Alex Alexin, Head of Demand Generation at Insightful, shares how she found her way into marketing and ultimately into demand gen. She unpacks what demand generation really means today, beyond leads, and why data, analytics, and operations are at the core of effective strategy.
Learn how Insightful uses behavioral insights to refine personas, the evolving role of employee productivity tools, and how aligning sales and marketing on metrics drives better outcomes. Alex also shares a standout campaign that cut the sales cycle by 52% and highlights the value of testing, iteration, and curiosity in modern B2B marketing.
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About Insightful
Insightful is a workforce analytics and productivity platform designed for modern teams looking to optimize performance, boost operational efficiency, and leverage data-driven workforce management. By integrating real-time activity tracking, behavioral analytics, and automated time mapping, Insightful simplifies employee monitoring, remote team oversight, and resource allocation, all within a single, intuitive platform.
Known for promoting productivity transparency, Insightful replaces scattered reports and multiple tools with a unified, real-time visibility layer that connects daily work directly to meaningful business outcomes.
Time Stamps
00:00:18 – Guest Introduction: Alex Alexin
00:00:42 – Alex’s Career Journey
00:03:14 – Understanding Employee Monitoring
00:04:04 – The Purpose of Insightful’s Software
00:05:36 – Reframing Employee Monitoring
00:06:15 – Marketing Approach Overview
00:06:33 – Defining Demand Generation
00:08:11 – Identifying Target Personas
00:12:06 – Balancing Brand Building and Demand Gen
00:12:23 – The Full Funnel Perspective
00:18:04 – SaaS vs. Other Industries
00:21:32 – Successful Campaigns and Learnings
00:24:25 – Key Marketing Advice
00:25:40 – Final Thoughts and Contact Information
Quotes
“I truly believe that the heart of demand generation is the operations behind it.” – Alex Alexin, Head of Demand Generation at Insightful
“It’s all about how work happens and how you can really help your workforce do better or those workflows and those processes be better.” – Alex Alexin, Head of Demand Generation at Insightful
Follow Alex:
Alex Alexin on LinkedIn: https://www.linkedin.com/in/alexandraalexin/
Insightful website: https://www.insightful.io/
Insightful on LinkedIn:Â https://www.linkedin.com/company/insightfulio/
Follow Mike:
Mike Maynard on LinkedIn:Â https://www.linkedin.com/in/mikemaynard/
Napier website:Â https://www.napierb2b.com/
Napier LinkedIn:Â https://www.linkedin.com/company/napier-partnership-limited/
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Want more? Check out Napier’s other podcast – The Marketing Automation Moment: https://podcasts.apple.com/ua/podcast/the-marketing-automation-moment-podcast/id1659211547
Transcript: Interview with Alex Alexin at Insightful
Speakers: Mike Maynard, Alex Alexin
Mike: Thanks for listening to Marketing B2B Tech, the podcast from Napier, where you can find out what really works in B2B marketing today. Welcome to Marketing B2B Technology, the podcast from Napier. Today, I’m joined by Alex Alexin. Alex is the Head of Demand Generation at Insightful. Welcome to the podcast, Alex.
Alex: Thank you so much for having me.
Mike: It’s great to have you on the podcast. What we’d like to do first of all is just let you give us a bit of background. So, do you want to tell us a little bit about your career and how you’ve ended up at Insightful?
Alex: Yeah, I would love to. So, my career in marketing started very randomly. I went to school for psychology. I was one of those kids that thought I was going to be a psychologist. And then life happened. I fell into marketing as one of three jobs that I had at the time trying to make ends meet as one did in their early 20s. And I immediately fell in love with it. After my first marketing job, which was this very small book recommendation website, I actually ended up over at Prequin, which funny enough, they just recently sold to BlackRock. They took a chance on me, and I started there. The best part of that was that Mark O’Hare, he did not want to spend money on software. So, we had an internally built CRM. And with that came its usual challenges, if anyone’s ever dealt with that before. But having to work with our engineers to really understand What data I needed and why and what metrics I needed and why and how to be able to get that. I mean that just kicked off my love of demand gen. I truly believe that the heart of demand generation is the operations behind it and how everything works and the data and the analytics to see what’s working and what’s not. So, from there, I spent five years there just having a great time. And then I went, and I tried my hand at a 17-person company as head of marketing, their first head of marketing, which also was a lot of fun. What I’ve learned throughout looking at my career, which has been longer than I would like to admit, years-wise, is that I really like going to a company at a certain size and a certain place for me to be able to do and build. So yes, I’ve had these Head of Demand Gen, Head of Marketing, Director of Demand Gen roles, but the reality is that I am the one going in and I am building out HubSpot or I’m building out Salesforce. I’m building out those attribution models and really understanding what data we need to capture and why to make sure that all of the things we do, we know if they’re working or not. And we know if they’re working or not quickly. All of that then led me down a what has now been a very long HR tack in the B2B SaaS world career. And so, yeah, I’m currently at Insightful. I would say that one of the main drivers that brought me here was curiosity. It was curiosity about the software, trying to understand what is it that employee monitoring software does. And everyone thinks it’s this big brother thing, but it’s not. It’s all about how work happens and how you can really help your either workforce do better, or those workflows and those processes be better. So, it’s been a really fun journey here.
Mike: So, I’m going to go back and talk a little bit about Demand Gen in a minute, but I’ve got to ask you about employee monitoring because I think, like everyone else, you kind of wince a bit when you hear about it. So, do you want to tell us a little bit more about why people use Insightful and what it helps them do?
Alex: Yeah, I mean, let’s go to the very base of employee monitoring. I too, I wince. But the reality is, and this is going to sound so ridiculous, but the reality is that it’s just like the force in Star Wars. There is a dark side and there is a light side. Yes, you can use software like this for bad, for trying to weed out slackers and who’s not working and who’s not working from where they said they were. That is not what we are here to do. We empower our customers to be able to find those workflow processes that aren’t working. Where are things dropping? Why are they dropping? How can you fix that? And the way that we do that is through being able to track things like the best way I could describe this is think about a customer support team. Ticket gets opened, certain ticket types. How long has that ticket been opened? How many applications did someone need to go into to fix that ticket and close that ticket? Hell, how many actual people needed to open that ticket? So, we can actually automatically capture all of that and say, oh, hey, listen, for your billing questions, you have your people going into four different applications when they should probably only be going into one, maybe two. And now you’re being able to see where these workflows are breaking down and be able to create best practices and training. So, I would say that’s one of many use cases that I have found here.
Mike: I absolutely love that example because it’s completely turning around the company spying on the employee’s kind of story. And effectively, it’s the company finding the mistakes the company has made, which I think is brilliant.
Alex: Yeah, and I would say that we are one of the very few that we have an employee dashboard. You see what you’re doing. You see all of your work. We obviously use it here. I would say I love going into it. I love seeing, again, how work happens, what’s going on, what are all the different applications that are being used? What applications are we paying for that aren’t being used and save money there? So yeah, it’s definitely, it’s not what people think it is.
Mike: That’s awesome. And I’m sure people will be really interested in the product. But I’d like to move on to talk about your marketing approach. And the first thing I’d like to start with is demand gen. People mean a lot of different things when they talk about demand generation. So, do you want to tell me what you think it means and particularly what it means in your current role?
Alex: Yes, that’s such a good question and I agree with you. The name of this has changed so much over the last 15 years of what it is that I do. I would go back to the beginning of what I said. I think that demand generation is very much analytical and its operations focused and it’s understanding how everything connects to itself. So I take content, and I take product marketing, and I take information from sales, and I put that together in a way to try to reach our target customers at the right place at the right time with the right messaging. But the real core that I feel it is, is how do I track that? How do I make sure that I know who I am reaching, when I am reaching them, what timestamps I am capturing? What timestamps am I maybe by mistake, you know, overwriting versus just showing a history of why does that make a difference? I think the demand generation is also understanding the differences in your audiences. You know, if you’re marketing to SMB versus mid-market versus enterprise, the data that you’re capturing and what you’re looking at and what’s going to be important is going to most likely be different. Sales cycles, they’re obviously shorter on the SMB side, they’re longer on the enterprise side. For enterprise, do you really need to track every marketing touch and every sales touch in the same way that you would for SMB? Some may disagree with me, but I feel that demand gen, it’s really about the data, the analytics, and how it all connects.
Mike: That’s fascinating. I mean, starting from what some people view as the end game, which is the data, it’s a really interesting way to do it. I think one of the things that always people struggle with the demand chain is who’s the right person to reach, who’s a good lead, who’s a bad lead, if you want to make it really simple. So how did you decide on the personas that you target and really focus on reaching them and not other people?
Alex: That’s a great question and it’s very topical for what we’re doing at Insightful right now. So, when I first joined about a year ago, we had an idea. We had an idea that we were targeting operations, IT, HR leaders at certain size companies. We believed that we knew what their pain points were and what their jobs to be done were and how we fit into it. We started testing that with messaging and trying to hit people up through paid advertising, LinkedIn, Google, nurturing the email. Our database is huge. Let’s see if we can engage them. it wasn’t really hitting the mark. And I would say that what really became interesting is once we finally filled our product marketing area, we were able to get more research into what these people were doing every day and how the differences were not actually by job title in the way that we had thought. It’s more of a behavioral persona. which is very difficult to target. So now it’s like, how do we figure out what those behaviors are? So what we’re working on right now, and it’s not as though it’s some trade secret, but what we’re working on right now is a maturity ladder of how to speak to different people depending on the behavior. that they are exhibiting. And so, we’re going to start very just right in the middle and we’re going to bring them through a questionnaire. Who are you? What are you looking to achieve? What is this? And obviously we have to do that with giving them some sort of either thought leadership piece or just something that they’ll feel good about and we have some ideas on what it is that we want to do there. But I really think that what’s interesting about here and this is different than some of the other places I’ve been to that had their personas built out and they were very clear. that this has shown me that what you think your software does, who you think your persona is, very well may change. And that’s OK. And I think that there are some really interesting ways to be able to see that you do have to relook at it and see that maybe the market is going in a different way.
Mike: And that’s really interesting, presumably because you’ve got behavioral personas. there’s a customer journey or a set of customer journeys you see that maybe are less dependent upon what role the individual has and much more dependent upon the situation of the company, is that right?
Alex: Yes, that is definitely right. It’s the situation of the company; it is what that person is looking to solve for. Some people, specifically for our software, some people are looking just to solve actual tracking, let’s see, what tech is being used, what tech isn’t being used. That’s all we care about. And then you have other personas who care about how to optimize their workforce. What’s that workload distribution look like? You know, You have a gigantic support center of 500 people, all different teams. One is doing much better than the other. Why is that? Is that because of certain ticket types that are going to them, the amount of tickets that are going to them? So, with that, all of those different things, you cannot put the same messaging to those two people.
Mike: And if we’re talking about messaging, I mean, let’s make this a bit broader. Demand gen people are sometimes painted as just focusing on leads and just like it’s contacts, that’s it. But how do you think the company needs to balance, you know, building the brand and building reputation versus some of the more bottom of the funnel activities?
Alex: That’s a really great question. I think that sometimes people talk about brand too quickly. That’s usually a problem that I have seen. Also, I would say that not every company needs to have a recognized brand. I’m sure there’s a lot of brand marketers that I’ve worked with that are probably cursing my name right now because I am not sure that brand plays as big of a factor depending on the company. What I would say, though, is that with demand gen and just the way of thinking about it, you have to be very open to it being different everywhere you are, what demand gen means. And what I mean by that is you can walk into a company that has a very strong top of funnel. They’re already doing very well. So, some people would say demand gen is all top of funnel. Like you said, it’s all leads. Well, maybe it’s not. Maybe now your issue is you’re getting a ton of leads, but you don’t know what to do with them. That too is demand gen. How are we going to nurture them? How are we going to weed out the ones that we don’t want? I would also say that one of the biggest issues that I find is that a lot of demand gen marketers get pigeonholed for just that pre, not even pre-sale, but pre-opportunity creation. While we really have to look at the full funnel, I need to understand what I call suspect, which is, let’s say, an email address with no name attached, no anything. I need to understand suspect to demo requested, to opportunity opened, to opportunity closed, and beyond. Let’s talk now really going into retention. adoption, renewal, all of this stuff. And I do think that a lot of places are like, no, no, no, no, no, no, no. You’re marketing, you’re demand gen. You only think about leads. I’m like, well, if I’m only thinking about leads, then it’s going to skew everything. Because then I won’t know the quality of the leads. I won’t know how they’re working down the funnel. I won’t be able to tell you a sales cycle that we would be able to predict from different channels, whether that be events or inbound or webinars, whatever it may be. And then from there, how am I supposed to forecast anything? And again, maybe people are thinking, oh, demand gen doesn’t forecast, demand gen doesn’t, you know, marketing doesn’t do that. In the B2B SaaS space, yes, we do. We wear many hats. And I would say that we are very close to Rev Ops because the majority of these companies, we don’t have Rev Ops. And so, marketing thinks about it. So yeah, I think that we have to think about the entire funnel, not just leads.
Mike: But that comes back to data. And I think one of the things that a lot of people find is getting that data and pulling it all together is incredibly difficult. I mean, how do you manage to pull data from presumably disparate systems and get it all into one sensible location?
Alex: Well, first, you have to be okay with knowing that it will never be perfect. It will never, ever be perfect. And every single company I’ve started at, I’ve been warned, the data here is terrible. The data here is dirty.” I’m like, okay, it can’t be any worse than any other place. And it’s not. It’s really not. It’s funny that everyone has this idea that their data is the worst. I would say that what you need to first start with is specifically alignment with the sales team. Let’s make sure that we’re having the same conversation and we’re using the same terminology. What is a lead? what is an MQL, an SQL? What is the funnel that we want to discuss? Once you have those definitions, then it makes things much easier. Our definition of a lead is most people’s definition of an MQL. That is someone who has filled out the demo form or our free trial form. And so that makes things fairly easy. And then it starts to go into, okay, let’s start talking about personas and segmentation and different Do we have our sales teams? Do we have our SMB team and our mid-market and enterprise team?” And I think that, again, it all starts with that alignment. And I know that for years it’s always been sales versus marketing, sales versus marketing. Marketing coming in and saying, we’re bringing all the great leads and sales saying, no, they’re garbage. Yeah, that certainly has happened. But if you started off with a conversation of like, all right, what do we consider a lead? Let’s talk it through. it starts to help that data cleanse work. And then, I mean, obviously whatever system you’re using, whether it’s HubSpot or it’s Salesforce, I would say especially to the marketers, learn the backend. You have to learn, and this comes back again, you have to know the operations behind it. You have to understand that if you turn off this workflow, what’s gonna happen? or if you turn on that workflow, what’s going to happen? It is the most important thing, and it is really about thinking about every potential little angle.
Mike: And when you’re thinking about that, do you think it’s actually easier to do that in a SaaS environment than maybe in, say, an engineering company? I mean, SaaS companies have a reputation of really having been able to tie in the whole customer journey, whereas when you’re selling complex engineering parts, sometimes it’s a lot more difficult.
Alex: I’ve spent my whole career in B2B SaaS, so this is kind of all I know. I would say that what I find to be difficult is having all of the people necessary agreeing. And then not having people understand that just because we agreed on this definition today, that doesn’t mean that this is gonna be the definition forever. It can change, that’s okay. I spent four years at a company named Ease, it was Ease Central when I first joined, and we had decided that our North Star metric, not just for the marketing team, but for the company, was marketing influence. We thought that that was a pretty good term. Now it was, what is marketing influence? And how do we get buy-in from everyone? And we were like, okay, marketing influence, we can speak to the board of investors and say, it is an opportunity that had a marketing touch within 90 days of it opening. Cool, great, easy. Then we could talk to our VP of sales and say, okay, listen, here are the actual rules. And we built it out in Salesforce. If the marketing touch happened within 90 days of the opportunity opening and a sales touch didn’t happen before then, it’s marketing influenced. And then again, that definition, once we started doing the reporting against it, that definition changed. every quarter for almost four quarters until we got it perfect because first we were like, okay, marketing influence contacts, that’s great and then we realized the numbers were skewed because you’ve got 10 contacts influenced but only one opportunity because those 10 contacts were at one company. Okay, let’s now change it. We’ve got to go back. We’ve got to redo everything, and we’ve got to make it unique accounts. Okay, how are we going to watch unique accounts happen? Okay, let’s redo and that was literally going back and reworking every single Salesforce report, which I will say my number one If anyone takes anything away from this conversation, when you create a report, whether it is in Salesforce or HubSpot or anywhere that you are doing it, use the description. Write out the description because you may think that you will remember what it is that you did and how your brain was working. You won’t. So, I had 15, 20, 25 different reports that all had a similar name and I had to try to figure out which one it was. That was horrible. And then from there we realized that it wasn’t just unique account that we had to do. We had to do a cool down period because now we were double counting accounts within a quarter and we needed to make sure that we were only counting it once, and that’s where that 90-day cool-down period came. Iterations, be okay with it. Be open to it. Yes, it’s going to be a lot of work. Yes, you’re going to have to get a lot of people on board but also remember that there’s really only a small group of people that you’ll be working with to really figure this out. I’m not going to go over to my head of sales and talk to him and say, okay, I rethought this, I redid all of these reports, because he doesn’t care. And that’s okay. It’s once I get to the end that I’m like, all right, here’s the report. That’s what he cares about.
Mike: I love that. It’s fascinating hearing about some of the challenges you face. But also, what we want to talk about some of the successes. So, do you want to tell us about, you know, some of the campaigns you’ve seen that, you know, for whatever reason have been really super successful?
Alex: Yeah, so actually, again, at ease, I did this incredible project with our product marketing manager, where she was trying to rework our personas, and we were both working on life cycle stages. So, trying to understand the entry and exit criteria of each life cycle stage by our persona. So, I did all of the data part of it, right? I was pulling every sales and marketing touchpoint and her and I were kind of going through it to figure out Where are those intersections? What are we looking at? And after, let’s see, that data, again, I want everyone to understand none of this happened overnight. This, just going through the data analysis took like two months. So that’s okay. But after getting that data, then we were able to start to pinpoint the different pre-opportunity opening places by persona that we could actually start playing with. And what that looked like was depending on, and this was for them because of what our personas were broken out as, depending on your job title and the page that you first entered our funnel into, we put you into a choose your own adventure nurture program. based off of what we knew people who started in that journey went to. And we got you to places faster than you would on your own. We ended up actually being able to bring the sales cycle down by about 52%. And again, that took three quarters to get there, but we did it.
Mike: I think a lot of people, if they brought the sales cycle down by 5% would be pretty impressed. So, 52% is amazing. And that really, I think, shows the value of what you’re saying about not only get the data, but use it as well.
Alex: Use it, test it, iterate on it. I will never forget as well, that first nurture program, we realized that we, by mistake, put the same people into three different programs because we missed something, because we were building it all out ourselves in Marketo. It is okay to mess up. The whole point is that those little mess ups, you’re going to start to think about all of those little things as you move forward, the more mess ups that you see. And then you will have fewer and fewer and you will get to that end faster and faster. And you’ll be able to see that progress faster.
Mike: Yeah, I think there’s very few overnight successes that didn’t take a long time.
Alex: Exactly. Even a rebrand, you know, think about a rebrand. I still get a twitch thinking about it. It’s not as though one day you flip that switch and you’re like, hey, our new name is Ease and every single piece of content now says Ease. No, I bet you anything that years later you can still find stuff that says Ease Central out there because we missed something.
Mike: Absolutely. Alex, it’s been fascinating talking to you about this. Before you go, there’s a couple of quick questions we like to ask everybody. So, the first one is, What’s the best piece of marketing advice that’s ever been given to you?
Alex: Don’t be afraid to fail. That is definitely it. Don’t be afraid to fail.
Mike: Awesome. Simple and very true. Love it. The next thing, and I’m kind of thinking you might repeat the advice now, is if you’re talking to a young person who was just embarking on a career in marketing, what would your advice to them be?
Alex: Test everything. Click on everything. You’re not going to break anything. Don’t be afraid. That was always my fear early in my career, that if I touch something or if I ask something that I’d be afraid of what the answer was or maybe I shouldn’t be asking that. Don’t be afraid. Just do it. What’s the worst that’s going to happen?
Mike: I love it. I love it. What a positive way to end. I’m sure a lot of people have really enjoyed this interview. If people would like to contact you and maybe ask you some questions or follow up what you’ve said, what’s the best way of getting in touch with you?
Alex: Yeah, I would say find me on LinkedIn, send me a connection request. It’s Alexandra Lexin and I’d love to get in touch with anybody.
Mike: Alex, it’s been great. I’ve really enjoyed talking to you. Thanks so much for being a guest on Marketing B2B Technology.
Alex: Thank you so much for having me.
Mike: Thanks so much for listening to Marketing B2B Tech. We hope you enjoyed the episode. And if you did, please make sure you subscribe on iTunes or on your favorite podcast application. If you’d like to know more, please visit our website at napierb2b.com or contact me directly on LinkedIn.
