Today, I’m thrilled to be joined by Asia Orangio, the brain behind DemandMaven, a growth agency dedicated to helping SaaS companies and their founders reach new heights. Asia’s unique approach blends data-driven strategies with deep empathy for customers, making her a sought-after expert - from bootstrapped businesses to some of the most established companies. Whether you’re a startup founder or a seasoned marketer, I promise you that her insights will challenge your thinking and inspire quite a few new ideas.
In this conversation, Asia shares her journey from marketer to founder, unraveling the lessons she’s learned while scaling SaaS companies and guiding others to do the same. We’ll explore her philosophy on growth, the common mistakes founders make when trying to identify their growth levers, and the power of understanding your audience on a deeper level. This really ended up being a masterclass in sustainable growth and customer-first business foundations.
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The podcast was produced by Den Delimarsky. Music by Wataboi from Pixabay.
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Transcript
Den Delimarsky: Hello folks. Welcome to another episode of the work item podcast. And today I have none other than the CEO and founder of DemandMaven, Asia Orangio. Asia, welcome to the show.
Asia Orangio: Thank you so much for having me. Such a pleasure.
Den Delimarsky: I’m excited to be learning from you today and specifically about your career and your career trajectory. And maybe we can start with DemandMaven. What is DemandMaven about?
Asia Orangio: Yeah. DemandMaven is, ultimately, we’re a growth consulting firm. We work with founders and CEOs on troubleshooting growth, finding growth opportunities, and helping them define a go-to-market strategy. And we work with companies of all shapes and sizes. We’ve worked with companies that have no product, that are pre-product, pre-revenue. We’ve also worked with companies that are publicly traded, in half a billion. Really, what we’re looking at is we’re looking at solving the same problems and helping people make really tough decisions and then helping them make progress towards their goals.
Den Delimarsky: So it sounds like the scale of customers ranges pretty broadly. What led you to building a firm that spans the customer needs of effectively everybody, like you named, you know, somebody that has no product to like a billion dollar company. That’s kind of a, you know, there’s a spectrum there.
Asia Orangio: Yeah.
Den Delimarsky: Why, you know, I, and I’ve heard, and the reason I’m asking this is because I’ve heard a lot of folks that when they start their businesses, they think about niching down to a very specific domain. So like, oh, we’re going to focus on, you know, pre-product market fit customers. We’re going to focus on big enterprises and you’re spanning everything. Why?
Asia Orangio: Yeah. Yeah. It’s funny cause I get this question all the time of, well, what stage, you know, should we work with you in? And I say every stage because we’re not really focused on stage.
Asia Orangio: What’s interesting is businesses have the same problems just at different scales and the problems that we’re focused on troubleshooting growth.
Den Delimarsky: Yeah.
Asia Orangio: You can troubleshoot growth at 10K MRR. You can also troubleshoot growth at half a billion ARR. So there really isn’t like, oh, we’re only going to troubleshoot growth for just this one stage. But it’s just because the way that we think about solving the problem is very, very similar. And when we work with larger companies, the only difference is that we have more stakeholders. We have more people to discuss with. The level of insight that we provide tends to be at a larger scale, but it’s not necessarily like a fundamentally different problem.
It’s just more things that you have to think about. Of course, this is not always true for for different types of agencies and consulting firms. Of course, like the stage of growth will matter depending on what it is that you’re doing, but it just so happens that when we’re troubleshooting growth, we’re always focused on providing qualitative and quantitative insights to help understand root causes and therefore provide solutions. And that’s, I mean, it’s just part of the process. I think it’s so funny though, because we do get that question a lot of like, well, which one like do you prefer? And like, which one?
And we we love it all. I think the MicroConf audience, if anyone’s listening from MicroConf, they’ll primarily know us for like the more early stage work that we do. But when we look at the enterprise B2B SaaS space, they know us more for the research and the insights work that we do. But it’s all in the… In the same umbrella, ultimately, of troubleshooting growth, finding growth opportunity, and defining go-to-market.
Den Delimarsky: I like one term that you use here that I have not heard before. And I’m fascinated to learn more of what this is. Troubleshooting growth. Why troubleshooting? Because I feel like if we talk to a lot of founders or folks that run their own business, usually they focus on, you know, like, what’s your growth? And just like, “Oh, it’s marketing.” It’s, it’s always marketing. Somehow it’s marketing, but using the term of “troubleshooting growth”, walk me as a newbie in the domain. What does that actually entail?
Asia Orangio: Yeah. This is another really interesting phenomenon. But whenever people hear the word growth, the first thing that they think about is sales and marketing. But that’s just acquisition. And if you’re in the SaaS world, if you’re in software, you should know that growth is not just acquisition. There’s other types of growth to focus on. There’s activation. So once you get people through the door, how many people actually then become a customer and get activated and they actually get value from the product. Then there’s expansion. Okay, great. They’ve become a customer. Can you grow the account? There’s retention, which is where a lot of folks who are striving for product-market fit focus, you know they want to reduce churn, but retention is another huge part of the growth framework as well.
And then there’s within expansion, there’s monetization. So what are we charging? How are we charging? What is the model upon which we’re going to charge? And even within this, so you know these are like, you know, pirate metrics to make it simple, but growth also can be operational efficiency. So when you choose your goals, when you set your KPIs, when you choose your targets, how effective and efficient is your team at discussing what the what the challenges are, making sure they have the information and insights that they need to help reach those targets.
Are they the right ones? There’s also growth efficiency there. There’s also headcount. Growth is actually a very big concept, and whenever we’re troubleshooting growth, what we’re coming in and we’re doing is we’re looking at the entire business, not just acquisition, and we’re saying, okay, great. What are all of your other growth opportunities apart from just spending more money on ads or hiring more salespeople. And if that is still the best way to grow, amazing. Then like, congratulations, you’ve got, you know, the simplest growth engine that, you know, you could possibly have, you know, just spend more money on marketing. But the reality is that in SaaS, at least there are other levers to pull. And most teams, I think in the earlier days, especially kind of forget about those levers.
Den Delimarsky: I really like that framing, and especially because you broke it down into the stages of acquisition, activation, expansion, and retention. Because when we talk about growth, oftentimes, folks get zeroed in on one of them in one of the years. Oh, like, we don’t get enough customers. Like, let’s redesign our signup flow. Or, oh, we think our customers are leaving. Our retention is low. Let’s figure out how to keep them in the ecosystem. But what you describe is that you have to look at that end-to-end story, the entirety of the frame, not just one section of it.
Asia Orangio: Totally. Leaving one on the table is leaving… Like, you’re just leaving money on the table, basically. So if you forget about the others, then ultimately you’re… It’s just like… It’s like turning a blind eye to to all of your other growth opportunities.
Den Delimarsky: Yeah.
Asia Orangio: It’s literally leaving money on the table. And conversely, to sometimes to a detriment by only focusing on acquisition, you could also be creating a very expensive business to run. So it could also be setting cash on fire in the front yard. So another really fun metaphor.
Den Delimarsky: I love this. And so personally, what got you interested in growth strategies and troubleshooting growth? What was that catalyst that helped you decide that this is something you want to build a career around?
Asia Orangio: So when I left my last in-house, my last full-time in-house role, I was head of marketing at a VC-funded startup here in Atlanta. And I had the idea of, well, what if I offered my marketing experience without being full-time? And so this is, you know, the super classic example of a marketer basically just being like, what if I just consulted in freelance for a while?
Den Delimarsky: Right.
Asia Orangio: And that’s basically what I did. I had a couple of opportunities on the table, but I really just wanted to know like, what would it look like if I were to just go on my own for a while and working with the very first few companies that I worked with… I worked with a few, I mean, most of these are PLG SaaS companies. Most are bootstrapped and working with some of these founders, it’s funny cause like they, they would hire me for like, we need help with marketing. And I’d be like, okay, well, that’s what I do. Let me, you know, let me go in and like, you know, do the thing. And what I would find is, it’s true that they needed help with marketing.
That wasn’t untrue. But what we found was even if I were to triple their funnel, like even if I were to triple the amount of trials that they got, they wouldn’t be able to convert them or retain them. And sometimes both. Like there was one scenario actually where I worked with a very early stage company. And they were, they had just come out of launch and typically with launch, you know, you have the big spike and then it’s totally flat and everything’s dead and you have to figure out how do we, you know, do the thing and make the engine go again. And I came in right at that, you know, they had their peak and then it was in the trough part and I’ll never forget. We were generating demand. We were capturing demand. We were getting trials. We were getting leads. They weren’t converting. And then on top of that, if they did convert, they’d only stay for a month or two. So they’d immediately churn. And it dawned on me that If I wanted to work with these earlier stage or even bootstrap companies that it’s actually not just marketing. You have to have each of these pieces running in order for you to have an effective SaaS business. Otherwise what ends up happening too is founders will invest in marketing before they’re, I don’t want to say that they’ll invest in marketing before they’re ready. They’ll hire someone in marketing before they’re actually ready.
You’re always going to make investments in marketing, of course, but they’re they’ll hire someone before they’re actually ready to, and then end up having to let that person go because they realize really quickly, oh my gosh, the rest of the funnel doesn’t actually work. We’re not making any money off of this. And if they can’t afford to have that person, then, you know, it sucks for that person. So it got me thinking, if I could learn growth, could I offer this as more like fractional growth services and help teams navigate though, you know, what comes first, what comes when. And after they get established, troubleshoot it because growth will absolutely slow down.
Like you’re going to have times where you hit ceilings. And how do we figure out what’s actually happening? So that’s how I started. That’s how I got into it. I worked for a few companies trying to do more marketing services, and then very quickly realized, oh, not everyone has it all together across the whole funnel. And at the time, because I was positioned as marketing, it it felt awkward to be like, well, you should be thinking about activation and retention and blah, blah, blah. So then I really moved more into growth work. Some people also consider this to be more product marketing work, but that’s how I expanded into that.
Den Delimarsky: So you worked at VC-backed startups. What was the point where you decided that, you know what? I can actually make this a business. So you found the problem. You found based on your insights that a lot of companies struggle with this particular piece of kind of the growth engine, where it’s like they they’re either not looking at it comprehensively or they’re looking a little bit too, too broad. How did you personally decide that, all right, I can quit now and I can start my company.
Asia Orangio: Hmm. You know, it’s funny. I’m one of those marketers and this is a very common experience, but I’m one of those marketers who, like on the one hand, like, yeah, sure. I, you know, finger quote, like decided that I was going to do this. But the reality is that I experienced layoffs and I experienced, you know, in this particular case, the company that I worked for. They had to let their entire go-to-market team go. And I didn’t have a super long stint there. it wasn’t like I think I was there for about six months, but it was eye-opening. It was one of the first and technically second experiences that I had where I was like, oh, just because I have a head of marketing title doesn’t mean that I’m safe.
And that was the second time that it actually happened. The other company that I worked with also had a series of layoffs. That was a scenario where the business unit actually… Like, I worked for a business unit within a startup and that business unit was shut down. So it was just really, it was interesting. So in a way I kind of felt like the the entrepreneur life chose me.
It wasn’t an idea that I had until my last in-house role. I got out, I’m entertaining, you know, different full-time in-house roles. And I met a few growth and marketing consultants and I was like, you know, maybe it’s actually better for me if I work with companies on like a part-time or fractional basis, so that way I’m not as risky for them to invest in, and also it’s less risky for me as well. And it just so happened to work out in in the best way possible.
Den Delimarsky: So on another podcast, you did mention that you had at the time a mentor that kind of discouraged you from starting your own company and they kind of… were advising you that maybe you should consider kind of sticking around. And you use the term in-house, which I’m assuming is working inside the company full-time. That is not your company. And so you’re encouraged to stay and work in-house for some company, reach some higher level of you know executive via CMO or VP of marketing, VP of growth, and then make the transition.
Asia Orangio: Right.
Den Delimarsky: What led you to basically, I don’t want to say discard that advice. It’s a little bit too rough to describe it, or more like, say, you know what, that’s great. Thank you, but I’m going to do it anyway.
Asia Orangio: Oh, that’s so fun. I love this question. What led you to, you know totally defect and do the opposite. It’s funny too because I still love this mentor. This mentor was responsible for me getting into tech in the first place. I couldn’t help but weigh the feedback that I also got from other people. And I think to be fair, I think this mentor had a point. I think that they certainly had very strong points here. Even now, some people may look at me and see success, but I still have insecurities about never having had like a full-time VP of marketing or CMO job.
Of course, so in a way, I think in some ways this mentor had a point. But what made me say I still have to go and figure this out for myself, I was looking at all these job opportunities and I felt nothing looking at them. And so that to me was a sign that maybe I should just freelance for a while. And then the other thing was actually another mentor, and something that they said, and it was, you know, I was weighing, do I start my own business or do I go back in-house, which you’re right. And so that’s what in-house means. You’re working for… Like you’re a W-2 employee for a company that is not yours. And something that he said was, you know, he was like, Asia, what is an MBA worth at Emory University, which is the university in Decatur, down the street for me.
And I was like, God, it’s probably like 180K. It’s like some astronomical number, to me at least. And he was like, okay, so the opportunity cost of you not getting your MBA is you know let’s say 150 to 180K. Starting your business is basically you getting your MBA for… What’s your pay cut going to be in the first X years? And so when I put it that way and when he positioned it that way, when he said starting your own business, he was like, you’re going to learn more starting your own business than you may ever learn getting your own and getting this MBA at Emory and spending this money.
And when he put it that way, I was like, oh my gosh. And it hit me like, oh, maybe I’m actually saving myself some money by doing this. Now, obviously, this is… When was this? This was 2018. So 2018 numbers, little the economy was different, the world was different. And not to say that like getting your MBA is not a good idea, but at the time when I was looking at the opportunities that I had in front of me, going back to school was a thing I had thought about, not seriously at least, but it was an option.
And yeah, I just was like, you know what, maybe going on my own for for a while, we’ll see how long it lasts, Maybe I come back in two to three years with my tail tucked between my legs. Maybe I won’t, but I just need to see where this takes me. And I’ll be honest, I’m so glad I did. I’m so glad I did because I think the world is even bigger now that I’ve done it. I think for me specifically, the world might’ve been a little bit smaller if I hadn’t.
Den Delimarsky: I also love that comparison because you mentioned earning the MBAs several times over. So did you learn more through DemandMaven than you did through an MBA is the question?
Asia Orangio: The world may never know. I don’t have an MBA, so I will never, I won’t know until I get one, but yeah.
Den Delimarsky: You’re a practitioner. That’s, see, that’s the difference. Like if you think about MBA for a lot of it is very theoretical. Like here’s how you should be doing things, right? Here’s how on paper this should work, but you’re practicing the craft.
Asia Orangio: Right.
Den Delimarsky: You’re actually, you know, boots on the ground, getting things done.
Asia Orangio: Exactly.
Den Delimarsky: And I think that, that experience is much more valuable than just a paper that says like, yeah, you know the theory.
Asia Orangio: Right, right. Like, you know how to think about corporate strategy. I would say from next February will be seven years of DemandMaven. And when I think about everything that I’ve been able to experience and accomplish and achieve and do and see and learn, I, yeah, I just, I mean, MBAs, I think are like, what, two years, most programs at least.
Den Delimarsky: Yeah.
Asia Orangio: Yeah, I would have done this. I would have done this, you know, four more times over but and I really don’t regret it. Now, of course, there’s certainly the opportunity for me to go back and get an MBA, but we can do that. You know, that’s in the future. We can do that later if we really want to.
Den Delimarsky: Yeah. MBA programs are not going anywhere.
Asia Orangio: Right.
Den Delimarsky: They’re still going to be there regardless of who’s working on what business, but in terms of you finding the essentially fit that DemandMaven is a viable business. What was the pivotal moment for you were like, all right, clearly, I can make money with this and this can sustain my lifestyle and this can grow and become bigger and better for my customers for myself for my family. What was the moment?
Asia Orangio: Yeah. Ooh. Interesting question. So I would say it was about end of year two, beginning of year three. There was an incredible momentum around understanding the customer, understanding the growth levers that you can pull, understanding the parts of the business that you can ultimately… Could make progress with and and grow. And I want to say it was around that time and gosh, this was, that was year two, three. So it would have had to have been 2020, 2021. It was right around COVID. That I think was when, like I can’t even explain how much demand we had for our services. It just was like, it exploded.
And I was trying to figure out how do I meet all this demand? What I learned was DemandMaven is not the kind of business that very easily scales, not without a dramatic sacrifice in quality of work or without bringing on an equally experienced and driven co-founder. So DemandMaven is very much expertise driven. It’s an expertise business. So until I replace myself, it’s actually really hard to scale it. And believe me, I’ve tried all kinds of ways of doing this.
But at the time though, I was trying to figure out how do I… There’s this meme, this old meme that’s like, how do I hold all these limes? And it’s this guy and he’s like laughing and he has like a hundred limes. And I’m like, how do I hold all these limes? And he’s like smiling. That was, that was me, but crying. I was like, how do I hold all these limes? And I think that was when I was like, oh my gosh, I could probably do this for like another 10 years.
But what I’ve learned though over the last seven years-ish is businesses do evolve, markets evolve, and therefore businesses evolve. And I tell my clients this all the time because I have experienced it firsthand. As the market changes, you also need to evolve and to change as well, and you’ve got to be dialed into this. And sure enough, the tides changed. 2024 was one of the most challenging years I’ve ever had in my business. It wasn’t as bad as the first year. The first year was trash. 2024 was rough, and I think it was rough for a lot of agencies and consultants. It wasn’t just me, but I learned so much though from this year.
Den Delimarsky: Do you think, because you mentioned that kind of the high demand during the pandemic was somehow correlated to the pandemic because more people were, you know, I don’t know… I don’t want to be overly reductive and say like, you’re sitting at home, all of a sudden you’re signing up for all these services that do all these kinds of things. Companies decided to scale a bit more online. So of course they need more SaaS offerings and they need to figure out how this works. Do you think there’s any correlation there?
Asia Orangio: Absolutely. Because of the market forces that happened in that two to three year timeframe, the customer markets also changed. My clients’ industry sector has changed, but then also their customers changed as well. And so what I think what was happening was there was a sudden need to like, oh my gosh, we have to learn about the customer. Like we don’t know anything about our customer.
And I think the pandemic kind of forced everyone to come face to face with that because they kind of realized their pipelines changed and then for some, they were almost like mitigating risk. They were like, oh man, we could disappear tomorrow because the market has changed and we have no idea. And so I think there was a combination of founders who were like, oh my gosh, we have no idea who our customers are, all the way up to founders who were like, and we don’t know who our customers are and we’re seeing it reflected in our pipeline. It’s like fundamentally changed. One of my absolute favorite projects that I worked on, I actually ended up working on for three years and I was essentially a fractional CMO, but I’ll never forget - we started February 2020 and their business was in vacation rental management.
Den Delimarsky: Oh, that’s perfect timing.
Asia Orangio: Oh, perfect timing. So when March came around, pretty much all travel stopped. And when that happened, their customers freaked out. So churn basically happened, like massive amounts of churn. The team had to work extremely hard to recover and keep those accounts. And I distinctly remember being like, LOL, joke’s on me, this is going to be a bad project because how are we going to survive this? And they’re probably going to have to cut me like immediately. And then joke’s on all of us, because that actually didn’t happen. We ended up recovering and then we tripled. We ended up getting to a few million ARR and then we eventually exited.
Den Delimarsky: Wow.
Asia Orangio: So yeah, so it actually ended up being a little bit of like a, oh, it all worked out very well for everyone. But at the time it was terrifying. So yes, I do think it was.
Den Delimarsky: Despite the pandemic.
Asia Orangio: Yeah, yeah, survived it and I would say overcame it and at the perfect time exited.
Den Delimarsky: Wow, that is a great case study for how, despite the obstacles, you can still overcome them and be successful. For your own work, do you think your previous experiences at, again, like the VC-backed startups that you called out earlier, did it shape in any way how you approach the work at DemandMaven?
Asia Orangio: Absolutely. Absolutely. The biggest thing is I really learned to value being strategic. What I found from the VC-funded experiences that I had was there’s, and and this is still warranted and I want to make sure it’s really clear to everyone listening. When you’re VC funded, you have to execute and you have to execute fast. It needs to be the like the DNA that you live by. But what I also discovered is sometimes, not always, but sometimes there are scenarios where that level of just rapid execution sometimes can put you in a corner that is really difficult to get out of, and you will hit ceilings really quickly.
In my first VC-funded role I was head of demand gen, I was in a scenario where it was all about just mass execution, like let’s do as much as possible as opposed to measuring twice and only cutting once. And that to me is being a lot more strategic and choosy about where we put our energy because the budget was limited. We didn’t really have that many resources. And it really taught me that like, oh, spraying and praying doesn’t always work.
And like, spending any amount of money also doesn’t work. Not always, at least. Maybe if you’re really lucky you’re in the right place at the right time, you can just spend and not have to worry about it. But in our scenario, it wasn’t that way. And then also, I learned about things like what is the executive presence that you have to have, even if you’re not an executive? And technically I wasn’t an executive per-se. I wasn’t like a VP or chief, but I learned that, oh, like the way that I show up matters. And when I started DemandMaven, that was one of the things that I really wanted to work on. I treated it like it was my MBA. I actually have a business coach and that’s what we joke about all the time. We’re like, how’s the MBA going?
And I’m like, well, seven years in, haven’t graduated yet. But those are the things that I wanted to work on. Yes, absolutely. When I think about how I approach my work now, it’s all about balancing strategy and execution. We’re not an execution house. We’re not an agency. But When we work with founders, we have to execute. We can’t just talk about this. We have to, you know, get going and get moving and do the thing. And we can help with that process, but there needs to be boots on the ground to actually do it. So so yes, definitely.
Den Delimarsky: So if you boil down this seven year MBA into things that you’ve learned personally that are key to you, now that you know this, what would those be? So you mentioned executive presence being one of them. Then I feel like that’s definitely one of those things that’s underestimated. Like the power of executive presence is underestimated because how you show up does matter. And no matter how much you wanna think like, oh, I’m this genius. I’m just gonna show up and solve your problems. Doesn’t matter how people perceive me. It really does. It does quite a bit. Other than that, what were the key lessons in your experience?
Asia Orangio: Yeah, there’s so many. So I’ll expand on executive presence. There’s also how you communicate ideas, how you get people on board with the way that you’re thinking and like what you’re seeing. The other thing I’ve learned a little, honestly, the hard way, the first half of DemandMaven I’ve learned this certainly the hard way, but ultimately, businesses aren’t hiring us for research. They’re hiring us to make progress. So jobs to be done is one of the frameworks that we use.
So if we were putting this in jobs to be done terms, their job to be done is not to do research, it is to grow their business. And one of the things that I have learned is how do we ultimately position the work that we’re doing.
And any executive is going to have this same exact challenge, and also I would say any contributor as well. So contributors, when they’re thinking about the work that they do, how do you position it to your boss? How do you position it to their boss? How do you position the work that you’re doing in a way that makes it clear that you are aligned with the goals. And when you’re not aligned with the goals, can you get really honest with yourself about that? How can you see when you are not aligned with what’s going on? And I would say that this is a craft that I’m still working on. I’m still mastering it. And I think for me, though, it’s just at different levels now. We work with even bigger companies now. And how we position the work to different key stakeholders and to different levels of organizations. That’s a skill that I’m still refining and honing. There are other things too, both from the practitioner sense, but also more from the consulting sense of, like, how do we think about structuring engagements? How do we think about operationalizing those engagements? How do we think about delegation? It’s not all on me. And like what’s the team that I build around me to help me do the work that I do? There are all kinds of lessons learned there. Then also too, how do you partner with your clients? What does that look like?
So many different things there. And then I think when it comes to more of like the hands-on marketing growth product work, I have learned that over the years, it’s… I don’t want to say it’s like not an excuse to not know things, but my insatiable curiosity is a a good thing I’m finding because the more that I learn about product management, the more that I learn about… Even within growth, also within marketing, the more I’m able to do just better work overall and have better conversations, have more productive conversations. There’s so many different directions I could go into, but yeah, there’s been a lot.
Den Delimarsky: So it is worth it as a seven-year MBA. It definitely seems like the way to go. If you really want to learn, learn by doing.
Asia Orangio: Oh yeah.
Den Delimarsky: I wanted to zero in on something that you also called out and that is scaling yourself and learning how to delegate. And you kind of talked about it earlier where you were finding a way to replace yourself as kind of the, not necessarily the CEO, but you have CEO things to do and there’s a lot of ground level work that needs to be done. And as the company grows and as your scope evolves, you can’t do everything yourself.
What was the point for you where you realized that, yeah, I can’t do this myself. I actually need to hire people and scale because it’s hard to give up control. It’s hard, especially when you have your company is your baby. You’ve built this up. You think you’re the expert. You think you have, you know, the levers and the mechanisms to control this. And now you need to say like, and somebody else can now help me build this and I have to trust them. What was that for you?
Asia Orangio: Yeah, two things. So the first was that that was around like year two, year three. And it was in the similar, like in that same growth spurt of “I can’t hold all these lines.” In that same timeframe, that was when I was like, okay, I’ve… Something has to, like something’s got to give. I can’t keep going this way. So right around year two, I brought on a research lead and it wasn’t called this back in the day. It was called something else. I think it was like marketing coordinator.
I can’t remember exactly what we called it, but it was essentially a research lead, someone who I could pass interviews to. And then also eventually someone who could help me build deliverables and this was the first role that I brought on. Honestly, it was purely because of scheduling and just human bandwidth. Qualitative insights gathering is part of every project that we do. It doesn’t matter what project we do. If we do activation work, if we do retention, monetization, if we do expansion work, it doesn’t matter what it is.
Qualitative is part of it. And if I had five projects going at one time, all of those have five to ten interviews each that I’d have to do. And it just very quickly, it just was like, I literally can’t hold all these limes. Like all of these interviews are not going to fit on my calendar all at once. So I had the “aha!” moment of like, okay, I’ve got to give this to someone else.
And when it comes to bringing in other researchers and interviewers, that I would say is the most successfully delegatable thing about demand management. As long as you have the right requirements in place, you have the right SOPs and processes, and and also you’ve got the right person in the right seat,
It is actually… It’s amazing. It’s one of my favorite things about what we do is getting to work with other smart interviewers and marketers, people who learn jobs to be done and other styles and types of interviewing and getting to talk to them about like, what did you hear?
Like, what did you see? And it’s actually at a place now where it’s not totally hands off. I actually attend these interviews as well. I just don’t run them and I can sit back and just listen and it’s, oh, it’s the best. Actually, it’s one of my favorite parts of the process, working with my team and the client on what did we hear. This actually is another big key insight over the years. Your work goes so much further, so much faster when you have people on board from the beginning.
This is going to sound really obvious when I say it, but we used to go off into a hole and do our own research and talk to customers. Then we come back to the founder and we’d be like, hey, here’s everything that we learned. Here’s all the research that we did. Here’s everything. And they’re just like, okay.
Over the last year, two years, we’ve actually changed that to include them in the research process. They don’t interview, they just attend, but we do debrief after and we discuss what we heard. And we find that in terms of the path to execution, teams and founders are way faster at executing if they get the insights upfront and they hear it live. It’s just like, no one’s gonna go back and listen to a recording. So as, I guess, growth consultants, we’ve had to figure out how do we motivate people to take action and making them attend the interviews hands down the fastest way.
Den Delimarsky: You know what, all of this resonates with me as a product manager because every time I’ve done customer interviews and you do that, you know you work hard to recruit the customers. You interview the customers for an hour - each customer, you have the recording, you have this email and email report that says, here’s all we found, here’s the product. And then nothing gets done because they’re like, oh, cool, thanks.
Asia Orangio: Not a damn thing.
Den Delimarsky: Appreciate you doing the research. Like here’s a thumbs up and we’re going to move on with our product anyway. But bringing in the stakeholder in the room and saying, just just look at what they’re doing. Just watch them. That is such an effective way to change minds that no report will ever do. Like, be in the room.
Asia Orangio: Nope. 100% agree. We noticed such a stark difference that it’s now like we actually charge more when when the teams don’t want to participate in the research. We’re like, okay, well now it’s increased by this much. We will give you a better rate if you do this with us because done for you is great. Don’t get me wrong. I do think done for you has a good has a place, but done with you is like… It just hits different when you hear the customer firsthand or the user or the prospect, whatever. It just makes you want to change. Change management is one of the most challenging parts of any growth work that we do. One of the things that we do know is, yeah, we include them. UX interviews are similar. Nothing hits quite like a UX interview. Nothing is more painful than watching someone navigate your product. And this also changes it changes minds and hearts very quickly about what should get done. And it’s not as much of a debate.
Den Delimarsky: Yeah, because then you were ending up with like, oh, no, it’s not confusing customers. Like, nope, they don’t understand how to use this.
Asia Orangio: Right. Yeah. They’re clicking the wrong button. Oh they’re not even opening up your little tool tip or whatever. They’ve skipped over this entire section. Totally. Yeah. And they’re like, Oh my gosh, how do we make this more obvious or clear or whatever? And yeah, no, I love it. I love it though. Those are the things that I live for because it creates change.
Den Delimarsky: Now let’s talk a little bit more about the work that you’re doing and because we talked a lot about different aspects of your career, how DemandMaven got started and all the kind of aspects around it. You work with a lot of founders, you work with a lot of folks that run companies in terms of growth strategies. What are the top mistakes you see folks do?
Asia Orangio: I think the biggest one is having analytics debt. And I’m going to say, I’m going to say like big analytics debt. Everyone has some sense of analytics debt. Like there’s going to be a lot of stuff that you can’t measure or is not perfectly attributable. But I think the biggest… I guess it is kind of like a red flag. It doesn’t mean that we wouldn’t work with this company. It just means that this is a problem. We got to solve this. But to me, the biggest like, do not pass go, don’t collect $200, is when there is very little tracking at all, analytics-wise, and this is very common. And I think there are some companies that they just get to a certain size. They never think about product analytics, or like I think most teams think about marketing analytics, but many of them don’t think about product analytics hardly at all. And so, by the time that we get into growth work and we can’t even measure what’s our new user retention after you know within 24 to 48 hours and no one has the answer. Or like there are some companies still that are rocking with no subscription metrics.
So what is your net revenue retention at 12 months? We have no idea. Those are the types of things where it’s like, all right, guys, we got to get some data around this. I think if you’re trying to invest in building out a growth engine and you have massive analytics debt, it’s just… It’s going to be really painful. So that’s something that you have to, a lot of people want to put the cart before the horse, but you’ve got to put the horse before the cart in this scenario. So I’ll say analytics debt. I think when it comes to… I don’t know if it’s a mistake as much as it’s a pitfall. I think it’s a like when people forget that if you make a change in your go-to-market strategy, it likely has an impact on other key areas. So for example, if you fundamentally change the market that you’re targeting, it might actually have a pretty big impact on both your channels and your model.
And vice versa, if you dramatically change your pricing, for example, or you dramatically change your model, and it’s not super duper aligned with your core target segments, you may attract an entirely different market. So it’s like, forgetting that those pieces are connected is another pretty big pitfall, I find. It’s not as common, but every now and again, I’ll work with a company that’s like, they’re completely overhauling pricing, but the new pricing is not at all aligned with their ICP, and so then it’s a shock later when like revenue goes down or whatever. And so it’s like, well, like let’s just make sure that these are all aligned and that they all work together. Other things I think are… It really has to do more with when you’re in the actual execution process.
With any growth strategy, this is pretty common and is still a challenge I think that a lot of businesses are trying to solve today, but just creating silos. And very unintentionally creating silos, whereas I think a maybe more fast-moving growth team is very aware and intentional about closing any potential silos or gaps. So marketing and product need to actually be speaking together. If you have sales, they also need to be invited to the go-to-market table.
That’s a really easy one. But then there’s even within marketing, like the acquisition team isn’t at all talking to product marketing, and then they’re not talking to… It’s just so easy to have that happen. But yeah, those are just some quick ones that I see at different scales of businesses.
Den Delimarsky: In terms of driving accountability, right? It’s like you said, it’s easy to do the research. Well, not easy. Again, I’m overly trivializing it and should not be doing that. But the research is done, somebody can go and recruit the customers, do the interviews, drive the conclusions. How do you actually drive accountability so that the companies that you’re working with, the founders, the product managers, the marketers, actually act on the insights and drive change. So the work that you’re doing is not going just in some, you know, pit somewhere where somebody’s like, yep, yeah this is where all the research goes. Thanks. What’s the what’s the process for that?
Asia Orangio: From a service model perspective, the easy answer is this is where retainers come in. And we’re we’re basically hand in hand with the team, working with them on implementation. But I think like if I were to think in a non-consulting way, so there’s a few mechanisms that we use in terms of like communications. The first is trade-offs.
We talk a lot about trade-offs whenever we do any amount of growth work, especially if there’s like a more robust go-to-market team. There is a head of product, there is a head of marketing, and maybe the marketing person has a team, maybe the product person has a team. Sales is included in this as well. The way that I position it is I think about it like, yes, like you could certainly spend X dollars here, but here’s the pile of money that we could get if we were to spend our energy here.
The same thing happens from more of a top down perspective. So I’ll spend a lot more time with the CEO and the founder, illustrating those exact trade-offs. So like, yes, you could certainly spend an extra 10K per month on ads or whatever, or we could double this activation rate because it’s pretty low right now, and we could literally triple our pipeline. Those are the types of things that I that i help people see. When it comes to any type of growth project, if we’re not clear on what the trade-offs are, it’s really hard to make a decision. From a communications perspective, I talk a lot about like yes, this is a path that you can take. But here’s the opportunity cost. Here’s what now we’re going to sacrifice. And then vice versa, I make a lot of comparisons. I compare different paths a lot.
And I make it really clear, like here’s what is ultimately measurable. And to be fair, some opportunities are unknown. We might not know exactly like what the lever is going to be. Or can we quantify it? We might not always know. But as much as we possibly can, that’s what I help teams see as well. And then usually if it’s a more quantitatively driven team, usually that is enough for them to be like, oh shit, yeah, it doesn’t make sense to put energy into this because we could literally just focus energy on doubling this part. And then that would be a faster path to growth. Now, obviously, we still have to do it all. But at least prioritization wise, we we start there.
Den Delimarsky: I really like the framing around trade-offs because that’s something that stuck with me from one of your previous podcasts where you mentioned, you know, if a founder or somebody who’s looking at customer input, they need to understand which customers am I listening to? And something you called out is that paying customers should generally take priority. And that is because those paying customers made a trade-off. They paid you. And like that framework on trade offs, like somebody has to make a trade off, what the trade off is, and that determines a lot of the priorities, is super helpful.
Asia Orangio: Yeah, I’ll add to this too, because one of the one of the ways that we also now determine growth opportunity and also prioritizing growth opportunity is, yes, paying customers take precedent. But for every control, we do need to understand the other variables. So for example, paying customers are also survivors. They’re subject to survivor bias. They’re the ones who made it. So we also want to make sure we understand people who don’t make it.
And we’ve got to decide, are they qualified? And if not, OK, fine. Why? But if they are qualified, why did we lose them? Like what happened? And what’s in our control? What’s not in our control? But yes, the paying customer, yeah, they made a trade-off. They paid you money. And that means something. It means a lot, actually, especially for early-stage companies.
Den Delimarsky: And so how do you go about delineating… You know, I want to say there’s customers that are paying that did the trade off. There’s customers that are, let’s say they’re on the free tier. They can upgrade to something else. And there’s, what’s a good way to call it without being derogatory… Or like freeloaders, I don’t know, people that are just using the service for free and they will never pay you. They’re just going to stick on a free tier forever. What’s the delineation like?
Asia Orangio: Yeah. So there’s a couple of ways that we could think about this. And truth be told, the only real way to know is to talk to those people and to understand. Is this someone who is trying to get the most value for as little as possible? Some people may consider this, you know, like, are they trying to take advantage of the platform or not? Or is it more contextual?
And actually, there’s something about our acquisition or whatever that is attracting like this type of user. And also, therefore, are these maybe potential champions to get closer to the actual type of buyer that we that we really do want. This is really tough, and I think like even companies at scale are also still trying to figure this out because ultimately, especially if you have freemium, you really have to have a huge market to make that work.
Just financially, monetarily, like all the things. And I think when it comes to freemium in particular, you almost have to go with a little bit of grace and goodwill and benefit of the doubt while also still being, I think strategic about, okay, well, they’re not all freemium users are created equal. So which ones are the ones that champion the product and get us, you know, get us closer. And there is also the question too of are these people qualified, but they’re not paying because something about our model is not optimized. Like there’s so many different potential opportunities there. But I would say like you almost have to kind of think about it. Like you have to be curious. I think, if you have freemium, you probably have a lot of people using the product and aren’t paying. You ideally have a conversion rate of like two to three percent into paying. That means that 98% of people might not ever pay. You have to understand that 98% because it’s just impossible to make a judgment off, you know, off of the face value.
Den Delimarsky: It just sounds like you should not be doing freemium because that that’s just… There’s better ways. It seems like it though.
Asia Orangio: If you’re a bootstrap founder, you know, it’s so funny, Rob and I actually, Rob Walling and I have have similar views on this and also slightly different views, but I want to say we’re mostly like, I feel like we’re like 90% overlapped on this. Yeah, I never recommend freemium honestly to any bootstrap founder, but it’s just because the market size that you have to have and the go-to-market investment that you have to make to make it work is substantial. And I don’t think a lot of founders think about it that way.
I think they think about it like, oh, you know, people will sign up and they’ll just, you know, they’ll tell others and it’ll be like, everyone always compares it to, what’s that company, DocuSign or no, the other one - Dropbox.
Den Delimarsky: Yeah. Dropbox.
Asia Orangio: Everyone’s like, Oh, it’s going to be like Dropbox. They’re going to sign up and it’s going to be like a flywheel. And it’s like, I’m sure, but you need hundreds of millions of users for that to work. And then you have to build the engine to make them come and do that. So like it’s it’s a lot. It’s a lot. It does work, I want to say, for ironically enough, the same conversion rate of freemium, which is like 2% to 3% of bootstrap founders, I think freemium works for.
Den Delimarsky: Yeah, it’s interesting, too, because a lot of this also hinges on the idea of a PLG motion of product-led growth was like, oh, well, you know what, like, it’s free. But then there’s all these bells and whistles that we can throw in that will just drive, you know, as long as you use the product, you constantly are like, in this ecosystem that we build, you’re eventually going to upgrade, you’re eventually going to pay us money. And sometimes that happens, like in the case of Dropbox, where it’s like, oh, sure. Yeah, I’ll give out referral codes on Twitter. Because, you know, that’s how I get more storage. And sure, I’ll use Dropbox for all my stuff. You kind of drive that growth, but oftentimes, and especially like except for bootstrap founders, we don’t have the same reach of Dropbox, you don’t have the same, like VC funding to throw millions of dollars on marketing everywhere so people know about you. That success is going to be much more elusive.
Asia Orangio: Absolutely. Yes, it the resources required are pretty big. Unless of course you have endless time, upon which case I would say go for it. But like yeah, if you don’t have endless time, if you need this to be revenue generating, maybe freemium is not the vibe. But it depends, obviously.
Den Delimarsky: Of course. Now you live and breathe quantitative and qualitative insights. That’s actually something that I’ve seen before where folks are usually split in two camps. Somebody believes that all we need is quantitative. If only we can throw more analytics, more instrumentation, we’re going to look at the telemetry and we’ll figure out what customers want. And then there’s the other camp that says, discard all the data, all these numbers are irrelevant, it’s all trash. Just go talk to customers, find out what they want and build that. You are in the position where you have to join those two worlds. How’s that?
Asia Orangio: To be honest, it’s really my playground. This is where I’ve always lived. I have always been the marketer, historically who has wanted both. Because I believe in both both. You need both. Quant tells you what happened, but it cannot tell you why. Qualitative tells you sometimes why. It gives you a lot of information about, you know, the who, the where, the when. It may not always tell you what. And that’s why I fundamentally believe that you need both. I don’t think you can have one in isolation of the other. Both of these are stories that give you a rounded full view perspective. And I will say I’ve never really had any pushback either way around combining both of these. I do think sometimes clients will, they’re like, oh, but like, do you need to do qualitative?
Usually it’s qualitative that they’re actually very like, I don’t know. Like we do, we talk to customers all the time and they’re not as excited always at least to do calls unless they know for a fact that like, no, we know we want this. Usually I think there’s a comfort zone with quantitative and being able to just look at conversion rates and being able to just guess, oh, this is why it’s happening.
But that’s, but that’s exactly what’s happening is you’re just guessing. You don’t really understand. Like, what is that? Like, why is this happening? And that was always to me the biggest opportunity for someone to come in and kind of show, no matter what problem you’re trying to solve, you need both. You have to have both.
Den Delimarsky: I think in my opinion, the qualitative is harder. Because for for quantitative, what I just mentioned is like, yeah, you can put some instrumentation, some analytics, the metrics are more or less well defined for a lot of companies, like churn, retention, all these things are there, you know how to compute them, there’s tools that you can use to compute that.
Qualitative forces you to get out of the room, get out of the office and go talk to people and not just talk to them, but actually understand what they’re talking about, what their problem is. And to me, that seems much harder to do. And maybe that’s where I… There’s a lot of hesitation to like, oh, we’ll look at the numbers. We’ll look at the dashboard. That’s fine. We’ll figure it out.
Asia Orangio: Yeah, there’s also I think a little bit of fear too of running either a more structured research project or hearing from customers. So hearing from customers in the support sense is very different than talking to them from a journey perspective. And then nine times out of ten, that’s the perspective I’m bringing the table is like, what is the customer journey and what are the aspects of the customer journey we can optimize?
So I think there’s also a little bit of like, oh no, like do they actually like us? Or you know… So there’s a little bit of fear there too, but it is all overcomeable and also the benefit is far, like it far outweighs any anxiety around the actual process.
And it encourages teams to to continue doing it. That’s what I always recommend. It shouldn’t just be, you know, you hire DemandMaven, you do it once and then you never do it again. It’s no, like let’s continue to have these conversations in this particular way, because it does ultimately give us a different type of insight.
Den Delimarsky: Love it. Now, to wrap this up, I have a few questions that are much more tailored about your recommendations for the future and that for any founder, anybody listening to this, what is your favorite resource on growth strategy? It could be a book, podcast, video, documentary, I don’t know. What’s what would that be? What do you recommend?
Asia Orangio: You know, the, the resource that I am still like in awe of even now is, is it Lenny’s? It’s Lenny Rachitsky, of course, but is it Lenny’s Podcast?
Den Delimarsky: Yes.
Asia Orangio: Is that the website?
Den Delimarsky: Yeah. Lenny’s Podcast. Yep.
Asia Orangio: Lenny’s Podcast. Oh my gosh. So Lenny has been an inspiration for me for several years now. And when I think about growth, product management, and also he gets, he gets a little bit into marketing too.
I’m always in awe because I’m just like, man, like this guy just like really… He just really knows his stuff. And because of I think his just experience and expertise, he is also able to attract very smart people to kind of to talk about, you know, the things that they talk about. And so I would say if you’re not subscribed to Lenny’s Newsletter, like you would need to be you need to get on that because the gems that he drops on the regular is… I mean, the dude knows what he’s doing. And I, for sure I aspire towards his level.
Den Delimarsky: He knows the stuff for sure. Yeah.
Asia Orangio: John Cutler is another person who I admire and respect as well. So cutlefish, I believe is what his username is on SubStack. If I’m not mistaken.
And then the last person all throughout there is Jason Cohen. So this was one of the, I think he was one of the co-founders of WP Engine, but his writing, I like… Expertise aside, his writing is incredible and amazing. And I am always also in awe of people who can not just explain concepts or ideas, but to go deep and to cover topics in the way that he does.
But what I like about Jason is that he describes challenges that are unique to the founder. And so I always recommend his blog to, I think it’s A Smart Bear, asmartbear.com.
Den Delimarsky: I believe so, yeah.
Asia Orangio: Yeah, but anyway, I always recommend him to other founders.
Den Delimarsky: Lenny Rachitsky, John Cutler, and Jason Cohen.
Asia Orangio: Yeah, and now I’m actually second guessing.
Den Delimarsky: Love it.
Asia Orangio: That’s his name, right? I feel like that’s his last name. I know his name is Jason.
Den Delimarsky: I think so. I think it’s Jason, the WP Engine guy.
Asia Orangio: Yeah. Yeah. WP Engine guy. Yeah. Yeah, but we love him.
Den Delimarsky: Excellent. Now, if there’s one thing that you want folks to understand about growth strategies, what is that one thing?
Asia Orangio: That they are iterative. A lot of teams and founders. I don’t even want to say teams. I think this is really more a founder thing, especially if you’re a first time founder, especially if you are a technical founder. A lot of teams and founders expect to set a growth strategy to execute against it. You get it working and then you never touch it ever again. and it could not be further… It could not be more opposite in reality. I cannot tell you how many times I’ve worked with teams who or founders even who they get something going and then they’re like, and then it just stopped. And it’s like, well, did you do other things? And they’re like, no. And it’s like, well, growth is iterative. And it’s not just, this is it’s such it’s such a difficult concept to grasp. I think especially for the first time founder, but it’s not even that it’s iterative. It’s not just that it is iterative, but it is also that it is success by a million cuts.
Some people say death by a million cuts, but that’s like, we’re not here to die, obviously. We’re here to succeed. Growth is like success by a million cuts. You have to do a lot. It takes a lot and it’s incremental. It’s iterative. They all stack, assuming it’s all the right stuff. I think a lot of a lot of founders expect to do something and then see an immediate result at the end of the day or like a very clear, measurable thing. And it’s just not how it works. You have to make many multiple investments over time across several different key areas. And it’s not just marketing, it’s across the whole business. And when you get all those things going together, that’s when you see the like skyrocket growth, oh my God, now we’re like exiting and it was amazing. But until you kind of just accept that this is going to be a lot of different types of efforts across the entire business, you may fall prey to over focusing on just one thing and not the whole thing. And that’s I think where a lot of teams get in trouble.
Den Delimarsky: Also fantastic piece of insight. The last question that I have that I ask of all the guests on the show is if you think of an unconventional piece of advice for somebody listening to this and saying, wow, I want to build a career just like Asia did. I want to start my own company. What would that be? And it doesn’t need to be focused on just growth strategy. It could be something that’s coming from you personally. What would that piece of advice be?
Asia Orangio: This is gonna sound very Lisa Frank, but I was gonna say like, follow your heart because that’s really what I did. I mean, I’ve had an unconventional career and we didn’t even get into my first career, which is being a professional artist.
Den Delimarsky: Wow. We missed out. This is the… We should have started there. What?
Asia Orangio: I was a professional artist for about two, three years and that and then I moved into tech and I was like, cause you know, I need to make money. But no, I… Yeah, as cliche as it sounds you’ve really got to stay true to yourself and you’ve got to be very real and honest with yourself about what do you actually want? What are you good at? And what does the world need from you? And some people call this Ikigai, which is a Japanese word and concept of combining these four aspects of oneself to find like, here’s the thing that the world needs that you can get paid for that you do really well, etc.
I think Ikigai is something that is continually evolving. I think no two careers are the exact same. I think so many of us do kind of you know fall into things, but I think it’s because we’re really being honest with ourselves about what’s interesting, what’s exciting, what’s new, but also what do we feel like we could really come in and excel at. And that’s that’s been the guiding light that I think I’ve had my entire career. And even now, I’m going to start looking at my next fractional CMO, I guess we could say role, but this would obviously be through DemandMaven, but I’m ready to kind of do another three year gig with a company. Like I’m ready to do that again, especially since the company that I worked with for three years exited earlier this year.
And I’m kind of getting the itch of like, I think I want to help build a team again. And that’s kind of, yeah, but I’m following that for myself. And I think that can only come with like really knowing yourself and understanding those aspects of what you need and what you’re most interested in.
Den Delimarsky: What a way to wrap up the show. Asia, for folks that want to learn more about your adventures, the work that you’re doing, where should they go?
Asia Orangio: There’s a couple of places. I am on Bluesky. You can find me @asiaorangio. I am on Twitter. I’m mostly a lurker there, though, these days. I don’t post as much, but I definitely post more in Bluesky these days. I also, of course, you can find me at demandmaven.io. There’s all kinds of podcasts and content I’ve produced over the years that you can find. I do also have a podcast of my own, and then we also have a newsletter. But I would say go to demandmaven.io. It’ll all be there.
And then find me on Bluesky. Bluesky/Twitter/LinkedIn.
Den Delimarsky: And the podcast that you have is called In Demand. Am I right?
Asia Orangio: Yeah. Good memory.
Den Delimarsky: And we’ll link to that in the show notes, so folks can just, you know, you don’t need to look far. You don’t need to type anything. Just click the links and you’ll find Asia there. Asia, thank you so much for being with us on the show today.
Asia Orangio: Thanks so much for having me. Pleasure.
