Oct 19, 2022

Driving Growth Via Questions, Curiosity, & Analytics, with Michael Freeman

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Michael joined Skilljar with 20+ years of marketing, strategy, and operations experience across a broad set of industries, from startups to the Fortune 100. Most recently, Michael was the CMO at Certent (acquired by Insightsoftware), a SaaS provider for equity management and financial reporting software. Prior to that, he held a number of roles of increasing responsibility and leadership at companies such as Adaptive Insights (acquired by Workday), Highfive, ShoreTel, Mecalux, Teleflora, The Walt Disney Company, and Maersk. Michael has a BA in Communications Studies from University of California, Los Angeles and an MBA, also from UCLA – The Anderson School of Management.

What you’ll learn about in this episode:

  • How layering a customer education strategy in with the rest of your marketing efforts can be a great customer attraction and retention strategy
  • Some of the ways that measure the success of a customer acquisition strategy
  • The difference between reporting and analysis and insights
  • What the keys were to great inbound marketing in 2022, and now heading into 2023
  • How platforms have evolved and changed to help us do better inbound marketing

Additional resources: 


Intro: Welcome to A Brave New Podcast. The podcast is all about how big ideas, brave thinking, and marketing smarts help businesses grow. Here is your host, Josh Dougherty.

Josh: Hello, and welcome to A Brave New podcast. My name's Josh Dougherty, I'm your host. I'm so excited to have you along for the episode today. Today, I'm joined by the VP of marketing from Skilljar, Michael Freeman. I think you're going to love this conversation. He has a really long breadth of experience doing marketing, strategy, operations. He's worked across a ton of industries from things like shipping to technology, and he worked for the Disney company for a while.

And I think I appreciate his holistic view of how to drive results. He's thinking not just about marketing, but he's thinking about how he connects with his sales team, with customer success and understanding what are the different ways that an organization ticks and the ways that an organization works, and how do you leverage those for success? So, that's one of the things I'm really excited about.

The other thing that I really enjoy about Michael is his commitment to curiosity and questioning the way things are. I think this makes him do great marketing, and it also makes all of us, as we talk with him and learn from him, question what we're doing, question how we could improve. So I'd love to introduce you to Michael, who's joining us from San Luis Obispo, where he goes beyond just marketing—a retired soccer coach, loves rock climbing, surfing, playing the ukulele, and a bunch of different talents. And I think you can see that curiosity and those different talents coming through in the way he approaches his marketing as well. Hi, Michael. So happy to have you on the pod today.

Michael: Hi, Josh. Thanks for having me. I'm very excited to be here.

Josh: Awesome. Well, I wonder as we get into the conversation, I'd love to have you share a little bit about your story. Tell me about your career path, where it's taken you so far.

Michael: When I think about my career, it's been a wonderful journey so far, and I’m excited to see where it goes next. But to get me to where I'm at here at Skilljar, I've worked in a variety of industries. I've worked in a variety of ownership models, business models, and company sizes. I actually started in the supply chain industry coming right out of college doing marketing for one of the largest global container companies. If you go look in the ports and you see a big blue and white ship that says Maersk, well, that was the company I worked for.

Actually at the time, it was part of the single largest company in all of Denmark before Lego had their explosion. And it's a company that no one's ever heard of. And I've had a habit of working for a lot of companies that people haven't heard of but who play a big part in our day-to-day lives or the economy.

But, I've progressed through a series of different marketing roles and even in the cases where I wasn't working in marketing. I was part of Web 1.0, the original .com bubble. I did the fulfillment systems at an eCommerce company. So everything—once you click the order submit button online, to a product showing up at your door—which people take for granted now. But in 2000 and 2001, that was not a simple exercise, technically, to pull off.

There's always been a strong technology component. There's always been a strong analytics component to everything I've done and really a deep understanding of how strategy informs the way the business needs to invest and grow. Since I finished my MBA, I've exclusively focused on marketing roles, again, at a variety of different types of companies. I've been at a number of startups over the last few years and currently happily helping Skilljar grow.

Josh: Great. Well, let's talk about Skilljar, and what you're doing now, because that's obviously the thing that you're most plugged into today. What are you focused on there? What are the exciting things that are happening?

Michael: Well, Skilljar is the leader in customer education, and it's a new category. Even though users have needed to be trained and educated on how to use their products—if you go back many years, there was no product that was purposely built for that use case. And every company virtually wants to be in the recurring revenue business these days.

Josh: Of course.

Michael: And the great insight of the shift in the business model to recurring revenue was that hey, we need to make our customers successful and happy. And if they do that, they'll reward us with their continued business in the form of renewals in the case of SaaS but also repeat purchases and other types of business models. And we have this fundamental core belief about what we do, which is that trained customers are your best customers.

But when you think about it, well, how do I train my customers? How do I educate them to get the most value from their product? A lot of companies are really still based off of a labor-based model that is very manual, exclusively focused on the burden of this falling on CSMs or support teams or implementation teams. And what we found is that the most customer-centric companies have looked to automation to help supplement what those teams are doing—in the form of self-serve education. But also, for things that are still taking advantage of instructors, using digital assistance in the form of virtual instructor-led training, et cetera.

And rather than having that operate in some kind of data silo, have that fully integrated into the rest of your customer stack. So tie it into Salesforce, tie it into Zendesk, tie it into Gainsight, you name it. And so what I'm focused on right now at Skilljar is just helping us continue to grow. So we're a small company, but we are the largest company within this space focused on this type of use case.

And we've been fortunate enough to work with some of the best brands in all of technology, and in fact, beyond technology as well. U-Haul is a huge customer of ours. Liberty Mutual is a customer of ours. So we've found that this basic but powerful premise of trained customers are your best customers is really starting to catch on. So for me, I'm establishing a brand, Skilljar. I'm also trying to help craft an understanding in the market about what this category actually is.

Fundamentally, as a product, we're an LMS—a learning management system. But the learning management system category has been historically dominated and understood as being something that is bought by HR and used to train employees on how to be either better employees or at least less risky employees. So you have to take all that compliance training around perhaps harassment or IT security, those types of things. Very different use case from needing to train your customers on how to use your products.

And the other big LMS category that's been around and really grew and became top of mind for a lot of people over the last few years due to the pandemic, was the academic LMS. If you search online and Google for LMS, at least in my case because I'm based in California, I think 3 of the top 10 results are all logins to Los Angeles Unified School District LMS or some other regional LMS.

Josh: I have the same thing in Washington.

Michael: Yeah, exactly. Exactly. So LMS as a term has been dominated by these other use cases that really have nothing to do with How do you train your customers to better use your product? So my mission, and frankly the mission of our customers as well, is for us to elevate the knowledge and the market about this special and focused use case that drives powerful business outcomes.

Josh: Yeah, cool. I love that. And I can see the super clear picture of how education, training, this type of platform can help with retention, it can help with increased adoption of a product. But I think something that's interesting is, you talk about and I can see it on Skilljar's site too, you're using it for customer traction as well. And so can you share a little bit about maybe how that education strategy layers on top of the rest of the stuff you're doing in marketing to attract new customers?

Michael: Absolutely. I think there's been some forward-looking companies that have done this really, really well whether they're a Skilljar customer or not. HubSpot comes to mind. If I think about the HubSpot Academy years ago, 80, 90% of the content was how to use HubSpot better. And maybe 10% of the content was really around the domains of marketing back then. Now, they're a multi-product company and a multi-category company.

If you look at HubSpot Academy today, the majority of their content is how to be a better marketer, how to be a better SDR, how to be a better CSM. And then, yes, they have content on how to use HubSpot better as well. And so I think that's a good example of using education for a demand gen brand building purpose that's really top of funnel.

We have a great customer, Hewlett Packard Enterprise, that has worked with Skilljar to power a top of funnel demand gen campaign to build awareness for their GreenLake product line. And, so, talking with the education leader there, her belief is that education content is authentic content. It's not salesy content. A lot of users are very skeptical and very untrusting of what they come across. I'm a marketer. We're famous for doing something great until we abuse it or overdo it, or making perhaps too large of claims. I try not to, but I recognize as a category of work, us marketers tend to overdo it a little bit on some of the claims.

And when you think about great education content, it's solving a problem. It's helping them understand, the end user, the learner, how to do something better or how to do something at all if they don't have any knowledge around it. And so that's extremely valuable, and it's extremely authentic.

And when you think about inbound marketing, that was ultimately the goal surrounding inbound marketing; create value and don't ask for anything in return. Be authentic, be helpful. By definition, that's great education content too. So I think from an attraction standpoint, if you can go answer questions that people have, and do it in a way and from a position of experience and authority, that will drive traffic, that will drive word of mouth, and, more importantly, it'll drive great customer or prospect experiences that help you with every other touchpoint along that journey.

Josh: Yeah. I love that so much because one of the things I think about as a marketer, and I know as well, we are prone to make big promises and then be like, let me now twist these numbers a little bit to show you how we fulfilled on that promise when we overpromised a little too much. Try not to do that, but it happens. So I love the emphasis on trust because a report I always like to look at every year that comes out is the Edelman Trust Barometer. I don't know if you're familiar with that, but that's such a great report to see.

There is so much of, at least in the last few years, a gap in that trust. People are digitally fatigued, they're tired of seeing content. They see through the inbound content that's helpful but only kind of helpful and not really. And, so, I'm very interested in what you're doing as a company to build out that content that's going to truly help someone feel like they're more competent at their job or they're more competent in our field, all those sorts of things. So it's very cool.

Michael: Yeah. Specifically in that area, we do things like in addition to offering a Skilljar certification that is free and open to anyone who wants to go to Skilljar Academy, we also have an industry certification. So if you just want to understand better customer education as a discipline, we offer a whole host of courses and the knowledge checks that go with it so that you can get your badge and post it up to LinkedIn with a single click. And it's really about just raising that awareness and knowledge.

So in our case, one way I know that customer education is not a fully mature category yet is there is not a market-wide consensus on where this responsibility or function should sit. We have customers where it sits inside of customer success, we have customers where it sits inside of support. Sometimes support is under product and engineering, sometimes support is under a customer organization. Sometimes education falls under product, sometimes it falls under customer marketing, sometimes it falls under product marketing. We've seen it in a number of places and it's just a sign that there's a lot more growth that's needed in the category and understanding.

But I think when it comes to how you can use it effectively, it always starts with understanding your end user and understanding what job needs to be done for them, at whatever part of the product or the interaction they have working with you. And I zoom out from that, and it's not just working with your product but working with the concepts that your product is meant to address.

So the example I'll give is Tableau is a customer of ours. And so I can take classes on how to use Tableau better. But to be a great data analyst or data scientist, I also should know more about the topics of building great visualizations, thinking about constructing the right types of queries in the first place, so that I can then use Tableau much more effectively. And I think if you're doing that, that is a great way to drive new traffic, a great way to drive new leads but also reinforce the claims you are making in your other marketing copy because you're proving it right there. We are experts, we know what we're doing, and here's how this can benefit you.

Josh: Yep. Amazing. I like that so much. I want to transition the conversation a little bit to that peer marketing conversation because you've been doing this for a long time. Before we started recording, we were having a conversation about measuring success. So we'll get into a little bit of the vagaries, how we've been able to get more specific, but it's still challenging to get completely there. But I'd love it if you could talk me through some of the ways that you like to measure the success of your customer acquisition strategy. What are you looking at to determine if you're headed in the right direction and you're getting the results you want?

Michael: Yeah, great question. I think with a lot of the answers I'll probably get from this point forward, it will largely start with, it depends. And you need to get alignment with your other peers in your go-to market organization. So I think fundamentally, success depends on understanding your business model and making sure that there is alignment and agreement on what your desired business model is. Obviously any business, revenue. Revenue matters a lot.

But sometimes your cycle time is too long to have quick feedback on, Are my actions having an impact to drive revenue? Well, if you're an enterprise software company that has a nine-month sales cycle for a million dollars, you're not going to know for at least nine months or longer the real impact if you're only looking at revenue. So I always try to start with revenue and then work backwards until you get to a time horizon and volume where you can start getting quick enough feedback that you can react accordingly in whatever your tactic or program is.

And then besides looking at that, like I said, getting alignment with your CEO, your head or anyone else in the go-to market team, again, depending on your business. In our case, my most important counterpart is our VP of sales. And I need to be in lockstep with him to make sure that we are working together to develop a pipeline that ultimately turns into paying customers.

And, then, added to that is to make sure that we're fully aligned with our VP of customer success. Because none of us are in the business of signing one contract. We don't want that. We want long-term relationships. That's the premise of our business. If we make our customers successful, if our customers make their customers successful, they'll be rewarded with a repeat business. Well, the same is true for us. So we want to make sure we have a delightful experience, not just on day 1, but day 362, day 747. And so it's really the three of us that have to be fully aligned on what those metrics are and what we care about.

Now in my particular case, I focus mostly on pipelines created. And because we do operate in different segments with relatively different ASPs, I look at what type of pipeline we're creating for each of those segments. Because I could generate a ton of pipeline in one segment, but that's only going to help one set of AEs retire their quota. I’ve got a whole bunch of other AEs that need to retire their quota too with close one business. So I try to look at it by segment, how much the pipeline was generating.

Josh: I love that, and I think that's the modern way to do it. I know, back in the day, it would be like, we threw a bunch of my MQLs over there, even SQLs, but now everyone that I'm working with is looking at the pipeline. You have to be able to prove the pipeline. And I think that's scary for some marketers because it means you are reliant in some way on the sales organization. But I think it's just looking at it from a clear perspective. You're already reliant on them, it's just admitting it.

Michael: Yeah, absolutely. And look, we all are here to grow the business, not build smaller fiefdoms. The company needs to generate revenue, and it should generate revenue profitably over the long run. So one thing I'll say to colleagues to show that we have a philosophical alignment, as I say, hey, cash compensation's great, equity compensation’s even better. And the equity compensation can only work if the overall business is wildly successful. So all of us here at Skilljar are in it to make the company and the category wildly successful. Because if we don't do that, then personally we can't be successful either, besides the fact that we fundamentally believe in just this mission.

Josh: Yeah, absolutely. So all this conversation about the metrics you're looking at, measurement success, leads me to a broader discussion about analytics. I know in our past conversation as we were prepping for this, we talked a lot about the difference between reporting and analysis and insights. And I think you're particularly passionate about this topic. So I'd love to hear your thoughts about the difference between those two, why you're so passionate about getting towards ACT true analysis versus just giving the data.

Michael: Yeah, absolutely. Over the course of my career, I've interacted with so many people that talk about really loving the data but they just want to see, if you've ever seen the movie Office Space, they're just looking for TPS reports. They're just checking the box. And so for me, when I think about reporting versus analytics, I think of reporting as the what, but analytics is really the why and the how.

And I'm a big fan of history. And if you go talk to historians—actually, instead of going into marketing, I almost became a historian when I was finishing up college—most historians, they really care deeply about the how and the why of the events that occurred. Not just the what; the what's relatively easy. And same with reporting. Reporting is just going to give you the data and it's backwards looking. Analysis is really trying to understand the drivers and what influence created that result so that you can apply those learnings with an eye towards the future.

So I think of reporting as exclusively backwards looking and analytics as a forward-looking activity, based on knowledge you can gain by looking at the past, but it has an objective of going forward. And I think that's way more powerful and actionable because any of us that want to be successful in our company, in our life, it's all about driving and finding opportunities for change. Anything that stays stagnant will not grow, it will not succeed. So you always have to be improving. And the way you do that is by asking why and how, and how can the data guide me to a better why and how to do things going forward.

Josh: Yeah, that's so good. I'm laughing a little bit as we're talking too, because I was a history major in college as well and nearly went in for my PhD in history. So that's like serendipity to have this conversation.

Michael: Absolutely.

Josh: And I think that's why I like to solve puzzles and think about what are the big problems or the big challenges that can be overcome. Because at the end of the day, that's what history is about. Everyone would always be like, why do you want to read these old books? I'm like, I'm trying to understand why the world is the way it is.

Michael: Absolutely.

Josh: How it got there.

Michael: And we like to pretend. We like to pretend that everyone is extremely rational, but fundamentally, we are emotional beings that use rationality to justify decisions we've probably already made based on an emotional feeling. Yeah, I don't want to go down that path, but there's plenty of evidence to show that facts don't always matter for people's beliefs or thoughts. And really it's because they have this sense of why and then they see the world within that framework.

I remember, you mentioned, all right, we were talking about HubSpot earlier and inbound, I remember years ago I heard Guy Kawasaki talk. And he was talking about the 10 key lessons he learned from working for Steve Jobs because he's one of the original Apple Day insiders. And his very last point was the best one. And it was, a lot of people say you have to see it to believe it. And he said, that's completely wrong. This is the saying that he was saying that Steve Jobs used to talk about.

He said it's completely wrong. It's the exact opposite. You have to believe it to see it. Because if you believe it, you can see it there. You can make it happen but you have to fundamentally believe. And I think that that has always stuck with me as something very powerful. And when you're thinking about how do you improve the business, should I do this tactic, should I do that tactic, well, there has to be a fundamental element of belief in what you're doing and why you're doing it and how it's going to help your business.

And then you're going to take chances that will pay off. Because if you only do the things that you can see in front of you, you will never get above average. You're just going to do what everyone else has always done. And so you're just regressing to the main.

Josh: Yeah, I think that's an incredible point. And I was thinking as you were talking, even about choosing the tactic, it also applies to marketing strategy. Because if you don't believe where you're trying to get with your strategy, you're going to ask totally different questions as you look at your data. Because if you have this north star you're pushing towards, it is a little bit aspirational. All of a sudden, you are digging into your data in a different way, you're asking different questions, you are charting a different path. You're saying, what if we might just try this out and see if it works because you know you're pushing for something greater than just the incremental percentage improvement from an A/B test or something along those lines.

Michael: Absolutely. Something I mentioned to my team a lot, probably more than they want to hear, is that I like to say, and I didn't create this, I just picked it up over the years…

Josh: Of course. Great marketer.

Michael: Yeah, exactly. It's better to ask the right question than to get the right answer. And so that really is powered by curiosity coupled with that vision that you're talking about.

Josh: Yeah. I think that goes well into my next question of, can you dig a little bit deeper into that questioning assumption. I've heard that a lot through our conversation that we've just had. And I think along with questioning assumptions comes this idea that we have to constantly evolve as marketers to be successful and to achieve what we want to achieve. How does good analysis, good data analytics, help fuel that process of evolution and questioning?

Michael: So, for me, it is trying to never be too comfortable in whatever you're doing and always channeling a little bit of the devil's advocate. And it doesn't have to be you, it can be someone on your team just built into your culture, into your process. But encourage someone to be a skeptic or to be a devil's advocate, to question those assumptions and make sure, is there something different that we could do or at least try?

And I think besides questioning, questioning can often be perceived and taken as a negative. Why are you doing this? Why are you questioning this? Leave good enough alone or you're just making it harder, and it's just testing. And as long as you do it with an open mindset, it's going to end up bringing into relief certain ideas that wouldn't have been created or stimulated otherwise. So I think you should just be wary anytime you're hearing this is best practice, and we just do it because it's best practice.

Sure, there are certain things that you can use those shortcuts to y'all just don’t invest the time to question that assumption. We'll just do it, best practice. Sure. But if you do that all the time, again, you won't find anything breakthrough, and you're always going to be following what is happening, not see what is happening or what will need to happen to move your market or move your company along.

Josh: Yeah, it's so true. And as I think about something, one of the places I wanted to take the conversation was in inbound marketing. Because you've been working, you presented inbound years ago and have been around that for a while. And I think there is a real temptation, if you are doing inbound like we're doing in 2013, you're probably going to be in some trouble. But I think there's also, so there's a required evolution. So I'd love for your thoughts on, what remains constant in that world of inbound marketing? And then where has there been evolution over that time to where we are now?

Michael: Well, it's gotten harder.

Josh: Yeah, that's true.

Michael: It's definitely gotten harder. But I used to joke with people back when inbound marketing was first coming up as a term. And I used to say, well, and I've actually made a similar comment with all the buzz around ABM over the last eight years or so. I would say, "Back in the day, they just called that marketing." Because great inbound marketing is about understanding your audience, understanding what they want, what they are looking for, what problems are they trying to solve.

People don't just wake up and search for no good reason. They have a reason. They're trying to find out some information. They're trying to get something that's going to help them take the next step in whatever they're doing, whether it's evaluating a vendor for learning management platform, or see if they have shoes that they're interested in or in stock, or see if they can visit their grandma in Toledo, Ohio. Whatever it may be, they're searching for a reason.

And so a great inbound marketer is knowing their audience. They are trying to understand, well, what are the things that they're trying to solve for? And then how can I generate something, again, not checking a box, but deliver something that is uniquely of value to that person and that's going to give me a chance and opportunity to get an interaction with them. And again, part of the secret of inbound marketing was also don't always just go for the hard sell right away. Build a relationship over time, continue to provide value, and when they're ready and as they're educated, then they're more likely to consider you in the first place.

So I think at its core, those are the tenants that will always be true. Those were true before Google existed when you were just hanging up a shingle and trying to convince people in your neighborhood to come to your store. It was true then and it's true in the TikTok era and it's true with whatever comes next after that. So that piece is constant.

Where things have changed, and like I said, it's become harder from a certain point of view because there are more people doing this and paying more attention. So, with increased content is increased competition for that audience. Our audience is more distracted and fragmented than ever with all the things pulling at their attention.

And the piece that I've seen on the search engine is that Google has gotten much better at trying to figure out intent. Now, not going just beyond the basic keyword analysis and that type of thing. They've really tried to understand concepts more holistically and really get at intent. They're much better at it in certain categories of the keyword universe than others. Still some education to go for the Google bot to understand true meaning.

Yeah, I was surprised by one. I had a one on one with someone the other day, and I can't remember what we were searching for, and what showed up in the results was definitely not what we were expecting. And it was an innocuous term. So anyway, they've gotten better at it. But as long as you keep creating good content that is relevant for your audience, you're heading in the right direction. It doesn't mean you're guaranteed first page placement. And you're still now below a sea of paid links that take up more and more real estate, but good content should win out over time.

Josh: Totally. I think as I reflect on my journey with inbound as well, it's just that the quality has to be so much higher than it used to be to stand out. Because back in 2012 when you were doing this, or 2011, for most categories there wasn't a ton of content out there that was super valuable. So you just start putting up stuff and seeing your traffic skyrocket because it's doing the work. It's harder now.

Michael: Yeah. That was back in the days of, that's when Penguin and Hummingbird, that's when Google used to name or people would name their algorithm changes. And that was back in the days when Penguin came out and Hummingbird and all those good things.

Josh: Yep. How do you think platforms have evolved to help us? So certainly Google's platform, it's still a bit opaque. We can guess at how it's ranking, all that sort of thing. But the tools that assist us in marketing today, where are they really succeeding in your mind and where are there still challenges or there's a ways to go? I'll stop there. But behind my question is always, is there a silver bullet platform that's going to make it easy for us to do marketing? What are the things you're excited about right now from a platform perspective?

Michael: I think the things that I'm getting excited about are less about how do I drive the traffic because I haven't seen the level of innovation that I think. I'll get to the bigger problem I see and then I'll tie it back. But where I've seen more of the innovation that makes it helpful for inbound marketing are the tools that are going to help you get richer data about that audience and richer data for personalization purposes.

So if I use a company like 6sense, and when someone hits the website, they've come in through inbound traffic but I'm able to identify what industry they're in, what company they're in, or what location they're at, size of the company, you name it. Now I can start personalizing their experience in terms of what they're getting on the actual website. I can personalize the offers. And so if the goal is, going back to their earlier comment, delivering, solving the problem for this person, that's how they started with their search.

Well, with that additional information that Google doesn't provide but I'm still able to get through another software platform, I can better tailor the content, especially if I'm reaching many different types of audiences with many different types of problems. I'm more likely to be able to deliver something that's of even more value to them than I could otherwise. So there's been a lot of innovation in that space.

Clearbit's another one that does a lot of things in this area. Demandbase has been around for a long time. But I think that's one of the areas over the last few years that has become a lot more accessible to companies to use price wise, breadth of technology kind of accuracy. The challenge I still see, though, is it's still very, very hard to have any certainty or predictability about the ROI or impact you're going to have by focusing on inbound marketing tactics. And marketers are under a lot of pressure to use their budgets wisely and in a way that they can prove that they've used it wisely.

And so what ends up happening so often is that marketers gravitate towards the tactics that are easy to measure. Regardless of whether that's the most cost effective thing long term to do, they tend to gravitate towards those tools and those tactics because it's easy to measure. And now I can go justify, hey, here's what marketing spent and here's the number of leads we get out of it, and I can prove that. And I can also say, during the planning cycle, I will spend this amount of money in April. I'm going to get this number of leads that will turn into MQLs, that will turn into SQLs, that will turn into eventual close one business. And so those types of tactics still tend to win out.

And so I think the challenge for that, for the inbound marketing kind of tool set industry, is it still needs to get a lot better at helping marketers measure the value of your content investments. And then also help you better forecast the opportunity assessment of like, hey, what's the probability that we can try to rank and get this amount of traffic by focusing on these types of searches or this type of intent? Well, we think this is the amount of volume you could get and here's the amount of leads therefore based on certain conversion rate assumptions.

And then, what your kind of CPC equivalent would be to generate the same number or volume of leads through that source. With some kind of time horizon of like, hey, within three months, you have a 20% probability of getting this amount of traffic and that type of thing based off the strengths of your domain, and assuming you create some authoritative great content. That's just a real gap today I think in the market from what I've seen. And so marketers are continually going to invest in inbound marketing if they can't prove the ROI or even predict what the ROI and time horizon might be.

And when I'm talking to a skeptic, I tend to give an analogy. And when I give this analogy, they totally get it. They tend to forget it when it comes to planning time or time to sign a check or those types of things. But whenever I'm dealing with a skeptic that doesn't fully understand the value of inbound marketing, I tell them this, I say, "Well, you want to improve your pipeline health." And they're like, "Of course, we want more pipeline. Who doesn't want a great healthy pipeline?"

Josh: Totally.

Michael: Exactly. Well I say, "Well, imagine you came to me and you said, Michael, 'I don't feel well. I want to feel healthier.' " And I take a look and I ask you some questions and I find out that you don't get a lot of sleep, you're very stressed, you don't exercise, you eat poorly, you drink a lot and you smoke. And I'd say, "Well, if you want to feel healthy and live a longer, happier life, start exercising, make better choices when you eat, stop drinking, stop smoking, reduce your stress." And I don't remember if I said it or not, and get some more sleep.

And you do that, I can't tell you how much longer you're going to live. I can't tell you on a percentage basis how much healthier you'll feel. I can't tell you how much weight you're going to lose. I can't tell you how long it's going to take you to lower your cholesterol or lower your weight exactly to the number you want to hit. I just know all of that is true, and it's about living a healthy lifestyle.

And I think from a marketer's perspective, we should all have a very healthy digital marketing presence. And part of having a healthy digital marketing presence is investing in inbound. I just, unfortunately, can't say you're going to get 200 more clicks in the next six weeks, I can't guarantee that.

Josh: Yeah, totally. And I think the connection between brands is so helpful or is so relevant here too because I think inbound helps establish your brand in a way that you can't do with any other marketing tactic.

Michael: I agree.

Josh: And that's intangible too. But at the end of the day, it gives you market share. We mentioned HubSpot a couple of times in this conversation, if everyone thinks of them as the inbound people, what's the ROI on that? I don't know. But everyone thinks of them as the inbound people. Now they're trying really hard to change into the CRM platform people, but they're having trouble outrunning their current brand positioning. But that's a great thing.

Michael: I was going to say, it's a good problem to have. Yeah, you bring up a great point. It's very similar to brand investments. I go invest in brand spend as opposed to direct response demand gen spend, that's a challenging conversation if you're talking to a CFO.

Josh: Hugely challenging,

Michael: Especially in difficult economic conditions, if we're in a bear market or whatever or interest rates have gone up, it becomes an even more under scrutiny type of decision. But when I look at someone like Apple, the brand seems to have worked out just fine for them over the last few decades. But even more recently, you take a company like Gong, Skilljar customer by the way, they've really defined their category. Their brand is the category to a certain extent around revenue intelligence. And those were not guaranteed bets that they made six, seven years ago, but they have clearly paid off.

Josh: Yep. Going back to what we talked about with Steve Jobs, the belief is required to build the thing that you want.

Michael: Absolutely.

Josh: It takes time. It takes time. Well let's finish up here. This has been a great conversation, but let's finish up with just a couple of questions. The first one is, we've talked about questioning assumptions, being open, and being curious. I'd love to hear with you and your team, what is one big assumption that you've questioned in the last year? What was it and how did it help you pivot to be better marketers?

Michael: That is a very, very tough question to answer as I think about it for the team. But I think for me, I wouldn't necessarily say it was a big assumption, but it's more a big question that we had to deal with. And that was, when is the pandemic over? And is there consensus on when is the pandemic over and or when is it safe to resume getting together in person?

Josh: Well, Joe Biden said Sunday it was over, so we're done.

Michael: Yeah. He said, "COVID's not over, but the pandemic's over." Yeah, I saw the interview. So my example of this is Skilljar Connect, that is our annual user conference. And before I was at Skilljar, in 2020 Connect was a virtual activity. The previous two years it was in person in Seattle. Well, we made the decision last year to have Connect 2021 in person in a very safe and controlled environment with a lot of outdoor activities in Sonoma.

And we had a really hard time predicting what would the demand be for an in-person event. Even if you are showing a negative test and even if everyone was masked up and everything else, really hard to predict. And then we had a very successful in person. In fact, I think it was the only in-person customer education event or customer education conference last year.

Well, fast forward to this year when we're planning and we're thinking about, well, how big are we going to make Connect this year in San Diego? And that was a really hard estimating exercise of not knowing and really trying to question. We did talk to our customers, but to a certain extent, we just had to play some bets.

And I'm happy and sad to say that despite growing our attendance by, it'll end up being I think 80% bigger than last year, we already sold out with two months to go before the event happens. And now we're running into fire code problems if we are to extend any more tickets than we've already sold. So good problem to have, but just one of those things that has been a challenge.

And so I think the lesson for it, though, is as you are thinking about the assumptions you're making, always look to create optionality in everything you're doing. And look for where there are incremental steps you can take to deepen an investment or reduce your risk. How do you build steps into whatever your bets are?

And it doesn't mean don't make big bets. You should definitely make big bets. The most successful companies are the ones that made big bets. But wherever possible, try to build optionality into your decisions. Because if you do that, as you get more data and you continue to question things, it's easier for you to pivot. Or maybe not a full pivot but at least make those adjustments to accommodate your new reality based off of that data.

Josh: Yeah, awesome. The flexibility, always keeping yourself open to change. I love that mentality. So the final question before we wrap up is something I ask everyone. It's kind of a corny question, but you always get an interesting answer. I'd love to hear what you think your superpower is.

Michael: Perhaps two, at least this is the way I feel about it. So one is I think one of my superpowers is being able to find the joy in life no matter the situation.

Josh: That's a massive one.

Michael: Life is incredibly short, you might as well go through it happy. And if you find that you're perpetually not happy, well then you need to change your circumstances. And, obviously, people have very difficult circumstances that they're put into, so I don't mean to speak for everything in life. But if I'm totally speaking from the comforts of being a knowledge worker in a remote-friendly economy in the United States in 2022, try to find the joy wherever you are with whatever you're doing. And if you can't, then do what you can to change those circumstances to the best of your ability. I think that's my number one superpower.

My second thing I might say is being able to drill into ideas or processes to understand things at the root level quickly. A lot of people don't like getting lost in the weeds or the details. Don't get into the minutia. I don't think you need to live in the minutia, but I do think folks are better served if they can try to understand what makes things tick, how do they work? Because if they do that, they're going to be able to use that more effectively and understand whatever they're working with, they're going to be able to continually question, what we talked about earlier, the how and the why.

To be able to do that effectively, you need to understand how things actually work. I can't build a better watch unless I know how watches actually operate. How do they know what the time of a second is? Why does quartz vibrate that way to approximate what a second is? And if we didn't have quartz, what would we do? Go off some random esoteric example. But understanding, trying to get to the root of understanding how things work quickly, I think is something that I've been fortunate enough to have as a skill.

Josh: Awesome. Well, Michael, it's been a real pleasure to have you on. How can people connect with you if they want to connect online, keep up with what you're doing?

Michael: Connect with me on LinkedIn. That's where I spend my time on social media. I haven't been on Twitter much in many years and when I was, it was really just to complain at United Airlines for doing something poorly.

Josh: Of course, like us all.

Michael: Exactly. So they can find me on LinkedIn and connect with us at Skilljar as well. Hopefully, we can help your customers by training them to be your best customers.

Josh: Awesome. Great. Well, thanks so much for the time. I've really enjoyed the conversation. Appreciate everything you brought to it.

Michael: Awesome. Thanks, Josh.

Josh: All right, talk later.

Michael: Bye.

Outro: Thanks for listening to this episode of A Brave New Podcast. Go to abravenew.com for more resources and advice. If you enjoyed this episode, show us some love by subscribing, reading, and reviewing A Brave New Podcast wherever you listen to your podcasts.

Josh Dougherty

Josh Dougherty



OCT 11, 2021


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