Why Your Sales Experience is Your Marketing Superpower w/ Tony Bradberry (Part 1)

Today we're joined by Tony Bradbury. Tony is an expert in B2B sales and marketing spanning the last 15 years. With a passion for strategy, analytics, and competitive problem solving, he's never afraid to ask why to uncover deeper insights that drive business growth. Tony thrives on leadership and high performance execution. He brings that same energy to helping business scale and refine their go-to-market strategy. Tony, welcome to the show. Hey, nice uh nice to be here. Thanks for having me. Yeah, no, thank you. Um, so we met um through Tribe, uh, the founder group that we're both a part of. And um we first talked, I think this was probably over a year ago now. Um, and that was when I was first exploring uh just an entry-level understanding of how to approach marketing as I scale my business. And uh obviously that sales and marketing is your your realm, and you you definitely have a different approach, uh, I think a more strategic and th uh wealth thought through approach than uh some of the other uh agencies that I've I've come across and talked to uh since we first uh we first talked. And so um and marketing and outreach and sales is is definitely something that's still very much today top of mind for me, and uh something I'm actively building systems around. But um the first thing I wanted uh wanted to ask you and talk to you about is uh about building gray matter from scratch and um what what did your your founder journey look like in the early days? Um what infliction points um and really kind of what what set you up to be able to scale it to the 30 plus person agency uh that you have now? Yeah, so it's kind of interesting. Um, I would say first off, I wasn't here at the beginning. Um, so uh I I kind of take took over from the original founder. Um he'd started back in 2016, and it was kind of an interesting lifestyle business for the first few years. Um they basically operated as as a were truly just kind of a a I would call it a freelancer company at that point. And so it was one full-time employee with a couple contractors that that worked with him for quite a few years, for probably the first four or five years of the business. Um, they had grown the business at that point to somewhere around a half million dollars a year in revenue, which was great business for um kind of that setup. Uh at that point, there was a private equity person that the founder originally knew that that wanted to invest, and so they invested a little bit of money at that point. And with that money, they came and hired me. And so the funny story there is I had never worked at an agency, I'd never worked for an agency, I'd never even used an agency uh in my previous role. I was a director of marketing for um a small IoT security business. And um, so they brought me in and they were like, hey, build out this operation. And what was interesting is I didn't really approach it like building a marketing agency. I was just kind of looking at uh the structure and functions of the business and quickly realized that there were ways that most agencies ran that just didn't make a lot of sense, especially in the early scaling days. And so we kind of took our own approach and we took our own path. And I think that was super helpful uh early on in trying to figure things out. Um, you know, I always joke with people before I got here, they were paying their contractors over Venmo, right? Like uh it was it was kind of a funny situation where you're like, okay, it's so payments due this week. Somebody pull out your Venmo and send money to all of our team members. It's like, okay, well, we can't we can't do that. So we need to start building some processes. And so early on, the founder had started building those, but we spent a lot of time just building the infrastructure, which I think is the most important thing to do. Um, I talked to a lot of small agency owners now, and the amount of people that may be great marketers but don't actually build a business behind it are numerous. And I think that's probably the biggest hurdle they end up running into as they try to scale, is they just never built the infrastructure. They never built the SOPs, the employee handbooks, the financial acumen and and res and and controls to actually be able to grow. And that's that's a huge part early on. Yeah, no, and I mean I couldn't agree more with uh you know just the kind of professional service agency model, whether it's in marketing or accounting and finance, like uh like we are. And I think um, and you know, we have clients that are uh agencies of different sorts as well. And um what I tend to see is it's it it creates a lot bigger headache and it's a lot bigger, uh it's a much bigger lift to implement those processes just on a even just a back office foundational internal level once you're already scaled to a certain size. So um I feel like you coming in at that time at half a million uh revenue kind of size, you were probably able to make that impact and lay that ground level of infrastructure before it was like a huge pain to to implement. Um yeah, yeah. And so what about on um outside of that kind of foundational internal infrastructure level? What uh what did you change in the approach when you took over and uh that you know allowed you to scale that was maybe not the way they were thinking about this before? You know, you mentioned it being kind of built to be a a lifestyle business in a way. Um and so then when the decision was made to turn this into something that could scale, like what else had to change? Yeah, I think another thing that's probably really common for folks in this space, especially professional service at a small level, is um founders tend to sell themselves, right? And so it's about how smart they are, it's about how great they are, which is usually true. They're usually very talented people, but the problem is um that founder or that uh owner is not gonna be on every call. You can't, not if you want to scale, right? If you want to scale, it's gotta be about the brand. It's got to be about, you know, gray matter, not Zach, who was the founder at the time. And so one of the big things we did early on was we had to completely remove Zach out of the deliverable side of things, and we had to even tailor what he was saying in sales. It can't be, hey, I'm gonna take care of you, or you know, I'm gonna do this or I'm gonna do that. It's we, right? That conversation has to become we very quickly because what happens is anytime there's a problem, instead of calling myself who was running the operations at the time, or the team leaders or whoever that was, they pick up the phone and call Zach. And, you know, as a small business with a few clients, that's that's manageable. But when you start getting up to at one point, I think we had 80 some clients. Uh that's not that's not manageable, right? That'll burn you out. And so a lot of the stuff we tried to put in early on was we had the SOPs to know how to function, but it was about getting the messaging right, uh, making sure we talk with you know, this V we uh vernacular uh to try to impress upon them that it wasn't simply our founder, it was a team. And we were a real team, and you know, we had a lot of smart people, and all those people uh could drive growth and really help people. And I think that helped us a lot, especially as we scaled in that first year. We went from um, I was employee four at the time. I think by I started in June of that year, by December of that year, we were already up to like 12 employees, um, including myself. So we we realistically tripled the size of the company in a matter of of you know six months or so, and revenue followed very similarly during that trajectory. Um, we've always been very fortunate we had a nice sales pipeline, but you know, operationally was usually the bottleneck, and again it went back to not me, it's a we, it's a team. Right. And your path into this um was uh was kind of different, right? So you do I have it correct that you you you had your degree in marketing, but then you graduated during like the worst job market in a generation, and marketing jobs were just impossible to come by, and then ended up in sales. Um did you at the time did that feel like a a failure or a or a bad thing, or were you able to see the opportunity in entering at that uh at that side uh in the sales side um and how that can how that did you were you able to see how that would later power uh how you view marketing and what you're doing now? Yeah, so I don't you know I I just graduated college at the time. I don't remember if I was uh that uh introspective, uh right. So I don't know if I really thought of it that way. I thought of it as more like, look, I need a job. Um, I've got an offer for a job. It's not necessarily the job I want, but it's the job that's available to me right now. Um I come from a background of, you know, I I wrestled, I wrestled all through high school pretty successfully, wrestled in college pretty successfully, and you know, built on this idea that like you can will yourself to be good at something. And so my thought was like, look, I can hustle. Um, and that's what I'll do is I'll get in here and I'll hustle and I'll see what happens. And if I don't like it or it doesn't work out, at some point the uh economy will turn around. At some point the market will turn around and I can go try to do something else. Um, and so I got in there and I started hustling, and you know, I was very fortunate that you know I kind of saw opportunities where there were gaps, and I always volunteered or offered that, hey, you know, I know a little something about this, happy to look at the website or happy to, you know, take over the Google Ads program they were paying an agency to do at the time. Um, and just kind of like start picking things up. And over time I kind of built my own positions by going out and kind of stealing things and consolidating them under me, uh, which allowed me to kind of slowly transition out of sales into creating uh the first internal marketing role at the company and then eventually becoming director of marketing for the company. Well, yeah, so because it the where my head goes too is like uh with uh the perspective of entering in the sales uh in sales, did that give you like was there were there things that you learned in sales early on that were integral to now how you view marketing, you know, like get that gave you different perspectives on how marketing uh can be more powerful or or benefit better that you may not have seen if you went straight into a marketing role and spent your entire career just in marketing roles. Yeah, I I think so. So we didn't have much marketing uh where I was, right? I got there and it was really a sales-led organization. And so being in an organization where sales is expected to essentially hunt everything, um, there really aren't inbound leads. I mean, people did find us organically, we had a good name, but we weren't actively trying to get leads. And so, you know, it really ended up falling on the sales and a lot of time inside sales to do cold calling and things like that. And I think one of the things that I took away from that, more so just in general, is client communication and really figuring out how to read people and understand, you know, mid-conversation where people are going and try to actually get in front of them. Um, because you can kind of feel when people are heading towards a no or a yes and kind of start feeling their objections. And that's basically what marketing is, right? Like all we're trying to do is answer questions for people. A lot of times here, what we'll tell people is sell the problem, not the solution. So, really, if you can point out the issues more so than even start talking about how you're gonna solve them, you get people to create agreement. And that agreement is what gets people to want to listen to that solution at some point. And so um learned a lot in that, and and it it compounded when we got to Great Matter because obviously uh the founder that was where he came from, was actually the sales side too. And so he and I really related well to understand that we've got to give you know sales qualified leads to sales, right? And that comes from understanding what uh the sales is looking for, um, and then building marketing that kind of matches that. Right. Yeah, no, and that's that's been something that I've been uh learning about as I've uh we've played around with different uh um marketing initiatives internally ourselves is uh the the qualifying part is so important and find that's seems to be uh at least for us uh the hardest part to to figure out is is the w the balance between like for example uh for a paid ad campaign, um like I found myself asking these questions like what is better, a higher volume of leads that are less qualified or uh tightly qualifying and weeding out uh more people because you're creating more friction to try and qualify them. And like what is that balance? And um for something like uh for a company like mine, uh, you know, where we sell um you know pretty you know relatively larger ticket uh uh engagements and services, um 100% geared towards uh small, medium-sized businesses and business owners. Um how what what have you seen for for companies like this, you know, that provide similar services um be effective in the way that leads are qualified? Yeah, so there's a couple uh I'll say lines of thought or or trains of thought uh on that. And so you ask a good question, is it volume or is it trying to wheedle them out? I I think usually it's a it's a combination of both. And so what I mean by that is the problem you're selling, if you really have your ICP defined really well and you understand what makes the problems of that group unique to you know somebody too small or too big to work with you, um, then your ads, when they target and and the copy of the ads should resonate with those groups at a higher rate than they resonate with the other groups. Meaning if you've called out the problem well, they're gonna click on it much more likely than anybody else. And then what you want to do is when they get to the site, you want to qualify them through a little bit more and say, hey, a perfect uh relationship for us looks like this. It looks like you know, roughly this amount of money, this size for revenue of you. Um, you guys have this kind of things in place, you guys are looking to add these kind of things. You basically self-select out so that by the time they go to fill out the form, we already know that they're gonna be a good fit for you. Um, what we've seen people get in trouble with is kind of that that classic, well, um, you know, I I want more leads, right? And you start sacrificing the quality of them. The reality is to qualify those out, hop on calls, that's time. And time does have a cost associated with it, especially as you scale. And so what may work early on when you don't have as many clients or you're you know okay with spending more time is it makes sense. But what you're gonna find is uh that leads you to start accepting clients that may be just outside of your target group, and those tend to be bad clients. And what I mean is the money's good, meaning they'll pay you, which is great, but the effort is off because it doesn't actually match what it is you want to do. Sure, I can do that work, but there's a reason I don't do that work usually, and that's because it's it's exhausting and it'll drag you down. And so we went through that a little bit early on, where um, especially in our growth phase, where we're like, cool, money's money, we'll take it, it's close enough, let's go. Over time, we found that those people are essentially vampires, they will suck the life force out of you. Um, and so you want to be very uh direct in that. And so when we talk about scoring those through, have those set criteria. Um, try to wave them off at every chance you can get, whether it's in the ad phase or in the conversion phase on your website. Um and if one slips through and you talk to them, don't be scared to push back. Don't be scared to tell them no. Yeah, no, I think uh, especially uh companies that are uh relatively new or in that growth startup phase where they really do want to scale. That seems, you know, and this is something that I've uh I've learned the lesson a few you know a couple of times the hard way as well, is being able to say no to engagements that you know are not the right fit. Um because you know, you you want to grow the company and uh you want to try and help everyone, but then there's you know, uh you can often see some of the f red flags right at the beginning, and uh, but then you kind of think, well, their money's green as well, uh, how bad can it be? And then it, you know, um I think we've all gone, you know, been there, especially businesses that uh provide services, you know, B2B. Um and it's not every dollar is created equal. Uh, and it's uh often the cost of that revenue is you know, are things that you cannot you know tangibly measure and and dollars, but the cost it outweighs the revenue that it even brings in. Uh and so and that's where I come back to is how can uh after those experiences, how can I how can I weed out those type of clients and engagements from the beginning so that I don't have to be in this position again, uh which is you know you know part of the learning experience. But um you know I I I see you talk a lot about AI use, and then I and I know your industry as long you know as far as well as every you know industry in the world is is being or will be affected uh and impacted by uh by AI and technology uh in the future, if not already, which I think you know we're we're well well beyond uh that already starting. And I kind of see two camps of thought of diff of different people and founders. There's the one that see the opportunity, and there's the ones that kind of see it as this bad thing that are trying to resist. And personally, I think it's like you're there's no resisting and stopping this from happening, and there's so many opportunities in this, and I'm choosing to view this through um that lens rather than a uh a lens of scarcity. Um but I'm curious what your uh what's your overarching you know first thought uh on just the world that we live in now and where it's going because there's so many different different uh thought trains of different people and experts and at the end of the day no none of us know where it's going to go. We can only guess where we think uh and have our own opinion. But I'm curious to hear your uh your thought on on where where this is all heading. Yeah, I don't know if we have enough time for that. Uh now it's uh yeah, I've got I've got opinion too for sure. I uh I will say this. There's a lot of thoughts around AI, and I think some are like most times a little bit um fantasy, right? And not to say we can't get to a lot of these these um places in the future. Um but understanding where it is today and understanding where it could be in 12 months is really, really important because I think sometimes people will try it today and then not get what they expect the outcome to be, and then just say, see, guys, our jobs are safe. Um in two weeks from now, that could be completely different, right? And the problem is anybody that makes a snap judgment right now on anything kind of dismisses how fast things change. I will say this we have fully embraced it. Um, we've embraced it in a way that recognizes the ability for AI to do the thing we do. So this idea that you're getting paid to do a task is going away. And it's going away across all industries. Again, I think you know, talking about you in like your industry, bookkeeping, right? Bookkeeping is something that the AI is going to be able to do very well because it's more of a it's it's more of a functional thing that just does. There's rules, you follow the rules. You do the thing, here we go. Same thing with marketing, right? Like there's tasks we do for every you know larger campaign or strategy we run that have to happen, right? And so using AI to do those things that aren't necessarily about using our experience or the nuance or context that we get from a client, but really leveraging it to actually do those things is such an efficiency driver. And so we super, you know, we're we're all in on that. I think where people get nervous is where we take the human out of the loop. It's where we basically say we're gonna put this thing on autopilot and let it make a bunch of cascading decisions. Because if the first decision was slightly off, then the next couple decisions it make are slowly going to drift you further away from what that initial decision should have been caught and corrected. And so I think human in the loop is still the way to go. It's gonna be the way for a while. Um, but there's a lot of work being done there, right? There's essentially like multi-chained agents that essentially create their own, we'll call it, gated area where bias is contained that then checks against multiple people. So it's moving fast. Um, I think you know, you have to embrace it. Like you said, if you don't embrace it, you'll get ran over by it. Um people thinking it's a bubble, the pricing, the valuations, the the unit economics, sure, maybe. Um, but you're never gonna put this genie back in the bottle because especially for that task work, it does work and it works very well. Yeah, no, I agree, I agree with uh a lot of uh the things you're saying right here. Um especially you know, like the the cost framework, right? I don't know how sustainable $20 a month subscriptions are. Um but you know, it's there's you know, uh I and I've heard examples also of companies that are you know spending uh that have come out and said they're spending more on their uh their AI consumption and than they are on the than they were on on the people that they let go to replace them with. Um you know, so like the cost thing is, you know, that's I mean that is what it is, right? And but um but I have the same, you know, you know, because in in the realm of what we do, um, you know, we have there's kind of the you know the bookkeeping layer layout layer, there's the you know controller accounting, higher level accounting uh kind of function, then there's the strategic finance fractional CFO layer. The bookkeeping layer, a hundred percent, like there's there's uh when you break it down to its core, there's just there are a lot of things that are just this are a set of rules. Uh but then even with uh something that is can be nuanced because I think that's where a lot of the a lot of the uh you know the software and the AI technology that has come out uh that tech companies have released for our industry um to automate tasks have missed the mark a little bit, is understanding the nuances that occur, especially within small to lower middle market size companies that might not be the same way applied to the next company. Uh they might do it slightly different. Um, and so it's not none of these tools have been uh very effective in uh you know rolling out blanket wide, because in um I 100% agreed there needs to be a human in the loop um monitoring uh the decisions that are uh automated. But like something something as simple as categorizing banking credit card transactions for a client inside their you know their QuickBooks Online. That's like the first step that you need to get the data, transaction data, inside of the financial world. Um and you know, like we had we built um a connection to uh on into its developer um where we can connect into QuickBooks and we can do things inside of Slack or inside of a clawed desktop uh with the MCP. We can do basically everything that you can do inside of QuickBooks logged in, um, but in a magnitude of different places and with natural language. But then the hurdle from what I envision is like this continuous close, where we will get to at some point in automating all of those close kind of bookkeeping accounting workflows to close out um you know the books and to have live financials is the categorization of those transactions because that's where they sit inside uh QuickBooks is is basically like on the front step, but not inside the house. So you can't access those to have um but with uh you know, we couldn't have done this a year ago, but uh a few months ago I built a uh a workflow built on a plaid application that then goes directly to the source, and then because the categorization part is fairly simple, because if you can explain the logic, even if it's nuanced from client to client, if you can explain that logic to a human, and the human can then carry out that task, then you can explain that logic to AI and get a pretty similar, if in if in some cases more accurate and consistent outcome. And so that's what we create, and we actually have a couple of clients live on that where their transactions automatically with that logic get categorized every single day. So that's live. A human is in the loop reviewing the work that happened, and then the system has got a a learning loop where the human will make comments on things that were done incorrectly or give it extra logic on why it did something incorrectly that it then learns from. And I think that's a powerful, you know, that's just one example, but it's where AI can become extremely powerful because not, you know, aside from a company becoming more efficient and you know, increasing margins and being able to bring in more business with less headcount, but in that example, it gives a client financial information, financial data live, and not having to wait for you know the month and to the month to close and then for humans to go and close the books and then get like it gives them real-time data, uh, which is a huge value add for a client. Um what have you seen inside of your uh inside of Gray Matter and the marketing industry? Like what's uh the biggest unlocks with AI um and how you guys use it? Yeah, it very similar, right? I I think this idea of um there's still nuance, right? And nuance is always gonna be tough to decipher for for AI because what may work, you know, we may do something for one client a certain way, but we change it for another because there's just certain things about their industry or about how they operate, right? Maybe their executive board needs to get something a different way, reporting-wise. Um, you know, those those things are very difficult. But for us, we're using it, you know, anywhere we can. We're we're diving in deeper with it. So we actually just launched a new website, uh, I believe about two weeks ago. And uh historically, we've always worked off of WordPress. You know, most of the internet's built on WordPress, and you have your plugins and you have your things, and that's probably one of the uh LinkedIn posts you saw. Uh it got quite a lot of traction from uh the WordPress community and and the non-wordpress community, which was really interesting. But um we had uh iCloud basically build the whole website. So essentially what we did was um we took our old website, uh, we had it scrape it, pull everything in, and then spent some time kind of talking with it about the changes we were looking to make, both from a brand perspective and a content and direction of the company perspective for that matter. Um so what it turned out was essentially a code base that I took into a tool called Replit and then worked inside of Replit to take that and build it out. What's really cool is you know it's not a small site, there's probably about 80 pages and another 200 blog posts on it. So um we ported that all over and we stood it back up inside of Cloudflare. So it actually runs from GitHub to Cloudflare. Um and now we're able to manage the website from there. And the cool thing is we want to spend up landing pages, or we want to do a new blog, or we want to do whatever it is we're changing. Um, I go into like Cloud Code and just tell it a little bit what I want to do. It makes the change, we push, we uh validate when we push the new code live to the website, and off we go. So we think about that as kind of maybe the future of where web's going. It it takes people that are comfortable with what that is, right? WordPress is easy, WordPress is familiar, it's a visual editor. This is visual too, it's just a different way of doing it, but it is truly all custom coded. So that's one side, and we'll put that over there. But like growth marketing is a huge part of what we do. Um, and so growth marketing is essentially this idea of we need to grow, how do we do it? And so that can be your SEO, that can be your paid ads, that can be email marketing, that can be content marketing, it can be social media. And so we use AI in different places there, right? And again, we're building systems right now internally that solve, I think, one of the problems you were just talking about to an extent. AI right now has very limited context windows, and it's hard to have context about what is nuanced to that client and what we're trying to do. And the more you put in there, it starts to degrade as it consolidates. And so you start seeing people veer off what is what good looks like. And so we've spent a lot of time working on building uh memory and um different types of controls that help us do that better. But I think that's the area that before AI truly quote unquote takes over, uh, it's got to go a long way. It's still not there. And so we handle a lot of that internally. Um, we still produce a lot of the finished product, but a lot of the outlines, a lot of the research, a lot of the stuff we're doing, it speeds that up immensely. Um, it helps put decks together faster, right? Like a lot of the busy work that in the day you had to have a lot of people to do, you don't need now, right? And one of the things we've noticed is it's actually required us to have less specialists in different things and more generalists. And so we like that because um the generalists see the whole field a little bit better than specialists tend to do. And so by having more of these generalists or strategists and people in that kind of department in Rome, they look at everything and they don't really necessarily bias towards one you know uh tactic for delivering results. With AI, we're able to allow those people that see the whole field a little bit better produce work and get to finished products faster than historically couldn't. So, you know, for us, that's where we've been leveraging a lot and seeing a lot of lift for it. And I think going forward, that's where most people are gonna find that lift is the era of the specialization probably is dying, and people that understand whatever it is your industry or your business is front to back will be your A players going forward.