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190: When To Hire a Director of Marketing and How To Do It Successfully

Posted by Austin Brawner on March 12, 2019


A topic that’s come up a lot in my recent conversations is how to hire a high-level marketing person.

Finding the right candidate can be tough, and when you’re a business owner doing a million other things, it can be even tougher.

In this episode, Andrew and I talk through the hiring process, from deciding when to hire, to where to look for the best candidates, and the questions to ask before hiring to make sure you’re getting the best person for the job.


Episode Highlights:

  • 3:41 How to know when it’s time to hire a CMO or Director of Marketing and one of the key signs to look for.
  • 6:28 Two main things to understand when you start the hiring process for a high-level marketing candidate.
  • 7:35 The most effective way to find the ideal candidate.
  • 9:23 Tips for working with a recruiter to find your next CMO.
  • 11:14 The two different types of candidates you’ll find when hiring a Director of Marketing.
  • 13:24 What to ask a potential new hire before you bring them in for an interview and the type of answers to look for.
  • 17:32 Once you confirm someone is a good fit, it’s time for the 15-minute phone call. Here are the questions to ask during that call.
  • 19:42 What is a “T-Shaped Marketer” and why you want to hire one.
  • 23:46 The framework for the in-person interview and what to look for.
  • 25:29 The last thing to do before hiring the person you think is the right fit.

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Austin Brawner: What's up, everybody? Welcome to another episode of The Ecommerce Influence Podcast. My name is Austin Brawner.

Andrew Foxwell: And I'm Andrew Foxwell back for another flash episode. I did that earlier on when we started these babies, but at this stage, I haven't actually said, "Flash," in a while, so I just felt like I needed to bring it back.

Austin Brawner: It's true. These have transitioned. What was just once an experiment now has become kind of a mainstay, and we've been kind of going into these episodes, doing these flash episodes, every other week. What's really interesting is that I find that every time I go through and spend the time outlining an episode ... So, a lot of these are inspired by conversations, right? You and I get an episode where we have a conversation with someone. We're like, "Oh, we gotta record an episode about this 'cause we keep hearing this conversation." It's interesting because I kind of have this feeling, like, have a bunch of conversations, bunch of conversations, they keep coming up with people about the same issue, and then it turns into an episode. This one has been one that's been screaming to be done for a while because I keep having these conversations with people as their businesses grow, and that's really the process of hiring high-level marketing people.

Andrew Foxwell: Yeah, absolutely. I mean, we talked about it originally in the context of hiring a CMO, but this is a decision a lot of business owners face. You don't know, when is the right time? You don't know, how do you even go about it? Then once you get people in, how do you start to interview them? How do you start to qualify them? And if you've not done this, it's not your core strength 'cause you're a business owner and you're doing a billion other things, what are the things you want to think about? That's really what we're gonna be covering today.

Austin Brawner: Yeah. The whole process of this conversation is really specifically when you should hire a Director of Marketing and how you want to approach it, and really, today, you're gonna learn the questions you should ask yourself before hiring, where to look for the right people, and then how to qualify those people and the process to find the right person for your business.

Andrew Foxwell: Yeah. Let's absolutely get into it. Somebody asked me this. When is it time to hire a CMO or a Director of Marketing? What are the qualifications that it's time for you? What's the answer you give on that one?

Austin Brawner: Well, I think that that question always comes down to capacity. As a business scales up and grows, you're going to move from a time, initially, when, as a business owner, you're spending a lot of your time in a marketing acquisition role, and as you grow, you need to spend more and more time in a CEO role. When the business is really small, there's almost no time spent in an actual CEO role, but as it grows, you have to spend a lot more time in the CEO role, and that involves more strategic vision, managing people, hiring those type of roles. I feel like the conversations I always have with people around hiring a Director of Marketing or a CMO, it's when they start to reach capacity and their CEO role is detracting from their role as the head of marketing.

Andrew Foxwell: Yeah, totally, right. They kind of become the bottleneck, right, to some degree.

Austin Brawner: Yes.

Andrew Foxwell: Does this happen in a revenue range, typically? I've always wondered that, myself. Where does that happen or do you see it happening most often?

Austin Brawner: I mean, generally, I see it in the $5-20 million run rate is kind of where people ... But, I think a lot of that depends on how active the founder is as the Director of Marketing. It can be lower earlier on if the founder is less marketing-focused, but in a company where one of the founders or the CEO is heavily marketing-focused, it tends to be a little bit further on. What's interesting, just to kind of ... I was having a conversation with one of my friends who runs a large direct to consumer company in Austin, and they were doing a website redesign.

Andrew Foxwell: Oh, yeah.

Austin Brawner: He was complaining. He was like, "This project has taken so long that I had to get it off my plate." He's like, "And it took so long because I was doing it. If anybody else on my team was doing it, it would've been done in, like, a month, but because I'm stretched so thin, I couldn't do it." That's a key sign, if that it's happening to you that it's probably time to hire a Director of Marketing or a CMO to take some of that burden off of your plate.

Andrew Foxwell: Totally. I think that's a huge sign. In terms of approaches as you go about it, I think there are two main things you and I have talked about, in terms of approach, of kind of just understandings, I guess, going into hiring a marketing person. One is hiring a high-level person like this is going to be different than an entry-level job, which I think is different than hiring an entry-level person. I think that's a big one. The second one is one I'd love you to get into that.

Austin Brawner: Well, the second one is that you gotta recognize when you're hiring a Director of Marketing or CMO that your ideal candidate is probably not actively looking for a job, and that's what's different about hiring for some other roles, is that you're going to try to pull somebody from another job that they might be satisfied with or only slightly dissatisfied with, and so the mindset is gonna be a little bit different than hiring for some of the other roles where people are more actively looking at it. You gotta approach it a little bit differently. It comes down to attracting how you actually attract your ideal candidate.

Andrew Foxwell: Yeah, so how do you go about finding the ideal candidate? 'Cause I've talked about, there are recruiters, there are other ways to go about it. What are the ones that, really, you've seen produce the best results?

Austin Brawner: I think that really, the most effective way is probably to go and ask for help from your network. I really like ... We had an interview with Mike Danner, the VP of Marketing at Ancient Nutrition, formerly Dr. Axe, and he has hired a ton, ton of people, and he's hired high-level marketers, as well.

He's the VP of Marketing of $100 million-plus company, so he's hiring the people that you'd be hiring if you were a smaller scaling business. His method, which is extremely effective, is to reach out to people who he thinks are actually really good quality candidates that would be a good fit for the specific position and ask them if they know anybody who would be a good fit for this role. The psychology behind it is not directly asking people, but giving them a challenge and saying, "Hey, I've got this really great opportunity for somebody who is an all-star, and they would be perfectly fit for it." Then you ask them, "Do you know anybody who would be a good fit?" It gives them the opportunity to respond back and say, "I might be a good fit for this role," or give you guidance towards hiring your first person. That's kind of the way that I would approach going within your own network.

Andrew Foxwell: I like that a lot. What if people go for a recruiter? I've helped a number of people go that route, which is, frankly, an interesting route. It really depends on the vertical you're in. Have you had good success with that? I mean, do you think that's a good way to get people that are really qualified that wouldn't have been normally looking, or what's your take on that?

Austin Brawner: I think it is a good way to go about it, or at least I think it's an option that you should be exploring if you're trying to find a Director of Marketing or CMO because you want to outline the type of person that you'd be looking for and have a close working relationship with a recruiter who might be able to find you some key candidates, just because it's difficult to get in front of the right people, and a recruiter could help you do that.

The success that I have seen has been people working with recruiters that have specific niches, a niche, meaning they know a lot of the growth people in San Francisco, and that's what they do, is they help people find VPs for the growth roles. That tends to be a better fit than just broad strokes recruiting, but yeah. Again, it's one of those tough things where everyone has strong opinions about working with recruiters because it can either work out really well or really poorly, depending on the person that you're working with. The key is, though, a lot of it can be incentive-based. You don't pay somebody unless they actually bring you results, and if you're in that position, then there's not much downside, besides the time invested in working with the recruiter.

Andrew Foxwell: Yeah, right. I think that's interesting. On the candidate side, you have the candidate understanding ... Or maybe you don't have a candidate, but you're thinking about framing this up. I've heard you say before, there are two different types of candidates. Can you go into talking about those two different types? 'Cause ideally, you're looking for these people that have, maybe, both, if you can.

Austin Brawner: Yeah. I was having this conversation today with a client in one of my brand guild coaching clients. He's hiring a VP of Marketing, and he's trying to figure out what he values most. The two types of candidates are this. There are people that VP of Marketing who have a lot of experience managing people, and there are candidates that have a lot of hands-on experience implementing campaigns.

Now, I wouldn't really recommend hiring either one of those. Ideally, you want to find somebody who has experience with both of those things. It's finding somebody who has maybe been at a company early enough that they have the experience of building the campaigns and then also managing people, but the question you gotta ask yourself is, the role that you're hiring for, how much hands-on implementation experience does your candidate need?

Because I can almost guarantee you, if they have a lot of experience managing people and you're asking them to start in a role where they need to do a lot of hands-on implementation, they're not gonna perform well. They're not gonna go backward and learn how to implement.

Andrew Foxwell: Right.

Austin Brawner: Where the flip-side, they might be able to learn how to manage people if they start out implementing. Those are the questions you just ask yourself and what I would think about when I'm looking for quality candidates.

Andrew Foxwell: Yeah. I love that. I think understanding kind of where you're gonna go of somebody that's really pulled the levers or not, or are they really just to kind of manage people? As you get into the screening process more, you're trying to refine who you have. You have said you want to get a picture, really, of how they kind of think and communicate, which I completely agree with from an email standpoint. What would be a question that you would ask them before you brought these people in for an interview? Do you ask a series of questions, or what do you think maybe ... Maybe it's one you've given them a broad question and see what they do with it.

Austin Brawner: Yeah. To put it in perspective, once somebody has been qualified, meaning you've taken a look at their initial ... Whether it's ... They pass the initial threshold. You haven't yet talked to them, but you know that they're potentially a good fit. The first part of the screening process that I would go through is to give them a broader open-ended question and let them ... This could be through email or it could be through, say, "Hey, follow-up with a Google Doc," something like that, but ideally, email is relatively straightforward. Ask a question like, "What would you do in your first 90 days if you took over as the Director of Marketing?" Or, "We're gonna be launching a product next month. How would you approach launching a product for us, knowing what you know now and nothing else?"

Andrew Foxwell: Yeah, right.


Austin Brawner: More of an open-ended question that's related to how they think about the opportunity, and a good marketer is going to realize a question like, "What would you do in your first 90 days if you took over as CMO?" That's a really hard question to answer without knowing much about the business.

Andrew Foxwell: Totally.

Austin Brawner: Well, what are you gonna do? Well, the first 90 days, I'd probably try to figure out what was important and figure out where the levers are, do an audit process, really dive into each channel, learn from the people that are the actual operators that we're working with on the team to figure out where the opportunities are so that the second 90 days, we can make it the best 90 days ever. You know what I mean?

That's kind of the type of an answer you're looking for, is realizing that it's very ... If somebody comes in with a lot of answers, like, "We're gonna do this, this, this, and this," well, that might not be the right fit because how do they know what they should be doing?

Andrew Foxwell: Yeah, right, making declarative statements about something. This is, to me, for those of us, many of you listening to this podcast, I mean, you want to have entrepreneurial thinking that you had, right? I mean, you're the founder. You're the people that had it, and you want people to be able to think on their own and in their own creative way because, in an ideal world, they're taking it and saying, "Here's what I've been thinking about in relation to marketing X, Y, Z." And so, giving them a question like that is really important.

I remember I was 28, probably, 26, 8, something like that, don't care, and I was asked for this company I was working with to be the Marketing Director, which was, frankly, a whole other can of worms of why they asked a 26-year-old to be the Marketing Director.

But, they basically said, "Hey, well, if you were, what would you do for a company presentation of your strategic vision?" That was all they asked me, and I ended up being able to do that, and I loved that kind of a challenge because it allows the person to put their unique stamp on it right away, too. I think that is a good open-ended question that if they ask too many follow-ups, then it's like, you're not understanding the exercise. The exercise is, what do you think? We're not asking you to get too specific here. We're asking you to think creatively. You have the email side, and there are also tactics like we did talk about-

Austin Brawner: 'Cause screening, yeah.

Andrew Foxwell: Yeah, we've talked about with Mike Danner where he's like, "Use this keyword," type thing, right?

Austin Brawner: Sure.

Andrew Foxwell: And make sure that when you send this response back to me, the subject line is, "My response to Mike Danner."

Austin Brawner: Sure.

Andrew Foxwell: Just to be sure that they're reading the whole darn thing.

Austin Brawner: Well, and I would say, though, if you're hiring at this level, the person that gets to this level is gonna be, hopefully, highly vetted, and so at least for a Chief Marketing Officer, you're probably not gonna need as much of those disqualifications, like wrong subject line, but you may want to ... More of the screening process is just like, how the heck does this person think? And would they be a good fit? Once you find out that, okay, they might be a good fit, the next step would be to kick off an initial 15-minute phone call.

Andrew Foxwell: Totally. On the 15-minute phone call, I think that's where you're trying to get a baseline understanding of some more tactical information about them. These are things like, "How many people have you managed?" Thinking about the role they're going into and, kind of saying, like, "Here's how many people we think you might be managing." So, making sure that those match, 'cause if they've only managed 2 people before and they're going to walk into a team of 15, that might not be a fit.

Austin Brawner: It might not be a fit, yeah, and how many people have they hired and fired? If you're expecting this person to come in and hire a team, which for a lot of businesses, they would, ideally, like the VP of marketing to becoming and hire their team, getting a better understanding of how many people they've actually ... Have they done that before? What their proudest achievement as a marketer is, that's an interesting question that you could ask and learn more about how they did it.

Andrew Foxwell: Right, right. I think the mistakes ... Another good topic of discussion, getting into ... All of us, in order to be good at what we do, I think that you have to understand that you make mistakes. That's totally okay. What's the biggest mistake? What are some of the biggest mistakes? What did you learn after from that experience? I think that's another really good question you want to get into.

Austin Brawner: One area that I think is very helpful, there's a concept ... I don't know exactly who initially started talking about this of a T-Shaped marketer. You want to hire a T-Shaped marketer. A T-Shaped marketer means somebody, if you look across, has a surface level understanding, so kind of horizontal level, surface level, of a bunch of different channels, and then a very deep understanding of one channel that's most important to you.

If your most important channel is, say, Facebook and Instagram, you're not gonna want to hire a VP of Marketing who has a deep understanding of Google Shopping and a light understanding of Facebook. You want to have a light understanding of everything and a deep understanding of Facebook. That's the idea behind a T-Shaped marketer, and so asking them what areas of marketing they're most skilled in and what areas of marketing they're least skilled in, and why, maybe, that is a weakness for them. I like asking questions about people where they feel like their weaknesses are because it's illuminating. We all have weaknesses in some area, and if you don't have the clarity to understand your own weaknesses, it's very, very difficult to continue to progress and grow because as you get higher up, you need to find people to help you with your weaknesses.

Andrew Foxwell: Totally, right. You need to understand your limits.

Austin Brawner: Yeah.

Andrew Foxwell: I completely agree. I think if they're gonna managing people, the good thing to ask, of course, is like, "What do you find most challenging about managing people, positive or negatively challenging to you?" I think that's a really big one because for me, the answer of managing people in the times I've done that in the past, the challenges, I love to see those people grow.

So, my challenge is, that actually becomes a really big part of my job, and I move out of some of the details, which isn't that helpful when I need to be in the details in previous positions I've been in. So finding what's challenging about managing people, I think, is a really big one, and I think real examples, as you've talked about.

You talked about before, real examples of what they've done in their previous work and talking about it in the context of a bigger company. Are they coming from a bigger company? Have there been blind spots you've seen there before?

Austin Brawner: Well, I think that it can be very impressive sounding if somebody says that they were high up VP of Marketing at, let's say, LinkedIn, or Facebook, or Google. These are massive companies, but even smaller large companies that have been growing. If somebody is high up in a VP of Marketing role at one of those companies, it can be hard to get tangible examples of what they actually did to move the needle because those companies are growing, with or without that person there.

So, if you're looking at somebody who has had experience at a much larger company, trying to drill down on what they actually did to move the needle, wherein a smaller company, it's very obvious if this person is the VP of Marketing at a company with 10 employees, and they've grown tremendously. It's because this person has executed.

I was at a conference, the Klaviyo conference, and I think it was the VP of Marketing for a company called Taylor Stitch. He was walking through some of the stuff that he was doing, and it was a lot of hands-on implementation, and they had a lot of success. It was very obvious that it was because of the thought process this person had gone through, that they had that success, versus just being on a team that was in a company along for the ride.

Andrew Foxwell: Interesting, very, very interesting. Well, in in-person interviews, you could do a whole other podcast on doing, how do you sit there and look at it? I mean, one thing I was struck by in a recent episode that we did with our friends from Boardwalk T-shirts, they were talking about one would ask interview questions in-person, and the other, when they were hiring, and another person would look at the body language. I thought that was really interesting. How do you see a framework of doing the in-person interview the right way?

Austin Brawner: Well, I think if you do this process correctly and you've screened, initially from ... You've got the person's response and the email response. You've had a 15-minute phone call and answered some questions. When you feel like they're qualified for the job by the time you sit down for an in-person interview, the main thing is, how are you going to interact with this person? How do you feel about them being on the team? Does it feel like a good fit?

Because, again, if you're hiring somebody, it's basically your role, you're going to have a lot of interaction with them, and trying to make sure that they're a good culture fit, that they believe the same things you believe, that they're gonna continue to believe the same things that you believe, that they have similar expectations to the expectations that you have for the role. Those are the things that I would look at for an in-person interview with the founder or to bring somebody in.

Andrew Foxwell: Interesting, yeah. Well, I think this has been awesome. I've definitely enjoyed going through this with you. Is there anything that you want to mention as a last final thing?

Austin Brawner: Yes, 100%. Do not hire them until after the in-person interview, you have a second follow-up that they spend some significant time with your team. Once you have the in-person interview and you feel good about it, schedule some serious time with the team and observe.

Remember, this person is going to be reporting to this hire that you have. You want to see how this person interacts with the people that will be on their team, even though they're not yet in a position of authority. You want to make sure, are they curious? Are they asking questions? How are they interacting? Go from a process of maybe have them come in in the afternoon, have them go around, ask people questions, learn a little bit more about the role, and then go outside of work. Go to happy hour or go get dinner with the team and see, is it a good fit? How are they interacting? Do they fit in right away? Is it forced and weird? How does your team feel about it? Because again, these people are gonna be really, really, really close and working day in and day out, so you want to make sure that the team interacts and you gotta have a good feeling about it.

Andrew Foxwell: That's such a good point. The team dynamic, obviously, is what really creates the magic. Well, thank you for this episode, my friend, talking about hiring, and when and how to hire a CMO or Director of Marketing. I have found this particularly engaging and interesting. Of course, if you have follow-up questions, you can always hit us up. If you really found this episode useful, please go ahead and rate us on iTunes and tell your friends about this episode.

Austin Brawner: Yeah. If you're interested if you're in this position and you want some help hiring a VP of Marketing, head over to I'm working with people all the time to hire the right team and scale up their business, so you can go head over to and we'll chat there. All right, talk to you guys soon.

Austin Brawner: What's up, everybody? Welcome to another episode of The Ecommerce Influence Podcast. My name is Austin Brawner.

Andrew Foxwell: And I'm Andrew Foxwell back for another flash episode. I did that earlier on when we started these babies, but at this stage, I haven't actually said, "Flash," i...

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