The Win Rate Podcast with Andy Paul

On today's episode Andy welcomes another engaging group of sales superstars, including Jeff Bajorek, Chief Sales Officer at White Glove, and Jason Bay, Founder and CEO of Outbound Squad. They reflect on the complexities of sales and the tendency to oversimplify the process. The panel's conversation highlights the importance of immersing oneself in the sales journey, acknowledging the difficulties, and appreciating the victories when they come. They reflect on the rewards of dedication and the intrinsic beauty found in navigating and mastering the sales landscape.

Host Andy Paul is the expert on modern B2B selling and author of three best-selling, award-winning sales books, including his latest Sell Without Selling Out. Visit andypaul.com to subscribe to his newsletter for even more strategies and tips to accelerate your win rate.

What is The Win Rate Podcast with Andy Paul?

The world's best conversations about B2B selling happen here. This exciting new podcast from Andy Paul, the creator and host of the Sales Enablement Podcast (with 1200+ episodes and millions of downloads) is focused on the mission of helping increase your win rates by winning a bigger percentage of the deals in your pipeline. In this unique round table format, Andy and his panel of guest experts share the critical sales insights, sales perspectives and selling skills that you can use to elevate your sales effectiveness and create the buying experiences that influence decision-makers to buy from you. Host Andy Paul is the expert on modern B2B selling and author of three best-selling, award-winning sales books, including his latest Sell Without Selling Out. Visit andypaul.com to subscribe to his newsletter for even more strategies and tips to accelerate your win rate!

  Hi friends. Welcome to the win rate podcast. I'm your host, Andy Paul. That was Jeff Bajorek and Jeff is one of my guests on this episode of the win rate podcast. Jeff Bajorek is chief sales officer at White Glove and my other guest for today's discussion about sales effectiveness, the buyer experience, and improving your win rates is Jason Bay.

Jason is the founder and CEO of the Outbound Squad. Now, one listener note before we jump into today's discussion. If you enjoy the show, please do me a favor, take a second right now before we begin. To rate and review this podcast on Apple Podcasts. It helps us to get discovered by even more professional sellers who are looking to take their careers to the next level.

So thank you for your help with that. If you're ready, let's jump into the discussion.

Okay, friends, that's it for this episode of the Win Right Podcast. First of all, I wanna thank my guests, Jason Bay and Jeff Bjork for sharing their insights with us today. If you enjoyed this episode, please subscribe to this podcast, the Win Rate podcast with Andy Paul on iTunes, Spotify, or wherever you listen to podcasts.

Thank you for that. And again, thank you for so much for investing your time with me today. Until next time, I'm your host, Andy Paul. Good selling everyone.

 hello everyone. Welcome to the win Rate podcast. I'm your host, Andy Paul. Really excited today, joined by Jeff Bajorek and Jason Bay, who not only share initials, but apparently share a friendship as well. So, , how long have you guys known each other?

Oh. 20. 17 of 2018, Jason, where was it? We, it was the sales success summit. Scott Ingram's event in Austin. We had, our paths had crossed prior to that. I was hearing you on these daily sales tips and Scott's other podcasts. I'm like, who is this Jason Bay guy? Why does he keep showing up? And then he's in Austin.

And then I think that's when we finally met and or was there, did you do the, why in the by with Christie and me first,

No, so we met at that conference and I remember Jeff tried to say hi to me and I was off running to do something else and

So you ignored

I can't you know, I was like, Oh, hey, sorry, man. Yeah. You know, and Yeah. And then we ended up going on. So there was a, like for dinner, we went to Salt Lake barbecue and there was a bus.

Went out and driftwood. Yeah,

They had beverages on there. And I thought I was drinking a real Heineken. I was drinking a non alcoholic Heineken and I felt drunk during the bus ride. I was thought that I was tipsy, but what we talked about though, and why we became friends was I said, Jeff, do you have this problem where you just, Yeah, you're kind of the only person that, you know, that does what we do, like sales training, consulting, et cetera.

He's like, no, actually, no, I know I got a lot of friends. Like, and the next week he just started introducing me to all of these people that are in both of our networks. And it was just, Oh, okay. It really made me realize how much, how important it is to know peers. It's good to have people that you look up to. And it's good to mentor people and all that kind of stuff, but to have peers, just like in this call, like people doing the same stuff is very invaluable. And if nothing else, it'll give you a space where you feel really understood and listened to because most of our spouses don't do what we do for work.

Most of our friends don't do what we do for work. Most of our families, especially don't do what we do for work.

So that's kind of the story around how we met.

of course, what you have to do is get to the point where I'm at where my kids work with me. So

they know what I

will tell you what my, my daughter's doing a little bit of work for me. You know, I mentioned the why and the by and you know, we it's not a podcast that we actively promote. I've talked about it more in the last three minutes than I have in the last three years. Well, maybe not the last three, but we've been doing it.

We've not been doing it for about a year and a half, but my daughter is actually taking that old stuff, taking it down and then reposting it up to LinkedIn and putting transcripts and some video stuff to it. And so it's kind of fun. Cause she's actually learning from me and listening to a lot of this stuff in a really osmotic kind of way.

Like. She's not just sitting down listening to me lecture. She actually is hearing me talk to other people. And so she's getting involved with some digital marketing and some tools and stuff. So yeah, she's somehow she still thinks her dad is pretty cool. I'm going to ride that wave as long as I can, cause she starts driver's ed in like two months.

So we'll see.

yeah. My, my kids are substantially older and they lost the idea that dad was cool decades ago. So yeah, I'm under no illusion about that at all. So that's fine. That's fine. So Jeff, you have a new gig. Tell us about that. Yeah.

I do every once in a while A client opportunity comes along. And I have really, and I fought this this opportunity for a little while, cause I really loved what I was doing as a consultant and the variety and everything, but there's just a really cool opportunity with a company, actually a merger of two companies called White Glove and Acquire Direct.

We sell seminar marketing services to financial professionals and the opportunity to bring together two formerly competing companies. Petitive with one another sales teams get them to sell the profound bag. If you will, of solutions for financial advisors and help them move from a transactional selling environment to a more consultative long term view model.

It just does that. Ticked every box for me. And there's a lot of talent that could use a little bit of direction and can really grow an opportunity to get involved and work with a team. We, Jason, you were talking about a team of people, peers. I've got a very experienced team of people that I really want to go to battle with every day.

And to think about the end result too. We impact the financial literacy of hundreds of thousands of Americans every year. And there's a broader impact that's, it's not everybody on the sales team gets out of bed with that as their purpose every day, but there is no diff there's definitely no no real discussion around the fact that we can feel very good about what we sell.

So when I think back on my the eight and a half, nine years that I've been doing. Consulting and training and coaching. This is right up my alley and got the offer right after sell like you was officially trademarked with the U S PTO. So there was just a lot of good news that week. So

Excellent. Excellent. Well, congratulations.

thank you.

Yeah. Well, let's, I guess we'll sort of play off that a little bit. So I wanted to talk, at least start talking about outbound a bit. Cause you know, Jason, this is your specialty. Yeah. And sort of taps on something we were talking about before I start recording, but LinkedIn is.

inundated, I'll use the word with advice on cold outreach, whether email or cold calling or whatever. And trying to help people sort of deal with this monster. I think sales technology has created, which is these incredibly noisy channels that buyers have and trying to get noticed in them. I don't know, Jason, is there a way to fix it? Right.

Good luck with that

one, JB.

it? I think that the reason why, if I kind of look back, why I developed such a strong foothold in outbound is when I was getting our business started with my wife, you know, back in 2016 and really started talking about it online more. There weren't really a lot of people talking about outbound. It was more just like, do it. There wasn't cold email templates and cold call openers, like all the stuff that you see now. And it's really gotten to the point to where it's become so prescriptive that it's almost like. It's shared as like get rich quick advice style,

where it's like, do this, use this magic 27

seconds cold call opener. Yeah, here's the exact thing to say, and what I like about it is that people are paying more attention to it, and it's becoming a more popular thing to talk about. And my experience in working with companies is there is. In general, just less fear of people picking up the phone. So it seems to be like a more normal thing for people to do.

All right. Okay.

So I think that when, so when you say fix it, that

sort of implies that it's that Oh God,

was thinking from the standpoint of, you know, our, I don't know, it's, I don't see a lot of data yet. Maybe you have the data and you can share it with us. Is that's. It's really working for a lot of people, right? It's, it's, I'm just based on anecdotal data more than anything else. But so yeah it's way for sellers to show up and get noticed more easily than they're doing now, or to build the connections they need to build more easily than they're doing now, or more effectively than they're doing now through whatever methods they're using.

Yeah. I think the best thing that's happened in, cause I spend most of my time in SAS and tech, I think the best thing that's happened for them is. The stuff that happened in Cuba of last year with the VC companies saying, Hey, we're going to stop giving people money until they turn a profit. You know,

that whole bubble that started to kind of burst has been the best thing because what that exposed was. I would see this, you guys, I would work with an SDR team. That's like 80 reps and maybe five of them were hitting quota.

And the rest are like below 50 percent of quota. So the SDR function as a whole at that company is not a profitable part of the organization. Like when you look at the revenue that is closed from the appointments that they set, it literally, it doesn't even get close to the cost.

And there was this, you know, hire as quickly as you can build the top of the funnel and kind of get there faster with money and complete disregard to profitability. I think that stuff is starting to fix itself though. What I see in organizations now is there's less SDR support for the account executive.

So there's more self sourcing that

needs to happen, which we could talk about that.

Yeah. Love to.

I feel like where people are like a closer should spend a hundred percent of their time in closing. I just don't think that's a reality for most account executives or sales teams for them to be so booked that the account executive. Doesn't have any time for outbound and doesn't is it has like zero responsibility for the top of their funnel. You know,

I agree a hundred

it's such a pipe dream. All of the data would show you the best account executives. They self source according to bridge group and sales loft about a third of their pipeline is what the really good enterprise folks do.

And they're working the referrals and they're able to start higher in an organization because they have the experience,

But. I'm starting to, in a positive way, see more of that motion where top down it is expected of an account executive to really be a full cycle seller and to not rely on SDRs and marketing for pipeline and to not look at the SDR org or the SDR.

If I'm an account executive, as I'm their boss, and they have to do the things that I say and reach out to the people that I say, I still see a little bit of that. So I do see it working more effectively because the people that are doing it. As an account executive, by definition, my job is to close. So I'm doing things in a way that will help me find more opportunities that can close, not just get more meetings in my

right?

And I'm starting to see a lot of SDR organizations in the last couple of years, especially where the meeting comp, they're either not comped on meeting set, or it's such a small part of their bonus in commission structure. That it's really like, is this turning into qualified pipeline? Is this closing? So the reward systems I feel like are starting to get more on the same page and there's more collaboration between the two. So I'm seeing a lot of things move In a positive direction in this area now, the advice online and like what to do with that. That's like a whole nother topic. We can talk about, like, the right way to go about doing outbound. We can spend a lot of time on that. But I'm seeing overall in software companies, at least a movement in the right direction as a forcing function of we're not going to just be printing money.

Our VCs are not going to be printing money for us anymore. And these firms are not going to want to buy us unless we can profitably produce revenue that we close. Thanks. Thanks. Thanks.

Jeff

I have to follow that. I agree with Jason and I think, and I've always agreed with the idea that When you over segment the sales process, you're going to create different problems than the ones you're trying to solve. And so without recognizing that, okay, if we're splitting the prospecting function away, if we are treating closing as a reward for being a good prospector, you're such a good prospector.

You don't need to do that anymore. Jason, congratulations. You've been promoted. You let the plebs do the dirty work while you get all the glory. It's just, nevermind the. The communication gaps that are now created, nevermind the fact that you are essentially segmenting off and vital function of the sales process and eliminating or discouraging at the very least the easiest way to create and self source new leads, asking your best customers for referrals.

And not just asking the referrals, but asking them the very specific questions that will help you learn the messaging and learn the words that you need to use to find more like them. Instead, you've got people who are being sold the opportunity that if they get really good at this, then they too will be promoted to the promised land and you're making them start to do the hardest work possible without a whole lot of guidance.

But here's your playbook. Kid, good luck. It's there. There are some fundamental problems with the model, but I think it's important to talk to about the differences in industry and what prospecting really means to different people. I've worked with people in business development functions and what you could call pseudo SDR functions where their customers pick up the phone 90 percent of the time.

So we have to be careful that what we see online isn't dictating our feelings about the broader market in general, because despite what you may have been led to believe, not everybody gets on LinkedIn every single day and scrolls and likes Andy's posts and likes Jason's posts and skips over mine.

Cause they're not Andy's or Jason's. And then, you know what I mean? Like we have to be very clear about the very small sliver of the Customer population that we're actually reaching. And it's easy to forget about those silos.

Well, it is, but it's a great point and lots of things I wanna talk about there is so, yeah, LinkedIn is sort of a view into a sort of a software dominated type environment and you're joining one that's not in that space, right. Is so what's been the experience. There, because I think I sort of more and more using this term is that, you know, what happens in the SAS world isn't real selling. Because it's, you know, small, very small fraction of the entire economy and business world. And yet again, you spend time on LinkedIn, you'd think it's 90 percent of it. And also given the fact that the systems are sort of set up, just the incentives are set up in the venture funded world, they don't really care about excellence to that degree.

Cause. Cynically, they're trying to get to an exit and make it somebody else's problem to deal with. So, it's curious what you're seeing so far outside of that, you know, echo chamber in terms of, you know, Jason's point. You know, what are AEs doing for, you know, self service? Yeah, I've been talking to some companies.

Hey, the AEs are doing 100 percent of their leads are self sourced, right? Yeah. I had the fire, their entire SDR team last year to Jason's point. Cause you know, they weren't producing.

Silence.

we would think in terms of tech enablement and everything.

They wear work boots and blue jeans and baseball caps and they get their hands dirty every day, right? But so much of it is dependent and I'm so new, you know, with this organization, I don't have data for you at this point in another couple of weeks. I will, I don't have data for you yet, but I know that a lot of this is done over the phone with email as air support.

But these teams are on the phone all day and they want to be on the phone all day. And when I say, Hey, do you want to come out here? Can we, you know, institute regular training, you know, for an hour a week? They're like yeah, can we do it at a time when we're not on the phone? Cause we really like selling and we really like making money.

It is the opposite of what the LinkedIn silo would have you believe. But I will tell you that it's really dependent. I've also got some questions. Clients and former clients in the professional services industry where they can't get people to pick up the phone, right? So to Jason's point that he made earlier about,

Can't get to pick up the phone to make the calls.

No, I'm sorry. I'm sorry. Can't that I've got clients where 90 percent of their prospects will pick up the phone because they sell to breweries and the tap room is open and someone is always there to pick up the phone and they kind of have to. And I've got, you know, other people who are selling professional services and consulting and of a different form and software, for instance, where.

Where it's really difficult to get an executive on the phone to talk about spending half a million dollars, you know, with them. So, so much of it has got to do with product market fit and knowing who your ideal client is. And I think getting back to what Jason mentioned about the perfect script and the perfect 27 second call opener, there aren't enough salespeople actually thinking about an empathetically putting themselves in the position of their prospects.

You know, what I like to think about is, are you able to parachute into the negotiation that your prospect is having with themselves inside their own head in order to enter that conversation and influence the decision? We're trying to catch people who are buying right now instead of influencing the 30 percent of the people who are problem aware but aren't ready to buy yet.

And so there's some approach considerations that I think need to be made, but they take longer. There's not an immediate dopamine hit and a return on you know, effort and it's, I almost want to say that we've forgotten how difficult sales is. Because we've tried to focus on how easy it can be.

If you just follow these steps. And I don't know, the three of us have been selling long enough to know that it's a drag sometimes. But the beauty is in putting yourself, immersing yourself in the work to figure out how these lines of code in the matrix actually lead to something, and then when you win, it's like the best thing ever.

And then they pay you like it's, you know, I feel like we've tried to distill things down to something so simplistic that we've forgotten the beauty of what we do.

Interesting. Yeah it's, well, I've said several questions. I came from all that is,

at

Yeah, is well, one, one star observation is done a bunch of work with clients looking at, you know, their win rates and see the fairly, and this is a software company, so, but it's, but a very distinct trend, which is when they, in the early days.

The AEs actually tended, and they were selling enterprise products. AEs tend to do more self service. First, first people in, right? Route, AEs making their own calls, self service in the leads. Win rates. These companies, you know, generally in the low 40s. So, decent, right?

Pretty good.

They turn on the spigot. For SDRs and outbound inbound. When rates drop below 20 percent in all the cases we looked at for the AEs, and it's like, okay, what's going on here? Suddenly it's like, and I think that's the point Jason was going for is when the AEs have responsibility for developing their own leads, self sourcing the leads, they make better choices about who they're talking to. And who they're going to invest their time in. And when the spigot gets turned on with marketing and the SDRs and inbound and outbound, and it's like, yeah, they suddenly become a lot less selective about who they invest their time in. And it shows up ultimately in win rates. Jason. Right. Yeah. Right.

of companies doing is I've just been advocating for this for so long because when we started our company at first, we were doing outsourced lead generation and appointment setting. So essentially people would hire us and I would send email campaigns and LinkedIn sequences and things like that.

When you could do a lot of automation and we just booked the appointment. Well, I was writing all of the base level kind of sequencing copy, but I wasn't researching every individual prospect. I wasn't looking for their email. Like we had a team of people helping with that. So instead of looking at the outbound function as I'm going to give an SDR, which an SDR is a big expense.

It's a 60 K salary plus bonus. Like Great SDRs will make 80 to a hundred K plus, especially the enterprise ones. And think about you have a salaried employee looking for people's email addresses, doing data mining essentially for the CRM. So if you looked at the account executive and said, Hey, this person's really skilled.

How can we just tee up as many live conversations with them as possible with these decision makers? And you start to break apart that task. Really? I think it's an ops. Solution. It's how from an off standpoint, can we say, Hey, here's our 50 named accounts. Let's do all of the research to our best ability to map within these accounts, make sure there's good emails, phone numbers, et cetera, and do all of the dirty work for you to be able to just pick up the phone and dial through your list with very little effort because the account executive, if you can give them something where. Like think about the workflow. This is the big thing going on in tech right now. I have Salesforce that I'm in and out of. I have LinkedIn sales navigator. I have outreach, let's say. And then I have zoom info for my data. I'm in and out of four different tools and the workflows don't really work that great between them. So I'll give you a really practical example. One of the number one plays to run. If you're a company is who used to be a current client of ours that moved to another company that is not doing business with us. How do we systematically reach out to our customer alumni? That sounds really great in theory, but you know, how many steps that creates for a rep to actually execute that play.

Yeah. Like they have to have something built in salesforce that syncs with sales nav that has to be manually put back into outreach and then they have to go find the task and that there's so many steps to running that play. I really think the future of outbound is we like very play driven and context and situational driven and how do we reduce the complexity in the tech stack to make it easier for the rep so that. Every week when I log in on Monday morning, Hey, here are five people that used to work at one of our current customers that are at a new place. The tasks are already queued up and someone's already put in a sentence or two on triggers that you could probably mention. Because that done at scale for an account executive and arming them with all that knowledge, I call it eating complexity.

Well, that's what I've heard it called in business, but with like the sales rep, you want to eat the complexity and the complexity for a sales rep is the workflow. That is the most complex thing for reps and tech that have these bloated sales tax is our bloated sales. Tech stacks is the amount of context switching they have to do. And the ops team, especially at a minimum, what they should be given is here is step by step how to execute these plays.

Here's the click path for that. And that's something that you can't really measure, but I bet if you were to observe. You know, hundreds of account executives, and you could film them and watch them through their workflow.

I guarantee you, like, a quarter of the time that they spend working is just figuring out, like, what tools to open and, like, what steps to do and, like, where to find stuff. It's crazy. That's, I think, the really big thing right now that we have to do is don't do the prospecting for the AE. Make it easier for them to prospect.

Yeah.

it occurred to me that the SDR was created out of a lack of effective sales leadership and management and the the complexity being there. But as the SDR function, you know, became more popular, it was less because of the complexity more because, well, if you're not going to prospect and we're going to find someone who will there, and you know, it's like, okay, it's a solution to the problem, but it, Are we looking at the problem the right way?

And Jason, what I think you're suggesting is it's a different way, right? It's like, okay, what's really getting in the way now that people are more comfortable with the idea of prospecting because that drum has been beaten so much over the last decade or so. It's like, okay, yeah, you're right. I probably should do it.

It's really hard to argue with it. But it's really hard to do it. Can I just have her do it? She's only 24 and We could, you know, maybe dangle a promotion in front of her and see if she can pick up the phone. It's like, no, who's better in this organization to prospect than you? Nobody, but I can't because of X, Y, and Z.

What if we took X, Y, and Z off your table? Can you make 10 calls a day? And does the qualification go up? Yes. Does the close rate go up? Yes. Is it easier to do? Yes. Well, there's all this talk about, well, no one's picking up the phone and outbound prospecting is failing and it's only available, you know, it's only sorry, effective, you know, one or 2 percent of the time.

And now that Google and Yahoo are taking a wall, all all of our scalability away from us. What are we going to do? It's gotta be about reaching out to your network and things. Yeah. Folks, it's always been about reaching out to your network. It's always been about expanding your circle of influence.

It's always been about going to the people who know you and learning a little bit more about why they like you. So you can take the right messaging to the streets and why you're at it. Why don't you look for people like them? It's, this doesn't have to be as hard as we've made it because of all of the segmentation that we've done.

I just, I can't give more of a plus one to what you just said there, Jason. It's eat that complexity and let's enable reps to do it themselves. In most cases, I think.

So what do you see as the future and sort of the role? Cause I'm hearing more about this and I was just going to talk to a couple of companies that are doing this actually one this week is again, it's not for all products, but they have product that sort of justifies this, say people back out in the field, calling on customers,

Oh, I love

that. I love getting out there in person and doing that. I think another element of this handy too, because this connects with the win rate All of the stuff I do with companies is so basic. By the way, the first exercise we do is we reverse engineer success. We say, Hey, let's look at the last hundred deals that you guys have opportunities, right? That have either closed water, closed loss. And let's just look for patterns and where you win and where you lose. I'm sure this is something you do in your closed one analysis, right? And I'll give you a really practical example. Like one of the companies I'm working with right now, they sell a DevOps solution. And basically, if a company has a lot of software developers, they create an internal developer portal, they call it, and they're basically doing sales enablement, but for the developers, because being an engineer, there's a lot of like, stuff they want to spend as much time on coding and less time on the other stuff. When we started looking at their closed one deals, it's like very clear that 85 percent of their wins come with like very traditional software companies. They win in FinServ, they win in insurance, but this is like less than 15 percent of their business. And you have some reps where almost all of the deals that are working are once they have the lowest ACV, they take the longest to close and they have the lowest win rate. And just doing exercises like that. Like I see this when companies want to move up market really aggressively to like another company. I worked with sales HR solutions and it's like, as soon as they wanted to start growing really aggressively, they open up the industries like this. And then now I have a rep, like, imagine you're an enterprise rep here for a second and you're selling to Nordstrom. You're telling you're selling to chase bank. You're selling to another fortune 100 company that no one's ever heard of before. Cause it's like an industrial kind of thing. These are like three. Like very different business models that talk about things very differently. Get you're expected to sell to all of them. And I think the specialization shouldn't have come through the role of AE versus SDR versus SE it's like true industry expertise.

Yep. I agree.

And an 80 20 rule, like saying no as a company and having a culture where you challenge where managers say, Andy, I noticed you're working these FinServ accounts right now.

What's up with that, dude?

You know, we don't win very much of those,

like what's going on. You know, like I see you have these other 80 accounts. In fact, I looked on sales nav and there's tons of new hires and new execs. Like there's tons of low hanging fruit there. What are you doing?

Exactly.

Like that conversation's not happening enough.

That's like step number one is. No matter how big you are or how soon or early you are in the process, it's just ICP. Dude, what's your ideal client profile? And use the data! To tell you where you should be spending your time that fixes a lot of the win rate issues right there where it's like, let's just not put in meetings where AEs have no expertise in those industries.

They don't know what the heck they're talking about when they hop on a call with someone.

absolutely. I, people are tired of hearing the story in the show, but it was posting about win rates and somebody, you know, founder pushes back, says, Oh yeah, I'm really suspicious of high win rates. I said, well, why? And he said, well, cause you know, it means my sellers aren't having enough conversations.

I'm like, well, if you've gone through your go to market learning curve and you've dialed in on your ICP. I don't want you talking to customers outside the segments that we're focused on outside the ICP. I don't want my sellers to have a lot of those conversations until we own a hundred percent of that segment we're after stay focused.

Yeah.

It's just

the willingness to say no.

Yeah it's no different than like when I have an inbound lead come through now and it's not a software or a professional services company that sells something very productized. The first email is, Hey, looking forward to chatting with you and he just letting you know, our program started 50,

exactly.

You know, and it's like giving them a chance to just opt out

And giving them all those expectations up front is it's so crucial. But again, I think the system I'll speak to software specifically with this is flawed because if you're being funded and you have these high pressure growth targets, of course, you're not going to say no to business.

Oh yeah. That's,

Of course.

Yeah.

but then you get the, what happens is, yeah, increasing number of complaints. You see it just recently got on LinkedIn is people saying sales is killing revenue. And it's like, well, what do you mean? It's like, well, because sales just taking anything, right. Cause I feel the pressure of the targets and then we can't expand and we can't renew them.

We can't upsell them. Because of the wrong fit. That's like, well, that's really a management issue, right? As you were just talking about, somebody has got to look at that and say, why are we doing that?

Right.

I think bootstrapped is Like the way to go, like there's so many great, like companies that I've worked with that are, they're not completely bootstrapped, but they're early stages, less than a 20 account executives. They don't have all this big funding

and they're taking their time and they're like scaling something that is actually scalable.

By definition, they take something that works and then they scale

it.

They don't take a shitty process or something that is not

profitable and try to make it bigger,

you know?

I always say the problem with SAS is they tried to scale before they learned how to sell what they have.

Yeah, so,

And yeah,

to your point, precisely. Well, I had another question for you is a little bit about the in person thing a little bit. But. Yeah, it's talking to a client and yeah, they sell a product that a lot of big companies, maybe not big companies, even small companies use it, but their target markets, you know, probably companies 50 million and above and so on.

And yeah, I suggested to them they're looking at their, they're relatively new, looking at their growth plan. And I said, well, why don't you do this instead of, you know, Setting up and building all your lists and for everybody around the country is why don't we say this year, you're only going to sell the companies within a 50 mile right radius of your office. More than enough process, major metropolitan area, more than a, more than enough prospects there. And it was just like, Something that never occurred to them is like, cause then you can go out and you can touch people, you can meet them and, you know, event, local events, you can build the relationships you don't have to sell, even though you can sell, you know, virtually when you're wherever anybody is, why not take a geographical look at it where you can actually go out and touch people and meet people and build those.

I'm just curious. You guys take on that.

Well, I might be biased, but that's literally how I sold for the first decade of my career in medical devices. I knocked on doors, I got in my car. If I made 10 good calls in a day, if I made 10, like, I'm walking into, you know, medical offices, right? If I got through 10 calls in a day, that was a busy day, right?

I was in a tightly, you know, bound geographical area. There were days, you know, there were trips I planned, you know, four days up and back up into the upper peninsula of Michigan from where I live in metro Detroit. That was the gig. So I may be painted by that, but I can tell you when, You knock on a door when you stand in front of somebody, it's really hard for them to ignore you.

When you stand in front of somebody and they can't ignore you, you can ask a question that'll help you learn something that might help you on the next call. It teaches you patience. It teaches you diligence. It teaches you to look around you and read a room. You know, it, there's, there are a lot of things that go into selling that are intangible for people who are in inside sales departments and are very good on the phone, but don't realize how much the phone limits them.

Who are very good in email, but don't realize how much email limits them. And I'm, you know, I'm a big proponent of doing whatever you can to immerse yourself in the environment that your prospect lives and works in so you can understand how you, one, if you can even help them. Two, how, and three, what's the best way to communicate that?

So the.

Well, I think if you're calling on, you know, more senior level people is they're back in the office, they've been back in the office for a while.

Lot of them never left.

yeah. So it's not like you don't know where they are and you can take an account based approach within a geographic territory. I don't know. It's just, it was me.

If I was a seller, it's like, that's what I would do is, yeah. Try and keep it as local as possible. Again, learn our lessons there. What do you think, Jason?

Oh, when you mentioned that, what I thought of was unfair advantages is what I wrote down.

And it's like, where you look for unfair advantages as a salesperson or as a business, the unfair advantages, if you're predominantly focused on companies that you can go meet in person, most people that sell to them are not meeting with them in person.

That's an unfair advantage,

like by a long shot.

And then to your point, Jeff, getting to really know, cause To bring the conversation full circle, we're kind of talking about messaging and do you know the products are the prospects world and all that other kind of stuff? Well, yeah, you know how cool it is when, like, when we go do sales trainings or events and we go in person and we get to see them in their office.

Like, this is how I learned so much about stuff. I was teaching around workflow was, oh, wow, the reps got 2 screens opened up. He's got his talk track on 1. He's got Salesforce outreach. He's got to bounce back and forth between these scripts that we create scrolling through a 50 page document over here.

Okay, the way that I've set this up for them is not good enough. Like, it doesn't fit into, like, their workflow and user experience, and you don't get that unless you're there in person. I think the other thing too, though, is I'm curious your guys's thoughts on this. The other thing I thought about was, is being a remote salesperson more productive than people that go. In person to meet customers because the number 1 thing I see with sellers working virtually is the distractions in their home.

Yeah.

was a guy on a training call yesterday. We had them in breakout room student exercise, and he's trying to feed his kids at the same time

Yeah,

don't get me wrong. I know there's like.

Yeah.

Making ends meet is hard, you know, I don't have kids, so I can't speak on that part, but I do know that if he was in person working with clients, he wouldn't be distracted by other stuff. He could just focus on selling. So that's kind of the other thing I thought about too is. Like, are we building a world of salespeople that for the life of them could not go in person, like into a conference room with 4 of their prospects and actually make that a productive use of time?

I think we're building a generation of salespeople that cannot whiteboard something, and not rely on slides and do all of that kind of stuff. I wonder if that's part of the windbreak problem. That's a, just a, that's just a soft skill. The presentation skills and getting in terms of people being able to teach with nothing but a whiteboard and being able to do that as it's, that's totally a lost art.

I think before, but even at a more base level of the whiteboard and the presentation, it's just the human skills, right? Is the comfort as you talked about is, you know, just having a conversation with someone that. You know, is not all about me. What I need, right? Is, you know, to build that connection with someone, build that relationship, you know, lead sort of naturally into the business discussion. reign to your curiosity. You know, move beyond the scripted discovery calls to really understand what's important to the buyer. I think those are the lost arts. Those are the things I've, I focus on is 'cause I think I'm sort of, of the mind that we could actually. Stop training sales skills, quote unquote, sales skills and focus on human skills, training and industry training and financial training and never trained sales skills.

And we'd be better off with the sellers, right?

it's business acumen. It's sociology. It's understanding how people move and move, not just physically, but emotionally, socially, psychologically, like it's not about the talk track. There's no magic 27 second introduction that you can say it's going to work every single time. We know that. So, but can you read a room?

It, can you know, appreciate, yeah. Can you read a person and can you read a person on the phone? It's tougher to read them over email. There's an art to that too, but just, So much of that is just there's a word I've thought to use and I'd rather not use it, but there's just, there's some, well, I almost want to call it adulting, except I don't like that word in general, but there's something about just growing up in a place and being able to interpret a lot of information around you and know that even if that's the perfect thing to say, now's not the right time to say

it.

Yep.

Or what Jason's talking about. It's like all the talk tracks in the world, all the templates. I've got playbooks for you. Look at all the stuff I created for you. Here it is. You walk into the office, you're like, Oh, you'll never use this. It's not that it's wrong. It's freaking perfect. You can't use it because I did not realize the environment in which I was asking you to use it.

And I learned that particularly over the last 18 months as I've worked more closely with beyond just the sales team, right? You, you get in, you get into the client Slack channel and you realize all the chatter that's going on. You're like, how do you even, how do you focus on anything?

You know, there's this expectation from a cultural standpoint that you're going to participate and you're going to wish everybody happy birthday and you're going to give them tacos or whatever it is, you know, on Slack that you're doing. And we have all these things and we forget that our job. Is to put ourselves in front of people who can say yes to us and all that implies.

And so there's a certain amount of, you know, what Jason mentioned before we were teaching people that there is the perfect thing to say to the perfect person at the perfect time. And there's just no such thing as

It doesn't exist. Right. Well, and I think that's the value of being in front of people, right? That's how you learn that. And. And again, I sense, yeah, more, so if you're talking to clients, there's more people traveling these days to see clients, but it's, it is an unfair advantage as Jason talked about.

It's funny you brought that because it's, you know, a friend, my friend, Stu Heineck, he uses that term, you know, creating unfair advantages and that is one. And it's, it seems like so intuitively obvious. And I think part of the problem is that. When you hear, like, CFOs hear about travel for sellers and so on, they think that they're just mindlessly traveling instead of saying, look, no, we're going to travel a specific point in time.

This is generally who might travel to help move the deal forward or whatever. And you use it judiciously. It can be hugely effective. I, in my career, I work for startups that We're oftentimes bootstrapped or very lightly funded and we're Travel for us was all usually overseas. So it very, you know, isn't judicious as I said in the way we use it

Yeah.

constraints like that you use it effectively it is that unfair advantage I just remember talking to this group in New York enterprise sellers and Yes, fairly large group.

And I said, you know, raise your hands if you got an ACV, you know, six figure ACV, you know, a lot of hands go up because they're selling to enterprise. And I said, well, how many of you actually go travel at some point to win the deal? Like two hands go up. I was like, okay, well, if I were competing against you, I'd go visit them and I'd win all those deals. Because I think that is an unfair advantage and it's, yeah, one that doesn't have to be.

You may win all those deals before the credit card bill is even due.

Yeah. Yeah.

Right. You want to talk about the money out to travel and all that other stuff. Like I get it. I, I don't know if this is a tangent that we want to go on, but let's talk about the time traveling and let's talk about that time that you spend with a partner, with a manager, with a colleague, with a mentor, whoever that is.

And all you're doing is thinking about and talking about what it means to be in sales, what it means to sell that deal. What are you, what are your objectives on the call? What did you just accomplish? What did you not? I joke with people. I tell them I, I learned how to sell by drinking beer. Because I spent a day with my manager, we'd go on all the calls.

And at the end of the day, we'd sit down and we'd have a beer somewhere. And we talk about what happened, what didn't, what should have, what will next time, what do we like, that's where I learned how to sell, you know, and it's like the nuance of reading the room. I learned in an operating room, we never have problems.

Because problem is a dirty word in the operating room. We will occasionally encounter issues, but we never have problem like because of the way it raises the collective blood pressure of an operating room. Yeah there's just, it's nuanced. It seems fluffy, but and Jason you made a point earlier about the stuff that you do, that's so simple.

I had a client, I just ended an engagement with them just in last winter. Yeah. And this guy is this particular rep for this company is crushing it now. And a lot of that's not due to me. It's just the tweaking a couple of things. But he said, Jeff, you know what? The biggest thing for me that you did was you reminded me that while I'm wrapping up one meeting, I should make sure that I.

Confirm the next meeting and keep this deal moving forward. He's like, it's so simple. I was embarrassed that you told me that. And I wasn't doing it. I'm not going to lie. I was red in the face after I got off that phone call. I was like, why aren't I doing this? He's like, but you know what? You're the one that pointed it out.

And it's just little things like that keep deals from stalling. And now his pipe is full and he's crushing things. And it's like, guys, don't give me credit for being smarter than I am.

Well, you know, Jason talked to simple things, you don't simple things is yeah, my first boss always reinforced selling simple, not easy. But it's simple. And if you can keep that in mind, then yeah, they can pay dividends. And it's, I try to do that with like my books and so on. It's reduced complexity, simplicity, and just, you know, here are two things, three things to hold onto for a mindset.

You know, Jeff, your great advice about, you know, setting this next meeting before you leave that the one you're in setting expectations for it. It's, I was having a conversation with somebody yesterday about this is just was just this habit of saying, as a manager, you can go through and ask your sellers on every opportunity in your pipeline, what's the buyer expecting us from us in this next meeting or next call, whatever, that's going to enable them to move closer to making their decision,

That's a question most people can't answer,

right? But you should be able to answer as a manager. I demanded my sellers answer that for every opportunity in the pipeline.

Right.

Otherwise, what are you doing? Why is, why are you taking, what is the purpose of this call? Why are you wasting their time in yours? Yeah,

wanted to circle back, Andy. They wanted to touch base

about something.

back.

want me to, they want me to touch bases with them.

Standardization around process is really. The key, right? It's what's the what's what are kind of the winning elements of the process. And how do we standardize that across the teams process does not equal scripting, though,

you know, and it's like, when you look at these things, I think there's so many semantics out there around talk tracks versus scripts versus all of this other kind of stuff.

And it's what you just shared there. Andy is an example of Standard operating procedure. This is how businesses scale is by standardizing things like that

and then checking for it. You know?

when I love your use of the word. Cause I, I prefer that you use the word procedure, not process for the very reasons, like process tends to come across as a sort of static, you know, systematized thing that, that doesn't enable. People, any sort of leeway to, you know, customize it within a framework, right?

And we sort of have a procedure and well, what does that procedure differ? Maybe in the hands of various people, but that's, we do this, right? We confirm. But how do I, people confirm the words they use might be a little bit different, but a lot of times, you know, people take this process and take it to the nth degree and so we are going to be very rigid.

And yeah, I grew up in the era when the Green Bay Packers were in the first heyday back in the first Super Bowls and so on. And Vince Lombardi, you know, famous coach and people always used to, you know, thought he was too rigid in his approach to things. So actually what we do to give people freedom within structure, right.

And people to bring their personality to the game, people to bring, you know, their unique skills and strengths within this framework. So let's provide frameworks. Absolutely. And then enable people to tailor it to themselves within that. Unfortunately, I think too many managers, at least in the software world, look at process as something that must be adhered to step by step.

And it, you know,

constrains people. Yeah.

Just creating robots at that point. And we're not good as we're not as good at being robots as the robots are, and we need to keep that in mind.

Yes. That's a great way of putting it. Yeah. Jason.

I was going to say one kind of last thing on that topic is this concept of objective strategy tactic. And it's before we start talking about tactics, if we're talking about cold calling permission based opener, say this kind of thing. The objective in that first 60 seconds that you need to understand is that's where 80 percent of cold calls are lost is in that first 60 seconds.

And you got to kind of reverse engineer why that is. Well, what do the people do in those calls when they don't work out? Usually it's some variation of, Hey, Andy, this is Jason with outbound squad. We sell sales training. I wanted to talk to you about training your team. It's some sort of pitch. So it's like our objective is to how do we gain entrance into the conversation by talking about them instead of talking about ourselves,

knowing that's the objective that gives you a lot of wiggle room around the different strategies and tactics that we can apply for that. And that would be one thing I would just leave with. Especially like enabling the rep as a leadership team is, do they understand the objective of every part of their job? Whether that be the prospecting part of the job, the discovery part, the demoing, the negotiate, like, what is the objective? Like, what is the thing that we are trying to accomplish by the end of this activity that allows people to actually be creative? And you get reps that can actually improve a system or come up with better tactics, honestly, than a lot of the people sitting in the ivory tower, you know, but objective is just so critical. What's the objective of this? What are

we trying to accomplish? Let's start with that first.

yeah. And I think there's a mindset behind that though. And I agree a hundred percent with what you're saying is what's the objective, but I think the objective can be, what do I need from them or how am I going to help them? Right. The one could be extractive. One could be supportive. And I think we tend to have the objectives be extractive, right?

What do

I need from the buyer as opposed to what's the buyer need from me? Right. And I think if we frame the objectives that way, then it becomes much more effective. Cause I think if you ask most salespeople and I've been doing this over the years asking groups and now sellers, you know, what's your job, it invariably comes down to something having to do with persuasion or convincing somebody to buy my product. And, you know, I believe a job of seller is to help their buyer achieve an objective. Right. And those are two different mindsets in terms of how you approach a similar task, you know, in terms of like, you know, outbound and gaining interest. So, yeah, I think absolutely right with having the right objective in mind, but it's gotta be the right objective, right.

Coming from the right perspective. And I think that's where we really have missed the boat in general in sales.

Absolutely agree.

Oh, good. Well, we'll end with that then. Gosh, I get a, I got a pearl wisdom in. Thank you. Guys, this is a lot of fun. Thank you.

And he appreciated that. Thanks for inviting me back. I was really excited to come back just to talk to you. And then all of a sudden I get a a calendar invitation with a J base name on it, and I'm like, Oh man, this is going to be fun.

Yeah, that was you guys are welcome to come back anytime. Jeff, this is what your second time on the new podcast.

it

All right. No, honest. Come back anytime. So, appreciate it. And some people can find you all on LinkedIn.

Correct. Best place to find me. Yep.

All right. Good. All right. Jason.

Go get

you.

LinkedIn outbound squad. com for me. Yeah. Thanks for having us on Andy.

Hey, talk soon.