Why mid market companies get sales wrong and what AI changes

Hey, thank you. I appreciate the invitation. It's so far so good. Thank you.

Well that was I know it th there's a lot of interesting, incongruent seeming things that seem together. so I've was a musician seriously and professionally from the time I was young. So was doing that and was in Nashville and then I moved to New York City, went to school in New York City, a college in New York City at the New School, which is a great jazz program. And you know, long story short, music was good, but I've wanted career-wise or playing-wise, I hadn't a lot of luck, played with lot of great people, and it was you know nice. but business-wise is you know, it's an idiot, everything's idiot idiosyncratic, but music particularly so. So I just by happenstance, I went to school at Columbia to learn more about business and statistics and et cetera. And while I was there, coincidentally, I met a hedge fund manager who was a brilliant bit of a character and a just a brilliant person. And he was a musician, a hobbyist musician, but a capable, capable nonetheless, and like musicians or whatever. So I did I interned there for a little while. And got a trading allocation and just built up from there. So that it's it was it was really a lot of happenstance and extra extraordinary good fortune because I learned more I learned more from him directly and in mainly indirectly, and in that context about a lot of things than than I would have in any business program or anything like that. I I couldn't I couldn't think of enough. and so that was good. That was a nice run and that that ended that's a that's a different story for a different time. but then I decided, well let me do let me do music again. Let me be more involved in music. Because that's my really w one of my first passions. As as people say passions, it's a goofy thing to say. and did that for years again in New York. studio recording, organizing, organizing production in different capacities, et cetera. So that was good and yeah, I had a lot of good fortune. and then for different reasons thought A was starting a family and et cetera wanted something that was more expansive because that was a good business but I wasn't it wasn't something I was able to scale meaningfully put it that way but was good. And so I got into quota-bearing sales essentially. You know what I mean? Because there's always been a sales and business component to all these things, but where you really had to hold quota and just do that thing. and that was some years back now. And so I've I had different positions and sort of, you know, essentially worked my way up through different companies in different positions through sales and business development, and and marketing tangentially. I'm not a marketer primarily, but through sales, especially the way sales exist now. You really if you're running teams and you're you're trying to get something off the ground, you need to have good copywriting, you know, because you can't you can't trust marketing with all due. You can't trust like mid-market marketing agencies to really do that kind of heavy lifting. it would be a wrong expectation. So when it comes to real conversion marketing for emails, even snail mail, I've even written you know radio and television, which is outside the scope but it worked out well because it didn't fit contextually. So anyway, so all those things come into play. So the yeah, so the short story, long story, longer, is that got into quota bearing sales and that just expanded. And then I started Barnstormer a few years ago, because it seemed It's there's always a market for people needing more sales. It's a revenue consultancy. And finding that balance where we offer direct sales, direct deal help. You know, we're we're not consultancy like here is a spreadsheet, here's something that you should do. We are hands on. You know, we we we participate and and and when you're dealing with mid market, SMB mid market and you're coming in to do these things, you need to be involved with deals, you need to be shepherding deals. That's just it's just part of the thing. if you're really gonna get lit. Well while you're training and while you're nurturing the team, it it's all sort of coincident. and and the the the marketing piece is th the the the connections between sales and marketing are just seem to be getting tighter and tighter in terms of necessity of action. Not really. Teams are still siloed. There's still, you know, there's still there's still challenges to be met. but joining those skills is it seems a critical thing going forward. So so that that that's the i in it is good for business. So th that's the the the that's the thing.

It yeah, so so the the the moniker consulting holds within it a whole bunch of stuff. And some of it's interesting and some of it is just hokum, just nonsense. It just that is just dismissible. just like anything else, right? That that that arc of things happens. so yeah, and when you're look when you're dealing with like like mid-market co you you you're dealing with people who they need to have something done.

They need it the when you get to a larger organization, you can get sort of, here's just strategy for its own sake. Good and necessary. They're thinking longer term. Everybody's thinking long term, but it it's it's a different thing. When you're coming into mid-market, they they need action, they need activity. You you you could strategy is important, but it's you can spend a couple of few days on a strategy and then get into the actual iteration in the market. Cause what you y you you have to have real world pushback and real world understanding so you're iterating your systems properly. too much sitting and strategizing is who's it helping, you know what I mean? It's necessary, but sometimes people give it give it too much weight. Yeah. In my opinion. I could be wrong. I could be wrong about any of this. So imply high.

between it could be any number of things. You mean i i i in the context of the company and the market or the context of the of their internal operations?

well that depends. It might not be It might not be a wholesale market misalignment. If it's early, so that it depends if they're relatively early and still finding something, that they're still c trying to find their market really. And they've got an idea, this industry, that industry, but where further is their audience and and how does that how does their sales process really shape up? Who do they need to talk? Who's cutting the check? Who do they need to talk to? Who who are who are the people influencing that decision? Who's who who's riding the dime? And if they're a little more developed, they have they'll usually be can they'll understand their market at least relatively well. so it won't be a misalignment. It could be more of how they're reaching the customer, what what they're saying, you know, when they're what avenue they're saying it in, what it's all there'll be many ways to approach the market. through marketing so outbound marketing and you you you find a different balance. But usually that's that's fairly developed. it needs some tweaking more than like wholesale alignment. Internally that is where you f it's a little more challenging and th that that sort of day to day really expresses itself. and You have the same issues of people you you have retention issues, especially in sales. You got to get a good team, you gotta train them, you gotta hire them. That is a that's particularly difficult in sales. generally speaking. Some people have you know high retention, they're doing great, but it it it th that is always a challenge. and increasingly And this has been worse post COVID. There's always it's it's an imperfect world, but you see an increase in companies trying to really finagle sales when it comes to the quotas that they're setting. They might set quotas that seem reasonable but are a little bit out of a little bit out of range. there you'll see more instances where, and I've seen this in a bunch of contexts. More instances where a company will try to somehow fish their way out of like a big commission on a big sale. They'll there will be more friction than you would imagine in trying to get get that rent paid outright. Or or w without too many frictions in every people want to be involved in deal. If you got a big deal, everybody wants to be involved with it and wants to take some kind of credit. That's a natural thing. but in terms of misalignments, that that comes to mind as an increase in some in the past years, especially post-COVID. that notion of, okay, well, we we take care of our salespeople. We got you, we understand that the more you make, the more we make, however you want to phrase it, that sort of guiding ethic. You see that expressed, but in real practice, it's less these days. Companies of all stripes are willing to Maybe ta I'll just say take advantage of the sales team. and so th that is a that that is a meaningful misalignment that you have to that you have to sort of deal with. So everybody's properly incentivized, parties can trust one another appropriately. Th that that is something I see that i is worth attention. Yeah.

Yeah. well I am meaningfully involved with sort of AI and I have I'm a partner in a New business, recent business, called Emberlink, with Josh Hudson, who is a fantastic infrastructure engineer. He was at Polymarket and some and some other companies. So he's a great guy and very knowledgeable about these things. So that business is taking authority governance for AI agents. So your AI agent can't encroach on your system, you know, ha has it it it does what you're asking it to do and not anything else. Else and then gives you receipts on the matter, is the short story. and more generally, I think that it is probably true that in some years it won't be that long before those, especially, and you can already see it taking over in customer service functions, because the it it is more dependable. AI agents can be well trained. They're more difficult to train than I think people think. Forgive me if I tangent too much here. You can reel me, but there's a lot to say. they're absolutely trainable in a way that is very effective for customer service and will be for SDR work and et cetera. And it because they don't they don't get tired, they know the product, they know the the mandates, they know the company immediately and accurately. they don't get moody. It's it it it it it for more transactional customer service it will it will win the day. And that technology, the AI technology is extraordinary. It's amaz it is truly amazing what can happen now. And some of the misgivings that people have, which are true, and I don't see a future like some sort of Arch Arnold Schwarzenegger AI takes over the world like maybe. I don't know. I can't I can't quite see that far out. but especially with LLM use, GPT

Claude, etc. often enough people misunderstand, and it makes sense why, that that they don't understand the power and what they can really yield out of the LLMs because of the way they're using it. They can ask a question and then query it, and maybe they push back a little bit on that query, and they get something that doesn't really is okay, but doesn't really fit into. I don't know, this they have misgivings about it. But you need other sort of master prompting, other scaffolding, that's other other agents potentially that are running in the background. Even simple scaffolding that you can design within GPT itself that informs your answers, that that informs what GPT gives you and materially improves your output. So, what is a so people often misunderstand what's available, and that makes sense. And also simple structural things like if I'm if I'm asking an LLM to write. write something and I I open up and I say, hey, write this, write a post, or write an article, or write this, write this internal memo, whatever it is. GPT thinks about that and let me write this. Here's a heuristic, here's a framework, and it gets, it'll be accurate and you'll have, it'll be better than average. And so it's it's it's a usable result. But what's happening is that it it's it's compressing. You'll notice compressed compressed language like in the room. If you see something I somebody you'll see blah playing but say, in the room, whatever you there's a there's a non-zero chance that that was GPT and that's fine. People should be using GPT all the time. If they're not, you're you're missing it. You're absolutely missing what's about to happen. No, there's not it's not a controversy. It's not You're I and I I I I can see people why well people are skeptical and that makes sense, but they are they're missing the train. so what you need to do process-wise is start back and say, hey, here's this topic. What's happening? Here are my thoughts on it. what are my assumptions? What what what's re what what's grounded, what's not grounded. You have to push back on your own ideas and also on the system itself, make sure the the the information is accurate. And the more you have that you have that adversarial pushback to GPT, the more it will give you better answers. And also outside of a writing prompt, it will give you better turns of phrase. It will give you more elegant outlines and turns of phrase. So you take that and then turn that into your finished product and have to prompt and there's other like I have the different like texture controls and other like writing things that I have running, scripts script that I have running in the background. that help all this stuff. so anyway, so I could go on, but s but between process and sort of understanding what's available, I can see where p people both have misgivings and also misunderstand what can really be done like right now with GPT. And it's only going to get better. So to corral that back into into an answer, I think that the customer service functions, anything that is relatively more transactional will be will be AI agents eminently. It and the there's always drift. There's some drift component. 'cause it it it's it's it's non-deterministic. So there's variation. And you just have to you always have to corral those variations and training and and make make sure there's a human in the loop depending on where where that needs to be. but it it it is here and it's not it will be taking over and it will be doing a great job of it and some of these tasks. Yeah. And there'll be other jobs and other expansion and other things that come from it. So I think it's it's a it's an i it's a thing of increase on balance, e even though there's th there'll be some some awkward transitions here and there.

Right, right, exactly. Exact well phrased, yeah, yeah. That's right. Yeah. Yeah, just to be here. It's been a while.

that no one talks about. I'm not sure about that part. I would say the The I would say getting the getting clients, finding the right clients, that is that is that is always the biggest challenge. And it's doable and there's business, there's there's there's good opportunities. But that is, I think that and just just taxingness. And even when you come from sales and you know that universe, because some consultants they come from a whole other space, they come from engineering space or whatever, and they don't know the sales dynamic. So it's just not in their blood to go, I need to do I don't they think that they can do five of a thing, like five like outreach in a day, you know, five email messages a day, whatever they think that's gonna pass muster. And I understand why they think that, but th it's easy to misunderstand the scale and like how much has to be done to get a certain result and what the process is. So even when you come from that world,

And consultancy specifically, because everybody's a consultant, everybody's got that banner, and you have to sort of you have to differentiate. and just like you're saying before, it's like, I hear consultant and I hear it too. Like I hear consultant and I think that's just bullshit. Can we swear? Sorry, I don't know what that is. You can edit that out. And so that's my consultant. It's like, they're just gonna make a spreadsheet or it's whatever, it's somebody's doing and again there's there's brilliant people in consultancy and we we bust balls on KPMG or whatever, but there's a bunch of really

Right people working there and they there's some interesting things happening. so no you don't wanna get get too too cheesy about it. but that that moniker is i i i is its own is its own challenge. But so yeah, I I'll say that and client work again has its own challenges, but I find that that is it's not smooth sailing because th th if they're coming to me or they're coming to the consultant, things aren't great. You know what I mean? Rarely do a does a company come to a consultant and go, yeah, everything's great. We just can't, we've got sales

Everything's taken care of. The team's great. You know, but we just want to kind of blue sky some ideas and we'll make something happen. Maybe somebody's getting that business. It's not me. You know what I mean? Yeah, yeah, yeah. Something terrible is going on. Either they're starting something and they don't know how to do it, which is which is more understandable, or something has just really gone awry. And probably has been going awry for a while and they need to fix it. so, but even in that context.

I find that the client work is even when challenge is is satisfying and is i there's a more there there's a different kind of buoyance there. But the the the the schlog of reaching into the market and finding your audience and finding the best f finding those best deliverables, those high quality highest quality deliverables in your context, that is a challenge, certainly initially. Yeah. Well w what what what have other people said here? What what what are you hearing is Is the th th th those main issues from your other guests.

Absolutely.

Capacity constraint. They're getting that that's right. But that can happen, but that's not the main story. That's right. Yeah.

Yeah, that's interesting. That's a I would say unfortunately I did this enough. I would say just get after it. And that sounds silly, but but but r realize that everything is at stake, but not as much, especially when you're 20. It's like get involved. It's like what you when you're 20, you can just get away with almost anything. And I don't mean, you know, any you anything silver bananas, but do what you do what you want to do and not, you know, understand the expectations, but Now's the time. Get into something. If you want to do something, now's the time. It's just going to get more difficult. I mean, I kind of think that way anyway. But anything that that moves you or that is interesting is fine. And if it doesn't work out, so what? Keep it moving, because a bunch of stuff won't work out. And you know what I mean? It's not there's you don't have to have as many questions answered as you think. When you're 20, it's just get figure stuff out. Just understand what's this? what's this? and whatever whatever that is to any individual's taste or temperament, just get involved and realize that it's probably gonna be. Fine that you don't have to have, well, this is gonna lead me to where I'm 40. Like you don't need to know, you don't need to care about it, right? Just just just engage with as much as is meaningful to you as you can. And if it goes awry, well, you'll be fine, you know, more or less. Again, I don't I don't mean to be cavalier about it, but you you you'll be fine. and don't don't don't be hesitant, you know. J jump in feet first. Yeah.

Yeah, I'm I'm easy to find. on on LinkedIn, William Kenny on LinkedIn. There's probably a a few names, but William Kenny at Barnstormer Consulting. you can go to the website, Barnstormer.co. and those are the best places. And yeah, my email is Kenny at Barn K-E-N-N E-Y at Barnstormer.co. So any of that, any of that'll work.

Hey, thanks so much. It was a real pleasure. Congratulations on your podcast.