Fractional Hustle

Welcome back to Fractional Hustle, folks. My guest today is Brian Koffler. I'm very excited to chat with him. Brian is a seasoned expert in demand generation with over nine years of b two b marketing experience. He's a SaaS demand generation leader, the founder of DIGS Marketing, and he currently resides in New York City.

Brian, welcome to Fracture and Hustle. Thanks for having me. Happy Friday. Happy Friday, sir. Happy Friday.

So, you know, founder of DIGS, right, Can you tell me a little bit about that? Give people an idea of, you know, what you do and, you know, that journey, how you started. Yeah. I can start with what what we do. So DIGS is a demand generation firm that works with b to b SaaS companies helping scale demand gen.

Usually, what that means is scale paid ads and email marketing to generate predictable new sales opportunities. So, yeah, mostly, we work with scale rapidly scaling b to b software companies that are usually between, like, 50 or 5,200 employees. And almost all of them have little marketing or no marketing. So, usually, it's like a marketing team of less than full time five full time employees that are really looking to generate pipeline, repeatable pipeline each month. They have aggressive goals, and they need help from experts to to hit those goals.

So, yeah, that's part one. Part two is, yeah, I worked in house for ten almost ten years and then started working a little bit on the side, with a few companies and realized that I loved it, and I love the opportunity to work with different businesses at the same time, really help these companies. And then I'm able to now take what I learned and what I've learned and really, scale results for, many companies. And achieving those results are are amazing, and everyone's happy. So Yeah.

Yeah. It's amazing. So when you said that you come into these these organizations and their teams are, you know, one, two people, that sounds tough, man. That sounds kinda difficult. Like, what is that what is that process like?

That's a good question. Usually, what I see in especially in b two b software is there's a team of less than five. They're try often the these companies are trying to scale multiple marketing channels at the same time. Yeah. So that's email marketing, paid ads, customer marketing, CRM and database automation and marketing.

And it's usually one of two things, honestly. One is that they haven't started that journey yet, but they're getting pressure from the CEO or board to start because they know they have product market fit and they know that they need to start generating predict predictable results, or they have a team, like I said, less than five people who are kind of responsible for everything. And they need to fill in some gaps, and they don't have headcount or budget for a full time, you know, director or head of demand gen like I would be if you hired me full time. And both of those scenarios really need somebody who can come in, be self sufficient, know what they're doing, and generate results without a ton of hand holding while also being able to kind of talk to CEO and strategy level of why we're doing the things and then also be able to do them. So, yeah, I found that the fit there is really nice with the 50 to 200 employee company that is, usually, like I said, less than five full time marketing team members.

Yeah. So you're coming in and just trying to help them get to that next step, maybe, you know, 500 employees, just trying to help them scale. Usually, they have, especially in the software world, you know this. They're very aggressive goals year over year. They're trying to scale the companies fast.

Often, it's like the pipeline and the revenue goals are two x year over year. Right. The budget may or may not be two x, so it's not one to one. And then, yeah, to your point, like, I'm trying to help them scale as best as I can to the point of where in a great engagement, I actually will help hire a full time demand gen director, demand gen manager, head of growth marketing. And then those people, when they come in, they have a great baseline and somebody like myself who can kind of understand and teach them everything that we've built because I've been part of it.

Yeah. So like you said, those are super aggressive goals for, like, a lot of those organizations. What have you learned in trying to hit them? Like, what are the things that you're like, okay. Like, I know that these things work, and, you know, we're we're gonna achieve them.

Yeah. So I have a two part answer. One is that I don't believe any two companies' demand gen or growth plans are templatized or boilerplate, so I don't think you can just run the same exact plays Yeah. And expect success. On the other hand, I do think, especially, again, b two b software companies of that size, the channels that I have seen that usually work the best at that stage to generate short term and midterm pipeline and growth are paid ads and email marketing.

And scaling those two channels is usually a priority, and that's why it's usually the two main pillars of my engagements. If I were to paint a broad brush, that's the answer I would give. Yeah. So how do you curtail to each act individual situation, right, or each in organization? You know, how do you what what are you looking for in terms of, like, just certain criteria to to to take each case as it is?

Yeah. It's a good question. So part of it is I rely and work very closely with the in house marketing team or person to understand the messaging and their ideal customer and their best customers that they have so we can try to get more of them. I am not especially at the beginning of my engagements, I'm not an expert in this product. Right.

I'm a marketing expert. So I I do work very closely with if there's a brand marketer or a content marketer or a VP of marketing to really understand who they're going after and why. That's number one. And then number two is I often often these companies have some kind of inkling of early success with one of these channels, and they really know or they think strongly that, like, if we do this correctly, it will produce exponential results. And I like starting there.

Rather than building something from complete zero to to one, getting something from one to two or two to three if they have some kind of baseline Yeah. Usually produces results quicker. So I like looking at data and asking a lot of questions of, has anything worked in the past? Is this why you're bringing me on? You know, questions like that.

And, usually, there is something that has worked at some level that we start with. Awesome. Did that answer the question? Yeah. Yeah.

Absolutely. Absolutely. So, you know, something I saw on your website, right, was transparency. Right? You know, you you you you like to say that, you know, you tell it as it is when you're coming into into an organization.

How do you navigate that where you're coming in saying, hey. You guys are doing a bunch of things wrong, you know, and and then you wanna change a bunch of things. How do you tow that line? Yeah. So, one, I think it's just my personality.

It's how I am in my personal life. That's how I am with friends. That's how I am with my wife. That's how I am with work. That's number one.

So I do think there's just some personality aspect to it. I also believe often people and this is a little bit of a phenomenon that I've learned, but companies actually listen to kind of outside voices sometimes more than they listen to internal voices, and it's almost like I'm validating their thoughts. And I've been in many situations where the internal marketing team is telling the CEO or telling the VP of marketing that x y z is not working, and there's back and forth. And then I come in, and I tell them the same thing, x y z is not working. And immediately, they're like, let's cut that.

So I think there's some level psych psychological aspect of when you bring someone in who is an outsider a little bit, and they tell you something's not working, you listen. And people actually have told me they pay me to do that. They want that. So in some sense, it's a lot easier to do it when you're not in house. You're not worried about necessarily getting fired or negative feedback.

Again, I'm I always position it as like, hey. I'm a neutral third party here. Right. I want the best results. I don't have to play any of the internal politics.

I'm not looking for promotion. Right? So I've actually found that people hire me for that exact reason because I will give them an unfiltered opinion. Yeah. Yeah.

No. You know, it's it's when the cool uncle comes over and tells you something instead of your dad. I should use that example when I talk. That's exactly right. And whether they want to admit it or not, I've seen it now 15 times, on a fractional basis where it is crazy how I could literally say the same thing that somebody internally has been saying, and then I get a message like, thanks, Brian.

I've been saying that for six months, and no one's listened to me. Like Yeah. Yeah. You have someone in your corner as a I mean, yeah. Because, you know, people are playing the politics game.

They don't wanna maybe necessarily rock the boat of an organization or, you know, yeah, put their job or reputation out on the line or at risk. So no. That's it's really interesting that, yeah, you kinda come in as, you know, like you said, as an outsider, and people, you know, they receive that information with grace. You know? That's yeah.

I've talked about this a bunch because it is like a phenomenon that I I wasn't necessarily expecting when I left in house role to do this. Yeah. But it is very obvious and evident. And the other thing is people understand that I've worked with many different companies that are usually in similar size and stage of scaling. So maybe the internal person hasn't, or maybe they're young or green in their career, and they don't have ten years or fifteen years of experience.

So I think there's also just that aspect of people understand that I'm an expert in this space and growing companies and from a marketing perspective have a good lens. But, yeah, I that is often the beginning of my engagements of saying, like, no. No. No. No.

No. We should focus on this one or two things. Yeah. Yeah. And so when it comes to the email side of things, right, how do you how do you even begin to start a campaign?

That is a loaded question. Again, my default is kind of, hey. Have you done anything in the past that's worked or has seen some some success, whether it's new business generated or good open rates or replies? Most companies that I come into have done something. Yeah.

And that's kind of based on the size of the companies. I'm not coming in, like, super early stage, like a company of 10 people, that has never done anything. So I start there. The other kind of place I I often start is where's what data do we have and what's our cleanest data from a new business perspective? So often, what that actually leads to is people have a good database or a clean database of lost deals, like people who evaluated the software and didn't buy.

We have a lot of data on those people. They were in the CRM. We've probably talked to them before. So I like starting there versus just, like, a cold audience that we may or may not ever have engaged with. Yeah.

So, yeah, that's kind of, like, the two part process of how I start or would talk about email marketing if we were just standing up the program. Yeah. Yeah. No. I you know, someone just tapped me for the sixth time via email.

Right? And I was like, alright. You know, let's get on a meeting. You know what I mean? Sometimes, you know, yeah, the cold leads are more receptive and warm because you've already established that relationship even if it's not necessarily, you know, a a working relationship at that point in time.

Correct. You know, you've already cracked the, the introduction. Also, you know, there's some level of those people, whether they've evaluated the software and not move forward or they've downloaded a piece of content in the past, they have some level of brand recognition. Yeah. You're not just, like, a name that they've never heard of.

I'm not saying that they're necessarily ready to buy this month, but, like, the chances of that person answering, like the example you just gave or downloading another piece of content or going to a webinar is much higher than random person in your database. Yeah. Yeah. No. Absolutely.

And so you're so you're talking about, like, a warm audience. Right? You know? And and yeah. Yeah.

And so, you know, already reaching out to those people that you wanna interact to. How do you establish, you know, maybe messaging or, you know, are you using what they already used? Are you trying to come in, you know, just from a completely different place to shake things up? Or, you know, is it AB testing? Like Yeah.

It's a good question again. Usually, I partner with someone internally for the I am not a brand marketer by trade. So often what I'll do is I will provide best practices on the actual emails. Like, how long should they be? What's a good call to action?

How frequently should we be sending them? For the for the content, like the tone and the messaging, I work closely with someone in house who understands what the brand wants to or the company wants to show or have people perceive them as, externally. So at the beginning of my engagements, it's a lot of, collaboration. And then usually what happens is when I work with my clients for six months or eight months, I have a pretty good understanding of how they want to speak or what their emails should sound like, and then I can usually do most of it myself. But, yeah, definitely a collaboration at the beginning.

So when you're coming in, you're mostly working with the marketing team. How do you transition into communication with other departments? You know? Sales is coming to mind. Right?

Yeah. You know? Like, how do you how do you make that extend that olive branch to those different people and and get that This is the fun part about working at smaller companies, especially, like, 50 to a hundred people. Usually, the marketing and sales teams are not that big in general, like I mentioned. Yeah.

So there are already established Slack channels or meetings or communication messages where everyone's in. So in that sense, it's it's not that hard. I've actually found that to be more of a challenge when I work with larger companies like 200 to 500 people where it gets a little more siloed. But the majority of my engagements, I would say, the sales leader and the marketing leaders are pretty in constant are in constant contact Yeah. And constant communication.

So in that sense, I kinda just get inserted, and I'm part of those conversations. And, again, at the beginning, probably a few more, frequent meetings to get to know those people and establish who I am and my background, and then it becomes natural pretty quickly. Awesome. Awesome. So how long are you typically working with a client, you know, to, like, really show that, hey.

I'm worth it. You know, you're you're paying me. I've been working with your marketing team, your sales team. Like, you know, I've I've brought in this, you know, this amount of, you know, leads or whatever. Like, how you proving your your value to these people?

Yeah. So one of the things I'm most proud of is that I actually don't have set engagement lanes, meaning my clients can actually leave any time. Yeah. So they're not locked in. I don't do, like, year to year contracts unless the client wants to.

Sometimes they do, but standard, I don't offer that or I don't, request that. What I've learned, though, is on average, my engagements last, like, eight to twelve months, which, again, I'm proud of because they don't have to. They could last two months or three months. And then, like I said, usually, what happens is I help hire the person that is the full time replacement for what I'm doing, or my role changes a little bit if the channels that we've been focused on are now kind of working on autopilot. My engagement might change to focus on something else in the future.

But, yeah, I think I think it's pretty obvious, and you need a you need, like, two months, I usually say. And if sixty days go by and you're not seeing results or you're not seeing progress, then you shouldn't work with me. But, yeah, I'm lucky to say that that hasn't happened. Yeah. And I think it's because I I understand what I'm doing.

And, also, usually, the people who hire me have realistic expectations, which is always needed on both ends, I would say. Yeah. No. Absolutely. You know?

Kinda undersell, over deliver. You know? I yeah. Like, there are times where somebody's talking to me and asking if they wanna test the channel, and I and I always I've learned to give an answer that instead of saying, okay. Let's do it is okay, but I wouldn't expect results in less than six months.

So if you're not willing to commit to six months, then it may not make sense. Yeah. And that's in the case where they have no previous data. They've never done the thing before. It's a little different if I come in in a situation where they do have some marketing programs running and there's some success and they just wanna scale because then there's actual things to base their assumptions off of.

Yeah. One thing I've learned is, like, hey. If I am getting brought in to do I'm making example here, but, like, Google Ads, and the company has never done Google Ads before, you're not gonna know in thirty days if Google Ads is a good channel. Yeah. Yeah.

It takes time to build things, you know, and especially in today's world. You know, people want results, you know, yesterday. Right? You know? So, yeah, it's a it's a it's a fine line of balance.

You know? Especially when, yeah, it might take, you know, like, six months to like you said, it takes that eight to twelve months to really spill that program and get everyone in sync and get the messaging right. And that's tough, man, when people aren't but like you said, it's easy when you can just drop that client if their expectations are unrealistic. Yeah. I think the biggest, unlock that I've learned is setting them up front before the deal is signed rather than signing a deal just to make the deal and then figuring it out.

So I will be totally transparent upfront if I think that their expectations are unrealistic, and I've told people are a better fit who would take this this assignment. I just don't wanna tell you something, and then, two months later, you're not happy. Yeah. Yeah. Absolutely.

So has client you know, has has it been through referrals mainly when you're getting your clients? You know? Has it been you know, are you are you promoting yourself? Like, how how has that process been? So it's been a mix.

I've actually been working on this for my business this past year and and this upcoming year. Mostly, it is still referrals, and there's a few different referral channels. But a lot of my clients are somebody I've worked with in the past at another client or at when I was in house, got a new job, or somebody they know got a new job, and it's like referral of a referral in a way. That's that's how always I that's always how I describe it. There are direct referrals that does happen too.

Like, somebody that I've worked with got a new job and wants to bring me on, that that happens. The other main way I've been getting clients is, I'm part of a few marketing groups, Slack groups, LinkedIn groups for b two b software. And pretty frequently, people are looking for help. And often, it's not they're not looking for full time help. So I do some proactive outreach when I see an opportunity that makes sense, and I've I've acquired a few clients that way, which is actually a focus of mine moving forward because referrals are great, but they're hard to predict.

And sometimes there's no referrals in two months, and then the next month, there's six referrals. It's just how it works. So Yeah. Going to also get my own business is makes my business more stable. So I'm focused on that.

Do you bring people on too, like, in these groups as well? Like, say you have a project that might be, you know, too big for just you to handle. Are you, you know, are you working with other people as well? I am, but I'm very kind of strict about how I do it. So, I am the point of contact for all of my engagements.

I am the one on the weekly meetings. I am the one on the Slack group. I am the one project managing. So all of my clients get me. They don't get someone else as the point of contact.

I do, however, have resources that I bring in who are who are experts in very specific things that help me on the back end. So an example I always give is I have a few people that I work with that are super technical at, like, Google Ads and HubSpot conversion tracking. It's like a very in the weeds thing that I can do, but it would take me three hours and it takes them ten minutes, and I know it's gonna be set up the same way every time. So I do bring in specific resources as needed. They're sometimes in the Slack groups with the the clients, so sometimes they are communicating, but they're never leading, and they're never the point of contact because I believe that people work with Diggs because they wanna work with Brian.

Yeah. So that's a huge value prop that I don't wanna ever change. No. Right. It's your it's your name, you know, your reputation.

Right? You know, it's like you don't wanna jeopardize that. You know, someone's having a bad day and sends a bad email or shows up to a meeting. You know? Yeah.

No. You're you're on the line. I completely understand that. I I really do. You know?

What I found is, my clients appreciate the other resources I'm bringing in and because more work's getting done. If they have a question or a problem or they have an idea, they want me to be the one that they talk to about that kind of higher level stuff or bigger picture stuff. Right. So, yeah, it's kind of the best of both worlds in that sense. The other value prop is the cost for my clients is not more when I bring people in.

It's included in the cost of Diggs. So they don't have to worry like, oh my god. I'm gonna have to pay Brian or Diggs more money this month because someone else is helping. It's a total value add. It's not an additional cost.

Yeah. Yeah. You factor that into the proposal where it's like, I might need, you know, this person this person to come on and help me, yeah, like you said, you know, in the Google Ads or the HubSpot or, you know, whatever whatever that specific case calls for. But, no. That makes a ton of sense.

That makes so are you are you looking to, like, scale beyond that or but, like, when you're also the point of contact. Right? Like, it's kinda your baby. Right? You know?

So, like, how are you balancing that where it's like, you know, maybe you wanna grow your company, but, you know, you also wanna make sure that the quality is there. You know? Yeah. That is a great question. I don't know if I have a great answer.

I I'm not, I'm I really still enjoy being in the weeds, being the point of contact. So I don't think, at this point, I would even want to scale to a point where I can't do that with all of the clients. That being said, the more part time back end resources I bring in, it does free me up to take on more clients if needed. Yeah. So until I'm at the point where I am at client meeting after client meeting after client meeting Monday to Friday, I think I still have room to scale.

Yeah. To answer your question, I think it's something I think about frequently, and I it's always this balance of how many clients versus how much time I'm going to be working versus how many additional research I'm gonna bring in. So I found a nice equilibrium where I'm at, but that doesn't mean it won't change at some point in the future. Yeah. Yeah.

And if it's not broken, right, you know what I mean? Like, you don't need to, like, you know, rock the boat too much if it's going well. Yeah. And I'm happy. So I've thought about that too.

Like, there's no reason to scale just to scale if I'm happy at the stage that I'm at right now in my life. Exactly. Exactly. So, you know, email's been around for a long time. Right?

You know, it's I feel like it's kind of this evergreen thing in marketing where, you know, how long have email addresses been around? You know, the nineties, I think. Or you know? So it's like it's they they've been around, and they've kind of stayed they've kind of stayed consistent in their relevance. You know?

Do you see that going forward? I don't I don't think I see that changing too much. Yeah. I think you just have to be a lot better with how you email now to get people's attention because their attention is everywhere. You know, Slack, Teams, email, Instagram, Facebook, TikTok, if it's not banned.

Yeah. Twitter, right, or x. And a lot of the email providers have gotten a lot stricter with what hits the inbox versus junk or spam. So I really just think it's a question of making sure you're in a you're doing it the right way and that you are being very thoughtful and not just blast emailing. Like, the days of mass emailing people who are not interested or who have never showed intent is a quick way to get your domain Yeah.

Filtered in jail. Yeah. Or flagged in jail. Yeah. And then and then you can't I've had clients that have had this before they brought me on and, like then they cannot send emails, and that's a huge problem.

So Yeah. So what's the right way then to to email in in today's day? I think it's what we talked about earlier, which is starting with people who have shown some kind of intent and focusing on those people. Email providers know if somebody's opened and clicked and, downloaded content, and they're not going to flag you or block you if you're really among those people. It's the same thing with making sure you're not emailing people who have opted out or email address has been quarantined or bounced, which is like a whole, subset of things that can happen that means you should not be emailing them.

You'd be surprised with how many companies still include those people in their email list, and it hurts their domain. And then the third thing is if you are emailing cold cold prospects, you wanna make sure you are doing it at a lower velocity and lower frequency. And, you know, there's a lot of best practices, but 50 to a hundred a day max, not a thousands of day Yeah. Or tens of thousands a day. And you wanna make sure you're sending them relevant information, not the first and second email should not be like, see our product.

It should be, here's a valuable resource, or here's a blog post, or here's an event we're running. Yeah. What I've definitely seen, especially in the past year, actually, is that email providers and CRMs are getting a lot stricter if you just blast everyone old school, like, spray and pray style. It Yeah. Hurts it actually kills your deliverability moving forward.

Yeah. So it's definitely a world of quality, not quantity. Yes. And I have dealt with people are actually pretty receptive to this, and people understand this because they have their own emails and they see. But there are, like, some of those old school leaders that I've talked to that don't quite get that yet and are used to the days of just emailing thousands of people every day from their sales and marketing team.

And, yeah, it's a quick way to get in a lot of trouble and a huge mess to dig out of. Like, it sucks if that happens to you. Yeah. Yeah. Because, you know, like, the powers are so concentrated with you know, if if everyone's operating out of Gmail or, you know, Outlook or you know what I mean?

If if you if you get flagged from any one of those, you cut off a whole sect of people that, you know and that, like, ultimately, it really limits your options if if one of those two organizations, you know, doesn't allow you to send emails anymore. I've been part of a recovery process for this, and it's, like, three to six months of just creating a new subdomain, warming that subdomain up, emailing people at a low velocity. It it literally is could be three to six months to get back to the volume that you were at, and that's a huge deal for a business, especially if they're leading on email heavily, which most are. Yeah. Yeah.

Man. So, Brian, any any closing thoughts, anything that you would wanna tell people in terms of if we haven't already talked about it in terms of, you know, email, you know, b to b marketing, you know, any any closing thoughts? I think the biggest challenge I see, and I think this is one of the values of working with myself or someone like myself, is that if you are building your demand gen and marketing channels in silos, you're setting yourself up for failure, and you really need to build and understand how email marketing works with paid ads, works with your CRM, you know, works with event marketing. And one mistake that I see a lot is these is companies are kind of building their channels in silos, and there's not a team or a person who is understanding how they all work together. And it leads to a lot of mess down the line.

So I think that's, like, one standard piece of advice I always give is, though, all those things need to be connected in the systems connected, also have the strategy needs to make sense together, or else you kind of get this haphazard marketing where the messaging isn't consistent. What you're trying to get people to do isn't consistent. Somebody a prospect could be getting six different emails. One is for an event. The other one's about seeing the product.

They're seeing Google Ads that say different things. Right? So I think especially early stage companies that are just moving really quickly, sometimes they they fall into this unexpectedly, and then they realize, like, oh oh, man. We really need to make sure our channels are working together. So that's kind of, one piece of advice that I give to everyone, and I try to communicate to all my clients.

Yeah. Making sure that foundation's solid so that you can build out of it, and then, you know, everyone's in sync moving forward. Yeah. It's funny you mentioned that. I'm actually redoing my my company's website, and the headline is going to be lay the successful foundation for demand generation.

So, like, that phrasing, laying the successful foundation, is exactly what I tell people. Because if you don't and you scale those channels, you run into major issues when you're spending three, four, five x of what you're spending currently if they are not built together. Brian, if anyone wants to find you or learn more, you know, what's the what's a good place for them to do so? Oh, so, I hope this isn't too difficult. It should be easy.

So one is I have my website, very simple, DiggsMarketing.com. I have a LinkedIn. It's my name, Brian Koffler. I'm pretty active on LinkedIn, so, you could shoot me a DM there, or you can email [email protected]. But, yeah, would love to talk with anyone who's interested in learning more or just interested in scaling their marketing if they're a b two b software.

Brian, thank you so much for being a guest on Fractional Hustle. We really appreciate it. I learned a lot, you know, in terms of the email realm, you know, especially, you know, it's just a whole new reverence for that area now. You know, it's really I mean, I knew it was important, but now I really think I understand just just how important it is, you know, and it's like cutting a leg off if, if you if you don't use it adequately and also if you kinda, you know, get into that that that, Google jail as I've heard. You know, some people call it or, you know, whatever with the emails.

But thank you so much. Thanks for having me. I appreciate it, Steven. Yeah. That's all, folks.

We'll see you next time.