Episode #002: James Winter, VP of Marketing at Brandfolder
Why are so many marketers so afraid of sharing what works and what doesn’t?
In this episode, we chat with James Winter, VP of Marketing at Brandfolder, who has a decade of marketing experience. His current company has been making big news lately after getting acquired by SmartSheet. James has also held previous marketing roles at AspireIQ, Dialpad, Nexmo, and Seagate Technology.
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Stephanie Cox: Welcome to REAL MARKETERS where we hear from marketers who move fast, ask forgiveness, not permission, obsess about driving results and are filled to the brim with crazy ideas and the guts to implement them. This is not a fireside chat and there's absolutely no bullsh*t allowed here. And I'm your host Stephanie Cox. I have more than 15 years of marketing experience and I'm pretty much done about everything in my career. I believe speed is better than perfection. I use the Oxford Comma. I love Coca-Cola and have exceptionally high standards and surround myself with people who get sh*t done. On this show, my guests and I will push boundaries, share the real truths about marketing and empower you to become a REAL marketer.
Our first guest episode of REAL MARKETERS is finally here and in true REAL marketer fashion, I had a completely different guest planned for this episode but decided to change my mind on Friday afternoon. Yes, I'm talking like two days ago. It turns out that I had an interview scheduled for the podcast on Friday and that person actually had their company acquired by Smartsheets a couple of days before. And so what do I do? I did the interview. Quickly afterwards, I decided to make him our first guest of REAL MARKETERS and my team helped quickly edit and set up promotion of this episode no matter of hours on a Friday afternoon. That's definitely the definition of moving fast. So a huge thank you to Michelle and Lorena for their ability to get shit done so quickly even on a Friday afternoon. Now, let's meet my first guest. James Winter is the VP of Marketing at Brandfolder. He held previous marketing roles of AspireIQ, Dialpad, Nextmo, Seagate Technology, and we're talking all about keeping the secret of an exciting upcoming acquisition, what he calls the Salesforce fallacy, how he can't turn off his desire to move fast, and so much more. Trust me you're going to like this one.
So one of the things I like to ask everyone, you know instead of the traditional introduction is tell me something that no one else really knows about you. So what is your one thing that no one really seems to know about you?
James Winter: You know, the question and the most interesting answer I can give will come with a caveat which is that people who have known me for a while do know certain aspects of this wage. But I grew up in a religious whole for the first fifteen sixteen years of my life and got out around the time of like my junior year of high school.
Stephanie Cox: I would not have guessed that I can imagine that's had a really big impact on your personal life, obviously growing up and also probably as an adult too.
James Winter: Yeah, it's certainly had a long term effect. That is for sure.
Stephanie Cox: Well, I don't know how I follow that one up because I was usually I like to share something about myself and now I'm kind of like don't know what to share. Maybe I'll start with, maybe the biggest thing about me that most people don't know is I actually had a brain tumor six years ago. I had brain surgery and it was so rare that they were only five doctors at the time in the United States that could operate on it. So I had to fly from Indy to Phoenix to have the surgery done. So I am a medical mystery as my doctors tell me.
James Winter: Wow. I'm glad that everything is alright.
Stephanie Cox: Yeah. It was what's funny about that is, you know, a lot of people know that I was a medical leave, but you know, when you tell someone that you had a brain tumor they kind of look at you weird and like what they don't know what to say or how to respond so I don't usually talk...I don't usually talk about it. And if you saw me today you wouldn't notice and so but anyways. My little tidbit. So let's talk about marketing now since we both share some personal life stuff. You have been at Brandfolder for a while now, so can you tell everyone just a little bit about your company, kind of what Brandfolder does before we get started?
James Winter: Sure. So I joined Brandfolder about two years ago and Brandfolder's in the digital asset management space. So we provide an intuitive, easy to use cloud-based solution to create, store, manage, and distribute and analyze all of your digital assets. So everything from photos, videos to PDF, PowerPoints even, more obscure things like 3D files and 360-degree viewer images so you can kind of think of it like cloud storage on steroids, but with a whole lot of cool stuff like Adobe Integrations and other things that make it really easy for marketers and creatives to focus on the more important work.
Stephanie Cox: And you've had some exciting news this week. What's happened at Brandfolder that's been all the buzz?
James Winter: Yeah. So super exciting to be featured on the front page of Bloomberg, but we got acquired by a great company out of Bellevue, Washington called Smartsheet, which I'm sure lots of people are familiar with so it's a really great outcome. The team over there has been awesome throughout this whole process. Everyone I've met on the exec team there has been amazing and I'm really looking forward to working with everyone. It's a great outcome with a great company and everyone's keeping their job Brandfolder is remaining independent for you know some period of time, so there is no disruption to the customer or anything. So it's really like the best possible outcome as far as I can tell. This is my first time going through an acquisition while I've been at a company so. But I couldn't be more excited to be joining my smart search team.
Stephanie Cox: That's awesome. How much like fun or stressful has it been a kind of leading up to that, you know, knowing that you were, you know involved to some extent during the process and you know, it's as a leader, right, you know a lot more than the rest of the organization might know, so talk me through kind of how that one that was.
James Winter: Yeah. It's been interesting and it's not the first time we've gone through it like Brandfolder, even though the last couple of years has always been intentionally a really prime acquisition target, like we haven't raised a ton of money, but we've had incredible growth and our net retention is awesome. Our MPS is awesome, customers love the project, and we as a leadership team really went back and forth for a while over the last year like do we raise another round? Do we just self on our growth because we're cash-flow positive. So we had a lot of optionality and we've had acquisition talks before and lots of investors were interested. So it wasn't, it wasn't novel but this was definitely a very serious one and I think the overwhelming feeling was like when you know an exciting secret and you can't tell people, it's like you're getting your significant other this amazing gift or something that's exciting and want to tell them and get them excited about it too.
Stephanie Cox: Yeah no. That's how I feel like most every Christmas on like Christmas, you know, I buy the gifts for the kids. I'm always like this is so cool. They're going to love it. I want to give it to them now. My husband's like it's not Christmas chill out.
James Winter: Yeah exactly, right.
Stephanie Cox: It is very hard and then it's also that thing where you don't know for you, but for me, I'll start being like Oh, I wonder if they notice like that I'm really excited or that I kept asking if they like this when I came on TV like am I giving away secrets and not realizing it?
James Winter: Yeah, there's definitely that like nervousness of like letting something slip to someone or something like that and I just had was like, you know to be careful about who was involved in what.
Stephanie Cox: Yeah, especially since Smartsheets is publicly traded as another layer of complexity to it around keeping it quiet that isn't necessarily the case with like if it was just another private company.
James Winter: Yeah, exactly.
Stephanie Cox: So you've had the opportunity to really build out a marketing team from like the growth stage, talk me about what that's been like. How do you get started when you kind of come in and you're building the foundation of just not just the marketing efforts, but also the team? What have you done and learned from that process?
James Winter: A lot of my career, you know aside from my first job which was at a Seagate which you know is obviously a huge established company has been a companies that were just getting started with the marketing journey in a lot of ways so. My first job when I moved to San Francisco was at a company called Maxima which was about thirty people and didn't really have anyone in the marketing team and I was hired them then we brought on leadership and they built out a team and I learned a lot about what not to do in that period.
Stephanie Cox: I want to know all about what not to do. So, and finish and we'll get back to that.
James Winter: I think the biggest mistake there was assuming that hiring someone who was at a big company knew how to build something that could sell to big companies. Like there was this assumption that just because someone had worked at a large company like, you know take Microsoft or Salesforce or whatever and I actually called this the Salesforce fallacy, which is because someone is successful in one environment it means practically nothing as to whether it'll be another one and a lot of people make that mistake when they're hiring. So naturalization learning experience and then I have the chance to go to Dialpad and I work for a really amazing CMO there named Morgan Norman and she built just the most incredible team I've ever worked on and super high performing and they all a lot of them still work together and a lot of them have gone on to do really awesome stuff. But I really got a great education in how to build a good team and what a good marketing program looked like and then I joined with AspireIQ to build out the marketing team for the first time. So I got to take a lot of those learnings from Dialpad and put them into practice and kind of the same thing at Brandfolder. It had some different marketing folks but never like a full-fledged team or you know, I guess what I would call like the best practices for hiring a full-on marketing team and leader so it was really cool to come in. And Brandfolder when I joined already had an awesome product that was getting better every month, a great sales team, and so everything...a great customer experience team, like everything was kind of primed for marketing to make a big impact and we were able to do that because great product, great sales team, great support team, and the resources to hire a best in class B2B SaaS team.
Stephanie Cox: So that's great to hear and I know you've probably had a lot of success as a lot of things that you're like, I wish someone would happen sooner but let's get back to the Salesforce fallacy. I love that because I have the same belief which is if someone worked at a large organization, was successful, and you bring them to a start-up or a scale-up they likely don't know what to do or they don't understand the like resources that are available and it doesn't mean they'll be ultimately successful in that environment. In your experience, what have you seen as the biggest struggles for people that have hired from large companies and brought them into more growth-stage companies?
James Winter: I think it depends on the role. So I think for sales people the hardest thing that when you're an established company that you often don't really have to sell the company at all. You're just selling a product and there's no validation stage that you have to get over. Whereas when you're in a company that no one ever heard of and you know is smaller and doesn't have the same resources or brand equity already, you don't only have to sell a product, you have to sell the entire company and the trust that this person or this organization needs to put in your product. So that's I think one of the biggest ones is like salespeople who would probably be killer enterprise reps, at you know Salesforce, for example, would struggle if they don't have that Salesforce name-back and you know, I'm sure and the other way goes as as well, which is like someone who's a good start-up like grinding account exec might not have the polish or know how to navigate certain things at the enterprise level like someone at Salesforce does. From the marketing side can be similar. I think one of the biggest things is just not being used to not having the resources and having to be a little bit scrappier and being used to doing things in a certain way where they had different teams of people to support them. They had all these different support functions and now they're having like really get their hands dirty and rolled their sleeves and like do something that maybe they haven't ever done in their career or haven't done since they were super young, you know, I still write website copy, I'm still making...I'm still involved in making collateral for sales team sometimes like at a small company you just have to do a lot. And some people who are you used to things being a certain way might not be ready for that.
Stephanie Cox: No, completely agree. I think I've seen that happen to my career and I think it's partially, at least from my experience what's been hard when you like from a sales perspective is, you know, to your point, they're used to the name, right? They don't realize how much like the name Salesforce or Microsoft or any of these big players that really everyone knows has on. The number of leads that drives, the quality of those leads the sales process overall right, you're selling more on, you know, are you a good fit for what they need versus like should they even seriously consider you and then I think you know, the other thing is that a lot of times like reps at larger companies, they have a pretty set sales process, right? They're all trained on how to use it. Yeah, they have their own take on it, but it's kind of like, you know, we do X, Y, and Z during the deal we have sole cons and then you get to more of a start up or scale up and you're like “Hi. We're still figuring this out. And we're laying the tracks as the train is going at like a hundred miles an hour and we're probably going to change it like ten times.” I would be like that and not everyone does.
James Winter: Yeah, definitely if you're like obsessed with following a certain process being at a start-up it might not be for you.
Stephanie Cox: No, and I think everyone...I think Silicon Valley and like some of the shows like glamorized it a little bit where it's you know, it's everyone enjoys it and it's so much fun. And I think it is true, but it's to me it's really like do you have the personality type for “Hey, this needs to get done” and regardless of what the title is or years of experience, you will roll up your sleeves get in and just do it.
James Winter: Yeah, exactly.
Stephanie Cox: I always find like when hiring everyone says they will but like the reality of that it's totally different. So one of the things about Brandfolder that I think is interesting is your product could work really for anyone right? Like theoretically any marketer could use your product. Correct?
James Winter: Yeah. I mean, we sell pretty much every single industry you could possibly imagine.
Stephanie Cox: So we have a similar situation at Lumavate too, so I'd love to hear like, how do you figure out like what to do and where to prioritize your resources when you could literally sell to everyone but you don't have the resources to sell and market to everyone like how do you handle that?
James Winter: Yeah, it's been interesting problem to solve and it's always a moving target too because changes to the product might unlock new age categories that were previously not a great fit for your segmentation. So when I joined Brandfolder I had heard, you know anecdotally from people like, “Oh, yeah, we do well with sports teams, we do well with you know, like whatever healthcare companies,” I don't remember exactly with all the work but when I dug in and tried to look at the data and Salesforce, it kind of told a different story like yeah, we had a lot of breweries as customers, but they didn't pay us that much and the sports teams that we did have took a long time to close and the sales cycle wasn't particularly smooth for the amount of revenue that they generated. So when we really dug in and this is something I would encourage everyone to do if you don't have a really good handle on this is Clearbit makes a product that's just a batch upload. And so what you can do is explort all of the domains from your Salesforce customer list or all of your opportunity data and upload that into Clearbit and it's like ten cents a row. So maybe a couple of thousand bucks for a lot of companies and it'll give you all the industry company size that gave you all the data that you wish you had on these companies and then throw that into a spreadsheet and just start taking a look at you know, which types of things correlate with better sales cycles. Like what is the sales efficiency of a manufacturing company versus a medical company or which industry has the highest ASP or which industry has the better winner or whatever. There's lots of metrics you should look at to try and determine what your ideal customer profile is and it's really easy to get that data now with Clearbit.
Stephanie Cox: Well, I loved that you just showed that example, that's one of things I know you and I are part of Revenue Collective and I love that you share some times are like these like really helpful like quick little like, “Hey, you should use this to hack your website. It's just a great helpful way to additional content. So thanks for sharing another example of that.
James Winter: Yeah. Maybe I'll make that one I talked about today.
Stephanie Cox: Yeah, I love that. Well, and that's to me like part of the reason why I reached out and want to get you on the show is I just find you have so many great takeaways and I feel like you try so many different things and tend to move, you know, pretty fast in your efforts to drive results for your business and that not all marketers do that.
James Winter: Yeah. I I can't really turn it off.
Stephanie Cox: Me either.
James Winter: And my mind is like racing all the time with like, oh, we should try this. We should do this like and sometimes I have to reign it in because it can be distracting but I think generally it's a positive.
Stephanie Cox: No, I'm the same way and it's so funny because I tell my team all the time like I have this unlimited number of crazy ideas in my brain at any one time and I just like try and figure out like how many the team can handle in a period. And like we're getting ready to do some big launches in the next couple of weeks and I literally said yesterday, I promised like nothing else is going to get added to the list. I really do promise this time because we're kind of like at our max capacity but I have like three other ideas and like well, it’d be really great if we could do this in the next two weeks, but that's probably not great to do.
James Winter: Yeah, one of the things I really try to tell my team to coach-up on is managing up. So like if I'm saying something and saying this is a priority and we need to get this done but then something else gets added to the play, you need to let me know that what the trade-off is like tell me “Okay, we can do that but it's going to mean that this thing gets pushed out a few weeks later”. I really learned in power of that when I was a product manager.
Stephanie Cox: No, that's such a good point. I said that yesterday to my team something similar, you know that you need to speak up. Or for instance, you know, maybe it doesn't get pushed off but you know we could do both, but if we did both it means they look like this instead of what you wanted. Are we okay with maybe like a more lighter way version of what we initially plan and doing the bigger part as a fast follow, you know, what's the I always tell people you need to ask, “What's the real driver?” is it time or is it function like functionality or you know content of something like what is the thing that matters the most?
James Winter: And I think too there's a really good opportunity these days for process improvement in automation and outsourcing. So I've run...I ran a contest with my team that everyone participated in to do a flow chart process map diagram of something that they do on like a semi-regular basis in their role and how they could either automated or outsourced or do something to make it much more efficient and it was really cool to see everyone whether they were on like the community marketing side or demand gen, or marketing ops or events like come up with these new ways to solve a problem that used to take them a little while and now they could get done in a much faster amount of time.
Stephanie Cox: Have you at all experimented with like Upwork or having your team use any of those types of platforms to get some of the more mundane marketing-related work that just needs to get done.
James Winter: Absolutely. I'm a huge fan of finding those opportunities. And when I was at AspireIQ before we raised our Series A, my budget was like $5,000 a month and it was just me for a little bit. So I got really good at figuring out cheap ways to do things and there's a lot of talented people around the world who are working remotely and don't like don't charge an exorbitant fee that you can just add on, almost like proofreading. For example, you can pay someone, you know, maybe twenty bucks per blog post or something and have them proofread for grammar everything that you're putting out and they'll turn it around really quick or I had this really awesome Polish designer who was this woman that did great work and super quick and like when we didn't have the design resources in-house, we would send it to her and she would do an awesome job. So I think if your resources are limited or you need overflow, there's a lot of good people you can tap for that.
Stephanie Cox: It's like I have the freelancers that are like so..that are really great at what they do. They're reasonably priced. I totally trust them and then I always always had this like kind of situation where people are like, oh who does your like who does that for you and I'm like, I don't want to tell you because I don't want them to do your stuff too because the now they can't do all my stuff when it's last-minute crisis.
James Winter: Or they’ll raise their prices too because they realize how much more they could be taking.
Stephanie Cox: It's like I kind of like first dibs or something. So thinking about just marketing overall, what do you think is the most undervalued area of marketing that people don't spend enough time or resources investing in that would have the biggest impact for most businesses?
James Winter: A least organizations I’ve worked at it's some combination of segmentation and focus. So, with a company like Brandfolder where you can sell the everyone sometimes it can be tough to to have that conversation with people who have been there for a while saying like “Hey, we're going to focus on these jobs and businesses maybe at the expense of these other ones because that's the right area for us to make the most efficient revenue out of and I know you've done things a certain way in the past, but we we need to focus on this area because you know resources are limited and and not everyone is created equal.” So I think the challenge and I saw this at Nextmo as well is when you can sell everything to everyone it's a lot harder to convince people not to do that and to focus on what's actually making you money. So I think getting a really good understanding like what are the most efficient types of companies in generating revenue and what can you do to help accelerate, even if it means not treating everyone the same.
Stephanie Cox: No, I think that makes a ton of sense. Now one of the things I like to ask everyone because if you've been doing marketing for any period of time you've probably had something that has not went as planned and has you know, either just failed a little bit or failed miserably. So tell me your story of something that in your career has not worked out as you had hoped and what you've learned from that so other people cannot do the same thing.
James Winter: I think the biggest mistake that I made in my first time as a marketing leader at AspireIQ was being too much of a ‘yes, man’ and basically the situation was like they would say “Okay here's resources and we want this.” And I didn't really have the confidence or the knowledge or expertise yet to be like, “Okay, that's great. Here's what you'll get for that. But if you give me this here's what I think I can produce.” So I think being more vocal in asking for things would have been helpful in that situation. So, I think it's really important to find that voice and like speak up and say “Hey, like you're asking for this and that's not really a reasonable request with the resources we have so if you want that like, we need this to do so or if there's going to be you know consequences in quality or speed or whatever it might be.”
Stephanie Cox: No, I think that's such a great point because so many people especially when they're younger in their career choice don't know how to say no and they don't know how to say like your request is unreasonable. I was talking to a friend that's a marketer a couple of weeks ago and she was given these kind of really outrageous goals by her leadership team and she was like, “What do I do? I don't have the resources to do that.” And I said, this is like on a Friday they had that conversation I said, “Okay. Well this weekend we'll put together a plan, like I'll help you put together a plan of what you need in order to do that and you're going to tell them what you need in order to hit those goals and then when you do that, you’ll have a conversation about okay when he sees all you need, whether it's you know additional help, its time, its commitment from them, you know or money to do that tied to the goal, then you get to have a conversation about it and see like, okay, well does the goal need to change or can I get the resources,” right and it feels a little bit more productive sometimes than just saying, “Hey, that's unreasonable.” So that's one of the approaches I love to take with people is “Hey, if you want to give me a really crazy goal. Awesome. Let me tell you exactly how I need it and like write it all down so you can see I put the time and thought into it and see you know, hopefully if we can kind of come to an immutable situation that's somewhere, you know, that meets your needs and is realistic.”
James Winter: Yeah, and that's I think something that a lot of companies could do a better job is whether it's top-down or bottom-up like coming to some reasonably data-driven assumption. So when we go through the budgeting process and setting targets like we have the sales targets from that the board sets and agrees to and we also have the reality of the budget and so we'll back into the numbers both ways where it's like, okay based on our historical data if you give us this much money and we have this many SDRs or whatever and sales generates this much pipeline on their own, we can expect this much pipeline at the end of the quarter. And then also if you take the revenue target and back into it saying like here's our win rate, here's the average selling price, how much budget would we need to hit this target? And we usually end up kind of somewhere in the middle of those.
Stephanie Cox: Well, compromise is so important these days I think especially as we're all working remotely right to kind of understand where everyone else is point of view is where they're coming from and find a solution that makes everyone win because I always say that's about like sales quotas, sales quotas are great and I love you know stretch goals and the big fan of them, but at the same token if they are so stretched that they're unreasonable, no one's motivated by any unreasonable goal. You can't get people like really to get to do what they need to do. And that's not on them. It's more on you as a leader to make sure that they have a way to be successful.
So in the true REAL marketer fashion of moving fast, here's one takeaway that James shared you can implement right now. So what I want you to do is take an hour and map out all of your repetitive tasks. So what are the things that you're doing every single day, every single week, or every single month and really think about how many of those that you can automate? What can take off your plate through automation or if automation isn't an option for some of them, can you get a small budget and use a platform like Upwork to outsource some of those repetitive tasks. Find ways to better scale yourself and that's a great example of how you can do it. So what are you waiting for?
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