Ep#9: Mastering Go-To-Market Strategy with Carol Malakasis

Welcome to Method, where we decode what it really takes to build and scale startups. I'm Andy Walsh, founder and strategist. Each week we'll bring you actionable insights and real stories. Let's dive in. Welcome back to Startups Decoded. In today's episode, we're going to explore Go to Market. For me, Go to Market is a pretty broad topic and we'll definitely tackle that today. But it would be pointless for me to do it without a great guest. And today I'm very excited to have Carol Malakasis on with us. She's been trailblazing the way that she approaches what she's doing, the success she's had. So, Carol, welcome.

Thank you for having me. Andy, good morning.

Good morning. This is for me now become the favorite part of my week. I get to sit down with people like you, pick your brain and learn, but also try and spark some conversation. And for today, if you're a founder and you're thinking about Go to Market, whether you're fresh and just starting, or whether you're series C and a long way down the path, Go to Market is important all the way through. So I guess kicking off in your mind now Go to Market seems to be a bit of a catch all. Is there a way that you'll be able to simplify what's sort of encapsulated in Go to Market?

Yeah, it's a good question and it is a very broad name to describe a thing. Right. What is Go to Market? Is it our overall strategy? Is it, you know, our sales funnel? Is it how we think of who our customers are and how we go after them? You know, it's selling and it's onboarding like it's a big category to basically describe how a business goes out and finds customers in a repeatable way. At least that's how I think about it. And now I forgot your question.

No, all good. So yeah, from a Go to market perspective, like a simple definition which you've kind of given there anyway, so maybe it's worth looking at some of the components of a Go to Market and we can look at where you start through to what are some of the ways that you would roll out that sort of Go to Market strategy?

And I mean, it depends on the, on the business and their stage. So as you mentioned, I primarily work with startups, usually at the seed stage, I'll work with technical founders, sort of giving them that first go to Market, that first sales playbook that's somewhat repeatable based on market signal for them to, you know, essentially develop a sales intuition and have a process to go acquire business and then, you know, as we get better at go to market, that becomes more specific, more granular, more robust. So on the series a side where I work with founders and sales teams go to market is so much more. Right. So it's more detailed scripts and sales collateral and segmentation depending on more customers are going after. And it's just more detailed and, and process oriented. Go to market really depends, you know, what it's going to look like and what it's going to entail depending on the stage of the business and the types of businesses that business is going after and who's the person sort of executing that. Go to market.

Yeah, there's a bit within that. So taking a step back, I had a guest, Lucy Wolfenden, on episode number two. Her business, the Scale Up Collective, does fractional CMO work and they're working a lot on marketing strategy at businesses at different stages too. So the process you just described then, I guess foundationally, how would you set up that if you had a marketing counterpart in that team or maybe there's a brand strategy in place, what are some of the things that you would have to have either done yourself or from someone else in the messaging framework through to any testing that they may have done from a marketing capacity to allow you to optimize your process?

Yeah, and I mean, usually the businesses I work with are so early on that they're not even at a position to, to have a more robust or repeatable marketing process. Right. The brand isn't even a thing at the states they're at, they're still figuring that out. But for me, when I work with a business, assuming they've already, you know, had some traction on their own, I think of go to market as sort of a deep dive to understand what they've already done. And I break it down into overall go to market strategy. So target market, icp, you know, current solution. And then I'll go more granular into the process. Right. So when I think of process, it's mostly the sales funnel and how we're moving customers along. So, you know, assuming that in the strategy we've identified ICP and you know, demographics, psychographics, pain points, et cetera, it's like, okay, now when we look at the process, what's the process to bring that ICP into the sales funnel? What are the different parts? You know, how do we do discovery, how do we do demo, when do they come in? What sales collateral do we use, how do we present pricing, Is there a POC that happens? How do we close and onboard? And then I look at execution. How is the current team, whether it's the founder or the founding sales team, executing on that process? Right. And if we have a team, then there's also another component that we look at which is like, okay, now how do we manage that team? And does everybody know what good looks like? And you know, how are we conducting sort of pipeline reviews and one on ones and coaching on calls, et cetera. So go to market changes depending on again, the stage of the business and who's. And who's executing and it becomes leaner or more robust.

Yeah. Great. And to play that back to you a little bit. So some of the components, which I'm always wanting to do is like, how do we come up with a simple model for people to think about their own program? So within that you talked about the customer. So within that there's icp. So who your primary audience are, some of their behavioral qualities, et cetera. You're thinking about messaging, what are you going out with? You're thinking about where your audience is. So you're thinking about planning from an outreach perspective. And then the effectiveness side is the metric. So is that, is that a good summary of sort of four parts of what you're doing? Okay, so on the first audit with a business.

Yes. That's what it entails.

Yeah. So on that first part about the audience, if you're working with the seed stage company at that point you've got a, let's call it a hypothesis as far as who your primary audience is. Sometimes you might have a few side by side that you've got good instincts on. You've done some, maybe some foundational research. There's parts that have happened at that stage to validate that customer. But through your process, are you also validating the most impactful ICP within that, as well as the sales messaging and sort of how that converts. Are those two things happening in parallel to make sure that you can validate that you're talking to the right person?

Yes, but I also want to take a step back here too. So there's something called founder market fit, meaning the founder, when they set out to, you know, when they come up with a problem and the sort of new solution around that problem that they're going to provide the market with. Ideally they've lived through that problem themselves and they know it very well in a very sort of intimate way. And they, they feel all the implications of the problem not being solved and whatever time or resources are being wasted and why the solution that they've come up with obviously needs to be tested is better than existing solutions today. So we need to start with a strong hypothesis there. Otherwise it's going to be hard to validate, you know, any of the ICPs or the solutions. And of course, you know, then you look at, there's, there's a lot of customer discovery that should be happening during that stage to see in which direction is there a stronger pull between all the different ICPs and titles and size of businesses that we're talking to to sort of decide, okay, this is what we're going to start with, this is what we're going to niche down on and we have a strong enough hypothesis around the problem and now we're going to go try to validate our solution before we really go into hard sales launch mode, if that makes sense.

Yeah, absolutely. So within that you're I guess, double checking validation. I say double checking because off that founder market fit model that you described, there's already good instincts and insights of a personal experience that a founder has had as far as the problem that they're trying to solve or opportunity they're trying to create. So within that, that double check piece, as far as that feedback that you're getting on that product and how it works, how it solves their problems, et cetera. So the, the second stage of that then, if you get to a point where you feel comfortable that you've got enough sort of of a quorum of people that have bought into what you're doing and you've got traction and when you're thinking about messaging and testing messaging, are you looking at both in person and digital communications at the same time?

No, I think it depends on the business. There are businesses where in person selling works really well and others where it's not required.

Yeah. So you need to think about in the instance where you would have both, if you're doing a digital sequence of messaging to target a certain customer versus an in person piece, how you think about those two conversations? Are you working with the sales team to help, like give them some questions or things that they can use in the sales process if they're having a meeting versus like something that's short, sharp and impactful from a digital message perspective?

Well, you bring up a good point. And again, I want to take a step back here too, because if I'm still at the stage where I'm trying to validate the problem and my solution and what pull There is in the market towards my solution and whether customers are willing to pay for it. Because if they're not, then what are we really validating? You shouldn't have a sales team that's too early to have a sales team involved. Right. If there is no repeatable playbook that yields X amount of predictability on a monthly basis and X amount of revenue, there should be no sales team involved. You're still at that founder led stage. So to go back to your question, yes, of course, if I'm working with founders, we'll test out messaging and test out scripts and test out necessarily sequences. Again, too early for that in my opinion. But more so, what does the sales funnel look like? And if we do the same things X amount of times with different prospects, is the repeatability, Is there patterns in what people say? Are the questions sort of yielding us the answers we're looking for? You know, how long are people staying in different stages of the funnel, et cetera. But no, there should not be sales teams involved at this point where it's still even unsure whether this is the right product for the right Persona for this current market.

That's a good point. And in those early stages of a startup, up into that seed piece, if you're trying to get revenue full stop, or maybe you're trying to get revenue momentum to find that sort of product solution fit in that stage where you're starting to get a little bit of traction, you need to have confidence in the pipeline from a revenue perspective to bring a dedicated salesperson on and leverage the insights, the momentum, customer database things that you would then start to build out. So focusing on the people side of that and hiring, I know it's something that I talk a lot about with founders and have questions in that space. If you're thinking about momentum of a company and roles and responsibilities, if you've got founders doing early sales, what sort of things do you put in place to be able to measure progress in traction in retained revenue, et cetera, to get to a path where you feel confident that once you hit point X or hit these indicators that you can actually hire a dedicated salesperson to come in and support and scale what you're doing?

I mean, again, it really depends on the business. The revenue indicators and the milestones are going to be very different of the businesses. SMB selling to small to medium sized businesses versus if it's an enterprise sale. Again, I'm more so looking for repeatability. First of all, in the funnel. Do I have a funnel where people are coming in Whether it's inbound, whether it's outbound, whether it's referrals, I don't care, as long as I know that on average, you know, for the last six months, I've been having, I don't know, I'm making this up, five new customer conversations a week, and that I have a playbook to take these five customers from new conversation to close in a certain amount of time. And I know exactly what all the steps in the process are, and I know exactly what objections are going to come up. And I am able to gradually keep going up with my pricing because this is a product that solves a real problem that customers need.

Yeah, that makes sense. So it's having enough intelligence, intelligence, I mean, feedback, et cetera, and a sense of how you're building out that customer journey and getting people through the funnel. So from that, like getting into that customer journey, what are some of the things you might look at as far as, like digitally and even from a direct person to person sales process? Do you put something in place to be able to track that, that customer journey as far as what stage they're at on the sales process? And what are some of the things that are blocking that potential progression to the next stage within that funnel? What are some of the things that you would do taking people through that journey?

I mean, the first thing I do with founders I coach is listen to all their calls, listen to all their calls and really understand what the blockers are, where we're getting objections, where we need to bring more decision makers in the process, where we need to become smarter in our storytelling, and what collateral and case studies we need to use to move people along. Again, my sort of biggest priority is to find where are blockers in the sales process and the different sales stages and what I need to provide my customers with in order to sort of unblock the certain stage and move them along.

Yeah, that makes sense. So within that, as far as then getting pipeline and pipeline momentum to be able to take that knowledge, what sort of things are you pulling out from that sort of insights and work that the founders are doing in that sales process to then turn it into a brief that you can bring an external salesperson in to help sort of escalate what you're doing? Do you pull that information out and then turn that into something quite structured to give to someone else, to be able to then use as a playbook to then to continue that?

And that playbook is built as early as possible. I mean, from the first calls, we're Starting to build scripts. We're iterating on our outbound messaging, we're iterating on our sort of objections. We're iterating on, you know, you want to use those learnings really, really quickly, but the idea is to give a structured of an approach to founders as early as possible versus a suggestion of, oh, you should say this but like, hey, here's a script based on what we learned. Try this verbatim on your next call. Try these questions and see, see what the outcome is and let's learn and work on it on your next call and your next one, and your next one.

Yeah, yeah. And that's, I guess that dynamic sort of loop being in place is critical. Right. Because you've already established a way to track and understand what you're doing, what's been effective and what's not. And it's a continual evolution to be the most effective machine that you can be as far as building pipeline, converting the sales and then the retention, which is obviously critical as well. So if you're thinking about hiring someone, it's a question that comes up all the time as well from conversations with founders is on the budget perspective if you want to hire a salesperson. I see a lot where salespeople are coming in if there's sales history and they can get a sense of conversion rates, the time to close the sale, what that sale amount is, whether they'll come in on a commission only type situation. In your experience, are you seeing sales teams looking to come in and get paid a wage plus commission, what sort of typical packages would you see within that as far as benefits and how do you.

It's always base plus commission. I mean, I've done commission sales only in the past and I think it's great. Right. Assuming you have strong belief in the product and the ability to sell the product and it comes with a conviction of can this product be sold and how fast and how much is there a need in the market and do I feel confident and my sales abilities and also what the company is providing me with to go and do. To go and do a good job. Right. But I haven't really seen any company. It's always base plus commission.

Yeah. And it's good to know if you're thinking about planning and you've got good instincts and insights around sales, momentum, pipeline, et cetera, being able to manage cash flow, which is so important. And right now we're seeing a lot of conversation around bootstrapping and where founders are not relying on external capital to be Able to have that fallback if pipeline doesn't play out. So that's a real delicate balance for a founder to be able to think about when they put someone on what they can afford to pay them, having the right incentives in place as well to reward the work that they're doing where there's a win win situation. So to be able to measure that then into a metrics situation. I am a big advocate for metrics and I love to be able to see data across the board on most functions within a startup. Setting that up, are you typically putting milestones, targets in place for the salesperson to hit? And that could be outreach, it could be conversion. What are some of the things that go into the mix on the metrics?

Yeah, I mean of course there's always a mix of both sort of daily metrics. Amount of calls, amount of emails, you know, amount of demos booked on a weekly basis, amount of deals closed. And then there's also the sort of hard quarterly or monthly quota of new revenue brought in.

Yeah. So it becomes a target that's a company wide target that's obviously set and then within that you're allocating responsibility to certain people and they have their own individual targets. But right now the piece that's happening a lot is the market is changing significantly and it feels like sometimes on a daily basis with new technology, new competitors, competitors coming to market faster and being able to navigate that is, is tricky as, as a young founder, maybe it's your first company. So within the, I guess the process of not just the outreach didn't really.

Have insight into that. They hadn't set processes, they weren't really set expectations in place of metrics because the sales team had been with the company since day one. And at the beginning they were also, they were sort of, you know, wearing all different types of hats and helping with everything. And as the role became more specific and streamlined, no one really checked in to see how are we using this tool and what is the accuracy of our data and how are we making revenue prediction, predictions, et cetera. I don't necessarily, you know, I don't have a certain tech stack that I suggest it depends on what the business is using. I don't have a Preference on HubSpot vs Close vs Salesforce as long as you know the job is being done. And it's funny because. Well, it's funny to me. Last week I had a call with a very early stage company that came in and you know, was looking for all kinds of advice of should we do this versus do that. And my advice was like, you're so early on, all you need to do is just sell. You don't even need me. Just go validate that customers are willing to pay for this. And the sales rep, what, you know, I appreciate the eagerness was like, well, you know, we're using HubSpot. Should we go use close and should we sequence versus Taylor? And if we sequence and we use Apollo, we can get more messages out. And I'm thinking you can use a whiteboard. Like, I don't care what you use. The point here is, and again, this was a company that's very early on, but the idea is use anything to give you the basic information you need that will inform your next actions. So if you're going to use a spreadsheet or a whiteboard to see, these are the leads that are coming in and these are the pipeline stages that I've come up with and these are the triggers that tell me when I need to move people down a pipeline stage. And there's sort of a method behind this that I can then build on as I learn. Great. I don't care what tech stack people use. And you know, warm leads, everybody warns warm leads. But again, that's, that's a whole bigger topic. We could talk about it for an hour. What I care about as a fractional sales coach is that the teams know what the messaging is. They know how to go find customers and move them along the sales funnel. And they know what they need to be successful. And whether what tech stack they're using or what methodology they're using, it doesn't is secondary to me.

I think to be able to understand that as a founder is important. And I've heard it described sort of in three phases before on a startup's trajectory. So in that early stage where you're trying to get first revenue and get some momentum, it's very much a growth hacking stage where you are having to be reactive all the time. And if you get something that's working, then chasing that and seeing where it stops and then maybe having something else that you're trying, it's a pretty nimble type experience. And then the second stage being where you've got revenue momentum, you're starting to build out a data set of insights that is more robust, that you can use to have some structure and then probably like a post series A, then you're into more hardcore metrics where you actually have got a lot of history behind. You can look at trends and patterns and then you can double Down. And even from a tracking perspective, you can start to see, well, if our web traffic declines 15% and our sales are declining as a result, it may not be a sales problem. It's, you need to get better traffic back to your website. So finding the source of the problem and having that data.

So while there are other motions like, you know, warm leads and website traffic and product led growth, my experience has always been in direct sales. Where are your customers? What are their titles? What do they care about? Where do they live? What's the right messaging to get in front of them? Okay, now go do it. And if it doesn't work, come back to the whiteboard.

Yeah, great. And we talked earlier around the personal side of it. As far as you, the founder, and getting that message out. On episode number four, I think we had Cindy Scalicki, who works a lot with tech founders in honing their message. And that can be in a boardroom, it can be in a pitch to get fundraising, it can be in sales. The confidence for a founder to be able to sell. Just because you're the founder doesn't mean you're the.

Is there a different. I like how you start with the confidence for the founder. Is there a different. Is there a way out? Is there an alternative?

Well, that's the question. I guess I was.

Well, that's the answer. There isn't.

Yeah. Yeah. So being able to have the ability. Because not everyone is a natural salesperson.

But it's something you can learn. I don't think there is a thing as a natural salesperson. There are people that are more extroverted than others and you could say more socially gifted. But my experience has taught me that it comes down to two things. Having a growth mindset and being willing to put in the work and. Right. Of course, I was having this discussion yesterday where, especially with a lot of technical founders that, you know, come out of YC have gone to an Ivy League school and are super technical and they have all these negative connotations around selling. I don't want to be pushy. It feels icky. It doesn't feel genuine. Well, I mean, the answer is tough luck. You're the, you're the person that knows your product the best and cares about it the most at this stage. So you need to find a way to get past those beliefs and get in front of your customers. And obviously I'm oversimplifying. Right. And I'm exaggerating to, to make, to get the point across, but it's, it's a skill that you can learn. And I've seen in my experience working with so many startups that, I mean I've seen founders putting on their sales hat and because they have so much knowledge around the problem and the solution that they've built, they're better than the best salespeople and they have so much charisma and conviction and can answer technical questions and can relate to their customers. Probably because at some point they were in their customer shoes. And again, at the end of the day, what's the alternative? Are you going to hire? I couldn't even sell for people at this stage, no matter my experience because when you're so early on, everything is so fluid that no one can really validate it. And that's why most startups in these early stages, I know I'm ranting, but I want to get this across. This is why most startups at this early stage pivot because there are so many unknowns and you just don't know what's going to be sticky with your customers that known outside you, no matter what their sales background is, can come and do this job for you.

Yeah, yeah. And it's that reality and there's no hiding it. To be able to get revenue growth, you need to sell. And in those early stages, unless you come with a lot of capital and prepared to hand it over to someone else to do it for you, that.

And you're going to burn through that capital. You're going to burn through that capital so fast.

Yep. Yeah. So being smart with your money from a budget perspective means that you take on that role.

Correct.

Okay. So turning that back on to you, like we, we didn't go into depth at all about sort of your background and your focus. But what would you say in a typical week is the type of things that your business does? So tell us a little bit about that reaction. Tells me that there's a lot of things that you're doing. But like, yeah, from the, like from an overall perspective, what are some of the things that you focus on with your clients?

Yeah, again I work with a very early stage companies and that's what most exciting to me because there was always new fires to put out and you need to get crafty and you need to move fast and that sort of adrenaline keeps me going as well because I've always been in startups even prior to getting into consulting. So the companies I work with are either founder led selling, helping founders really validate their first go to market motion and building a playbook that's repeatable, that Assuming the, the go to market is successful, we can then, you know, interview and hire and onboard sort of their founding sales team. And I also work with series A sales team so I'm working with two series A sales teams today. Very different sales motions. One is SMB which is the environment I sort of was brought up in, just very fast transactional selling. And the other is a more enterprise state to commercial real estate companies. So very different sales motions for one of them. I am currently wearing the recruiter hat and I've done this for the last one and a half year where I've hired 25% of their company and for the other one I'm doing anything you would imagine from a sales manager. I am listening to every call and coaching and holding one on ones and training sessions and I've also recruited twice for them now and I'm onboarding those new sellers. So it's, it's very, very hands on work.

Yeah. And that's the part that most founders I think don't realize that goes into scaling their business. Like the product is one part of it, but the people become like so, so important and you end up spending most of your time. And I've scaled a business to 35 people and within that I went from being the person who was so passionate about the problem that I was trying to solve and getting my hands dirty. Yeah. And then you end up running the business. So you're spending your time in legal documents and cash flow and managing personalities and hiring, firing, all that part of it. In those early conversations, do you give them that reality check? Are most people naive?

Yes. Yes, absolutely. Yes. And it's funny because after every engagement I asked customers to leave me a testimonial. I should have had this ready to play it for you. But you know, there's a couple of new ones I got from early stage companies that they were essentially saying that from the first call we had with Carol, she sort of really put us on the spot. And this was not a fluff call because to your point, there's so many things that go into it that founders don't necessarily expect. And when you have someone very technical, the tendency is to hide behind the product. Right. Versus sort of want to tackle good market and hiring and firing and training and all the stuff you mentioned. So yes, I am very honest and direct about what needs to be done because at the end of the day these are not my businesses. So I need full collaboration from the founders to make the most out of the engagement.

Yeah, there's a trust that has to be the standard, right? That's just the foundation for your relationship as a consultant with their business, is that you need to trust each other, have transparency, and tell the hard truth. You don't have time to tiptoe around and tell them that everything's going to be all right. It's like, this is the reality of the reality of where we're at, and this is what we need to get to. But then off the back of that, like the experience that you've had and the success that you've had with your clients, they know immediately that you can help them go from that point of, you know, maybe pre revenue into getting revenue momentum and the stages to do it. So you know that even with that first confrontation, that it's going to be progress after that. It's just that first part to kick off and go, okay, this is what you've created, this is what you need to do. And we all need to accept that to be able to work together and make this be an effective partnership.

And, you know, it really depends. Again, I'm thinking to a company I worked with earlier in 2024, where I was fully aligned with the founders, and we agreed to start with an audit, sort of a deep dive to see, you know, how many dead bodies are in the building. And we did the audit, and we agreed both on what the audit uncovered as well as what, you know, I came up with a plan. This is what we're going to do based on what we found out, and this is how long it's going to take us to achieve it. And this is what I'm going to provide, and this is what I need from you. And everyone was. Was in agreement that this is the right way to go. And what happened is the sales team that was in place, even though prior to me coming on, they were saying, we need coaching, we need training, we need best practices, we need a manager. One month in the engagement, we're kicking and screaming how hard they were working and how terrible all this visibility was and how they were being micromanaged. And what ended up happening was we fired the sales team, all of it, every single person, which is awful, right? Like, it's a big decision to make. And then we had to hire a new team. And guess what? This company is so much better off. And that was not the plan going in. The plan was not to fire the sales team. The plan was to give the sales team a better process and accountability and to help them do what they were already doing in a much easier, streamlined way. But what you often see in these early companies is because, you know, rules change and expectations aren't being set, it's hard to go from 0 to 180, and a lot of people don't really want that. As painful as it is to let people go, it's going to cost you a lot more money and headaches to keep people in your organization that don't want to be there. So, you know, it ended up working out really well eventually. But it was a very sort of. I can't even think of the right word. It was a very stressful moment for everyone involved, including myself, to come to the realization and to push that this is the right decision for the business. These people need to go.

Yeah. And typically in a founder stack, you're not going to have someone who comes from a sales background. So having someone like you has that experience is critical to be able to acknowledge that and you're not there to upset people. It's all around progress and growth and getting momentum on the sales side.

So people get upset. That's fine. As long as the decisions that we're making are the right ones for the business.

Yeah. Yeah, absolutely. So this has been amazing. I know that we're at time. So one last question. As far as people reaching out to you, have you got room for clients at the moment? And if so, what's the best way to reach out?

The best way for people to reach out to me is on LinkedIn.

Okay, great. Well, I'll make sure that I'll put some contact details in the show notes and then obviously it'll be on my LinkedIn as well. But Carol, this has been so good. I appreciate you making the time today.

Yeah, thank you so much for having me.

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