deal with a bigger company and add a zero on the end like this is a completely different feel yeah and like having as you mentioned outreach having worked at outreach and having seen like their smb team just killed it just smashed it right and so it's like they were making really good money.

13:47And so like, if you can do that, you know, they're like, Oh, well, I want to move up. I'm like, why? Like, you know, I mean, like, you know, in many cases, they were making as much or more as, as enterprise for sure. And you're like, dude, stay where you are. Right. Um, so I think people have to be really real with themselves about what they're, what fits their personality and how they want their days, how they, what they spent their days, how do they want to spend their months? Right. Like, can you do without the dopamine that you get from closing a deal in 90 days, you know, four months, six months, because there's a lot of loneliness in enterprise sales where you're just like, feels like screaming into the void, right?

14:25Just like to try to get someone to pay attention to you or try to get a 50 ,000 person company to move on something. And so like you have to be really real with yourself. Otherwise you will make yourself miserable. Like no title is worth spending your days in a way that you don't like. Yeah. Yeah. So let's get into some of those things that are going to be helpful for the enterprise and really any rep listening, but especially the enterprise and strategic reps. Yeah. So before we get into that, how do you how did you land into like starting your coaching practice? Because a lot of what we're going to talk about today is from like the many AEs that you have coached through this process and like you have some really awesome frameworks and all of that kind of stuff.

15:09Why start a coaching practice? um it happened accidentally on it started accidentally which was i started trying to figure out linkedin around like 2019 2020 because at tableau they were always pushing like social selling on us like oh like do this on linkedin and i'm like why do they care so much about this like it just was fascinating to me and that was when gong was really like doing really well at putting, having people be the face of the brand. And I was like, Oh, I get it. They want somebody to be the face of the brand. So then I started figuring, trying to figure it out. And, and so I made God a lot of mistakes and really horrendous posts.

15:49But what I started to figure out was when I, I mean, God, it's so embarrassing. If you go back to the early days, but what I started to figure out was when I taught something, when I broke something down, like, Hey, this is something nobody ever taught me, but I had to go, you know, bumble around and figure it out and broke it down into steps. Those things were the ones that took off. And then from there, then people would message me and be like, Hey, can I, can I, can I pick your brain? Right. Like, can I, can we talk about this? And so, and because I am at heart a teacher and that, like that helping piece really like does it for me I was like yeah sure absolutely and then it's and so and so like oh my god well what can I do for you like well you can write me a recommendation for this because I was like you know this may someday turn into something and if nothing else it shows I'm a team player right if all I ever do is work you know in a corporate job and so then that just kept happening more and more and then I was like I should charge I'm gonna see if I can charge for this because I don't have enough time with my like my real job and so then it just kind of went from there and i think i i was like why do i like why does this feel like such a good fit and it what i realized is it really just put a bow on like and brought everything full circle from like teaching experience to like stuff i learned in tech sales it just tied everything all up together and i tell like sales managers i get the best part of their job which i don't have to fire anybody i don't hire anybody i don't have to interview.

17:22I just get to help people with their deals and help them win. And it's fabulous. Yeah, it's the best. Yeah. Your content is so tactical. You do such a good job of breaking down these, like a really complex topic, like multi-threading. It's such a nuanced thing. And you do such a good job of just really breaking it down with a fresh perspective, but then also making it like, oh, I can literally use this right after I consume the content. So let's talk about the first kind of big topic that you help account executives with and how to tackle a new territory. So for anyone listening to this that's like less than a quarter maybe into the role or it's, you know, the first, you know, it's a key one and they've been assigned a new set of accounts, etc.

18:12can you walk us through maybe before we get into the tactics the mindset because this is very much not a a quantity game you're in fact the exact opposite i was taught the martini glass shaped pipeline which i always loved it's it's like shrink the top of funnel down and go really narrow and deep but can you talk about the attitude and mindset around this before we get into the tactics yeah like not everything not everyone is the right just like dating right like not everyone is the right fit for us yeah right and so we have to be able to do that and really focus and that's one of the disciplines of enterprise and strat sales is there's all these things we could do yeah but fine but like narrowing that down into what we should be doing and that is right account, right reason, right time, right executive.

19:06Yeah. And those, those are the way that we narrow down like what we should be going after and how we should be doing that. And I'll point out that, uh, whenever you talked about my coaching practice, starting a new job is probably the number one, like compelling event that seeks, that causes people to like work with a coach because they knew it worked in their last job and they want to make sure that it translates into their new job. and they also don't they want to like learn as fast as possible right cut the learning curve and also get to the get on the board as soon as possible right what we all want in a new job and so like i work with a lot of people that start this and so this is a really this is this is like the first what i'm gonna tell you is like the first session that we do almost always yeah which is we get their accounts and i tell them before before we or as we get this started the first thing we're going to do is run the why we win or where sorry the where we win report so we go into CRM and we look at closed one deals for the past two years and and if they're in enter you know if they're an enterprise segment then we narrow it to like enterprise deals closed in the past two years and then we start to look for patterns like in you know CRM basic CRM reporting you can filter by industry yeah right you can filter by geography like we just start looking for patterns because what we're looking for is our true ICP, which is who spends money with us, who gives us money.

20:33That is in my mind, the only criteria for what makes ICP. It's not what our founder thinks we should be selling to. It's not what marketing is going after. It's not, you know, the, the, the new vertical we're trying to break into. It's like, no, oh, these are the people that have given us money. So this is what we should be looking for. So we start there and look for patterns as far as like those. And usually there will be three, maybe four industries that stand out. We're like, this is who buys this. Right. And like that's true across. I work with reps that sell anything and everything. And that is always true.

21:13There's just always three or four. Yeah. That are like, this is, this is for whatever reason, this is what makes sense for them. So then whenever the rep loads their own accounts into SalesNab, then we start to filter down. We start to filter by industry, size of company. You look like you had a question. Are there any other less common things outside of – because industry is a big one. Is there anything other – or is there anything else that is maybe not so – or even counterintuitive? Yeah. Yeah. So one is number of employees, meaning like company size. Right. So sometimes if you're selling enterprise, sometimes that means accounts that have like 10 ,000 employees and above.

21:56Well, somebody that has 11 ,000 employees looks very different and operates differently than someone who has 30 ,000 employees, than someone who has 100 ,000 employees. So be a little more granular with a lot of these filters that have very wide ranges. Yes. in sales now yeah and looking at and that's part of the patterns too right is like looking at yeah how many employees do they have the personas involved another one that is maybe counterintuitive or maybe just less thought of is how old the company is and and how fast they're growing but i remember when i started um at at a role and i i went to the and our you know our sales source data wasn't very good and so I went to somebody I was like hey tell me like tell me where we went tell me the low-hanging fruit accounts and one of the things that I mentioned he was like we did really well with companies under 10 years old yeah after that they really slow down in how they you know are thinking about it and I was like I would have never thought that that made a big difference but once you see it you can't unsee it is this something now that you would ask a rep to use clod or something like that for to analyze yeah yeah Yeah, you can frequently find that out.

23:11And Claude is like a really good, or any AI, is like a good gut check for whatever your CRM data says because sometimes it'll mislabel things, right, whenever it doesn't have the employee band correct. Another thing that I like to look at in LinkedIn, and now they've put it into SalesNav, is for the personas or the departments that buy our thing, looking at how fast that department is growing. That's like another really nuanced thing. I feel like you got to dig a little bit deeper that can be really revealing for sure. Yeah, and depending on what we're selling, sometimes it may be good for us if headcount is growing.

23:46Sometimes it can be great for us if headcount is shrinking. Yeah, right. We just have to know. We just need to look for the, but yeah, those patterns I think are not things that people always think about. But one of the things that we talked about that is definitely a pattern, is definitely a signal, and you can filter for it in SalesNav, is companies that have new leadership in the past three months. It's a lovely little toggle in SalesNav, and it just unlocks a lot of magic. There's a quote from a previous leader that you like to recommend here that I love. Yeah, yeah, so why that is. And he said, no leader gets hires to keep things the same.

24:25Yep. You're like, when I heard that, I was like, no. like yes that's a hundred percent true so you know we're filtering by you know all the patterns we've all the patterns we've noticed all the things that make up the accounts that spend money with us and then we're filtering by those that have new leadership because like those are you know there's lots of tech now that like determines they'll say like oh this is a signal and this is a signal they're researching you yeah and none of no shade to any of that but like new leaders in the departments that we care about, probably the number one thing that indicates they may be open to doing something differently.

25:02So I'm curious how your guidance might change with this because I'm sure there's kind of a range depending on how enterprise or strategic a rep might be. But what is the goal of this exercise? Do you just want a couple of accounts? How do you determine how many accounts and which ones to start with? What is the result? I guess, of all of this. Yeah. And, you know, what enterprise is or what strat is varies by different company, right? So some true enterprise or strat reps, they may have three accounts. They may have five accounts, right? Versus I work with people that they have enterprise in their title, but they might have 117 accounts.

25:45They might have 74, right? Especially if they're in an early stage startup or lots of reasons. And so it just has to be, it has to be doable. But what I find is when you narrow by all those things, like what are the right industries for you? What are the right, what's the right like employee size for you? And one of the other things I mentioned, or one of the other things we should look for when we're looking, when we're running that sale or that CRM report about where we win, we also want to look for the outliers, like the large deals, right? Like, is there an industry, Is there an age or size of company that or a certain buyer that when they buy, they go big?

26:26Yeah. Right. So when we filter by all those things, it is usually not hard. It's usually not overwhelming to figure out, OK, well, what's our next step? Because there's usually just not that many of them. Yeah. So you really want to substantially cut the account list down. And once we do that, what's next after we've determined the accounts? Yeah. So we use all those filters in SalesNav and then we add those to our high value account list. Then we flip SalesNav to the lead side because now we want to look for the right executives. So then we put in our executives. And I really like to go deep to figure out the right executive.

27:16Like what is the right executive? And there's a number of patterns that I look for there. Does this, number one is like, does this executive have a pattern of achievement? Do they get promoted every couple of years? Are they, especially in industries where people stay or are not promoted quickly and somebody is moving up that ladder, like they have figured something out. Yeah. Executives that go from that start out in a really kind of new, like fast moving industry, but get hired at an old school industry. That is that company saying we have to do something different. Yeah. Right. Leaders that get brought over.

28:01You know, you might have a new C-level leader that brings everybody over. Right. um so looking at any anybody who's had exposure to our our uh product or service before they might not have bought it but and maybe because maybe they didn't buy maybe they wanted to but they didn't so like anybody who's had exposure to so like there's a number of things that we can look at as far as like what makes the right executive i also if you go into um you know you find your you know a new leader and you go into their linkedin profile many times they will in their not their current role in their prior role, they will tell you all the things they did and all the things that they accomplished or the things that they were responsible for in their prior role.

28:44That right there is telling you what they got hired to do. Yeah. Because leaders are just like salespeople. It's a performance thing. And like salespeople get hired to reproduce their past success. Leaders are the same. And so if, even if they've had the new role for two days and it's nothing is built out yet, go look at their prior role and the one before that because 90 % of that is going to be what they got hired to do in the new place. Yes. One other one, I call it the ship jumper. I don't know if you've seen this one or not. I think Nate and his Rala might have shared this on a LinkedIn post or something.

29:26Sounds about right. You look for the folks in the C-suite or at the VP or SVP level, and let's say that you're currently VP of sales outreach. What I would look for is other directors and VPs whose previous company was whatever your previous company was. And then I could see people that might've followed you to your new job. Sometimes that's a big list of people because the great executives will bring other execs over. Sometimes it's a small list, but essentially what we're talking about here in challenger speak is finding the mobilizers. The people that are really going to care about making change.

30:05So I really like that one. So we're doing the sales nav filters. We're trying to find the right contacts. We're trying to find execs that were newly hired. I love all the detail you gave around like there's such nuanced things that you can do to figure out like if this is a change maker or not so with the account research are you using like sales nav like they're i forget what the functionality is called they have like a little like account mapping like kind of stuff like what do you like to use for account mapping because this that sounds like a really big part of this process it's like really sitting down and looking at the account mapping it as best as possible etc yeah it's really an influence map i guess really weird right and so i'm really looking for the right those the first right executive right the first right people and then mapping or and then putting in like who who do i think reports up to them who do they report up to there's a number of of tools that there's no particular one that i use because i work with so many different reps that they have access to like different you know different lots of different tech that that does that for them my main concern is like and one of the things we've talked about is finding the right executive and then finding the warmest way in yeah that's the thing because once we get once we get in and start understanding some of the inside baseball right some of the things that are happening behind the scenes that's where we can start mapping making a map that makes sense right versus i think there can be some tendencies in in sales especially in enterprise and strat for analysis paralysis to be like i have to make this perfect account map and understand this and you're like there's gonna be some people that you didn't expect that are important like we talked about like mobilizers so until you start having conversations in those accounts you're not gonna know we don't necessarily need to build out like this super complicated map so it's really you're you're looking at the people that are most likely to champion change and let's talk about the warmest path then because the thing you don't want to start doing is just like firing off a bunch of emails making a bunch of calls like you're very strategic about like warmest path then and what's the best way to get in contact with this person?

32:19What are some of the strategies that you typically recommended and have seen success with here? Yeah. Yeah. So, I mean, of course, everybody's looking for anybody that's connected with them in their company, you know, any connections with leadership. One of the things that I found is executives don't, executives are not fanatical about reaching out to people they know and connecting with them on LinkedIn. And so one, you know, obviously if they're connected with them, that would be a good thing. But one of the things I like to look for is did they go to the same college especially if it's like a large school like did anyone at that for this executive that I'm looking at if they went to Howard did anybody a lot of execs have gone to like Ivy League schools right you know right and so like and those things are a small world right and it's a super big commonality yeah and there's like some sort of like phrase in their fight song or some sort of catchphrase that they can instantly understand yeah um the other thing is if there's not that one of the more unusual things we've done is look for did they go to like a rival school right because like that can be like you can get it you can provoke a response pretty quickly if you know in the subject line you're like you know you say something about that rivalry right so there's just like unusual kind of outside the box things but even that's kind of cold ish right like you want to ideally you want warmer so you know looking for obviously anybody that um oh this is another thing we do in sales nav is i have reps take their go through and look at like their customer stories like who are their reference customers and even run a crm report of like every account that has bought and then that are like you know the ones that really have bought big that love our company put that into sales nav as a um past company and then and then look for employees that had that as their past company that are now at our target company yeah right because they've probably had some level of exposure to that um another kind of warm way in is there's a there's like a there's like a brotherhood of like sales people and even if you don't sell to sales leaders sometimes you can reach out to sales people in that account and be like listen like i am trying to you know yeah i'm trying to understand you know what's going on here is is your cfo the right person for this or am i really looking for operations and sometimes people will help you out like that so i like to look for like like little known maybe because i think everybody knows like the most generic or most used warmest way in type things yeah so let's talk about referrals real quick.

35:02So let's say that there's someone I'm connected with and I want to ask them to introduce me to someone. What's, what's the proper way to do that? Yeah. So it is to, is if I send you a list of people that you're connected with, let's say I send you a list of, and I don't want to send, I should not send you a list of 40 people. I should also not ask, Hey, do you know anybody at these companies? Like I should, again, like so much of sales especially enterprises friction reduction we need to make this as easy as possible so i said send you a list of like probably under 10 people yeah and when i send you their names they their name should include a link to their linkedin profile so you can be like oh do i know this person yeah right and then ask okay you know these are people that i'm trying to get to know would if if uh an introductory email would be like a natural motion given how well you know this person, I would be happy to write like the first draft for you.

35:58And especially if we only are finding three people, sometimes what I've done is just ghost write that first draft for them, especially if it's pretty clear how they know each other. And then also we want to make it again, okay to say a hard thing to be like, and Hey, if this wouldn't be a good idea for right now, totally okay to tell me that too. Totally fair. Right. Because maybe they had a falling out or, you know, there could be a hundred reasons. And so we just want to make it easy for people to, you know, tell us no, if, if that's the thing, but most of the time, if we, if we make it easy, people usually want to help.

36:34Yeah. So I'm going to do the work of finding people for them. I'm going to do the work of potentially ghostwriting an email for them. And in terms of like what we're asking for, is it just, Hey, I'm going to ask this person to send an email to the person I'd like a referral to and just ask for an opt-in if they would be open to an introduction to me I think that's the best way right because that that feels better whenever somebody has agency to yeah to just be like yeah that's totally fine yeah is there any other tips you have around ghostwriting the email and like just what might be included or common mistakes I think you never want to mention your like the name of your product like it is not about the product.

37:18It is about legitimately how you think you can help. Yeah. Right. So Jason, I noticed you're connected with Alexa. Alexa just took over as the CFO of this company. And from what I've seen, like they're undergoing hockey stick growth. What that usually means for finance is that they're growing way faster. They're keeping up with all these different things. And so my product or service can usually help in this way, this way, this way. Right. So that you understand what it, like the reason I have, not just like I found, not just that Alexa has this title. Right. But like I am, and I'm saw, and I'm communicating to you, I'm showing you, I've done my research.

38:01I've done my homework. I know why this makes sense. I'm going to, you know, this is not a referral or an introduction that you're going to be embarrassed about. Yeah. So I think going that extra mile with that is super, super important. What about when we have an executive? So you mentioned the same school staff, but let's say that the executive is a first degree connection with someone. Is that the same kind of thing there where I'm going to ghostwrite for my sales leader, let's say, or let's say I sell an HR solution. I mean, I ghostwrite for my CHRO who's connected with another CHRO. Same sort of principles there.

38:37Yeah. Yep. Yep. Always. Cause I mean, our executives, every executive is busy. Everyone is busy. Right. And so like, we want to make it as easy as possible for them to reach out. In fact, whenever I do this, whenever I go straight for an executive, I will literally, I will send them the email and in the email, it will include like customer email, customer LinkedIn profile. Here's the subject. Here's the entire email. And they, you know, obviously it's a first draft. if they can choose to not do it, but it just, I want it to be so seamless, just easy peasy, copy paste, right? Like make the, one of my sister's like things that she always says is like, make the right thing easy and the wrong thing hard, right?

39:17Like this is the right, this is it. We should just make it as easy as possible for them to, to do that for us. Yeah. Love it. Um, let's shift gears a bit and talk about POV and like hypothesis creation. Obviously a very big part of enterprise selling that applies not only to pipe gen, but also some of the stuff we'll talk around uh disco so what are the nuts and bolts of a great like point of view or hypothesis on you know why it makes sense for this account to engage with us yeah and the good news is like with ai it has literally never been easier like if we are not doing a point of view on accounts in enterprise or strat like well we're not building much pipeline probably yeah because like it's just never been easier i mean it used to take us back in the day like hours and hours to like go through you know earning statements or all these different things and so i like have a prompt that i have built but what to to help with a pov but it takes into account like company news has this person been on any podcasts have they given any interviews and great thing about ai is that maybe they haven't given any interviews stateside but maybe they gave some in Europe, right?

40:29So it's going to hunt down those things a lot faster. Um, you know, any, you know, any indication about earnings also looking at what are their current open roles? Like who are they hiring for and what does that tell you? And then the, and then the P and what's happening in their industry, the, and then the POV should tie them all together. So I'll give you an example of one that I did for a rep, um, that was actually trying to get a job at Samsara in 2023. Yeah. And so we were looking, he was like, I want a way to stand out. I want to get hired. This is my top company. I want to get hired by them.

41:05I was like, you need to, we need to go into this interview. Like you're going into a, a, you know, a discovery meeting and have a point of view. So we looked at all the stuff and what we found in, in the, in their, um, earnings report, what they, what they said, or their end of year report, what they said was the previous year profits had been up like a wild amount like 40 and what was driving that was deals over a hundred thousand dollars and they also had open roles for um enterprise aes and sdrs and so the point of view that we developed there was like hey notice that you know you're that the what's driving the 40 you know revenue bump is deals over 100k so i would imagine as you're building out your enterprise team what you're looking for is reps that understand how to have a conversation with c-level executives reps that are comfortable with the trans with the um what's the word trans transformation reps that are comfortable with the transformation conversation because samsara kind of deals with old school industries but that's just what i noticed like what did i miss that you guys are focused on as far as like building out the sales team yeah when you walk in like that you have demonstrated i understand what's happening within the org i understand what's important and how i can add value so it's the same for any you know it's the same for as we look at companies and i can give you an example on the comp like what a on the company pov side like if that's yeah i think what i'm curious about here is that

42:45the mistake there's a couple mistakes usually that i see and i'm curious on your perspective on this it's one the altitude of the goal or challenge in the pov is too low yeah so it's like if we're using outreach in as an example and we hop on a call with a sales leader it's like hey i saw you're hiring aes and imagine that you know self-sourcing is going to be a really big thing for them um and that you're really focused on like making sure they complete their call tasks and like okay the bb of sales doesn't give a shit about that um so i think the altitude of that is interesting and then the multiple choice list like like one of the first exercises that we'll do with a company when we work with them is we'll build out a messaging matrix for their key personas and usually we have um we call it the three t's it's trigger tension trust that's the reason to meet the trigger is the why now what's happening right now the tension is the problem and then the trust is the social proof.

43:46It's the who we've helped with this. So usually we find that there are two or three tension buckets, problem buckets, that we have triggers that lead into those tension buckets and then trust statements below that. If you imagine like kind of like a waterfall kind of graphic, those tension buckets I find are really hard if an enablement team has not done a great job of saying here, these tend to be the problem buckets that we help with. A rep is kind of left to their own devices and it can be really hard to kind of find that. How do you, how do you help reps find what those kind of patterns are that we're looking for?

44:22I don't know, maybe with like these really, cause I don't work really big strat deals. Maybe it's like very different across the accounts too, but I'm sure there's gotta be some patterns I would assume that align with your solution. And there's like a nice Venn diagram there of stuff that you kind of find in the center of what your clients are working on and having challenges with and what your solution helps with what are your thoughts on that how do you guide people through that i like your word altitude and because i think that whenever we talk about you know there's multiple personas that are involved in buying our thing but within those departments there are multiple levels yeah in those departments right so let's take the example of selling to hr departments which is what i used to do so at at in any department like end users the end users of our thing only care about, does this help me do my job easier, faster, better?

45:16That's it. Managers of end users, no matter what their title is, and managers of end users can look like, it can be managers, it can be directors, it can be VPs, depending on your industry. But if they manage end users, what they care about is, does this thing help me with a metric my team is measured on? Can help me look better. And then at the executive level, it's, does this help us meet our goals or mitigate our risk yep and if we are speaking at the wrong level when we you know when we ghost write a note or send an you know an email or send a linkedin message that if we send somebody who's an end user of our product and we want to you know talk with them to help kind of build a point of view about what's happening in the company and we send them a message about increasing their market share yeah they're like what i'm not i don't even know what our market right like oh yeah no and if we enter your point earlier like if we send an executive something about like making life easier for you know their hr managers or their hr analysts they're it's like delete yeah right so it's really important to think about not just persona but like but like you said like the altitude like the level in each department because it does make a huge difference And that's actually one of the things that we have a prompt for that we use, but anybody can make one just about personas.

46:38Like, help me understand. Here's the three. Here's the three departments that buy my product. Help me understand at the executive level, the manager level, at the end user level. How do these people spend their time? What do they care about? What are the problems that they have? What do they try to do that, you know, that's hard for them to do right now so that we get a feel? And I like building that out. And I literally will leave it up on a screen as I'm working on pipeline. build or working on discovery you know prepping for that call because i want to make sure that i am speaking the right language because i can have the best like most life-saving message in the world but if i'm speaking italian you're speaking and you speak german yeah not a lot's gonna get through there yeah so it sounds like having this cheat sheet and knowing this in advance is going to be really helpful with pov and hypothesis creation so this is kind of a good segue into outbound led discovery so you have a great discovery framework that i would love to dig in but i i also would love your take on like how is doing discovery for the first time when i secure an intro let's say with this executive who was not already shopping for something right versus someone that comes inbound and we're working a deal where there's already a buying committee and there's this budget set aside and like all of that kind of stuff how is outbound led discovery different And then let's talk about your discovery framework.

47:57Yeah. So like when you talk about like martini glass, like that funnel, right? So there's different levels of awareness and intent, right? Somebody who comes in with, you know, a buying committee already set up and a line item in their budget, like they're pretty far down that funnel, right? Of awareness versus intent versus somebody who may not even have known like our thing existed. Yeah. Right. And so then we reach out to them and, and they are like, oh, well that, that could be interesting. They're open, but they, the level of intent is, and the level even of understanding is way different.

48:35Yep. And we have to, and we would not, we would be wise to like think about that in how we, in how we approach that. So, and there is a difference in like discovery when people come inbound versus outbound. But the other thing I like to just like the asterisk I put on like inbound is inbound does not necessarily mean like done deal. I know. Right. It doesn't mean that. It means like we don't actually even know why they have a higher level of intent. Yeah, I have. Maybe nobody else has had this experience, but I've had people seek out calls with me when I was a rep because they were actually the champion of a different solution.

49:16and they needed to get to other vendors, right? Especially if you're doing an RFP, especially if you're doing like larger companies, sometimes they have to show that due diligence, right? So they just want to get that call, you know, on the books and they know the vocabulary, they've got the buying committee and we're like, Oh my God, this is the best thing ever. But we have no idea. We don't know always what the intention is, even if they have a higher high level of intent, like, but we see, we don't know always what's driving that. Right. So we have to be careful not to view inbound as like, oh, they want it.

49:47Well, they may want to solve the problem, but they may not want us to solve it yet. So there's that to like, to be aware of. Um, and then outbound is, yeah, definitely. We called that, right? Like we reached out to them so we can't be, we can't be like, Hey, so Jason, thanks for taking the call. Like, you know, tell me kind of what you're experiencing right now. And you're like, really? Yeah. You called me, right? Like That's going to be a way to make someone get in the call or just immediately check out. Especially for outbound-focused stuff, we have to come with a very tightly messaged POV that we start the call with.

50:27In your experience with the reps you work with, I would assume that a lot of the strategic deals are more outbound-oriented and that execs aren't coming out and filling demo requests and doing a lot of other kind of stuff. So let's talk about your discovery framework. So what are kind of the key parts to this? And we'll talk about how that kind of adapts for outbound. Yeah. Yeah, you're right. Pipeline has never been harder to build. And I think AEs have never, sellers have never been leaned on as hard as they are now for self-sourced pipeline. Yeah, it's crazy out there. Right. And also, can we really reasonably expect a 24-year-old SDR to understand how to communicate with a C-level executive of a Fortune 500 company?

51:14Probably not. I don't think so. Yeah, I think the Enterprise BDR SDR game is a very different game from the SMB and mid-market kind of stuff. right the business acumen it's it's like oftentimes the person's first role and it's like i'm a very big fan of sales development and like all of that kind of stuff but yeah absolutely 100 yeah i mean that's that's an unreason that is just an unreasonable expectation to put on them right like so hopefully if you're in like enterprise bdr sdr role like hopefully i had i've worked with some amazing enterprise bdr sdr but you're right this it's not their first sdr role and they to our point about ego and understanding yourself sometimes these are people that love the sdr world they might be 40 50 years old and just be like this is this is what i like and god bless those people like i i do not i've done a lot of cold calling and i have never been great at it and never enjoyed it so like that to be like good on your feet like that is you know is absolute absolute skill for sure so but yeah aes have never been called on to do more of that and so yes we are going to have meetings where we called them.

52:22You know, we message them. And so we want to start and we want to start with, I, whenever I think about structuring a discovery call, I think about EMT, right? Acronyms, this is the teacher in me, like acronyms make everything easier to remember and prospects are in pain. So they need an EMT. So when we think about starting that discovery call with an E, that is excavate pain. We want to get beyond just surface level pain. And so we're going to start excavating with, with some multiple choice questions, which I call like a menu of pain, right? We're going to let them pick what is, what's valuable to them to talk about.

53:00And when we give those multiple choice options, we are showing that we understand and that they don't have to educate us or educate us as much. Yeah. Right. So when I was selling HR software to school districts, now we get, you know, an HR and most of the time, executives are not the ones taking those first calls either. It's like managers and directors, right? And so we want to tailor our messaging appropriately. But if I was speaking to a manager director of HR, I might say, you know, Hey, Jason, appreciate your time meeting. When I meet with HR directors from large school districts like yours, what I see is, or what they tell me is it's really hard to hire good teachers.

53:44And so when they do their onboarding process, they want that to go quickly, right? Like they don't want their systems to be the reason that somebody checks out, right? They also are being asked to do a lot more with less. So there's a lot of stress on their people to do maybe what would have been two people's jobs two years ago, five years ago, and that can lead to mistakes and that stress. And it's also compliance issues, right and then also sometimes they are they are worried about like retirement packages and how they're handling that those are the things i hear but i'm curious like you may be far different like what did i miss that you guys are really laser focused on and what you're looking for there is like you know actually the a lot of this is is true you know we're dealing with like x y and z and there's this an immediate moment of like you get me as a buyer i feel like it gets you like on the same side of the table, so to speak.

54:35Ian Altman wrote a book on same side selling, I think it's called. So that POV, the goal is to really like have some resonance there with the buyer. Yeah, a thousand percent. And we do not have to get that a hundred percent right. And in fact, it's better if we don't, because what we're looking for is enough resonance that it's that you get me, we speak the same language, but enough that needs to be corrected that they're like, yeah you know it's not really so much their retirement piece but yeah we have a very hard time getting teachers in the door and so our process has to be super fast we are in an urban school district we have suburban school districts that pay more and people may want to be in those environments you know and so like we have to be not just as good we have to be better right and so like we want that correction because where they correct us that's where the gold is that is where and it doesn't, it gets to that deeper level pain, but we haven't made it feel like an interrogation.

55:37They are volunteering the information, right? Because they are, they're leaning forward. They're like, oh, you understand enough about my world that we can skip the 101. I can tell you the 201 or the 301. And that makes it so much more productive of a call right up front. Yeah. The gold is in how they talk about those things. And again, even if we're only 50 % right, the fact that we've done any homework at all and made any effort at all at understanding earns enough credibility that they'll be like, you know what, I can see why you'd think that, but actually here's what. That's 100 % fine too.

56:17And it also establishes really quickly, like I think one of the things that could be kind of hard in an initial intro call is if it takes you 15 or 20 minutes to get to something really meaty in a 30 minute call, you've blown most of the call. This gets you hopefully there in the first couple minutes. So the E is for excavate pain. We need that POV. We're going to get that through our account research. What's the M stand for? Yeah. So after we get them talking about, you know, we excavate pain, we get them talking about what's important to them. We need to ask a couple of deeper level questions.

56:51We need to talk about our offering enough that it speaks to those things. Let's talk about that, actually. Because that's, I feel like that can be so hard with an enterprise solution that does so many different things. So how do you give, I call it a teaser statement. How do you give the teaser statement or the elevator pitch or whatever you, nomenclature that you use for it? Like, how do you talk about your solution in a way that doesn't like derail the call? Mm hmm. Yeah. So digging deeper, getting them to kind of laser focus on those things that are really important. And so like if we go back to the school district's example and they want to onboard people quickly so they don't have people drop out of the process.

57:27You know what I could say there is, well, hey, like our solution actually takes you instead of having people handle like 20 pieces of paper and trying to collate that and misplacing the file in the file room. they can see like a checklist all you know all the way in front of them so that they can see the whole process just the whole chessboard does that does that sound like something that's worth spending a little more time on or i mean just you know barking up the wrong tree there right so like we we talk about enough of it the other thing is i like to have a couple of customer stories that where i think will resonate coming in where i can say oh you know what hudsonville was dealing with that exact same thing and their problem seemed like it was, you know, really in like getting in, you know, TB tests or, you know, whatever.

58:15Is that, is that kind of where you guys are or is it different? Right. So we, we, we build credibility even more by talking about how we've helped, but we need to, however we're doing it, we need to give them enough that they're getting some information because to your point, if we are waiting, if we're messing around and we get 15 minutes into a 30 minute call. And all we've done at the end of that is gotten their answers to a couple of questions. They leave very frustrated, right? Because let's be honest, the reason that they've taken a call with us is we've said, we sent some message that has given them some level of interest to understand something they can't understand with outside research, right?

58:56Because they're looking, they're looking at our website. They're, they're asking AI, you know, they're asking friends, like there, there's something that they can't, that there's something that they can't find out without talking to us because most people do not want to talk to a salesperson. Right. So like they're, if they're doing that, there's something that they want to know. And we want to leave enough room in that call for them to get some information about us. Right. So we talk to them a little, that's kind of the meat, that should be the meat of the call. That should be like first five minutes is, you know, credibility building statements, POV at the beginning, 10 minutes should be kind of going back and forth, helping understand, is it worth looking at?

59:34And then we get to like the M and the T of EMT. So the M, this is like last, you know, five, 10 minutes is matching urgency. Especially important. Actually, this is especially important with inbound. If we have a lot of inbound because people can be a fan without being a champion, right? Like they can absolutely love our thing and not be willing to introduce us to a single person. Yeah. Right. And so like we have to kind of sort out where are they or they can also agree that this that our thing looks great but they may not be able to budget that. Right. They may have just bought something that they thought would do something similar.

1:00:14Like we have to match whatever urgency like they're feeling. And so again I like I love a multiple choice. You know Jason thanks for taking it. I'm glad we're able to connect. It sounds like you know what we have may be interesting it may be interesting enough to have a next conversation because it sounds like may help with a couple things you're facing and also i find that really there's three reasons people show up to a call like this one is like they're in education mode they got a problem they're just figuring out what's out there right second is this is they have a big problem they really want it solved six months ago they're hoping to find somebody that can help and figure that out quickly yeah next one is they got a problem it's not a huge priority they're probably gonna do something about the next year but it's not on fire and i'm just curious kind of where you'd place yourself on that scale and the reason i ask is i never want to be the one to chase anything i don't want to blow up your inbox if today was education mode 100 fine yeah right gives them permission to say that hard like just looking yeah right and when we give them permission then sometimes that's where they lean in and they're like actually my boss yeah really wants this evaluation done or i had the higher also the higher up we go if we do get a vp or c level to show up for those calls that's where they will be will level with us and be like nah i gotta get this figured out this is i had a vp of sales be like this is my top priority for q2 if i don't figure this out i will get fired yeah i was like oh my god this is this is our first call okay and so then then because then whenever we're we are able to match their urgency that helps us figure out should there even be a next meeting yeah right because maybe not especially if we have a ton of inbound and then and then if there should be a next meeting because this is a priority they have to get this done then the t of emt is teach them to buy so we can have our prospects are smart smart people they are experts in how to do their job but they are not experts in how to buy our thing nobody when they take their job nobody hands them a six inch binder and like here's how to evaluate every piece of software I'll ever use for this role.

1:02:16That doesn't happen. They don't know. And most companies, even the largest ones, don't really have a buying process. They have a procurement process, but the actual, like, here's how to evaluate a vendor and the steps we're going to go through and the consensus that's needed. I've never seen that. That's a really important point. And I like that. They have a procurement process, but they don't have a buying process. They don't know how to do this. But nobody wants to admit that. And so we can lose a lot of time, and especially in an enterprise sale of them going to, you know, different departments and trying to figure out how do we evaluate this?

1:02:47Who needs to be involved? Versus if we say, you know, Jason, it sounds like this is something you guys want to get solved before you're trying to onboard teachers for your next school year, right? So typically what happens next is one of a couple of things. We might need to do a kind of a demo that is more custom to your role as an HR director. So you understand, is this even worth putting in front of more people in your org? sometimes we need to bring in finance because they're going to have a say right away and that's just better to check that off right away sometimes we might even need to bring in it right at the beginning because they have certain like compliance things it'll be a no-go so that's just what those are the three things i see typically happen but your team might be different you know would a different motion be better right so they can react to something and be like oh you know what i should probably bring in it just to make sure we can keep the trains running on time that way they can react and if they're a super savvy buyer and they've bought something like this before that leaves them open to be like nope actually you'd think that but in our district it's chief of staff got to go to them first yeah but we've given them options right and we've told them what we've we've told them what comes next um also really important there is the word typically typically is a magic word because what typically does and i and we have to be careful it's like typically what other folks do typically what people do in an evaluation not typically what i recommend typically what i think should come next they don't care yeah but typically when we tell them typically what other people do we are signaling this is what's safe right this is people like you do things like this and so they feel safer that's why whenever we are picking a new mexican restaurant we are not looking at what the restaurant says about itself we are looking at google reviews yelp reviews right like people care about what other people do and so like that is one of the things that i like i love a multiple choice and i love typically yeah typically is magic because it just subtly communicates you can feel safe doing this because this is like the normal path yeah dude you're freaking locked in the zone right now i love it this is so good like the match urgency is something i actually want to start doing in my sales cycles where i do ask about timeline but i'm not getting a really good like urgency is it it's an emotion right like what did what do they feel that needs to happen and like that energy and uh i want to match that i love the teach them to buy piece where everyone always talks on linkedin like the sophisticated buyer and i'm like most buyers are not very sophisticated most of the time they haven't purchased the thing that you're selling before or it's been a while since they have or they don't understand quite how that works so i love that so excavate pain match urgency teach them to buy we got to move on to the rapid fire questions we could have done a whole hour episode on that and maybe we'll have to do another one just on the discovery framework i love that framework um okay you ready for the rapid fire questions i'm so scared yeah okay these are these are softballs um how do you leverage ai in your day-to-day oh my gosh uh mostly right right well um for research right to make things that take a long time like to compress that timeline for sure um and i also love to use ai as a brainstorming partner yeah um i just find it's great just to go back and forth but i'm still doing the critical thinking but it's not just me like in my own head right so that and and also like those are the biggest two three uh those are the biggest two of a close third to that is helping quantify cost of inaction roi no one believes our roi calculators yeah they just don't yeah um that was novel i don't know 10 years ago 15 years ago no one believes no one believes our forester research thing they know that we paid for that yeah right but cost of inaction um is is huge and ai again can be a great, I have a prompt for this, but AI can be a great partner in figuring out what are some things that they might be losing by waiting that they haven't even thought about.

1:06:57And that is when we help buyers think through that, we are helping them make a good decision. And again, we're sitting on that same side of the table as them. And it's because it's urgency for a reason that makes sense to them versus like, here's how much money you'll save. They don't know that. yeah i love that so cost of an action um how do you like to decompress after a long day or week i think we have this in common so orange theory because i posted about that one time and you're like oh i do that all the time i haven't done otf as much recently but i was super into it for a long time yeah just i should have done an otf workout i'll know that next time i kick my butt at that um no but just like i like that because it's like somebody else guiding me through the workout it makes me pick up the pace it's i'm also pretty competitive so you're like yeah i'll definitely go faster now than i than i would and then after i you know i can be absolutely dragging going into there but then when i you come out like you're just like re-energized love it exercise for you is a big one yeah love it last question uh if you were a first time enterprise ae all over again what advice would you give yourself knowing what you know now

1:08:07pay the most attention to buyer problems and buyer psychology and drown out the noise that is going to be thrown at you around product training and and more activity everything else the more like your company is going to train you on the product and they should you should know about your product but laser laser focus in on the problems you solve and the psychology of the people that are going to be taking those calls with you i think those are the two biggest gaps in in sales training because that's way harder to train on right then then sales you know or then then just straight up product training but i would have focused on that way harder way earlier if i I had it to do over again.

1:08:56Any resources you recommend on the buyer psychology side, books, podcasts, articles, people to follow, anything like that? Yeah. I have a book that I'm absolutely obsessed with. It's not a sales book, but it probably changed the way I think about just psychology in general and influence in general. It's called the six minute X-ray. It's by a guy called Chase Hughes. He was a former military interrogator. He's got like a million followers now on like YouTube, but what he says makes so much sense. But what he talks about is not personality style, but decision making profiles. How do people make decisions?

1:09:30Because like to your point about emotion, they make decisions based on how things make them feel. So he talks about like the first three things are like significance, acceptance or approval. These are the three things that people want. And like in so if I'm sitting across from you, how do I figure out like in what order you place those things? Like what's the most important thing to you? And he talks about like all these different ways to understand that. And like, again, not a sales book, but just like a human understanding book. And once you read that and see those things, you'll never like look at Thanksgiving or a family reunion ever again.

1:10:07Just like you'll be like, oh, I see now. Yeah, it's super enlightening. I love that. So we got to check out that one. Thanks for coming on the show. Thanks for having me. This is super awesome. Where can people go to connect with you? and then tell us more about your coaching practice if someone's interested in checking that out yeah so obviously yeah they can find me on linkedin kristin with a y um and from there they can get connected to free stuff like newsletter website you mentioned ai prompts can they find some of that stuff on your linkedin um i really on on linkedin i really talk about like more about the ingredients to it and then to get the actual prompts that's those are things i talk about in either like individual coaching or like group coaching.

1:10:46And as far as, um, it's amazing. Like when I got my first tech sales job, I hired a sales coach. I didn't even, I didn't even call it that. I just was like, I just found this guy that had like, I had, I was connected with, um, personally and he had been a VP and a sales VP and, uh, and he was, I was helping him with a project he was doing. And I was like, listen, I don't know what I'm doing. and like I will trade you time on working on your project if you help me understand like this thing because I knew I could learn it but I also knew my learning curve would be a lot shorter if I got somebody to help me but now it's like way more common than it than it used to be but the people that come and do like individual coaching are generally like reps are starting new jobs that want to be able to have like fast success right like get to the top of that leaderboard really quickly get get on the board make an impact um and they're they are people that are top performers that want to be like consistent top performers not occasional right and they want systems and rip stuff that's repeatable so that they can do that you know next week but also like in their next role and in their next company like having an actual process because the sales process that we're given is really more like forecasting process or like CRM process.

1:12:08It is not a, it is not aligned to how people buy things. It's like, that's what people are looking for. And like to be able to do that quickly and repeatedly rather than working like 80 hours a week all the time and really not even knowing what you're doing that's working. Awesome. So check out kristinconner.com, correct? Yep. And then connect with you on LinkedIn and that's a wrap. Thank you.

1:12:36Thank you.

From the publisher

In this episode, Jason and Krysten Conner, sales coach at krystenconner.com, talk about the where-we-win report every new AE should run, the ship jumper move and other warm-path openers, ghost-writing a referral email your champion will send, and running EMT discovery on outbound-led calls.

Check out more free content and get help with outbound at ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://outboundsquad.com.⁠

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