EP. 8: The Biggest Growth Lessons I’ve Learned the Hard Way

by | Jun 18, 2020 | Marketing, Podcast, SaaS

Some lessons in marketing are easy to learn. You pick them up from a book, take a class, or hear a talk and get it immediately. Other lessons are harder to come by. They are the ones learned over time and through experience. The ones that we look back on and think about the head start we could have got from applying them earlier. 

In this episode of In Demand, Asia Orangio of DemandMaven shares the four biggest lessons that she learned the hard way. From customer journey’s to funnels and go to market strategy, you’ll learn growth lessons you can implement today to avoid learning them the hard way yourself in the future.

Extra Resources

  • none this time~


  1. Not Focusing on the customer journey: 
    1. Marketing is a dance. Customers lead and we need to learn to read and move with them. We have to match our content and marketing work to the places people are and the way they make decisions.
  2. It’s harder to build a funnel from top to bottom than from the bottom to the top: 
    1. You can build an awesome marketing funnel on paper from top to bottom but then realize that you no one is going through the funnel!
    2. To create a funnel that works, start with the bottom of the funnel activity, learn from your customers and create the middle and then top of the funnel activities.
  3. Your market determines how you go to market
    1. If you are entering an established market, with established competitors, you need to look around at the market to see how you fit in. If there are established norms (like free trials, needing to enter credit cards, etc.) not following those in your go to market plan will create a lot of friction. 
  4. Balancing long-term vs short-term efforts
    1. Especially in startups with VC funding, there can be lots of pressure from investors to create short-term wins at the expense of losing focus on long-term marketing efforts. Marketing wins in the short term are great, but you should always have an eye on long-term marketing plans and activities that compound over time. 



What’s up founders. And welcome back to another episode of the in demand podcast, where we talk all about how to reach your very first 100K MRR. My name is Asia. I’m your host. I am also the CEO and founder of demand Maven where we work with early stage startups on reaching their very first growth milestones. Today, we’re going to talk all about the biggest growth lessons I’ve learned. The hard way part of this is me admitting to making these mistakes in the end. A part of me is declaring to literally never make them don’t ever do these narratives. They’re awful. I, as a very junior marketer, I’ve done these things and, uh, I’ve, I’ve had to learn the hard way. And then there are some that even in some client projects, some of them have resurfaced and others were totally new. So I hope that you, enjoy this.

There’s only, let’s see, I’ve got one, two, three, four, so this might actually go pretty quickly, but these are strategic mistakes. Some of them are a little bit tactical and I’ll, and I’ll give you context on when some of these work and when they don’t work. But overall, I definitely had to learn these the hard way. Okay. The first one, I hate this. It’s ignoring the customer journey. I’m trying to think of a time where ignoring the customer journey has ever done me a good service. And I’m, I’m certain that there’s outliers of products in certain markets where, the customer, you know, doesn’t really know the, the best way to do something or, um, you know, sometimes the customer is wrong and sometimes you have such a small sample size that you really don’t have the full story or the full spectrum. I think that those are probably edge cases.

I think most of us are in businesses where listening to the customer journey and actually, mapping it out and also mapping out your acquisition to that. And your activation to that, those are, those are best practices. Those are things that you absolutely should do. It’s very rare that you ever would not do them all that said I have definitely been in situations where the customer journey was an afterthought and not something that we really focused on. And what I mean by that is it was almost like we didn’t really care how our customers actually made decisions, how they actually did research on their problems, what they were researching, or if they even were researching, what were, what were their concerns? What did they really fear and whether typically, I’ve worked in a B2B capacity. This could also be B2C as well, but w who really was this customer?

There have also been times where, especially as a junior marketer, you get kind of caught up in like the tactics of how to actually execute something. And I’ve definitely been guilty of that. In fact, I think most marketers start out with heavily focusing on a particular or a tactic. There’s some thing that they’ve been tasked with. And over time they become more strategic and they are able to see more of the whole story, especially from the business side and the customer side. But what I found is customer led growth was something that I learned over time, and I became far more proficient in it when I was more focused on SAAS and just overarched startup startup in general, when I was precise and pre-start up, I definitely was not focused on the customer journey and don’t get me wrong. It, it was pretty evident. We would produce campaigns that just didn’t net the results that we were expecting.

And I also think too that our strategy, our approach to how to acquire a certain kinds of customers, it was just, it was so misaligned. And it was, it was so clear. It’s clear now it was never, it was not clear at the time. It definitely became clear over time. Especially as I’ve grown as a marketer, but looking back at my, you know, at my entire career, it just became so obvious that, um, there were just things that we did that just didn’t make sense. I’m going to give you a few examples. Pretty much every single business is going to create some kind of blog. I don’t actually don’t think that, um, I don’t know necessarily that any businesses going to not create content. I think we are, we’re all creating content all the time and we don’t even realize it, but the kinds of content that I was creating way back, you know, when I was early, early marketer, didn’t really know a ton about growth in the way that I do now, but I was creating content that on paper was very well executed.

It looked great. It read very well. It probably told a compelling story, but when it came to that, our customers care about it. Absolutely not like at all. And when you think about it that way, it suddenly seems so obvious. It’s like, Oh, well this is a giant waste of time. Maybe not the content itself, but, um, or excuse me, maybe not creating inbound interest. Inbound was still a core function of that particular business, but it was just the content itself. Like the content itself was really the part that wasn’t strong. And this is where I had to really learn the customer journey is we’re, really kind of wrapping ourselves around that the customer journey is not influenced by what I do, if that makes any sense, really we’re discovering the customer journey and it’s a dance we’re kind of matching our steps to theirs.

They are the lead and they don’t really know it. And it’s our job to kind of dance with them and match our steps to theirs. It’s, it’s really not the opposite. So it’s, I think it’s very rare that we force customers to go through hoops. Um, it’s really much more like they have a way that they like to buy. They have a way that they like to be approached. They even have a way that they like to be convinced and we really have to match ourselves to that. I think even in the cases of doing like really interesting things from a customer journey perspective, I think even those are still technically inline with what the customer would expect anyway. So for example, you’ll see companies like drift, even Intercom, I would say, who are really challenging how they go to market. And they’re challenging a lot of the best practices and status quo things.

But what I actually think what they’re doing is they’re, they’re typically marketing to marketers or they’re marketing to people who want to see that and who want and expect that, challenging, like the best practices in the status quo. I think that’s something that is attractive even to that particular market. You probably could not do this, do the same exact thing for a different market. I don’t know. I think that that’s kind of where looking at the customer and the customer journey, it’s just so critical. And it’s something that I have made. I’ve made that mistake countless times in my career. I would say it’s something that I’m extremely passionate about now, but I would say when I was like a junior marketer straight out of college and like, you know, first few like real career moves back then it, it definitely wasn’t that way.

Huge mistake that I’ve made. I’ve learned the hard way now. I know what it looks like to actually map to a customer journey and to really care about it in the way that, um, actually nets out a positive outcome and actually nets out growth and results. Okay. The second lesson, trying to build a funnel from top to bottom, from super high level awareness, all the way down to high intent, bottom of the funnel activity or practices, it’s actually much harder than reverse engineering it. And what I mean by that is it is just so much harder to start at the very tippy top of the funnel. Okay, well, we’re going to build all of this awareness and all of this traffic with no where to lead them down that’s and like, we’re going to try to build the funnel along the way. I actually find that’s way harder than reverse engineering it.

And starting with people who want to solve the problem now and figuring out what the steps are above that. And then of course, above that. So starting with bottom of the funnel first, and then moving to middle of the funnel and then moving to top of the funnel last, I actually find that building it out that way, way better and faster, and usually more informed. This is one of those growth lessons that you really don’t realize that you’re making it until you arrive at this robust funnel that you’ve built, that doesn’t convert anyone into anything at all. And you just find yourself incredibly frustrated with the entire marketing foundation that you’ve built. And this is why personally I have come to really value a strong marketing foundation. And also I’ve come to really value bottom of the funnel activity, whether that’s sales activity or just marketing activity in general, bottom of the funnel activity.

If you’ve, if you’ve heard my re my previous episode about funnels, then you know what I mean? When I say bottom of the funnel activity, these are marketing practices that attract people who are most likely to buy and who are closest to the bottom of the funnel, meaning they’re about to take that next step into becoming either a paying customer or that very first conversion point that puts them into the sales funnel, whether that’s a demo request or whatever, these are the kinds of that we’ll ask the customer activity that we want. But then the marketing activity that happens around that, it’s about the website. It’s about case studies. It’s about pricing. It’s about how well do your features communicate the value of what it is that you’re doing. And then of course, there’s bottom of the funnel activity like paid search, which in theory generates a conversion pretty quickly.

That’s just an example, of course, could be a few different channels that are considered bottom of the funnel for you. But those are just, you know, very basic best practice examples. It’s actually easier to start there than to start all the way the tippy top and have no idea if what you’re building actually will convert into paying a customer or not what I find. And this is a huge mistake that both marketers and honestly founders make, but they start with this like top level awareness marketing activity. They’ve never even tested if someone, if they could just generate a conversion now based off of some search query or something. And they started this like very tippy top of the funnel and they build all this content, they build all this awareness and then they take people down to another part of the funnel that they’re kind of guessing at this point, because they don’t really know if it’s actually going to generate the positive result or not, which is a purchase or a conversion.

And then they do even more activity here and they bring them out down to like this next step of the funnel, way harder to actually know if you’ve got the right message. If you’re even targeting the right person, if what you’re doing even remotely matches what a customer journey could be. This is why I almost always say, if you can help it, don’t start with this like super top of the funnel awareness building, start with bottom of the funnel. First, can you attract people who are ready to buy now, do those people exist and who are they and why? So this is a lesson that I’ve learned the hard way, and that I have built out entire marketing campaigns and practices and just strategies I’ve executed, like, just so much before where we started top of the funnel first. And then we kind of, we hoped and prayed that we would understand everything by the time that we got to the bottom of the funnel.

But the reality was that if we had just started bottom of the funnel first, we would have learned more and we would have been able to build the right kinds of top of the funnel and just middle of the funnel activities. This might sound really nebulous and really, um, or maybe the opposite, maybe this sounds like really high level and kind of fluffy. But I think the best example I can give is we can target people who are actively looking for a solution right now, or we can build a bunch of stuff that hopefully educate some about the problem. And maybe also hopefully makes them realize that they have a problem and actually motivates them to solve the problem with our product. Don’t get me wrong. You can totally do that. There are some businesses where you need to do that. But what I find is it’s actually much harder.

You do a lot more guessing, and this is where customer research really comes into play pretty hardcore, but it’s just, it’s just so rare that, um, you will be in a situation where building top of the funnel is more important than building out bottom of the funnel. Usually building out that other kind of like awareness model. So like, let’s say you do start at like really high level top of the funnel activity. And you do that first. Usually it’s because you’ve got a lot of funding, you’ve got a lot of runway, you’ve got the time and you’ve, you’ve got the resources and the funding to actually carry an entire market all the way through to I’m converting now. And I’m purchasing from, I don’t even know what the problem is to I’m now a paying customer. That’s a huge, huge buying cycle. It’s absolutely huge.

Or at least it could be. I find the only times where it’s not are actually, like B2C and e-commerce kinds of, plays. I find when it’s B2B, however, pretty much never gonna start super top of the funnel. Pretty much always going to go for the bottom of the funnel activity first. And then as we learn more about the best paying customers and also about the buying triggers in general, then we can start to say, Oh, okay, well maybe this kind of middle of the funnel activity actually nuts out the kind of people that we want to be talking to in the first place. And then from there now we can kind of start at the more top of the funnel activity. But basically if you can help it start with bottom of the funnel activity first, don’t try to like, guess your way down a funnel that doesn’t make any sense.

Number three, your market heavily influences how you go to market. This is going to sound so obvious. It’s gonna sound so obvious saying it, and it feels obvious saying it. Now your market really heavily influences how you go to market. And what that ultimately means is when you sit down and you define your go to market strategy, go to market meaning, well, what’s my pricing model. What really is the product that I want to take to market? What’s my MVP, who am I ultimately targeting? And what channels am I going to use to acquire this part of the market? So much of the market itself dictates that almost to a point to where it might not make sense necessarily to dramatically change one part of that for any other reason than like, it’s just for fun. I’m like you just want to, there was a product that I was working on a actually recently, and I actually worked with this business for quite a while.

So they, they were, they were a pretty long time client for me for Demand Maven. And when we first started working together, the go to market strategy, it kind of went against everything that would be expected of them in their particular market. So instead of having a 30 day free trial, they opted for like the 14 day, even though other competitors were offering a 30 day, but it seems like every single go to market decision, we made like directly defied, like what the rest of the market would have expected from us. So instead of making it incredibly easy to sign up, it seems like we were making it actually even harder on top of that, the product itself, we couldn’t really compete with the big guys quite yet. Anyway, there were so many decisions that we made that seemed to completely go against what the market would have responded to anyways, all the way up to like required, like requiring a credit card, which don’t get me wrong.

Totally works in some cases. But when the entire market does not expect to enter a credit card, and you’re the only one who does, it’s just adding another friction layer. And so there were so many of these go to market decisions that had been made that seemed to, again, just defy what the market would have expected. Anyway, it’s probably one of the hardest lessons that I personally have had to learn, but it’s also, it’s so tough to teach this because you really don’t understand or realize it until you’re actually doing it the best way that I can offer advice though, to people who are struggling with us, where they’ve got to go to market strategy, but they don’t know if it’s going to work. If you have competitors in your space, that’s actually in many ways a blessing and a curse, obviously you’re competing, but at the same exact time, you kind of have an inkling of what your market might expect.

The other thing that you can, of course leverage is your own customer research. So by leveraging customer research, you can also understand if what you’re building go to market wise is actually going to stand if it’s actually got legs, and if it doesn’t have legs, you will also be able to learn pretty quickly. Not that not that businesses don’t have power. Of course we do. It’s just that we’re so much under the influence. If you will, of our potential customers, then we realize, and we really don’t know until we talk to them about it until we actually start to market ourselves or start to sell ourselves in some kind of way. And then we start to learn pretty quickly like, Oh, okay, this is where maybe things don’t fit, go to market wise, or maybe we’ve missed the Mark in these ways. Or people are not as interested in this kind of model, but they’d rather pay for this kind of model.

And if you don’t have competitors, there’s usually some kind of competitive alternative that, businesses are weighing or people are weighing in general. So for example, like if you’re competing with Excel, you would have to offer something so much more, incredibly high value, time saving, cost saving and some kind of way that it’s just going to have to be much less friction for people to use your product over Excel and so much of how the market, or at least part of the market that you’re views your product and also views the problem that you’re trying to solve for them. So much of those things have to be incredibly aligned. And if they’re not, then you never really achieve product market fit. It gets really hard to sell your product or to market your product in any kind of meaningful way. And on top of that, you end up with more unknowns than knowns, which is incredibly frustrating.

I think not being aligned with the market and not being aligned with the expectations thereof. It’s, it’s definitely a trap I’ve fallen into before. And it’s one I can recognize now, but I would say years ago, definitely not something I would have ever even really realized to be honest, but seeing it now, it’s so clear when a product is not quite aligned with the market that they’re in or the one that they’re trying to target. And this is something to, of course, to distinct cause there’s where you’re at and where you want to be. But when you are aligned, it is reflective in every single part of your go to market strategy, your pricing, your model, and everything that you produce from a marketing perspective, who you’re targeting all those things, even, even down to the features that you release, all of those in theory are working together and you’re not going to get, you know, perfect scores on everything.

There are some things that are going to be able to be a little bit misaligned or put you in an entirely different market. In which case you’ve got to now find product market fit there as well. But overall, so much of your market dictates how you go to market, which means that if you want to go to market in a certain way, you need to either change your market or change your product or both. That’s just the kind of implication that you’ve got. So if you’re misaligned in any kind of way, it will reflect and which case you would need to make adjustments. This is why so many businesses I think, changed their pricing. So often they changed their models. So often every now and again, they’ll even pivot and maybe even change the product or change the market, change their positioning. There’s just so much, so many levers that you can pull, but it’s, it’s really to, to achieve that.

Ideally all of these pieces would work together and you would see the growth in a way that seems so natural, but I find that not always the case and a lot of that really just is because of the market that you’re in. You’ve really got to be critical about what market do you ultimately want to serve? Is there a better fit for your market or is there, is there a better market really that you can actually go in and be in and based off of what you’ve built based off of the model that you’re comfortable with? What makes sense here? And a lot of that might not be negotiable depending on who, what you’re actually building and who you’re serving. And some of them are, some of it might be some of it sometimes it’s as simple as, Oh, we just, we just focused on this segment and not the segment.

And then it’s like, okay, well that’s fixed. And sometimes it’s not as simple. And that’s where so much more work has to go into it. And it’s, and it’s work that goes beyond just marketing. This is work that goes beyond just sales or just any one department it’s really full business strategy. And that that’s something as a marketer I’ve had to come to terms with, but then also, manage around because, you know, obviously we all want to grow, but, uh, I find that when there is such a clear misalignment, we’ve obviously got to put in the work to fix it. All right. The last one, number four, this one is one that comes up quite often, especially whenever I’m talking to founders who, who really aren’t certain, what is actually going to give them the best bang for their buck. And then also what’s actually going to take them to the state that they’re looking to be in.

And it’s balancing long term versus short term efforts. And when I say that this has been one of the hardest lessons for me to learn as a marketer and it’s, and it’s one that I have to I’m naturally sensitive to. So I have to temper accordingly depending on who I’m talking to. But what I do find is that, especially in a funded company, I find that short term wins and short term outcomes and short term, efforts are usually more valued than the longterm efforts. I don’t think that there was ever a conversation I had ever had with an investor where they weren’t wanting to know, well, what, what was the win this week? Or what was the, when this month or what have you. And I found what it, what it did was, it created a culture of really prioritizing short term wins.

What’s a win that we can scrap together in the next week and don’t get me wrong. That’s not necessarily a bad thing. In fact, it’s actually really cool to be able to come every week to the table with a win of like, well, we did this and this and this, and this was awesome. And like we saw these results, but what it kind of also did was it kind of made some parts of the go to market team, forget about long term and longterm activities are things that might not have short term wins every single week in terms of like results or outcomes. It might just be that the short term wins for those longterm efforts are really more around execution or they’re really more like tasks in a way, but those tasks over time build up to a larger effort. A great example of this is actually organic search.

It’s not that you can’t see short term results with organic search. It’s just much more that you have to know and understand that this stuff compounds over time. If you get hung up on the short term results, you’ll forget to build the longterm stuff too. It’s that kind of balance that I worked to achieve for all of my accounts and my clients now, for sure. But I’ve definitely made that mistake as a full time marketer, you know, previously and some of my previous roles before. I just think overall, like we just get, so again, we get so obsessed over like the small wins and we were disappointed by the longterm outcomes, but it’s just because we never made those longterm investments. We, there were, we weren’t taking steps or taking action every single day or every single week towards that longer term vision. And part of this is because we might not know enough to have it.

And the other part of it is sometimes the environment that we’re in or the culture that we’re in. It just, it caters more to those short term wins than the longterm ones. So I would say as a founder, if you’re obsessed with the short term wins, that’s absolutely fine, but just make sure that you’re balancing it with okay, but what are the things that I can invest in that will net a longterm result? Organic search is just one marketing or growth example, but there are plenty others. So for example, community building, building out partnerships, co-marketing relationships in general brand building even sometimes not all the time, but sometimes, sometimes that’s an important thing. The other thing to is, and this is something that I wish I had done earlier as a marketer, but there are some investments that just are worth making now because of their longterm net result.

So for example, you’ll hear a lot about, well, when you first start, you don’t need the best website in the world. And, you know, to an extent, I agree with that, but eventually you kind of come back to my number three, which was your market, ultimately does determine how you go to market. And if you’ve got a website that looks terrible and it doesn’t do the best job of converting people and you’re competing against others who have a much more polished look, uh, you might suffer, maybe especially if your product is not better. So if your product isn’t better, you’re definitely not probably going to see a better result, but overall, like, those are the kinds of things that, can sometimes hold us back and investing into a website. That’s to me, at least that’s for sure, it’s like a, it’s a little bit short term, but it’s also a longterm investment.

Like we’re hoping to stick with this website for a couple of years, at least. So it should be something that we’re pretty comfortable with and that we’re pretty happy with, but there’s all kinds of other examples. I think product marketing is definitely one of those. Um, these are things that produce longterm. They can also produce short term wins, but it’s really a longterm practice and a longterm investment. Those are just some examples again, but those are the kinds of things that, um, in a previous life, as a marketer, I did not do the best job of balancing those and the businesses that I worked for. I definitely paid for those something. It’s a mistake I’ll never, ever, ever make again, but it’s definitely, it’s definitely a possibility gets a thing that can happen. And it’s something that, I would just say to all founders, just to make sure that if you can balance your approach balance it, not just with the short term, and if you’re building a culture around short term, then your future vision will only ever be three to six months out.

We want to be in a place where we can see two to three years out. That’s the kind of longterm vision that we want to have, which means that we’ll need to make longterm investments. If you have a marketing team, there’s a really good chance. They already kind of have this in mind. And depending on the culture in your business, you should be able to ask and say like, Hey, like we love the short term stuff, but what about the longterm? Ask them, see what they have to say about it. And if it’s just you in the business, let’s talk about that. That’s something that, I can absolutely help us out. I would just say from a short term versus long term perspective, you want to have a balanced approach. You want to make sure that you’re taking steps in both areas, even if it feels very weird too. I really hope that was helpful. Thank you so much for listening. I really hope that you’ve learned something today. I hope that I helped at least unpack one particular thing or at least maybe helped you avoid some terrible lesson that you’ll have to learn the hard way. Let me know what you think. I am always available on Twitter, @AsiaMatos. Thank you so much again and have an awesome day.