The DTC Enterprise Tech Podcast

Julie Crabill (00:01):
I think you'll see that a lot in very technical founders where they respect marketing even more because they understand that it's something they can't do. Where they need help often is that they need help understanding what marketing as a whole can do for them.

Ronda Scott (00:14):
Welcome to the DTC podcast, a series of conversations between the investors and operators at Dell Technologies Capital and the people who are building what's next in enterprise technologies.

Ronda Scott (00:26):
Today I'm joined by Julie Crabill, a seasoned marketing pro who's made the transition from comms to entrepreneur to CMO, and now today is a fractional CMO working with early-stage technology companies. We'll talk a bit about what exactly a fractional CMO does on her journey to becoming one, and then we'll get tactical about how early-stage companies can take advantage of a fractional c-suite model as they scale their marketing and go-to-market teams. Welcome, Julie.

Julie Crabill (00:52):
Thanks so much for having me, Ronda.

Ronda Scott (00:54):
I am happy to be connected again. Julie and I worked together, I don't know, a few years ago. I

Julie Crabill (01:00):
Think the counts are more decades at this point, but Sure it was a few years.

Ronda Scott (01:04):
That's fine. So we've both been in the early-stage startup game for a while, so I'd love to hear a little bit about your background. Tell me a little bit about how you got into comms, and how you got into comm specifically with Silicon Valley startups.

Julie Crabill (01:17):
Yeah, I mean there's probably a longer story in how I ended up getting into comms, but I think early on it was I realized that I was not fearful when speaking in front of large groups of people. So I thought that must be what comms was all about. Got much deeper into it to realize that there was a whole lot of writing involved, which required me to do a lot of work and get myself where I needed to be. This is, again, decades and decades ago, but kind of fell in love with the idea that I could help companies bridge the gap between the technical elements of what they were doing and what the market actually cared about, which were often the human elements. So then, after 10-plus years of working for other people, I started my own agency in San Francisco called Inner Circle Labs, and our focus was really on passion projects.
(02:03):
And that was a big part of why I wanted to start the business is that I looked around at people working in comms and saw that a lot of people telling the story of the business didn't care. They didn't care about what the company was selling or worse, they actually didn't even believe in the product or mission. So by starting an agency where we could focus on working with early-stage companies that we really loved and that we were really excited about telling the story of, I think we were able to hit the market in an interesting way and bring a lot of great companies to market with a team of about 20 people over about 10 years.

Ronda Scott (02:38):
That's great. And you started the agency with a few people and you scaled it to 20 people over the course of about 10 years. What about that process gave you maybe more empathy for the founders you had worked with before? What kind of surprised you about the process? You're like, okay. Yeah,

Julie Crabill (02:54):
For sure. I mean, I think that it was sort of understanding the amount of intensity of the rollercoaster ride of you have these great days where you're like, this is the best thing ever and I'm so glad I did this. And then you have days where you're like, why did I leave a job where there was a regular paycheck, and I had benefits? So I think being in their shoes for a little bit where they understanding what it felt like to be on that rollercoaster was one way. And then the other, I think, is that oftentimes marketers and PR people will get into these calls with clients, and they'll explain their position of what they need done, and they don't often take the other side of what is the entrepreneur's position, what is the founder's position? They're just so focused on, I mean, I guess now that I have a 10-year-old, it feels a little bit like they're focused on getting their way.
(03:43):
They're focused on making the other side understand their position of like, we need to do this. We need to get this press coverage, we need to talk to the supporter. And I think starting my own agency and being the entrepreneur, being the CEO in that moment, I started to understand that there are many facets of what might matter to a business. And it's not just about this is a good thing to do on the whole, but how does that good thing weigh up against all of the other many things that are priorities for the business? And kind of creating that more holistic view, I think, came along with that.

Ronda Scott (04:14):
That's great. And you started off in pr, which is media relations, branding, positioning, that sort of thing. What did you need to do to scale your skillset to become a CMO because it's a much broader role.

Julie Crabill (04:28):
Yeah, I mean I think it's about surrounding yourself with great people. So, I think any C-level executive who claims to be a complete generalist is exaggerating. The truth is everyone comes from some tactical background. We all have some experience that we grew up in, and the key is to find people who you can trust and that can complement the expertise that you have. So, when I became full-time CMOing, I think it was about hiring or engaging the right people to balance out the skills that I brought to the table. So I was always going to be more kind of comms driven, maybe, than other CMOs. And that means I'm not always the perfect CMO for a company. There are people who really need that sort of very specific digital and customer acquisition, somebody who has that sort of data mindset. I hire those people.
(05:21):
I engage consultants. I have a network of people that I work with regularly on different projects like that who I trust and I bring them on to help me with the areas that I don't know about. And then I learn from them, I grow them if I'm building a team and if I am growing them, I help them succeed and help them learn the more holistic sides of things that I might bring to the table. I think that comms and marketing are deeply connected. The role of translating is where comms and marketing comes in. So it's translating product to market needs to sales, translating technical to human rights, translating culture and mission to hiring and growing the right team of people to help scale a business, and translating vision and success to fundraising. And then from there, you just need experts in the different areas that you're not an expert in. For me, it's marketing ops and data. It's digital; it's designed and creative. And I always go out and hire those people.

Ronda Scott (06:14):
Absolutely. I have a lot of early-stage founders who come to us and say, Hey, I need to make my first marketing hire. I've heard about this thing called fractional CMO. Is this where I should start? Or do you know somebody who's really great who can come in, or oftentimes I need to make my first marketing hire. Do you know someone who's really great who can set the strategy and execute against it all the way down? And it's very hard to find, and now the conversation often shifts to should I hire A CMO? Are we ready for A CMO? And what is this fractional thing I've been hearing about? Could that work for us? So I'd like to get tactical and dive a little bit into the fractional part of it because it seems like a very attractive way for early-stage startups to successfully scale their marketing function without having to commit to a really big expensive hire or make the decision between a very expensive experienced person or the doers as they're approaching building out this team and maybe they can only make one two at the most hires. So having said all of that, I'd love to hear a little bit about what does fractional CMO mean to you? What does Julie Crabill do as a fractional CMO? How do you engage?

Julie Crabill (07:33):
Because I like to work with their least-stage companies. I sort of start out with three to six months. It's either early-stage companies or for me, companies that are in times of rapid growth and transition. And by starting out with that sort of initial three to six months, I can help them quickly determine the needs of the business and how those needs of the business can turn into a strategy that prioritizes and connects those needs through the realities and the budgets that they actually have. So it's always fun to be like, if I had an endless amount of money, here's what I'd do for your business. But the work really is to say, here's what matters most to your business, and then let's stack rank that against what you have to spend the people on your team, what can actually be accomplished from a product and engineering perspective and how we're going to get that out to market.
(08:18):
So maybe it's fractional consulting, CMO versus pure fractional if you listen to some other people's definitions. But for me, if it's the right thing to do for the businesses that I stay on long-term, then I'm there. But oftentimes it's more that they need to hire somebody and I'm going to help them hire those right first couple people or build that initial team, or if they need to fix a few things before a lot of marketing is going to make sense, I think I can come in and help them with that advice of what will really drive revenue and growth and what will set up that foundation to allow marketing and sales enablement to really flourish. And sometimes that means I build a plan with them on what needs to change, what needs to be fixed, what needs to happen, and we keep in touch and then we reengage in six months or eight months or four months, however long it's going to take for them to get that thing done so that it can all be streamlined for rapid and smart growth.
(09:11):
It was kind of a two-question. So in terms of how I work with companies, it's oftentimes going in and saying, okay, from a strategy perspective, a foundation setting perspective, and a go-to-market perspective, helping you make money, what are the things that really matter for a lot of people that's creating a hiring plan to build what I call their alpha team. And that oftentimes is maybe one to two internal hires plus a network of consultants who are engaged and contracted to work when the work is required of them. So it doesn't become an administrative headache for them to get those people under contract. I help them have sort of that network of people that can be tapped into and green lit when the time is right for them. A lot of it is really getting clear on OKRs, KPIs, whatever you want to call them for your business. A lot of companies I see, they have a founder who thinks everybody knows what the goals are and thinks everybody's aligned on the goals, but really those goals have never been articulated in a way where people can clearly understand them

Ronda Scott (10:14):
And every founder's going to have their strength and weakness. But what do you see founders, what do they generally get when they're starting to answer some of these marketing questions?

Julie Crabill (10:23):
Yeah, it depends on the founder, but I think living the story and vision is really one area where I see founders excel. They're out there talking the talk, and when their team has access to them, there's a lot of great coalescing that can happen, which is why I fear for those founders when they start to scale really quickly because they're only one person, they can't live that vision and that story, well, they don't scale in that sense. So you have to figure out a way to get that done for them. I think understanding the upside of good coverage, I don't know if it's because they'd like to see their name in print, they like to be a little bit famous, but I think most founders are really good at understanding that PR can be a good inexpensive driver early on as they live that story and live that vision to the market. I think connecting marketing to sales and revenue is one area where they excel early on, the understanding that we're not just in business to have fun and tell stories; we really have to make money. So making that connection is one area.

Ronda Scott (11:24):
The other side of the coin, when you engage, what is often the stickiest points that you run into?

Julie Crabill (11:32):
I mean, I think it's shiny object syndrome for sure is a big one. So executives who set the goals and they get their team started on the right path, and then they say, well, this thing came up, and this big partner needs my help with this thing. And they pull focus from those things that just weeks ago they agreed were the one big thing or the couple things that needed to happen for the business. So that's one that I think is sticky and then not being focused enough on the value of the time that they're spending. One of my good friends and agency owner out of Austin has told me that he always knows it's time to raise his bill rates when people start wasting his time. So I think wasting the time of the people that you have engaged to help you with marketing is kind of a sticky point and an indicator for me that a business isn't ready.
(12:27):
I don't think that my time supersedes the importance of every little thing that can happen. There are fire drills that happen, there are personal life things that happen, but founders who are not ready to really partner on finding solutions to their toughest problems are usually the kind of founders that I say, Hey, let's talk again when you feel like you're ready or in six months when this problem that is currently always on fire for you has been solved. And if I can help solve it, obviously I'm there to help solve it. But I think oftentimes those are sort of the sticky areas.

Ronda Scott (12:58):
So many of the founders that we invest in, because we invest exclusively in enterprise technology startups, are deeply, deeply technical. How do you think about approaching those teams that are deeply technical, so they're very heavy in the technical area, and now you need to engage with them to pull them out of the technology and, as you said before, make that technology to human connection. How do you think about engaging and what does that look like?

Julie Crabill (13:27):
I think some of the most interesting founders I've worked with are the very, very technical ones, and not entirely, but I would say this group of founders are often more open to understanding that they're great at certain things, but they're not great at everything. So, one of the founders of Descartes, I think, was one of Descartes Labs, my first full-time CMO gig. He was one of the people who I felt most respected what I could bring to the table. And he was also one of the most brilliant, smartest people I've ever worked with. And I think as long as there is mutual respect, I knew I could never do what he did, and he knew he could never do what I do. And I think that that is a really beautiful relationship and I think you'll see that a lot in very technical founders where they respect marketing even more because they understand that it's something they can't do.
(14:20):
Where they need help often is that they need help understanding what marketing as a whole can do for them. So they may respect and understand that you, as an experienced marketer, do things that they can't do, but what they don't understand necessarily is what can the marketing function actually accomplish for their business. Some of it is about sitting down and saying, I'm going to help you understand where marketing makes sense for you. And to gain their trust, you also have to tell them where marketing doesn't make sense for them. They're very analytical, deep thinkers. So I think they need to be given that, Hey, here are the areas where marketing can help. Here are the areas where I wouldn't throw marketing at the business right this minute and maybe ever. And then really helping them see that there is a path forward to obtaining their larger goals for the business using marketing as a tool set.

Ronda Scott (15:11):
That's great. And so for these early-stage companies, again, oftentimes technical leads, they're building out their engineering side. They might make a couple of go-to-market hires or sales hires or business development, and now they're starting to wonder, are we ready for a marketing hire? And so when you're engaging with these early-stage companies, and you're talking to the founder of the leadership teams, how do you help them navigate whether or not they're ready for a dedicated marketing hire?

Julie Crabill (15:42):
Yeah, I mean I think some of it is understanding if you have enough of a need at a specific level encompassing a specific expertise set that hiring against it makes sense. I think some of it, this magical thinking of I'm looking for, you've mentioned earlier somebody who could be A CMO and run my strategy and write every piece of content and take all the notes in every meeting, this sort of magical and do more than even those things, but this magical unicorn who can do all of these things, it's just not realistic. So thinking about you don't want to pay somebody a CMO rate to do something that you could have a coordinator-level person, like an entry-level person do, but you may not have enough entry-level work for somebody if you don't have that senior person sort of running things. So I think making sure you have enough of a need is thing one.
(16:33):
And I would say if you're just going to go out and hire one person being ready to spend, say, three times of that person's cost to enable the marketing work that they'll then need to do, whether it's via consultants or via paid services. So if you're going to hire somebody who costs say a hundred thousand dollars all in, so you're going to take their salary plus the cost of them being a full-time employee, and that's going to cost you a hundred thousand dollars, do you have at least $300,000 earmarked to spend against marketing all in? Because otherwise, you're going to hire that person, and they're going to say, okay, here are the 10 things I want to do, and you're going to say, I can't afford to do any of those things. So I think those are ways to think about full-time hiring. And otherwise, if you're engaging sort of many consultants, many expert level people, you may want to have a coordinator person. And that person doesn't have to necessarily even be purely a marketing hire. You may want to have an administrative hire who could help coordinate workloads so that you can streamline things and not be paying my bill rate for scheduling work, let's say, right, as an example. So those are some ways to think about it.

Ronda Scott (17:38):
I think that's brilliant. The three to one, whatever you're going to spend on your hire, make sure that they have the budget because otherwise, you're not really set up for a successful marketing campaign or successful marketing efforts. That's brilliant. And so, actually, it seems to me that most early-stage companies should really be thinking about a fractional model because it sounds like you can have someone come in and deliver a lot of that strategy and a lot of that higher-level thinking without committing to that CMO salary and potentially start to fill out your team. So it seems so obvious, but obviously not every single company is doing it, so it's not a fit for every company. What companies do you think it is a fit for and when do you think it doesn't work? The fractional CMO model?

Julie Crabill (18:23):
Yeah, so I'll start with the second half. The types of companies that it's not going to work for are companies who are, and I've seen this happen, looking to bring in a correctional CMO and have them do everything for them themselves because not that I can't do that, but I'm going to bill you my bill rate for doing the junior level stuff. So if you're not ready for me to make recommendations for you on other consultants, you might want to hire agencies, you might want to partner with, internal hires you might want to make, then it's probably not going to work very well for you as a long-term solution. It could be a good like, Hey, we're going to do a short project, or we're going to figure out our go-to-market strategy, some key messages. We're going to get our website and our sort of external look and feel and the way we talk about ourselves in order, and then we're going to go do some other stuff before we bring on somebody correctional or higher against any marketing.
(19:17):
I think that's a potential use case, but if you're looking for it to be sort of this one-stop-shop solution as an individual, it usually doesn't work. You have to be ready to spend a bit more against it, just the same as you would if you hired internally. And then the types of companies that I think it works really well for are companies where the CEO and the executive team are bought to addressing some of the bigger problems that the business is facing with an outside party. So I can come in and I can just work with the product person to help figure out product messaging or just work with the sales lead or the chief revenue officer to help figure out sort of sales enablement tools and things that they would need. But it works best when there's sort of an entire leadership team bought into how we are going to supercharge our business through marketing and go-to-market strategies that somebody like me can bring in.

Ronda Scott (20:13):
That's great. And then is there anything else tactically that I should be asking about how to engage with what a fractional CMO can bring to an early-stage company?

Julie Crabill (20:22):
Yeah, I mean, I think there are times when it does make sense to hire a person, a full-time hire versus going fractional. And for me, you have the perfect hire. This person, you know that they're going to be a great hire for you or they fall into your lap. I think we can't ignore serendipity in the universe. Sometimes things do fall into your lap. So if you have that perfect first hire who you think will be more of a player early on and that you can build around, that's great. Or if you have more than half a million dollars a year earmarked from the beginning to spend on marketing, if you're at that stage where you're thinking about this and you're like, I'm ready to spend half a million dollars, it might be that you can potentially, you find a fractional or a strategic consultant who can come in and help you figure out how to spend that initially. But that's got to be somebody that you can trust, and then they can help you build that team and that strategy that can help create scale for the work that you're going to do from there.

Ronda Scott (21:20):
And in your experience, do you see more success when an early-stage team hires that eager manager who's stepping up into the role and executes for a year or so, and then they hire someone over? Or do you see more success the other way, hiring somebody who's more senior who can then come in, has a decent budget, and can start to build out the more junior doer part of the team on their own?

Julie Crabill (21:45):
Yeah, it depends on the business in most cases. But I would say that on the whole best first hire is going to be sort of that mid-level rising star who you probably will if you're growing a sort of business that's going to scale quickly and grow quickly, you're probably going to hire above them, but you're going to give them in that period, you're going to give them room to be a utility player for a bit grow and figure out what they want their specialty to be so that when you do hire above them, it's known that that's going to happen.

Ronda Scott (22:16):
That sounds like a solid game plan.

Julie Crabill (22:18):
The one last thing I'd say is kind of while you've got that mid-level person rising star in their seat, please, please, please start recruiting for that most senior hire that you're going to need in a year or in two years from the beginning because that recruitment process is slow, and this is not, I think traditional recruiting. You're not posting ads, you're not opening up job specs, but it is getting to know and talk to the people who are likely to be a fit for that in the future. So they probably have jobs somewhere else. They're not looking to move, you're not looking for them to move, but get to know them early and start to build in that workload from the very beginning because those people, you don't want to necessarily hire somebody who comes to your VP of marketing job posts. You want to hand target and select the person who you think is going to be right for that early by getting to know them, networking with them, and then making sure that any hiring plan you build from there has flexibility built in.
(23:13):
Because if that perfect hire for whatever level does come out of the sky, you're looking for that rising star mid-level person, but instead, you find a rising star junior-level person built-in flexibility to allow that hire to come in and then the way that they work and the things that they do will, of course, have to be different. But you don't want to walk away from a perfect tire, and you don't want to move too slow. I've seen way too many startups these days moving way too slow in their hiring, and they lose really good people for it. Other companies are moving faster than you, so make sure that you have a plan, swoop in quickly and be ready if a good hire does fall into a lot.

Ronda Scott (23:50):
So I'd like to dive into that a little bit deeper because one of the leave behinds as a fractional CMO that you provide for the companies you work with is a hiring plan. What does the time horizon look like for that? For

Julie Crabill (24:03):
The entry level folks, it's one to three months. For the mid-level folks, it's three to six months, and for the most senior folks, it's six to 18 months. It takes that much time to get the right hire in their seat.

Ronda Scott (24:18):
So it sounds to me that recording this in December, 2023 where we keep reading headlines that the labor market isn't as tight as it used to be, it sounds like it still kind of is for these roles in these companies.

Julie Crabill (24:31):
I mean, it still is for the best people. I think that that's why there are a lot of people who are always worried about the effects of AI on their jobs. I think if you kick ass and you work hard and you make yourself indispensable, then these things aren't going to have as much of an effect on you. Same thing with these economic changes of the hiring market. It's really hard to find a job. Well, I think if you really are great at what you do and you really want to work, you will find a position. And if another company is ready to move more quickly, then company A is left in the dust. So make sure that you're not company A in that position. Make sure that you're at least authorized to tell the person, I'm going to figure out a way to get you an offer in the next two weeks. Please wait. And yet you have the talking points about why waiting for this particular company is the right thing for them so they don't move more quickly. I think there's a lot of value in that.

Ronda Scott (25:24):
That's great. And it's a perfect segue into what I wanted to ask you next, which is one of the other things that's very timely for us marketers is, and it's a CEO-level conversation, is what parts of our company processes can be automated with all of this great generative AI technology that is dominating the headlines? And to your point, good people will always be in demand, but what's your sense on this? Generative AI is going to replace all junior marketers and junior PR professionals and comms professionals in the next three to five years.

Julie Crabill (26:03):
I think generative AI will make some meaningful changes to marketing. I think it will change the way that written content is created. Creative content market research and segmentation is going to be done differently. Advertising S-E-O-S-E-M, optimization data analytics. But while it is a massive shift, I think it is a massive shift in the same way that the internet was in the same way that mobile and social was. So we as marketers just need to learn the new tools and figure out what they'll mean to the way real people connect with businesses. And when it comes to junior people, I think it is imperative that marketing as a business unit, as marketers as a whole, we need to figure out how to continue to engage and grow and train and sort of apprentice junior people, or else we are going to lose our pipeline of those future great hires. So the rest of the business maybe doesn't care. They're like figure out a cheaper way to write things, to create things, to do the marketing, and we do need to do that. But there has to be a human layer. The roles will change, but that human layer will be required as long as the buyer on the other end of the process is also human.

Ronda Scott (27:17):
Anything else that we haven't covered that you would like to cover?

Julie Crabill (27:20):
I mean, I think my advice to founders at this time would be to build marketing into the DNA of your business. Think of it more as a go-to market than marketing. I think that marketing kind of has a bad rap as a thing that people perceive it to be more about sort of just promotion and telling stories. It's not that. It's about connecting what you have to sell with what the market wants to buy. And that means the survival of your business if you don't think about it. So we have to think about how the community that we're selling into is going to react to what we're selling. And even if you are a B2B business, the buyer at the other end is still a person. So what are you trying to get across them? How are you going to make their life easier? How are you going to solve their problems? And if you're not able to articulate those things to them and get that articulation of those answers in front of them regularly, you're not going to survive in a very busy crowded market.

Ronda Scott (28:19):
Well, thank you so much for joining us today, Julia, this has been very insightful. I appreciate your time.

Julie Crabill (28:24):
Thanks so much for having me. It's been super fun to talk with you about all this interesting stuff, and we're in a good place, marketers. Don't freak out. Keep up with the changes. But don't forget the fundamentals. Don't become that AI guy. We all remember that social media guy. So don't be that for AI

Ronda Scott (28:41):
Stage advice. Thanks, Julie.

Julie Crabill (28:43):
Thank you.

Ronda Scott (28:45):
Thanks for listening to the DTC podcast. If you like what you heard, you know what to do, like, share and subscribe wherever you get your podcast.