Ali Schwanke - Founder & CEO at Simple Strat: Leveraging YouTube for B2B Growth, Harmonizing Sales and Marketing, and Cutting Through the White Noise of the Marketplace

Ali Schwanke  00:00

Had I put it on paper and said, "Yeah, let's invest this whole guy's salary on building a YouTube channel," I'd have thought, that's crazy. But I mean, sometimes your gut is the best informant. It makes zero sense on paper, but your gut sometimes knows you better than the paper does.

Callan Harrington  00:17

You're listening to That Worked, a show that breaks down the careers of top founders and executives and pulls out those key items that led to their success. I'm your host, Callan Harrington, founder of Flashgrowth, and I couldn't be more excited that you're here. Welcome back to another episode of That Worked. I'm excited for this week's guest. I'm joined by Ali Schwanke. Ali is the founder and CEO of Simple Strat. Simple Strat is a marketing and sales firm that helps you get more out of HubSpot. From CRM strategy and setup to marketing automation and content creation, their services are tailored to fuel customer acquisition and retention. Simple Strat is also a Diamond Solutions Partner with HubSpot and the host of HubSpot Hacks, the number one unofficial YouTube channel for HubSpot tutorials. Ali is a data-driven marketing professional with 15+ years of experience in B2B strategy and content marketing. Most of all, she's hilarious. We talked a lot about Ali's journey as an entrepreneur, and she gave great insights into the challenges she faced and how she overcame those challenges. We also dove into some hot-button questions, such as how to drive sales and marketing alignment, should sales development reps report through marketing or sales, and how AI will impact the role of a sales development rep and marketing and sales in general. Now, I was most excited to hear how she built the top YouTube channel for HubSpot videos. She's turned this YouTube channel into a complete machine, and it's been a gold mine for driving new business to Simple Strat. Taking advantage of YouTube is something I'm very interested in, and I think it's a really underrated lead source for B2B companies. So with that, let's get to the show.   All right, today's guest, we are joined by Ali Schwanke. Ali is the founder of Simple Strat. Ali, welcome to the show.

Ali Schwanke  02:36

Thanks for having me.

Callan Harrington  02:38

I'm excited because you are somebody I love our sessions when we go back and forth talking about content, entrepreneurship, growing a service business, just in general. And one of the areas that I want to kick this off with—I know you had a really successful LinkedIn post back in the day, and it was, "What is the one question every entrepreneur hates?"

Ali Schwanke  03:00

Well, first of all, let me tell you about my stance on LinkedIn. I'm going to get to that in a second. But second of all, this is one of those examples of it’s not a platform to just post things; it's a platform for engagement. And so one of the reasons why this did so well is, I think it struck a chord with people, and that is, I had been two years into what I was doing. I previously was employed, and I had gone off on my own. So again, not unlike some folks who go out as a consultant. The thing I didn't understand at that time was, when you leave a company and you start a new company, everyone around you is waiting for you to give up or fail, and they're not doing that on purpose. They're doing it because you had the guts to do something that they didn't have to do, and they hope that if you fail, it makes them feel better about not taking that risk, right? So the question that every entrepreneur hates is, "Are you still doing that thing?" Because you, over here, are executing like a boss. Think about this: everybody at the first of the year, they get up, and they're like, "I'm gonna run a marathon," or "I'm gonna do this, like I'm launching a new business." And then they silently, six months later, are like, "I took a full-time job. Don't tell anybody." Everybody announces the start of things, and nobody celebrates the "I'm continuing to execute on the thing that I did two years ago, and it's going fine, but I'm not shouting from the rooftops every day like I was when I started."

Callan Harrington  04:19

It's so true, and it's funny. Once I got into it—now, I'd worked with a lot of early-stage companies, but once I actually founded a company and started my own business, I just had so much more respect for all those companies that were just grinding it out. Because it's so hard. I wouldn't have it any other way, and it's the hardest thing to describe, but it's so difficult. Have you found that to be the case with yourself once you founded your own business?

Ali Schwanke  04:45

The biggest thing that you realize, especially if you're in an industry like software, is you're not starting necessarily this product-led company. You go raise funding and build a product—like you're starting a service business, and service means you're selling knowledge and time in exchange for value. So you go out on your own, and what you quickly realize is that this thing that you really loved is something you're gonna do like 20% of the time. You're going to spend 80% of the time chasing down invoices, trying to figure out how the tax laws work, and like, "Oh, crap, I got audited by the Department of Labor." Welcome, everybody. That's a terrible experience. And let me tell you, all of the lessons that I've learned as an entrepreneur come from those hard knocks. If you're not up for that, you're not going to do what you love as a practitioner in a service business. If you don't understand how that works, you're just going to be a paid freelancer, right? So that's huge. 

Callan Harrington  05:35

It's a good point. And one of the struggles that I had early on was—and I had known this—everyone said, "You know, it's really lonely when you start a company." And I was like, "Okay, I get that. That makes sense. I don't feel like that's a big enough reason for me not to do it." That said, I remember the first time I got something and just didn't know what to do. And it was a very small thing. When I look at this in hindsight, it had to do with an invoice, and I just remember stressing out like crazy. And I was like, I don't have anywhere to turn. And funny enough, I ended up going to one of my close friends, and it's like, okay, this is 100 times better. And then I joined Collective 54, where we had met, which is...I've met a ton of great people through Collective 54, and having that peer network was really important. Did you have that when you first founded Simple Strat?

Ali Schwanke  06:27

I would say yes and no. I mean, I had other business owner friends that I leaned into. I'd worked in a company I was fortunate when I first started out that advised a lot of business practices and leadership, so I got to be a fly on the wall with a lot of those executive coaching sessions and that sort of thing that I didn't realize at the time was so valuable later on in my career because I got to watch from a distance. I would do this; I wouldn't do this. And so I kind of kept a journal of the things that I would do as a business owner versus what I wouldn't do. And I will tell you also, on the other side of that, if my former boss was listening, he'd agree with me where it's like, when you're an employee, you don't get it. Like, "If I have my own company..." Just like kids, "When I'm a parent, I'm not going to do it this way." And then you become a parent, and you're like, "Oh, that's probably why you should have done it this way." The reason why there are curfews is because nothing good happens after midnight. When you're an adult, you're like, "Yeah, all the bad things happen after midnight." So as an employee, I had some good opportunities there, but when I went on my own, I think the loneliness that you talk about, Callan, comes from three different areas. One is not having people who understand the new problems that you have. So your former friends, who are also employees, have employee problems, and you're like, "Yeah, I can't talk to you about this because it's weird." Two, some of the people that are now your friends also somewhat either partner with you or are your clients or whatever. So you have this weird place where you can share some stuff, and you can't share some stuff. And then the third part of that is just like, literally, your own ineptitude, where you're just like, "I didn't realize that. I didn't know this, and I feel like a complete idiot." And being okay with going into a situation where you can let that vulnerability down and find those people you can trust, that takes time.

Callan Harrington  08:00

That's so true. And for me, I had always operated from a P&L. Many of the companies I was with were venture-backed, and I never cared about pure cash flow. And then I got into this business like, "Oh, we just landed a really good contract. Oh man, this cost a lot to deliver," and that's fine if I got paid on the day that that signed. Yep, that was a rude awakening. What I tell people all the time now, it's like, look, going bootstrap is a great way to go. I love it. I don't know that I would have done it another way, but just make sure you're operating off of a cash flow forecast as opposed to a P&L. What was that moment for you? I'm curious, what was kind of that first moment that you had in founding this company where it was, "What do I do here?"

Ali Schwanke  08:54

I mean, bringing on your first employee is always that challenge. And so I'll say this: a friend of mine says that all advice is autobiographical. And for a long time, I was like, what does that mean? What it means is we give advice based on our own context, within our own paradigm. And so someone may have had a really great experience hiring contractors, and that's how they recommend you build your business—all contractors. Well, then you talk to someone else who has a different experience hiring contractors, and they're like, no, all employees. And so you kind of learn to have your own filter you run this stuff through. But I hired my first employee and then quickly realized that I'm like, oh, yeah, do I have to report them to the state? How do I do this? Do I have to offer health insurance? And so suddenly you've made a job offer, and then you realize, I don't know if that's legal. Do I write a job offer? Is that something that they need? And you just get caught up in this situation. And my first hire was wonderful, absolutely one of the best humans on the planet. So I completely lucked out. But I've talked to other founders where their first hire was a disaster, and they've avoided hiring for a very long time as a result of that. How I really started in that Simple Strat as an entity started in 2016.

Callan Harrington  15:04

Did you jump straight into Simple Strat, or were you starting that on the side before going full-time?

Ali Schwanke  15:08

 I mean, you know, I named my company, like every really great marketer does, Schwanke Marketing. So that was my first foray. That was back in like 2013 and in 2012 maybe. I named my business that because I was just doing consulting. I had no idea what I was doing. People knew me. They knew I could help them with their marketing and sales, and that's about it. So I actually would do more like CMO-for-hire type work, kind of like you're doing with the CRO side, but it was just helping them structure their marketing strategy, bringing them into a department, hiring people, then kind of stepping out. So that was successful, but it was just me when I would bounce around to different companies helping them with that. So Simple Strat emerged because I realized that the execution was oftentimes a lot harder than the strategy itself, so I just needed to have a back arm to support the strategy, and that's really why the company launched.

Callan Harrington  15:57

And you mentioned, you know, the good thing about those contracts you described is usually pretty good cash flow, and it's a nice way to segue into a bigger business. When did you make the change out of that into whatever came next?

Ali Schwanke  16:13

Yeah, I had a couple of milestones for myself financially that when we hit this, we kind of do this, but it wasn't like when we hit X amount of cash or X amount of revenue, we bring on an employee. That really kind of wasn't it. But that first job that I was telling you about, it was a leadership development company, and I really was ingrained with the idea that your time, as you escalate in your career, needs to be worth more, and you need to delegate the things that are not worth your time. And so that was my idea. I thought, I'm gonna scale this. I can either charge more, which then also still means that, like, Ali Schwanke charges more, Ali Schwanke still makes $0 when she goes on vacation. So trying to provide some leverage for myself was when that really switched. But I would say I also started to get a lot of just, I could see what was possible. And so I think having a better vision sometimes you don't know what you want until you start seeing what other people either do or what you don't want. And I did not want to be stuck in a freelancer business by myself for years and years and years. So that's why I wanted to build a team, and that's kind of the shift I made.

Callan Harrington  17:12

How long were you in this freelancer business before you started to add employees?

Ali Schwanke  17:17

I mean, it was about four years that I was, you know, I had a couple of big contracts where I would actually be on-site with companies a couple of days a week, and I enjoyed that because I was part of their team. But you know, when you're a company and you're looking at growing, it's like, "Hey, Ali, do you want to...Should we just hire you on? Should we bring you in-house?" And that's when I really realized, like myself—I don't think this is true of everybody, but it's true of me—if I'm in-house at one company and I get really, really deep in one company, I miss a lot of the bigger trends that are happening in the marketplace overall, and I love being out in front of what's happening and advising clients. And so ultimately, that just wasn't a fit for me. But that's kind of where I sit now, which is a good spot for me.

Callan Harrington  17:55

During those four years, what was it that prevented the business from getting to that next level?

Ali Schwanke  18:02

There are a lot of things. For me, personally, I had a very young family at that point, so I've never been a business owner and not had children. I've never been a business professional and not had children. Like, I've had, you know, a small child since I started my career, and I think for a lot of people—and I've had a mortgage—I've never been a couch-surfing post-college, live-on-ramen entrepreneur. Some of these, like, hustle-and-grind type of stories, like, yeah, I hustle and grind like the best of them, but, man, I gotta have some cash at the end of the day. That's more than, like, a little story and some F-words on TikTok, you know, like, I can't do that. So when I was operating in just that solo environment, I had pretty strong contracts, some good revenue that I knew could support us, and quite frankly, just the rest of it needed to not be touched for a while. Like, I needed to just execute and support my family and build my reputation, which was a good thing for me.

Callan Harrington  18:53

What was the turning point?What was the turning point? That's a good question.

Ali Schwanke  18:56

That's a good question. I remember sitting at my kitchen table, and it was New Year's Eve, and every New Year I sit down and do a planning session. This is a behavior and a habit that I got from that first leadership job. And I sit down and write down everything that happened in the year prior. So not only, like, what are the things that happened with family, I go through the months, and I start writing, "What would I have done differently this year had I known the things that I know now?" It's like the exercise of "what if?" What if I did this? How might we do that? And I started to realize that I wanted to live in a world where marketing had a better reputation than what it does now. I mean, granted, this was, what, six years ago? I wanted to live in a world where I influenced that for people, and I knew that by myself, I couldn't do that. And so I wrote out this manifesto, and I had no name for the company. So it bothered me because I didn't know what I wanted to name it. So I wrote this manifesto. A couple of days went by, I got the name kind of came to me, but I thought, this is it. This is it, like this is the change that we're going to make. And it took very little time to write up an employee job description and just post it online. So I think for me, as a business owner, an entrepreneur, and a leader, when I'm ready to make a decision, I just make it. And I can't tell you what happened. It was just kind of a timing thing, and this manifesto had to be written, and I just did it. And at that point, like, you couldn't not do it.

Callan Harrington  20:13

Was it driven from, "I want to build a business," or was that driven from, like, "I'm feeling a ton of pain. I'm juggling too many things right now. I need help."

Ali Schwanke  20:24

For me, it wasn't that. It was, "I know I can make a bigger impact," and that was the answer to making a bigger impact, was building a team and a company around that. It wasn't financial; things were going fine. I mean, I think, again, the challenge of I'm out for a couple of days and nothing happens, I was certainly feeling that. Now I'd be lying if I told you that, yeah, Callan, I can go on vacation for three weeks now, and nobody needs me. Okay, we're still working on that, right? Still working on that, yeah. But at the time, I think it was all about impact, and I knew that the people I was working with at the time were experiencing great results and changes in their business, and I knew if we could reach more people, more companies with a team, that that would accelerate.

Callan Harrington  21:07

Gotcha. So for you, it was more mission-driven than mercenary-driven. Gotcha. Well, one of the things I'm really curious about—I’d be remiss not to talk about this, because you're such an expert on it—when did you start to get more involved with HubSpot?

Ali Schwanke  21:22

That was 2017, so about a year after we started the company. At that time, I brought on a business partner, who at the time, we had agreed on moving into business ownership together, and he's a minority owner in the business. You know, ultimately, that was kind of something that we were testing out. But he said, "I think that we need to do something that allows us to put a stake in the ground for some sort of expertise." So it was really kind of his driving that brought us into the HubSpot ecosystem. He went through the partner certification, so, you know, he was a big catalyst in all of that before I was involved. But I still had a pretty strong brand reputation in the industry at that point, because I'd built a pretty strong career. I'd been the Marketing Association president in our local chapter, so I did have some good networks to sell into when we became part of the HubSpot ecosystem. We realized that HubSpot was still pretty new because they just released their CRM that year. But becoming a partner with HubSpot, we thought was like this, you know, all of our revenue problems would be gone because we were going to have leads coming out of nowhere, and that was a big, giant zero. So, but it did launch us into this "how do we differentiate ourselves?" question that we ultimately solved two years later. So, overnight success, right? Two years later...

Callan Harrington  22:30

Fast forward to two years. What was it that solved that problem?

Ali Schwanke  22:35

Yeah, we decided—well, it was pre-pandemic. So for folks that leaned into digital content during the pandemic, good for you, but we happened to luckily do that prior to the pandemic. So we leaned into video as a main way to connect with people online and then launched a YouTube channel called HubSpot Hacks. And everybody who had been part of our network before all of a sudden was like, "Oh my gosh, you guys are the HubSpot people." I'm like, "Yes, we are, but we have been for two years. You just didn't know it."

Callan Harrington  23:01

Did you jump straight into video and YouTube, or did you try other content avenues prior to getting there? What did that look like before that? 

Ali Schwanke  23:11

We did. We tried blogging, and I'll tell you that one of the things we learned—one of the things that we learned—was that a lot of agencies were already doing a great job. So this is, I mean, this is SWOT analysis 101, where, like, what is outside in the marketplace, and where can you compete? What are the gaps? And the gaps were not "the world needs more HubSpot written content." That was not a gap that existed. But HubSpot also does a good job of giving their partners content to lead with. And so again, if you think about like, "Alright, any team that goes to the NFL, if, you know, the NFL commissioner gives everybody the same playbook," okay, congratulations. You all have a playbook. Everybody has it. So we noticed that not a lot of people were using video. So that's really kind of why we leaned in. We had written blogs prior to that, but nothing was really leading to, again, that differentiation aspect. So I had brought on a videographer, and I have been bullish on video since "quote, unquote" year of video. I'm doing air quotes. That was, we'll say, 2013. That was supposedly the year of video. I'm sorry, Callan, every year it's the freaking year of video. And yet, we're still talking about it. And what I realized in that was video has typically a pretty high dollar perception. So the market that we were in was like, "Oh, that's so cute that you guys have video. Yeah, we're just not going to buy that right now." And so we had this videographer on staff that, had we not had that full-time person in-house, I don't think we would have started the channel because we wouldn't have had the resources. And so it was like, as luck would have it, we were just, "Well, we're already paying this guy. Let's just lean into it." That's literally how it happened. And then we started seeing that people were watching the videos, picking it up. We had identified the strategy and the gap, but until we started actually executing, you just don't know. So had I put it on paper and said, "Yeah, let's invest this whole guy's salary on building a YouTube channel," I'd have thought, that's crazy. But I mean, sometimes your gut is the best informant. It makes zero sense on paper, but your gut sometimes knows you better than the paper does.

Callan Harrington  25:10

You know what? A couple of things that I find interesting about what you just said. So, one, if I'm hearing you correctly, you hired this videographer because you were going to start selling video packages to...

Ali Schwanke  25:19

Oh, I sold one video...

Callan Harrington  25:23

...which, you know, most people, I would say, would probably just let that person go, save the money. You decided to keep him, roll the dice, and start building high-quality videos on YouTube. And then also, just for the audience, if you're unfamiliar, Ali absolutely dominates all HubSpot videos on YouTube. If you search HubSpot on YouTube, you're going to find Ali all over the place. And as people know, you know, YouTube is hard, but it's also really doable. I'm curious, what were some of those early mistakes that you had when you started to kick this channel off, and what were some of the early learnings that you had? 

Ali Schwanke  26:04

Yeah, one of...I'll never forget...one of the first things that I learned is there is a big difference between a video strategy and really great video production. And what I mean by that is, there's, I mean, just like if you go out and say, "I'm gonna find a marketing plan to grow my business." Okay, your marketing plan is going to vary based on what resources you have, what your goals are, what your product is, you know, all of those kinds of things. All of the inputs vary, which means your outputs vary. And if you look at a lot of the advice around growing YouTube and growing a channel, you get these creator-type insights. And so our videographer, we didn't know this. He was in charge of uploading, and again, he did a great job. Like, I am forever indebted to his kind of vision and the creative element that he brought. But we were posting in the description...we put, like, the soundtracks that we used, and we put that they were edited in Adobe, and, like, we put all the stuff that creators care about, that...who cares? Like, no business owner is like, "Good job. I'll now work with you because you edited it in Premiere," you know? Like, nobody cares. And then I just laugh now, because if anybody knows anything about YouTube tags and, like, SEO strategy...oh my God, our tags were things like...this is terrible..."Midwest" and "marketing" and, you know, "HubSpot." I mean, that's like walking into a room and saying, "I am woman."

Callan Harrington  27:22

And myself included. I'm not as familiar with tags and such on YouTube. But what should those tags be?

Ali Schwanke  27:30

Yeah. So, I mean, YouTube SEO strategy is boiled down to a couple of things. One is, what is the search string or something when you're doing a search-driven strategy, anyway? What is something that someone would go searching for on how to do in YouTube, and how would they say it? So, 101, if I was in your shoes, like, "How to build RevOps"...even, like, let's start with, like, "What is RevOps, and what does it mean?" Right? The name of the video would be, "What is RevOps, and what does it mean?" Okay, that's the name of the video because it's literally the string. Well, so that's the title. You write a description on YouTube, just like you do in a blog. And so you write the description, and you have to include those strings in your description too. You have to include them as tags. You need to make sure you have relevant links to any other content, any other videos that you might have called info cards. So all that's going to be super important. And I, unbeknownst to me, didn't know what I didn't know. And so I had two people on my team running our channel, and I got in there about five months in. And one, we had enough content at that point to optimize. So people will often say, "Oh, you know, our program's not working, whatever." And it's like, "Dude, you're on, like, day five at the gym." Like, you know, you lost your water weight. Good job. I can see a little bit of your bicep. We are nowhere near the finish line. And then you just don't have enough data to do anything with. "Oh, we're going to analyze the watch times..." Dude, you've got, like, 1000 hours. Wait till you get way more than that. So anyway, I re-optimized a lot of that and ran some experiments and started to learn with all that data. And I will say, as a sales and marketing professional, if you don't have something to learn on, this is why people start their own channels, because you can't sometimes experiment on company stuff. Clients weren't letting us do some of the stuff we knew that we wanted to do because we didn't have, like, a case study. This is very new territory, Callan. Like, who, in their right mind, is going to give us thousands and thousands of dollars to invest in a YouTube channel if they can't figure out what to do with it? So this has been our experiment. I've been the one taking the risk on it, and now people are asking me, like, "How did you know?" And I'm like, "You know what, jerks? I didn't know. I totally just bet on it, and it just happened to be a good bet." I can tell you all the stuff that's been a terrible bet, but this has happened to be a good one.

Callan Harrington  29:39

Interested in some of the terrible bets. 

Ali Schwanke  29:42

Okay, well, terrible bet number one I just told you about, which is, "Oh, everybody's gonna buy video," and they didn't. So that was terrible bet number one. You know, terrible bet number two was we thought at some point we would lean into helping fitness brands because that's an area that a lot of our team had experience in. We were passionate about...oh my God, talk about, like, the worst learning ever is we started ranking for some of these keywords, and then we discovered that nobody, seriously, nobody had a budget. Great. Now we get all these inbound inquiries that nobody has any dollars to spend with us. That's a great marketing plan if you want to try that one. I mean, we bet on this local user group we were going to run in our region, and unfortunately, where we're based in the country, everybody has a very DIY mentality. So they were just, "Thanks for the advice. Bye." So, you know, free lunch and free advice. That's a great marketing strategy. I highly recommend that one. So, I mean, there's a whole book of these. If you don't have a book like this, you probably aren't trying enough stuff, to be honest. You got to have some failure stories; otherwise, you're not risking enough.

Callan Harrington  30:43

That is so true because you don't figure it out from the successes. And 2021 was a big one for me, for sure. I could tell you that was a big one because 2021 was shooting fish in a barrel. I was getting clients left and right. They keep saying, "Hey, can you do this? Could you do recruiting? Can you do sales training? Can you build out our CRM?" and all these different things. Now, fortunately, that last one stuck, but prior to that, all these other things, I had no business doing any type of recruiting, like there was no reason to be in there, but I just took anything that came across. And then in 2022, all the fat was cut from budgets, and you had to focus, and you had to get serious on that. You hit on one of the things I'm interested in. So as I understand it—and correct me if I'm wrong here—at first, everybody was local to where you're at, and I'm in Columbus, Ohio, so I'm not in a huge market either, and a lot of your clients were also local. And then from there, you expanded to go fully remote and then got clients all over the country. Is that right?

Ali Schwanke  31:50

That's true. The way we looked at it, the pandemic forced some of that for a lot of us, but the way we looked at it was when I first started, we knew what business we could get based on our current networks and referrals, which is true of any new service business. That's how you start. But we had a list of who we would have competed with in our local market, and our goal was to be the best agency that people who wanted to work with us couldn't afford us because we were charging prices that were...we had a reputation enough, and we were charging what we know nationally was a rate versus...again, we're, I'm right outside of Omaha, so we tend to have a lower price or a cost of living here. We came up with a list of agencies regionally that we wanted to be competing against. So when you start finding yourself in the same conversations as XYZ from two cities over, okay, now we've started to build a regional footprint. And then we had a list of agencies that we wanted to be competing with nationally. And I remember that day we had our first...who we beat out in a sale, and it was one of those agencies that we had put on that list nationally. And now that's where we are because we have a national footprint. But we went that way because we knew the type of company we wanted to build did not have the customer base locally that would support us. Like, we would never have revenue. We would not even have enough customers locally that had the budget, the size, the sophistication, and the know-how to work with us.

Callan Harrington  33:08

Yeah, it makes complete sense. And we feel pretty similar when we look at especially when it comes to RevOps talent that has really, really niche skills, like CPQ within Salesforce, or working with DealHub or different groups like that. You know, there's only a handful of them that are out there just in general, and they're not going to be in Columbus, Ohio. Maybe one by chance would be here where I think it's so important...I think it's important for all businesses to have some sort of remote presence. I definitely understand the appeal of in-person, and I, of course, would rather meet with somebody in person than digitally. But from a competitive perspective, I feel that you have to. You know, one of the things I'd be remiss not to ask, since you are so ingrained on the marketing side, is when you look at how sales and marketing interact with each other, what do you feel needs to be there for that to be successful?

Ali Schwanke  34:03

I think there's a lot of talk around SLAs, because that's the word we're supposed to use. Do you have an SLA? I think a better way to look at it is, what is the understanding of the marketing function inside of the organization? And the reason I say that is if you haven't yet asked your team what marketing means and why we do marketing at organization or company XYZ, you will find that there's most likely, even if you have an SLA, there's different understandings of what marketing is, what it should do, and how you hold it accountable across the organization. So, and you have to constantly do this. So think about this: if you bring in a new sales leader, maybe a VP of some sort, the organization that they came from, they bring along their understanding of marketing. And so this is why you have so much push and pull of, like, "We're going to pull this program. We're going to start this program," because the way they understand that function varies. And where I see marketing and sales fit together is marketing is either a sales support for a sales-driven organization, or it is a lead generation demand function in an organization capturing demand that people already know exists. So if you don't have either of those scenarios lined out, you are probably bouncing back and forth between the two and having a lot of inefficiency in how that marketing function works.

Callan Harrington  35:12

I'm gonna ask you a hot-button question: where should the SDRs or sales development reps report? Marketing or sales?

Ali Schwanke  35:23

I mean, ultimately, it depends on how that's coming together. So I've been part of SDR programs where the marketing has zero say on what the SDRs are saying. And there's a lot of, like, we'll call it brand anarchy, like, "Whatever we get to open up an email..." So reporting is one thing. I think there needs to be a...SDR, you know, it involves a lot of what I'd call repetitive execution, and so you have to have an experimentation mindset as an SDR. You have to have creativity, but you have it within a box, right? This is your message, this is your audience, and here's where you go. It's a numbers-driven game. At the end of the day, though, if there's one person that's doing things that are slightly off, and they're getting great results, like you as a sales leader, should be like, "Hey, marketing, we might want to talk to this person, because they're doing some interesting stuff." Whereas marketing's like, "No, they're not. They're off the brand. Like, kill them." Now I think we have to just be constantly curious, because our playbooks change all the time. And as a sales leader, your job is to help your team get the best results possible. Most marketing leaders, in my opinion, purely my opinion, have not worked in sales. So if you were to put them in an SDR role for two weeks, like, they would die and quit and die. Like, it's just hard, it's just hard.

Callan Harrington  36:34

It is. It's a super hard role. And I used to be pretty hardcore that they should only report to sales. Now I've turned on that a little bit, and I think it's more such. There's that in my answer, you know, I love the answer that you gave. There's not, in my opinion, a right or a wrong. If it's really lead qualification, and they're just taking in, you know, a quick, "Hey, I just want to check XYZ." It doesn't need to be under sales. But if there's more, like, deep qualification discovery before getting sent over, I like it under sales. But I don't know. It's a question I've been asking. It's a hot-button question. I wouldn't be surprised if you get a question on this from the actual interview itself.

Ali Schwanke  37:12

Well, I mean, let's, let's, if you're gonna go there, then we have to go into like, "I'm sorry, are SDRs going to become obsolete? Isn't AI replacing them, Callan?"

Callan Harrington  37:20

Ooh, now we're really in the hot-button territory. You know, I will say this: I think it's going to be interesting. Enterprise, it's going to be a long time before AI replaces that. Well, you know what? This is a tough one, because I think a lot of the functions of it, AI will probably be able to do a lot of that. And I think full-cycle sales reps will get larger, ones that are prospecting and closing, because they can also run the AI and things like that. If it's an SDR selling into more of a traditional industry where a cold call still really matters, I don't think so. But we could talk about this all day. That is the hot-button topic right now, for sure.

Ali Schwanke  38:01

Yeah, so where does the AI report? Sales or marketing? Yeah, 100% marketing.

Callan Harrington  38:07

I mean, it's just that, because I know my opinion is so much more content-based. Great question, though. Love that. As you've grown Simple Strat, you've grown it. You've got a number of employees within the company. What does that next evolution look like for you as the leader of the business?

Ali Schwanke  38:27

Yeah, it's something that we're working through right now. And I would say, I mean, again, I have a business partner in this endeavor, and he has focused a lot on growing a specific side of our business and building some processes there. I'm working on the content side to do some of the same things, but it's elevating myself out of a lot of the delivery so I can spend a lot more time on market research. And by market research, it's really like having conversations and understanding problems in the context of new product offerings. So we've got a content multiplication framework that is, or actually, it's a content multiplication toolkit that's coming out in a couple of weeks. And so, because so many people like yourself are doing long-form content, videos, podcasts, whatever, they're not honestly giving them the distribution power that they need. So we're working on, you know, create once and multiply forever. And so we've got that coming out, we're working on helping folks better leverage LinkedIn—oh my goodness, it's such a goldmine. And people think it's all about posting, and actually, posting is like 1/100 of what you do on the platform. So I think where my superpower is, is listening to people—terrible to say this—but listen to people complain, and then in their complaints, there's typically a problem to be solved. And if I can get myself out of some of the delivery work with better systems and processes in my company, then I can spend my time on that.

Callan Harrington  39:44

Yeah, absolutely. So if I'm hearing you correctly, it's we're at that next stage of the business. In order for this company to really be able to continue to grow, expand, and add new offerings, I need to be out of the actual delivery of this service on behalf of our clients. And I know you're a lot farther removed from that, but all the way out, is that right?

Ali Schwanke  40:06

Yeah. I mean, I think I'll still be involved in some of the things where, you know, in a service business like ours, people do pay for time with the founder, and they do want some of those ideas and fresh perspectives. But from where I sit, I'm looking at, "Okay, how do we run meetings at Simple Strat, and what are the five types of meetings that we have, and how do I make sure an employee is, quote-unquote, certified to hold one of those meetings, and it would be consistent across the organization?" And I would say, in the last probably three to four months, I've started building out all of these things in Notion, and we've got a pretty strong initiative here in Q2 to really make sure that that gets...we have a webinar series launching. Ali is doing the first webinar, but Ali's not going to do all the webinars. So how do I certify people to host a webinar at the same level I would and not make you want to go to sleep? Simple Strat does not put on webinars that put you to sleep. That is not something that we do. So how do we make sure that that doesn't happen?

Callan Harrington  41:00

Absolutely. Last question, if you could have a conversation with your younger self, age totally up to you, what would that conversation be, and what advice would you give them?

Ali Schwanke  41:12

Take bigger risks sooner. We always talk ourselves out of risks, so we go into this, like, worst-case scenario planning. And the further I've gotten in my career...one, the worst-case scenario nobody planned on was COVID, and if your business survived during COVID, or you made some significant life progress during COVID, welcome to the thing none of us ever figured out that we would be able to do. But two, you're much more resilient than people might think you are. Like, everyone wants to talk about failure. Your failures are just learnings. So take bigger risks sooner because you execute at the speed of learning, and if you take a long time to learn things, you just grow slowly.

Callan Harrington  41:50

That's excellent. Starting my own business was a big fear of mine, and even the first couple of months of doing it, it was on my mind, "Oh my God, this could fall apart at any time." And then, for whatever reason, that just started to become less and less and less and less. It didn't mean that the risk still wasn't as great. I just didn't care as much. It's really interesting. So I love that advice. Ali, as always, it was great talking with you, and I appreciate you coming on the show. You gave so much great advice today.

Ali Schwanke  42:22

Yeah, thanks. Well, I'll have to have you on my show, and we'll talk about the AI/SDR conversation, maybe a little bit deeper.

Callan Harrington  42:29

I love it. I'm 100% game for it. I hope you enjoyed Ali and I's conversation. I loved hearing the strategy behind the YouTube channel that Ali built. It's definitely a route that I want to try myself. If you want to learn more about Ali, you can find her on LinkedIn in the show notes. Also, if you liked this episode, you can find me on LinkedIn too—let me know. And if you really want to support the show, a review on Apple Podcasts or Spotify is very much appreciated. Thanks for listening, everyone, and I'll see you next week.