Growing your business and growing into your role as a CMO

In a recent episode of CMO Convos, we were joined by Patrick Edmonds, CMO of Propsify to discuss growth in relation to both the business and your own career. Patrick discusses his journey to the C-suite, how he approached his role, and lessons for others embarking on a similar journey, his personal philosophy on learning and ideas, and more.

You can find the full episode here, but check out the write up below to see what we discussed.

Patrick's background and approach to the CMO role

To get started, can you tell us a bit about your background, how you got into the CMO role?

Yeah, absolutely. I'm the CMO currently at Proposify, they're an online business proposal software that gives you control and insight into the most important stage of your sales process, which is the close and the sign-off. I started here, it'll be five years, actually, next month, in about a couple of weeks.

I started as a growth marketer, not in the CMO role. At that time, the company was only about 10 people, about a million in revenue and since then, over the last five years, we've scaled to be over 100 people close to 10 million in revenue. And I've seen a lot of evolution and scale from there.

So my background, previous to that, was in a lot of paid advertising and analytics, kind of in the early 2010s, when Facebook advertising really started to become a major channel for marketers in addition to Google and other paid advertising things, it was a great way to, basically I worked at an agency where I would work on multiple different campaigns and plans, a good way to cut your teeth as a marketer and learn what really works and what doesn't.

My CEO even called it once: it's like you're a private shopper for other people. You're leveraging all of these big budgets from great brands and great organizations and learning what really works and what really doesn't work, targeting lots of different target audiences and different products and different markets.

And so that was really exciting but I kind of found out that doing that for a lot of different companies, you can only get so far, you can only scratch the surface to a certain degree of what is possible. So I really wanted to take a lot of those skills and apply it to one particular company, and I was lucky enough to be able to do that at Proposify.

Awesome. Did you approach the CMO role when you got to it with any philosophy? Or have you developed a philosophy as you've gone on? Is there something that drives you as a CMO?

Yeah, definitely not going into it. I didn't have an inspirational quote on the wall or anything like that. But over the years, you learn things about what's worked and what doesn't. I'd say right now, if I had to say what's my overall philosophy, it would be to go all-in on whatever your given strategy is at a time, but always be prepared to fail, because you probably will fail more often than you will actually succeed. So it's this kind of give and take where if you don't shoot for Mars, you're never going to get to the Moon sort of idea.

Inspiring a team to be able to do that and make sure that you're really pushing yourself to succeed is really, really important. But you have to realize that those big shots, not all of them are always going to be successful. So make sure that you're aware of what you're doing, what the risks and rewards are, make those big bets. And the only way for them to really, truly be successful is if you put your all into it. So that you're giving every opportunity the best chance to succeed.

But then be prepared to be like, "Okay, well, what's the next thing?" If this didn't go as good as I want it to be, you always have scenario planning and backup planning and what's the next thing that you're going to do so that you're always incrementally making a little bit of improvement every single time that you do, but you can't be overly conservative with that sort of stuff too or else you won't scale and you won't grow.

If you did have an inspirational quote on the wall, it sounds like it'd be that Wayne Gretzky quote, what is it now, you miss every shot you don't take?

Yeah, you miss 100% of shots you don't take. Exactly. So yeah, take the shots, make sure that you and your team have everything possible to succeed within that. But always be aware that if you're putting all your eggs in one basket that there's always that sort of risk and reward. But it's not to say don't be overly conservative too.

So it's a fine balance that you have to strike because if you're overly conservative about "I'm going to try this and kind of dip my toes in the water" then you're never gonna give it its fair shot, you're not going to take the shot, you're likely going to miss. So it's not an easy answer but it's something that I would think other leaders and marketing leaders are probably experiencing the same thing.

How did you bring that philosophy to growing Proposify in that way? What were the methods that you took? Did you go in with a playbook planned out?

No, I was not the type of CMO that you hire because they've been there and done that before sort of playbook. I mean, that's kind of how Proposify has grown is like it started small, and it's a lot of first-time people in their roles that have never done it before, which is a little bit different than some startups and scale-ups. Some companies raise a bunch of money right away, and then they bring in the people that have been there and done that before. And other times you can kind of scale and grow within it.

So we may be a little bit unique in that but that's the approach that's happened so far for our success. But at the same time, our CEOs told this story, so I'm not worried about saying it, before he hired me, he interviewed somebody that was at Yahoo at the time, and at the time, Yahoo was actually big and still pretty large at that time.

But they were demanding this crazy, not crazy, probably worth that salary at the time but it was something like more money than the company made in the last six months combined for just that one person. And they weren't prepared at the time to bite that off. I guess I was the second choice or something like that, which is a very different approach.

But I think leaders in organizations make that choice sometimes it's like, okay, are you hiring someone who's been there and done that? Or can you invest in somebody with the right raw talent and raw skills to bring to the table? I mean, we still have those conversations now when we're hiring new people, it's like, well, do we go out and find someone that's been there done that and we've seen a lot of success with that model.

Also a model with investing in some raw talent so I didn't have that playbook to answer your question but definitely over time, there are things that you learn and take from and one of my recommendations for other people is, you don't necessarily have to have the most creative or best idea every single time. And if you think you are, then you're probably fooling yourself.

But you can learn a lot by seeing what other people are doing really, really well. And I think the real key talent of good CMOs is those who know how to take the right pieces and apply it to their business, and not be distracted just by shiny objects. We've all heard of shiny object syndrome, like, "Oh, they're doing that, I'm just gonna try and do that for my business too".

Trying to take someone else's ideas and apply them for your own verbatim one-to-one is just a recipe for disaster. But the real talent is looking at a market, seeing what's working well, seeing how it applies to your business, and taking that nuance and tweaking it and applying it to what you do. I think that's a unique skill and a lot of people don't focus on a lot is how to steal ideas but make them your own.

Think of Apple, Apple has a lot of creative ideas, but if you think of some of their best products, someone came up with it first, they just did a way better job at that product and ended up totally owning a market. They weren't the first smartphone or the first smartwatch or anything from that perspective. But they take the pieces that work really, really well and put their magic on it and that's where it really works.

Is that your main philosophy when it comes to ideas, it's doing better than other people?

Yeah, it's learning, it's a lot of listening and learning. It's a lot of being aware of the market and being aware of not just what your competitors are doing but what people that are in the same space as you. I think of them as like competitors from a message perspective. There might be people that don't have the same product or service at all, but they speak to the same audience. So who's speaking to that audience? What does that audience get excited about?

And I'm not just talking about generic adults 25 to 54 sort of demographic fits, it's like who's your ultimate persona, your ICP, ideal customer persona profile for that market? What do they get excited about? What do they like? And it may have nothing to do with your particular product or service but there are nuances as to why they get excited about that, that you might be able to learn from and apply to what you do.

That's kind of a unique thing. There's this SaaS, Software as a Service, coach named Dan Martell, and he calls it R'n'B. It's called rob 'n' duplicate. And don't take shame in it, it's not stealing anything, it's not copywriting, but it's just creatively understanding what works well and putting your own spin on it.

So how did you take that method towards growth for Proposify, what were the big methods that you took? Where did you get them from? How did you adapt them for your own...?

Absolutely. So when I started as a growth marketer before kind of evolving in the CMO role I brought that paid advertising background experience. I asked our co-founders like, I don't want to do this right away, we were outsourcing that work and I wanted to continue to outsource it for a little while because I wanted to dive into all of the other aspects.

That's just one mechanism for growth and it's definitely not the only thing. I wanted to figure out what are the real mechanisms for growth for this business? Because it's not going to be the same for every business. But I did look at people in the same market.

So we're in kind of like a software startup market, I'd look at companies like HubSpot doing really interesting things on inbound marketing and growth and what they're doing from an SEO perspective. I'm not just gonna copy HubSpot, I don't know exactly what that is, but I'm trying to learn like, okay, they're getting a lot of traffic in these sorts of ways so I went heavy into the SEO aspects of our business and improving our site ranking and content and optimization.

It ended up that would have been a bigger lever to pull than any of the paid advertising stuff that I had brought. So our co-founders might have thought, oh, we're hiring this guy who has a lot of paid advertising experience, he's gonna come in and just do a really good job at leveraging our paid spend and growing us that way.

But I took a different approach, which is let's just leave that, I don't think that's going to be the main thing that's going to be the driver. Let's figure out what the landscape looks like and figure out what are those channels that can drive us because, in the startup space, we talk a lot about product-market fit, which is can you sell your product to a certain market?

But then there's market channel fit, and then there's channel model fit and then there's, what's the other one, totally blanking on it now. But you have to have that whole ecosystem working with the product and the marketing and the channel that you're going after and how you're selling it. It needs to be a holistic picture. So it's not a tried and true method but it's really just evaluating what is unique to this business, what levers can I pull to create growth within?

How the role has changed as the business has grown

Being at Proposify from such an early stage supposedly gave you the opportunity to get your hands dirty, get to know all these different moving parts of the business. Has that changed as Proposify has grown, how has your role changed?

100%, I'd say every year if not every six months it looks like a different role, basically. I'd argue back then, even when I was given the title of CMO, I was not a CMO. I'll be the first person to admit that it was probably too early to actually call that and our CEO and I, transparently, have had the same conversations like sometimes young growing companies want to be like, "Oh, you're the head of this and you're the head of this". And maybe that was a little bit too early to be able to say that because I wasn't, you look at other CMOs in other organizations, I didn't meet what a typical description would be of a CMO.

But in the last maybe year and a half, two years, I think it's definitely changed. I was definitely very much more hands-on as the growth marketer, even into the first year or two of being officially the CMO. Something our CEO Mike Kyle has said, you're always trying to hire yourself out of a job. That starts as the CEO, you wear all the hats, you are sales and you are customer support, and you are product development as that role.

And eventually, you hire a leader for product and you hire a leader for sales and a leader for marketing and that sort of thing. So you're hiring yourself out of all of these jobs in a growing company. Same thing can relate down to the marketing level, where when I started, I was leading all of the paid advertising, the analytics, the funnel building, a lot of the growth aspects, conversion rate optimization, that sort of thing too. And I had co-collaborators on some of the creative sides from design and copywriting, positioning.

We ended up hiring more people as the team grows and that sort of thing too so I'm taking this idea of hiring myself out of a job, but really what I was doing was hiring things I wasn't good at, which is another good mechanism, hire people that are better than you at whatever their specialty. So hiring way better copywriters, and way better designers, and that sort of thing that weren't my strengths. But what I didn't do was really hire myself out of a job I still kept a lot of those hats.

I was wearing too many of them for too long. It definitely was a learning lesson and had to evolve over time to find people with similar skill sets as me that were actually better than me at what those things were. That's a really big takeaway for someone that's maybe just starting growing into that role of CMO before they've really got there is make sure that you have the team in place to support whatever the company needs.

Do you ever miss it, do you ever feel like you want to put on a disguise, go back into the trenches, and "I'll see what's going on on Google Ads" kind of thing?

Yeah, I'll admit sometimes it's like a guilty little pleasure to be able to do that. But it's not necessarily always the most productive and actually can step on other people's toes and that sort of thing. So I have to claw myself back a little bit sometimes. But there's a balance there, I guess with being informed with what is possible and trying to paint more of a strategic picture for where we can go and letting other people make the tactical decisions on how that gets executed strategically.

And there's a certain level of servant leadership there too where you don't want to just be sitting on your high horse and showing that you can go into the trenches with your team. If something's broken, or everyone needs to band together as a team for morale and cultural reasons that yeah, you can do that, you can roll up your sleeves and do that.

But it shouldn't necessarily be the day to day sort of thing, if you've done a good job as a CMO, you've hired people that are better than you at those things and so you stepping in to try and do some of it's probably not the best idea.

Because you're not in the marketing team anymore, you're in the C-suite, that's the team you're a part of, and you're just in charge of managing that marketing team as part of the being in the C-suite.

Yeah, you make a really good point, that's actually something I'm talking with people about lately is some people don't realize who their teams really are. And that's at the C-suite level, and then even your management level. So I am part of the executive leadership C-suite sort of team and that's who I'm collaborating with for strategic vision, objective planning for the organization.

But then also, you have to think about the team that you have, depending on how deep, how many layers there are, we do have this management level there, too. And they aren't just individually reporting to me, they are a team in themselves. They are collaborating a lot, even if they have direct reports as well, there's this idea of which you kind of belong to multiple teams, but ultimately, where do you fit into that picture.

It's really about communication and collaboration and that's the only way that you can really get work done effectively is if you know who your teams are and if you can work collaboratively with them at the executive level, or at the management level.

Refining and testing different frameworks

It's something that a lot of growth CMOs, particularly first-time growth CMOs are going to have to get used to is trying out these different models for teams, different models for how the company functions, how it fits into the rest of the organization.

Yeah, we've gone through a couple of models ourselves from that perspective, because it started off with just a group of a few people. So three marketers, myself and two others, we'd end up hiring, "Oh, we've got some more budget resource, where are we bottlenecked right now?" we would just always hire to unbottleneck certain functions.

Like we need to write more, we need to produce more content here, we need more email nurture campaigns, we need to focus on... That was like the first intention of when we were hiring more people was just removing where the current team was feeling pain.

But that model does not scale very well, because it's not structured, it's not organized. What you end up having is a team of a lot of specialists in particular areas and the generalist or marketing strategy, then is still siloed to one or two people.

It's not very empowering for the team when they're only responsible for one specific aspect. They're basically just waiting to do their particular thing, at least in the scale of organization that we are right now, it's a lot more empowering if you have people that can tackle a larger project and own that kind of from start to finish. They don't need to be an expert in every single category, but they can see and speak to it and work with other people effectively to make that a reality.

The way that we position it internally is this idea of the T shaped marketer, if you've heard of that before, where you're broad on the top of the capital T, you're broad in a lot of aspects of marketing, so copywriting, SEO, optimization, paid, co-marketing, sponsorship, all these sorts of things that a marketer could be doing at any given time. And then you're usually deep in at least one or maybe two of those categories.

So when I started at Proposify I was a T-shape - broad across many but deep in the paid advertising space. And there are some others that are deep into the design or deep into copywriting. If you have a team of those types of people, they're broad enough that they can own a project and they can see the vision for what it looks like and they can bring their specialty into that one vertical. But they can collaborate with other people much more effectively because they can all speak the same language, at least at the top level of what they're talking about.

But if you have just people that are specialists and deep in one category, but don't have that breadth, they don't have the ability to necessarily carry a project forward. So building a marketing team, something I've spoken about to other people is to make sure your team's full of a bunch of T-shaped marketers.

Time for us all to update our LinkedIn profiles to include T-shaped marketer.

Yeah, I think it was Brian Balfour who was previously at HubSpot who might have coined that term, I'm not going to take credit for it. And then you can actually evolve that, there's a someone else I know, his name's Ross Simmonds and he evolved that to the capital I shape, which then at the bottom of the T when you've got that is a breadth of skills that are more soft skills of leadership, coaching, managing budgets, that sort of thing.

That's when you really identify who your marketing leaders are going to be or managers, where they have that T shape, that depth in one area and breadth, but they also bring these other skills that you need to lead and to project manage the rest of the team to make your project successful.

Circling back to two things you said earlier about not being conservative with the shots you take and also moving away from that reactive hiring model that you were previously using. Were there any other things that you realized weren't working as part of your development as a CMO, things you had to learn not to do?

Yeah, one's more business in general, I'm not scared of sharing this, is that if you're trying to evolve into a new market, or add more to something that you're doing currently because typically that's something that will happen in scaling organizations is they call that hockey stick growth right away, where it's like, "Okay, product-market fit and stuff, people like what you're doing", and you start to see a bunch of growth.

Eventually, though, that's gonna peel off and plateau, and every company, if you look at generalized has a scale period, and then a flattening period, and then they think of something else, there's a scale period again, and then there's a flattening period.

So whenever you get to the flattening period of your growth trajectory, you ultimately think, well, what's the next thing that we're going to do that will cause us to win? And from a marketing perspective, you might think that's a new channel that you haven't experienced before, it could be a new market you're going after. And the hardest thing to then do, especially if budget is a consideration, is do I take stuff away from what's currently working and apply it to the new area?

That balance between keeping what you know has worked and is working, versus investing in the potential future. There's no easy answer there because if you don't invest in the future, then you're SOL, you're not gonna get there because you'll probably stay flatlined, and someone else will figure out what the next thing is if you don't. So you kind of have to experiment there.

But if you go down that direction, this is my point of going all in your strategy but being aware of the impacts of that, if your bet doesn't pay off, what are the risks there? And how do you evaluate that? And how do you maintain what currently works with additionally what's new? And it actually relates back to the idea of hiring yourself out of a job.

You just need to make sure what you're doing right now, you're optimizing and you have it better. It might mean that there were five people involved in it before, can you optimize it to three people and a third of the budget at the same return so you can take that budget and those people and apply them to a new experimental method and mechanism.

As opposed to just taking part of that budget and those people and applying them somewhere else and you're really just stealing from one area of your business and potentially giving it to another which could totally pay off but if it doesn't, then you're in trouble.

Are playbooks possible?

You said you didn't go into the role with a playbook but do you think you have one now? Or is that just not something that's realistic? Does it need to be unique to the time? Or could you step into another CMO role at a startup and say "this is what we need to do based on what I did at Proposify"?

Yeah, I think there are potential dangers there for that example like not every business is the same. That idea of just stealing some other company's ideas and trying to apply it to a different business, there's no guarantee that's gonna pay off. But the playbook would then have to be broad enough in general so that it applies to how any business could potentially leverage this.

I think of it as a "What are your growth engines within the organization?" which is like how you make money. And ultimately, that is marketing's role in collaboration with product and sales, depending on what your business model is, you just need to figure out how to make more money.

And so the marketing engine is kind of this combination of all the touchpoints from traditional top of funnel down into the bottom of funnel, it's your pirate metrics, AARRR: acquisition, activation, retention, revenue, referral. And it’s all of the pieces that fit into that. So if I have a playbook is really just saying, you need to understand what your revenue engine is, and you need to understand, what's the market that I'm going after?

How am I positioning my product or my service to that market? What channels am I choosing to communicate that message of the positioning to that market? When I communicate to that market, how am I capturing it? So is it like in our case, transparency, we have a free trial or software, we have lead magnets we call them, like ebooks and white papers, you can request a demo, there are lots of mechanisms for capturing our audience.

Then there's a nurture sort of sequence after that, how am I communicating and educating through this buyer journey? Whether that's through email or retargeting ads, or just communication on our website, or webinars that we go on that we do or things that we sponsor in the market? How do we make sure that once we've captured them, that they are able to make a buying decision if that's the right decision for them? And then what's the ultimate conversion point?

How did they end up buying? And do you make it easy for them to do that? Is it an easy choice? Have you communicated your value effectively, so that mechanism of revenue capture makes sense? Then are you continuing to keep them after that capture? So it's understanding how all of those pieces play together and if you change one, it might impact the rest of them.

Being aware of all of those sorts of things is super important. Because if you change your positioning, your channels might have to change, especially if you change your market, all of that stuff down is going to have to change and one thing might fall apart, and it could break your entire revenue engine.

You may also want to create different revenue engines which require different positioning and different channels and different messages. So it's understanding ultimately, how do we get money from people? How do we make revenue? And what were all of the touchpoints that had them that preceded that?

So in order to truly understand that you need to know your data pretty inside and out. And you also need to know your customer from an anecdotal interview perspective and listening to calls with sales if that's part of your business model or interviewing them, surveying them, knowing what the market is doing. So it's not much of a playbook really, so to speak but those are just key aspects that any business would need to do to be successful.

Do you think you were better suited to understand that revenue engine because you were an internal hire? Do you think that was an advantage rather than an external hire might not have the opportunity to know that from day one?

From day one yeah, they wouldn't. I'd recommend anyone who is joining a company try and figure that stuff out as soon as possible, that's your first job is like, "Okay, what is the revenue engine? How does it work? How can I make it better?" For me particularly, why I think it came easier, is my background was in not just marketing, but in finance and a computer science background a bit too.

You wear many hats in a young startup, we didn't have a CFO, we had an external outsourced sort of CFO, so any business financial questions, especially when it comes to software and a recurring revenue model, we talk about monthly recurring revenue, annual recurring revenue, our churn, and lifetime value of our customers, I ultimately owned all of that on top of the traditional marketing metrics.

So it came very naturally for me to think about the revenue engine and how it all works, where are we making money from, which helps make marketing decisions a lot easier, because you know where to invest, you know where to put your time, you know the right sort of things, because you're looking at the metrics and measures of success a little bit more globally than maybe traditionally, a marketer would have 10-20 years ago.

So would you describe yourself as a growth specialist CMO? Is that the hat you'd wear?

Yeah, it's not a bad picture to paint for sure. I definitely lean heavier on the systems, process, analysis, and data side of marketing. There's another person in our company who is the Chief Creative Officer, and I'm the Chief Marketing Officer and we've worked closely together over the past few years and we have a running joke that we're like a two-headed monster sort of thing.

But really, it's the right brain left brain sort of idea where I'm definitely much heavier on the analytical side although arguably there's a lot of creativity that can go into that. Then she was much heavier on the traditional creative marketing side of positioning and messaging, that sort of beast.

You need both, you really need both to be successful, I don't know if it's common if you really get both out of one person every single time, but in our model that's worked for us. But if you don't get it in one person, you want to make sure you have that covered in your team.

That kind of goes back to the idea of hiring yourself out of a job and making sure you have people that are better than you. Because if you aren't as strong on the funnels system analytic side, I would hope that you would have a Head of Marketing Operations that is able to fill in those holes for you.

Or if you aren't as good on the positioning side, you have a product marketing expert that is really solid at doing some of the positioning work. So that's something that we've had to learn over time as well.

The future

Speaking of learning, what's next? What are you working on in terms of your skills? What does Proposify need from you now?

Yeah, since I think I've really more evolved into being a more CMO role over the past few years that it has been a lot of learning and that sort of thing. To be a CMO, it's to admit that you aren't actually doing a lot of hands-on marketing, tactical things anymore.

So I am trying to educate myself just on basic coaching concepts and ideas that can be applied to coaching the marketing team, as well as painting a clear picture to that team of what that success looks like, that communication of what does the marketing team need to do for the company to be successful?

Really, my role is making sure that the company vision is possible within what is possible within our marketing team, given our people and our resources. In order to do that the people on our team need to enact that so it's my job to paint that picture, to make sure that I'm removing bottlenecks for my own team that they are skilling themselves up to be able to make those realities true. So it's a lot of coaching, training, process so that the team has the resources that they need to be successful.

Where are you learning these skills from? Do you have certain touchpoints that you go to, certain wells that you go back to for these kinds of lessons? Or is it just something you're learning on the job kind of thing?

A lot of on-the-job, to be perfectly honest, I'll do some audiobooks just because I can usually try and do something else physically, not mentally, while I'm doing that for a sense of time. So I'll listen to a bunch of audiobooks where I can, reading - thought leadership from other people on the web, there's so much free, amazing content out there that I'll go there. I apologize, there's no one big thing that I'll go towards.

But our marketing team has actually started doing a book club so every Friday we get together and we've read a chapter or two of a piece of content. And it doesn't even have to just be a book, we're doing webinars or ebooks, or other forms of content and learning together as a team with things to change.

One example I'll just give is that we recently migrated to the OKR model, objectives, and key results, for our quarterly planning, we previously used the employee operating system EOS model, which is like rocks, pebbles, and sand, this idea that you need to fill your jar with the rocks first, before that. We've kind of moved to this objectives model so our team read a book, it's an OKR book, together as a team, called Radical Focus by Christina Wodtke.

It had a fable about an example company implementing OKRs within their organization. We learned together as we were implementing this system, and I think it worked really, really well, because we all learned at the same time this new concept within the organization and implemented it fairly quickly, within that quarter.

This is the second quarter that we're we're doing it and already seeing major improvement in terms of our ability to think about what objectives we need to hit and what initiatives we're choosing to drive those. So that's a good thing of kind of bringing the team together.

The two-way street learning model sounds interesting: you're listening to the rest of your team, and you're working together to drive the company forward. Is that something you think all CMOs should be doing? Or are there pitfalls in that maybe you're not taking the leadership role in some situations?

For sure. Something, as our entire leadership team, we've realized, and this is one of the reasons why we adopted the OKR model is we were being too much of a top-down directive-driven organization, which doesn't allow for a team to feel like they have the power to make choices or effective decisions. And the OKR model kind of flipped it for ourselves where it is a lot more bottom-up in terms of decision making.

It's ultimately the executive leadership team is to paint that picture of what is possible, so that everyone else in the organization can just look at what that picture of success looks like, and when they're making their decisions to say, does this work within that vision of the future?

That's all it really is, is a vision of what the future needs to be. And the leadership team comes up with that vision based on research and data and what we're seeing in the market and where it's going, what available resources we have on hand. And this is the picture that we're painting for everyone. But then so many decisions are made on a day-to-day basis by everyone in your organization.

You can't dictate every decision, you don't want to dictate every decision so it's really important to make sure that picture is clear as possible when those decisions are being made. And then ultimately give the ability for more of those decisions to be made from your organization. That's when you can get things done faster and more efficiently and you'll probably see better ideas because if you've hired correctly, you've got a lot of smart people in your organization who don't need to just be told what to do.

They just need to know that when they're making a decision that it's aligned with the direction of the company, and so that their decisions are, yes I'm making a decision and it's aligned with the picture that's been painted for me. That ultimately should be the right decision. But also create an environment where failure isn't a bad thing. That goes back to that semi philosophy, I guess I had before, which is to go all-in on your strategy, but realize that you're going to fail probably more than you're going to succeed.

You have to make sure that your team is comfortable with that concept because otherwise they'll be scared to make that decision or if they do fail, they might try and hide it or something. You want that to come open and say "Hey, we tried this idea. Didn't work. But we learned this, this, this and this. And here's what we're trying next". That's what we're trying to establish within the organization with this idea of enablement and objectives.

If you're hiding your failures, then you're not learning from them. You don't grow at all, no one knows what you've done wrong, and no one knows what you're doing better next time.

Exactly and sharing that information is the biggest part. So making sure other people know what's been done before, what's been tried, and what has worked and what hasn't so effective communication and sharing within our organization will just open up so many doors.

From all these lessons you've learned from your first CMO role, what advice do you have for people who will be stepping into a new CMO role soon or looking to make that jump in the near future?

Yeah, I'd say understand that being a CMO means that it's way more than just being a good marketer. That doesn't have to be the only path if that's what you think it is. Being a CMO is about empowering people, it's about coaching, it's about other people combined with a lot of cross-functional business acumen and working on that executive leadership team and seeing where the next revenue engine is going to come from. Making those decisions.

It's not necessarily about being the best tactical, paid advertising specialist or SEO specialist or whatever vertical that you brought. You can bring that experience with you and it can be taken as an advantage within your role but I guess if someone's wanting to be and choosing to be that CMO, just acknowledge to yourself that it's a lot more than just being a good marketer. It's about being a good executive leader and a good mentor and a good coach above a lot of the rest.

How do you go about learning to do that? Learn by doing?

That's a hard one. I'm probably maybe not even the best person to ask that question.

Is that a conversation for another time?

Where I'm sitting right now, that's the continual challenge is just trying to evolve yourself to be those sorts of things. I think you always have to acknowledge in whichever role you're in, that you're always trying to make yourself the next best person for that role.

Because at any given time, and this actually came from that book that I read, Radical Focus, it was an example of the two co-founders of the company, this is a fake story but they were potentially going to get kicked out of the organization - spoiler alert - and one of their board members basically says,

"Well, I could just go find someone else, another CEO, and hire them to do this job. Or you can become that CEO but you have to adapt and change to become that role". And that takes investment in yourself from a learning perspective and investment and reflection on what you're really good at doing and what you're not good at doing and seeing what the company needs and marrying all of those things together.

You may decide that's not you, and maybe it is better for the company to have somebody else and you can focus on some other area that is your strength. Or you can say no, I can be that person, I just need to get way better at this aspect in this area, which might be something along with coaching. We'll see how that goes, you can bring me back and I'll give you an update.

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