Episode 30 Edited
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Richard Ellis: [00:00:00] Research conducted by the Content Marketing Institute found that most marketers, 68%, feel that it's more challenging to get a job in the field now compared to five years ago. And less than 5% of the two and a half million marketers in the US are VPs. Making executive positions highly competitive. Today, we consider some goodness around how to build an executive level marketing career in tumultuous times.
Richard Ellis: Welcome to some goodness where we engage seasoned business leaders and experts to share practical guidance and tips to help new and future C-level leaders maximize their impact. My guest today is Drea Armstrong, a dynamic marketing executive with a passion for simplifying the complex and driving real impact across organizations.
Richard Ellis: Drea is currently the VP of marketing at Kubit, where she's known for her innovative approach to growth marketing and her ability to [00:01:00] turn big ideas. Into actionable strategies with a career spanning leadership roles at companies like Three Flow Modern Hire Walla and Workiva. Drea has built a reputation for blending creativity with operational excellence.
Richard Ellis: She's led teams through major transformations, champion digital marketing initiatives, and helped brands find their authentic voice in crowded markets. Drea, welcome.
Andreya Armstrong: Thanks so much for having me, Richard.
Richard Ellis: So let's dive right in. You've led marketing at multiple innovative companies, right? And all of those I think were during times of change, and I'm just curious, when you look back over your earlier career, is there anything in particular that kind of prepared you to really be equipped for that volatility, that complexity that we're finding in today's environment?
Andreya Armstrong: For me, change has always been the constant. I've been in startups for the majority of my career, and so if one thing has been the same, it's that everything is constantly changing and evolving [00:02:00] and we're making business based on that fact. Innovation is the bread and butter when you're working in tech. I think for me personally, and around 2010 was when I first got into B2B SaaS, and I think really what normal.
Andreya Armstrong: Career trajectory is everybody gets in line and knows with the most experience, 20 years of marketing experience are at the top. And then those of us that are just getting started in a field, you know, we wait at the bottom. We all follow each other. And in 2010, all of these tools started to emerge. And automation was this drumbeat.
Andreya Armstrong: How quickly can we get to this? Key of automating this stuff and it was like the great equalizer. No one had 20 years of experience in these tools. So for me it was really that attitude of fortune favors the brave. It's those who are not afraid of the change, who lean into the new, who are like the risk takers to take that step and say, I'll figure that out.
Andreya Armstrong: Those are the folks that we see now as. Starting to lead departments and [00:03:00] lead in organizations. I think that leaning into the newness of all that these new tools have to offer was kind of a major springboard for me.
Richard Ellis: Yeah. So certainly as just the tech innovation accelerated. Right. Just from a business standpoint then that kind of drug along marketing tech.
Richard Ellis: Right. And that kind of change. And then I'm assuming that that then really kind of shook up the rules of marketing and how you market. What were some of those changes that you had to adapt to?
Andreya Armstrong: Yeah, it was really just the big piece that emerged that I witnessed was from doing it to proving it. This huge emergence of marketing tech and marketing operations that kind of came up in that 2010 to 2015 came from the need for marketing leaders, CMOs to prove the money that they were spending was impacting the business in a positive way.
Andreya Armstrong: And I think that's always been. An assumption that yes, marketing is [00:04:00] influencing, but it was always kind of a dust in the way, like feeling for that change and seeing it in dashboards and in numbers was this new requirement not just from the companies but from the investors and the boards that were driving them.
Richard Ellis: I see that a lot in terms of just that trend from maybe over rotation of activity to outcomes. Right. And there's been, you know, I think just the nature of marketing and M MQs to SQLs and SELs and all of that stuff, right? There's been a natural kind of measurement of KPIs or conversions, but not necessarily all the way to revenue impact, right.
Richard Ellis: That we're seeing now. And I think you were touching a little bit upon that.
Andreya Armstrong: Yeah, absolutely. It can't just be the vanity metrics of old this many followers, this many clicks, this many downloads. We're really being held now as marketing leaders to owning a bit of the business alongside a full partnership with the sales organization.
Andreya Armstrong: So it's no longer two [00:05:00] separate teams. It's a go to market revenue organization that has to work together. And have the data to back it up to show that what they're doing is active, actually working.
Richard Ellis: So that's from a marketing leader standpoint, you have to be prepared to, you know, kind of prove it right.
Richard Ellis: Back it up. But what are some of the other shifts you've seen just from a marketing leadership standpoint? I assume one is, you know, having to chart the course through which tech to use and what innovation to take advantage of. But what are some other things you would highlight just from a marketing leadership standpoint?
Andreya Armstrong: Yeah, I think really being a technical leader is. Definitely a benefit, but having that recency of remembering what it is to be in the weeds with the tactics and being fully aware of what it is that your team is, you know, uncovering and embarking on every day, and what roadblocks they're running into, and having that empathy as a leader is more important now than I think it has ever [00:06:00] been.
Andreya Armstrong: Primarily because we're moving at light speed on a lot of these initiatives, and when you get pushback from your team. Being able to sit in their shoes and say, okay, I kind of see that, and let's find a way around it. There's always a way around it. Let's work together. 'cause as a leader, your job is to remove these roadblocks.
Andreya Armstrong: Right. And I, I think another really important part is being on that strategic level with the organization, having a seat at the table on where the business is going. Not so much as a loud thought leader, but more as a authentic member of your market. And that time to really invest like my time into being where my audience is.
Andreya Armstrong: So whether that's on subreddits or LinkedIn groups or Slack communities that they have developed to solve their problems and lean into each other. Just being a quiet listener and an observer inside the market and then bringing that back to the organization, not just to like. Influence my messaging with authentic [00:07:00] problems, but also to influence the roadmap and talk to the sales organization and say, these are actually the people that are having these problems,
Richard Ellis: right?
Richard Ellis: We're
Andreya Armstrong: off a little bit on our target, or we're off a little bit on where we think this problem is the most prevalent, and that definitely has. Impacts on the marketing organization, but the company as a whole can benefit from that as well. Otherwise, you get into a pattern of following the competition and following others down the path that's already been paved and no one becomes the market leader for following.
Richard Ellis: That's right. I love it. I love it. Well, and one of the things I just wanted to highlight so the audience doesn't miss it, is, you know, we always talk about how important the voice of the customer is, but I, I love the phrase that you used. You, you need to be an off. Authentic member of your market. And that's not just asking, Hey, what do you want?
Richard Ellis: What do you need? But actually embedding yourself in that environment, in that market so that you can really learn from a different perspective perhaps.
Andreya Armstrong: Yeah, absolutely.
Richard Ellis: That's awesome. Well, let's kind of double click a little bit [00:08:00] underneath that leadership. I think one of the things you were sharing with our team is that you need to be, uh, willing to experiment.
Richard Ellis: A little bit and not all experiments pay off. Right. So what's your philosophy on experimentation and failure and Yeah. Any advice you have for us there?
Andreya Armstrong: Well, I think first of all, failure is so important, not just as a department or as a company, but as an individual. If you don't have that personal experience that makes the blood drain out of your face when you think about it, very, very difficult to bring that empathy.
Andreya Armstrong: And create a safe space for your team to be bold. They're going to be a lot more cautious if they don't feel like their leader is going to have their back if they make a mistake. But those mistakes come from trying new things and trying new things is where you know, you excel. I think from an experimentation, no one really knows what's working, especially in this super fast changing environment.
Andreya Armstrong: And if you're not testing. Again, you're just following the leader. You're just copying everyone else their guesses. So [00:09:00] I really look at best practices as more of a starting point, you know, not gospel. A lot of times it's like common sense. It's like, yeah, we should send emails Tuesday through Thursday between 10 and two.
Andreya Armstrong: That makes the most sense, right? But. Deviating from that and discovering your own best practices and changes. So often, what was best practice in 2020 doesn't apply today. What was best practice in 2015 was completely out there. In 2020 especially is all of the tech changes. I mean even things like email marketing.
Andreya Armstrong: Uh, it just, it was our bread and butter in 2018. Mm-hmm. And I don't know that it's working in the way that it used to, because those systems have evolved in such an amazing ways. I think experimentation is where the money's made. And as far as like when to cut your losses or when to double down, I typically do like a two to four week testing period.
Andreya Armstrong: Okay. If you're not seeing what you think should be an outcome. In four weeks, it's pretty safe to cut it and say, this isn't working, this [00:10:00] message isn't working, this channel isn't working. And if you are, the double down isn't just to like dump more money in or put more con, it's a tweak on what's working, right?
Andreya Armstrong: So, hey, this message has been really effective. Let's tweak it to a different, let's segment it up and split it up by. Industry and then, oh, that's really working. Okay, instead of doubling down on industries, let's tweak it now, do it by persona. And we're seeing a ton of really exciting, positive numbers playing around with those different experiments right now at Kubit, and that's been really exciting for us.
Richard Ellis: That's good. And when you think about experimentation, you know, it goes beyond just the typical kind of AB testing of a message or maybe a channel, or are there any kind of just interesting experiments that you guys have tried recently that either worked or didn't work that you would feel comfortable sharing?
Andreya Armstrong: Sure. I mean, it really, it's interesting. I think five to seven years ago, I would never have thought about doing my marketing campaigns on a weekend like businesses for [00:11:00] business days. And now the weekends are some of our. Highest performing ad days. It's really funny. We would've pulled that budget, or potentially, depending on the organization and the size and our budget, we would've maybe completely turned it off and said, no one in B2B SaaS is working on this on weekends.
Andreya Armstrong: This is not their time. That's not true. People are on their device all the time. They're consuming. Content. If it's keeping them up at night, they're downloading it in the middle of the night. Right? And then, so I think that's been a big wake up call for me, is even just the time of day that our audiences are participating in our marketing.
Andreya Armstrong: Places I would never have imagined.
Richard Ellis: That's interesting. Yeah. It reminds me of Astoria. Years ago I ran an inside sales team calling on doctors, and they found that if they left their voicemails or if they called during the week, they would either get blocked by the office manager or you know, it would go to voicemail or what have you.
Richard Ellis: But if they called Saturday morning, oftentimes the doctor was in there kind of catching up on paperwork and [00:12:00] he would answer the phone. And they would get them live and be able to tell their message and it wouldn't go through somebody else or potentially get blocked. And so that was interesting. And then just thinking about like my LinkedIn habits.
Richard Ellis: I mean, I'm busy all day. I catch up on the weekends. I'm like, well, let me go see what I'm missing on LinkedIn. And so you might be onto something.
Andreya Armstrong: Yeah. And it changes with audience. It changes with offerings depending on what you're selling people or marketings, people might have more appetite for something like that.
Andreya Armstrong: In times that didn't work. And that's where, you know, we've always done it that way. And best practice kill me. I'm always like, well, what's the harm? What's the harm in trying? And if it doesn't work in a month, we'll kill it. Got it. But I think, yeah, that's just a fun,
Richard Ellis: fun. Be willing to risk. Yeah. Be willing to try some new things, but then be intentional about cutting it off and moving on if you're not getting the pay off.
Richard Ellis: Well, let's transition a little bit into kind of the topic of the day, right? We talked about innovation and the MarTech stack and all of that, ai, right? Yeah. Everybody's [00:13:00] wondering about ai. Where does it fit? Where should it fit? How should we or shouldn't we be leveraging it? So while I have you, what's your perspective on using AI in marketing as a marketing team, et cetera?
Andreya Armstrong: Yeah, I think AI probably feels really daunting for a lot of teams who haven't started it yet, or it feels like a big mandate, like a big, heavy. Handed the board is saying, or the CEO is saying, or we're being forced to learn this and work it in to become more efficient as a team. And so it feels like another thing, another tool, another initiative that's like, put it in the backlog.
Andreya Armstrong: I'll figure it out. Your team at. Revenue innovations has heard me use this analogy like no less than five times, and I can't remember, so I can't reference where I heard it from, but I was at a conference probably 15 years ago and they said, there's a man and he's got this bike on his back and he's running down the road as fast as he can and he's just, he's working so hard, but he's gotta carry this bike.
Andreya Armstrong: And somebody comes by and says. Why don't you ride the bike? And he screams back. I don't have [00:14:00] time. I feel that way sometimes with these tools. Right, and especially with ai, it's take the time to weave it into your day and not just as an extra thing to add on to the end of your day. Another tool you have to log into another thing.
Andreya Armstrong: It should be woven throughout everything, right? It should be in your design. It should be in your content. It should be, you know, to me it's not replacing anything. It's giving you. The time to complete this stuff. You've never had time to do so. It's about speed. It's like it's those dreaded tasks. Need to reformat a workbook because it doesn't fit into this thing.
Andreya Armstrong: AI need to turn a messy brain dump into a brief to disseminate to your team. AI need five different versions of it. I need a Slack update so they know about it. Now I need an email so they can find it. When they ask me about it, I need to put it in Confluence so it lives on forever. Ai, here's my notes.
Andreya Armstrong: Give me 15 versions of it. I mean, these are the kinds of things that marketers have been dreaming of [00:15:00] doing forever, but that rounded out beautiful package of a marketing initiative has never been possible because we do not have time to do it. Even so far as customizing content, if you take the time and you invest so much blood, sweat, and tears into putting together this beautiful piece of.
Andreya Armstrong: Gated content, and now you have the ability to customize it 15 different ways for all these industries or personas or use cases with the help of AI and getting that done in a week where it would've taken huge marketing teams months to customize that across. Right. Right. So that's the way, and I have to shout out my team.
Andreya Armstrong: I am not the AI queen, I am the ai like. Learner. Right now I'm the student and it's a lot of unlearning, right? It's a lot of unlearning. The hard work that we've always had to, there's no way through it, but to do it kind of mentality. Killing that in your brain and saying, actually there's a shortcut and it takes no [00:16:00] quality away.
Andreya Armstrong: It just saves me six hours of retyping this whole thing out. Yes, and I think that's the real superpower, is it's about efficiency and time saving, and it gives your team the power to finish the job, not just start.
Richard Ellis: How can they leverage AI to augment their workflow, right? Create scale, create efficiency.
Richard Ellis: And one book that I read recently is COT Intelligence by Ethan Molik. And it's just a great overview of AI and where it. Fits in our world today, and really thinking of it as your personal assistant that's there to do all the grunt work that you don't want to do, and to automate repetitive tasks to speed you up and create efficiency.
Richard Ellis: And so I love what you were saying about you need to think about. How to just weave it into what you're already doing.
Andreya Armstrong: You little shameless plug on the Kubit side right now. I think really beautiful job of leveraging ai. When I joined, it was like AI is analytics [00:17:00] intelligence, not artificial intelligence.
Andreya Armstrong: Oh, I like that. The concept there was. We're doing the transparency work. We're making sure that the data is accurate, coming directly from the warehouse with no duplication, no ETL, like none of that stuff. The AI that we're weaving in with Kubit. Lumos is this helper. It's like, Hey, by the way, did you know that report already exists?
Andreya Armstrong: Or here's some interesting insights in your dashboard that you didn't see. Yes, it's that. It's that. Two. You know, that 20 minute work that you're like, do I really have to go digging through all of these reports and dashboards to make sure that this isn't there already? Right. So I have to try to describe in SQL what my Cubit RAI tool is taking care of all of that for you, which is exactly how it should be used.
Andreya Armstrong: It's just like, what's that task that you're like, oh, I have to do that again. You don't have to.
Richard Ellis: Right, right. And, and just the more you use it, the more you learn how to use it. I used to pride myself on being an Excel guru and knowing all the formulas and I can concatenate different things and use VLOOKUP to [00:18:00] do fancy stuff.
Richard Ellis: Right. Yeah. I don't have to do that anymore. I can just pull up Gemini or chat GPT and say, do this for me. Here's my dataset. Exactly, and I don't have to worry about, oh, I forgot that old formula.
Andreya Armstrong: I know, and it's almost a shame, honestly, because I tip a lot of pride in all of my really beautiful formula dashboards, and now to be able to say, you know, build this for me, or change the format, or, oh, I want all of this split into text to columns and pull out anything.
Andreya Armstrong: The reference is this, I mean, in 10 seconds. It's done. So I think that that's the magic of AI is not thinking about unique. Another thing you have to do, it's just the fast tracked everything you wanted to do.
Richard Ellis: And I think it frees us up and it frees up a marketing person to be able to apply their skills, their experience, yeah.
Richard Ellis: To their work, the business, et cetera, in a more efficient way, because they're not bogged down with some of the stuff that AI could do for them.
Andreya Armstrong: On that topic too, I think it [00:19:00] expands the skillset of marketers. So I'm a technical marketer. Which means if you ask me to make a flyer, you're gonna be hugely disappointed.
Andreya Armstrong: I cannot for the life of me design, but I can with the help of AI and tools like Canva that are making it so much easier now to come in and just be a. I don't know how to make this, show me how it should look, and also just simple things. I have a member of my team who does a lot with events and sponsorships and kind of more external facing, and with the help of chat, EBTI can be like, let's work on you building this email by yourself and HubSpot, some skills she's never, ever done before.
Andreya Armstrong: Right, but you walk through with the help of chat, GPT and I constantly will get content that's just, it's so long and it's so impossible to like consume. And I'll put it in chat GPT and say, put this in bullets like m in fifth grade and help me understand it and it will do that for me. And so I, I've find endless uses for it.[00:20:00]
Richard Ellis: That's so great. Well, we're almost out of time and I wanna, uh, ask you one other question and then we'll wrap up, and that is, marketing's changed and continues to change, right? Change is the new constant. Now, as you mentioned, I, I recently read a stat that less than 5% of marketers reach the VP level. And so, uh, you've had a stellar career and, and I know you're gonna go above and beyond and do more great things.
Richard Ellis: So, what habits, mindsets, choices do you think really set you apart or set you up for success that others could kinda learn from?
Andreya Armstrong: Yeah, thank you. I think the first thing to acknowledge is that imposter syndrome is very real. Those folks who are potentially thinking about leadership and feel that they might have what it takes to do it, but are skeptical about their abilities are probably.
Andreya Armstrong: The most fit to lead because they're the most self-critical, which I think is a really important thing to be constantly like evaluating your own performance is the sign of a really strong leader and the kind of leader that teams will [00:21:00] be happy working for. I think a genuine desire to fix problems to not.
Andreya Armstrong: Rely on the status quo and to be constantly asking questions with a desire to understand, not to poke holes, but to truly like, Hey, I really wanna understand why we do this. Why do we do it this way? Mm-hmm. And if nobody has a really strong answer, that's an opportunity. To find your place in building, bringing value to the company, which ultimately leads to that leadership role.
Andreya Armstrong: So I think it's a combination of learning, understanding, collaborating, and being empathetic, not only to, you know, to the company and saying, Hey, as a leader, I'm not just responsible for my function, I'm responsible for the success of the entire organization, but then also to those team members that you're bringing with you.
Andreya Armstrong: And that you're responsible for their success by making sure that you're creating an environment that allows them to grow to.
Richard Ellis: Right. So well said. [00:22:00] Love it. Thank you for that. Well, we are out of time and so we're gonna close with my closing question and you probably know what it is, if you listen to the other podcasts, any of them, and that is we love to just share goodness in all kinds of ways.
Richard Ellis: And so outside of what we talk today, outside of business, is there any kind of little goodness that maybe you've experienced recently that you'd like to share with us?
Andreya Armstrong: Yeah, I've, you know, from a work perspective, I've been really enjoying learning more about our audience and seeing myself 15 years ago in some of the data product managers that we're talking to and working with right now, and seeing the potential and the opportunity that they have to attach themselves to.
Andreya Armstrong: The value of like bringing data to the organization in a trustworthy way and then letting them ride that success, that kind of cooperative partnership between a tool that enables them. In the same way that marketing automation systems enabled me to become valuable to my company [00:23:00] and find my path, I.
Andreya Armstrong: That opportunity. Seeing that opportunity in the data personas that we're servicing is really exciting and I can't wait to see where we're able to take them. So that's been
Richard Ellis: great. Huge potential there for them personally and professionally. That's awesome.
Andreya Armstrong: Yeah.
Richard Ellis: Well, thank you again for being here. Thank you for your time.
Richard Ellis: I loved our conversation. I think we had lots of great practical tips for our listeners out there.
Andreya Armstrong: Wonderful. Thanks so much, Richard, for your time.
Speaker 3: Some goodness is a creation of revenue innovations. Visit [email protected] and subscribe to our newsletter.
