Getting to Know the CISO: Dani Woolf

Listen to the podcast or read the transcription below. 

Chris: Hello, everybody, and welcome to the Security Sisters Network podcast. Getting to know the CISO. today. We are lucky enough to have Dani Woolf with us, and Dani will talk more about her experience from a marketing perspective. So we’ll get a different slant on getting to know the CISO. Anyways. So Dani, tell us a little about yourself. What brought you to start Audience first and your podcast?

Dani Woolf: Well, thanks for having me on. I’m thrilled to be here and looking forward to having a conversation. So my name is Dani Woolf. I’m the founder and CEO of Audience First. It’s actually really weird saying that because I just left my full-time job as a full-time director of demand generation for cyber security firm to start Audience First as an official working agency. Yeah. I spent the last decade running digital and demand at high-growth B2B technology startups. Around 2018 I ventured into the cybersecurity industry and quickly and painfully discovered that the way marketing is done in security is not the same as any other vertical I’ve worked for. I’ve worked in pharma, and I’ve worked in general cloud tech. Security is its own monster. And when I ventured into the space for a good while, I was doing many things based on assumptions and gut feelings. And when I had to look at performance and all the metrics that tied back to the business goal, it was really underwhelming and didn’t cut it. I felt really disempowered. I was defeated. And that’s when I realized that I needed to change how I’m marketing to my buyers, and to do that, I need to understand them. So how do you understand your buyers deeper? All right, Dani, let’s go to Salesforce. Let’s take a look at Salesforce. What did I find? Absolutely nothing. Why? Show me a salesperson who updates Salesforce regularly. Right?

Chris: Not unless they have an ISR that works for them full-time that can beat their admin.

Dani Woolf: Exactly. All right. So I told myself, let’s look for the next best thing. Let’s go to customer success. Hey, customer success, can you get me in front of =

Come back in a quarter, I’ll get you in the queue. I’m like, well, what the hell? What am I going to do in another quarter? I have to hit my goals. I got to double revenue. I have to 3X revenue. So that was frustrating. And then you could go to analyst briefings, but who gets invited to those? I didn’t get invited to analyst briefings. Let’s go to the marketing budget. Let’s see how much do we have for customer research. Zero. So I was like, okay, we have to flip it on its head. I got to take matters into my own hands. And that’s when I said, F it. If I’m going to thrive as a demand gen and revenue marketer who needs to double revenue net new ARR, I have to do this by myself. So I looked online. All right, let’s learn how to do customer research. Let’s learn how to do user interviews. Let’s learn how to recruit and find customers.

What I found on LinkedIn was really underwhelming because a lot of marketers talk a big game and say, oh yeah, okay. It’s really important. You have to do customer research. All right, cool. But how? Okay. And, more importantly, how do I apply the insights to strategies and tactics? Most marketers say, to do customer research, but they just don’t do it. So the natural thing for them to do is to resort to the status quo. Again, do nothing about it. So I was like, okay, I’m going to target my ideal customer. I’m going to reach out to them and ask for help and ask for a couple of minutes of their time, a few minutes of their time, for feedback on the specific campaign I was working on. And a few were open to helping me. And the snowball grew from there.

And then I realized the insights were so great I couldn’t keep this to myself. And that’s when Audience First was born. I was like, I was in a forum conversation with other marketers, and they were talking about all these shady tactics and tricks, and I was like, there’s no way you’re doing this. So Audience First was launched much earlier than expected because cyber security marketers and salespeople needed to hear these insights. And so it just grew from there. And it really resonated with the audience, not just the go-to-market teams but also the practitioners themselves. And someone didn’t get the memo I’ve been recording all day.

So yeah, it’s been six months in, and it’s turned out to be a really successful project. So successful that I left my full-time job as a demand marketer working for a security firm. And I decided to double down on my mission to help customers obsess cybersecurity firms understand their buyers better so that they can gain and retain their customers.

Chris: That’s awesome. Yeah. So I’ve been marketing for a lot longer than you. And I think all the digital stuff has really stopped that human interaction that we used to have because I’ve been in cyber security off and on since 2003. And we would have focus groups with our customers. The product managers were required to meet with X amount of customers to get their feedback on the product. And we did boards, and suddenly, after the Dot-com blow-up, everything changed to where we were just praying and praying. Interesting.

Dani Woolf: I want to throw one question at you, which I’m curious to understand why. So you have focus groups, and even today, in today’s market, you get a lot of vendors running focus groups. But why don’t the executive leadership and the people who need to listen to the insights to understand what doesn’t come to the table for those focus groups and chime in? Why is there no urgency to absorb and act on those insights?

Chris: Ego, maybe? The interesting thing is, sometimes when you’ve built this, and I’ve been in tech my whole life, but when you’ve built this company, and you’re the founder, you think you know everything and forget you’ve been in the Kool-Aid for too long. But I would like to believe that everybody I’ve worked with, the executives, would want to be in these meetings. As an executive in marketing, I want to be in those meetings. That’s gold. I’d be recording it on my phone secretly and taking notes, whatever I had to do to get that information. So yeah, I think it’s ego.

Dani Woolf: I thought it was just me, and that was my perception. But I’m relieved, but I’m not relieved that it’s not only me.

Chris: Well, then, we have something to change. That’s why you have a great company, and you’re doubling your business. People recognize it. Okay, great. So let me ask you a personal question now. We kind of go back and forth asking businessy and fun questions. So what is the one thing you refuse to share? Me, it’s dessert. I refuse to share dessert. If you want dessert, order your own dessert. Do not-

Dani Woolf: Ice cream. Ice cream. My wife tells me if I could choose ice cream or me; I generally hesitate because it takes me time to think about that answer.

Chris: All right. What’s your favorite flavor?

Dani Woolf: Ooh, that’s the hard question. It depends on which ice cream joint; what do they call it? Ice cream joints or parlors?

Chris: Parlor.

Dani Woolf: Well, we have some pretty good gelato here in Tel Aviv. I had really great pistachio ice cream in Spain not long ago. But I love a good vanilla. And I’m pretty; I love almonds or something with almonds inside. I like that crunch.

Chris: I like a little crunch in my ice cream too. Well, you shouldn’t share your ice cream if you don’t want to. Okay. So you’ve been doing marketing for a good amount of time. What do you think is the most important role of a marketing leader?

Dani Woolf: When you say role, do you mean trait and characteristic?

Chris: Role, characteristic, or focus. What’s the most important thing they should do as a marketing leader?

Dani Woolf: That’s a great question. I will answer in terms of trait and in terms of focus. This is my opinion. Okay. So in terms of traits, empathy, great at delegating, making bets, and analytical. In terms of focus, customers all day. More and more about customer experience. I mean, marketing is not a service function. And I learned this from one of my previous bosses, CMO; it’s not a service function; it’s a customer experience function. It’s the whole life cycle function. It should not be the only focus on net new revenue. And I feel like there’s so much pressure to focus on generating new revenue in the security space, particularly VC-funded and VC-backed firms.

Chris: New logos. New logos. Where are those new logos for?

Dani Woolf: New logos. Yeah. Well, what about the customer? That customer, nurturing your customer, you’ll more likely be able to generate new ARR when you nurture your customer, particularly in the security space, more so than just going after new customer acquisitions. So I think that splitting that into two-part questions, yeah, that would be the role.

Chris: Great. That’s awesome. Okay. What hobby do you enjoy, but never seem to have time for?

Dani Woolf: Hands down gardening. I love gardening.

Chris: Are you a flower gal or a veggie garden gal?

Dani Woolf: Flowers, for sure. Yeah, flowers and… Yeah, definitely flowers. I mean, I wish I had the time for it. I know it’s excused, but it’s so calming and therapeutic.

Chris: I have about 30 Dahlias, and I ordered 20 more next spring.

Dani Woolf: Oh, that’s beautiful.

Chris: You talk about relationship capital on your podcast. What are the steps we should be taking to develop rate relationship capital? And maybe define it too. Define what it is, and then tell us how we work on building that.

Dani Woolf: Relationship capital builds the relationships you have in your back pocket for long-term career growth. Because those could potentially turn into revenue for your business or referrals for your business. I believe there needs to be an inner shift, not just from an organizational perspective but from a human perspective. People need to make an inner shift. Currently, sellers and marketers are focused on the transaction and the persuasion. You cannot persuade someone to do something before you are actually generally curious and empathetic to your audience.

Chris: 100%.

Dani Woolf: That inner shift has to happen before you can act on the outer shift. The outer shift is that initial connection, meeting them, engaging them, demonstrating value, and asking for the transaction. So those words I just stated are essentially the steps. Right? So you have to establish curiosity and empathy, which is understanding your audience. Do you even know what your audience needs? What are their challenges? What are their pains and motivations? Only then can you establish that initial connection. And then you can meet them. Once you establish the initial connection and meet them, the inner shift comes back up, which is likability. They start to like you, and you start to each other. If you don’t like that buyer, that relationship isn’t a coin and lasts. It’s a bidirectional relationship. It’s not a one-way street.

Chris: I think that’s the problem. People look at it like it’s transactional and so much more. I can’t tell you how many people in my network I’m friends with that I met in 2003 on LinkedIn, and we became friends on Facebook. It was like, I don’t know, channel partners, even building relationships with everybody in and outside the organization.

Dani Woolf: 100%. So I want to reiterate that this bidirectional relationship is important and part of building relationship capital as a business professional. It’s asking for help. It’s asking your buyer and your audience to demonstrate value to you. Because you cannot thrive in helping them if they don’t provide value for you either, right? Ask for help, ask for feedback. How do I get better? What are the challenges are you experiencing? Be transparent so you can build that trust, credibility, and reliability. Only then can you ask for the transaction. And then I think a key element in building relationship capital is retrospection. Look at your relationship and what’s worked for you and your buyer in your relationship. Right? What didn’t work? What do I need to get better at? Measuring both their and your goals so that you can work together as trusted advisors. I think it’d be interesting to see how to systematize this, but I think we won’t be able to do it unless people nurture their soft skills, I think on both sides. Both on the technical side and the business side.

Chris: I agree. I almost feel like the loss of the phone conversation’s part of it. We’re sending emails, and we’re sending texts, and nobody answers their phone anyway. I don’t answer my phone. If I don’t recognize a number, I don’t think I’ll… Please leave me a voicemail, and I’ll call you back. But I think that’s part of where we’re losing stuff, too, is just not having that personal phone call.

Dani Woolf: I think there are modern ways to bridge that gap that’s been created. Again, I’ll refer back to the podcast. I mean, it’s a great way to meet people. It’s a great way to learn. It’s a great way to give value and help other people learn. It’s a great way to teach my guests. And so when you start becoming creative and how to demonstrate value and how to meet people.  You can do so many cool things these days with technology. You need to think about them in contextual ways and thoughtful ways.

Chris: 100%. If you owned a boat, what would you name it?

Dani Woolf: This is a hard one.

Chris: Really hard one.

Dani Woolf: I mean, it’s nothing creative. I think I just name it a midlife crisis or something like that. But that’s when I buy a boat.

Chris: I wouldn’t buy a boat, so that’s a hard one for me.

Dani Woolf: When I lived in California, my time living there, we had a couple of boats, and it was such great fun. Again, also very therapeutic. So it was great. I got to do some skipper courses and a great hobby. But yeah, midlife crises are like-

Chris: I love it. That’s a great one.

Dani Woolf:… a majestic pearl or something I want it to be. I don’t know.

Chris: I love it. Okay. Let’s see. What are some suggestions you would give the vendors out there on building their relationships with the CISOs? They’re spamming them with emails, and maybe we’ve covered some of this, but I mean, there are certain marketing tactics you have to do, right? You’ve got to send your emails but be mindful of it. So what’s some of the advice that you would give to a vendor that’s trying to get in touch with these CISOs? Because I know you’ve been talking to a lot of them.

Dani Woolf: First and foremost, get started yesterday if you haven’t done so already. Not in spamming them but in building relationships. Second, it goes back to what I originally talked about in terms of relationship capital. Don’t expect transactions. Vendors are there to help, at the end of the day, help practitioners do their job better. At the same rate, tying back to customer experience, they are also there vendors are also there to learn how to do better. That relationship has to be bidirectional. So ask for help. Do not be afraid to ask for help.

And I think a great way in a great conversation starter is to ask for help. Most of the success, I have a 97% success rate in hooking conversations with CISOs because I’m asking for feedback on how I can get better in my marketing message or my marketing campaign. And they’re astonishingly and surprisingly so many executives willing to help. I think there’s a stigma that security practitioners and executives are hard to tap into. But it’s not the case unless you come up with an authentic approach and transparent and honest approach to get better.

Chris: I think they tend to be a little prickly just because they always have people constantly coming at them with, look, come to a baseball game, come to our steak dinner, do this, do that.

Dani Woolf: 100%.

Dani Woolf: They’re not doing the research. They’re not doing their leg work and research, initial research. It really takes 10 minutes. It takes 10 minutes to do the research. At the end of the day, CISOs know that we have to put food on the table to buy. It’s how you approach it; approach them. It’s the context you put within that outreach message or LinkedIn message. It’s the way you get to them that is critical. Not through shady tactics, like using them as a stepping stone or whatever. They’re not dumb. They know that we need to sell. It’s just how you approach it.

Chris: As a marketing executive, we get hit all the time too. I’m always surprised to get some tactics people to come up with. Okay. So I was looking at your LinkedIn, and you mentioned you were a competitive swimmer. What are some of the lessons you learned from swimming that you could apply to your career?

Dani Woolf: Oh wow. So much. Just, first of all, I miss competitive swimming so much.

Chris: I swam in high school. I wasn’t very good, but it was really fun.

Dani Woolf: Yeah, it’s so much fun. It’s hard. It’s hard as hell. I mean, I do not miss 5:30 AM practice. Let’s just say that much. I’d say, I mean, just diligence and consistency. Because as a swimmer, you’re practicing nine times a week, and you got to go to practice and wake up early, and work ethic and diligence to succeed are important in sport and my career. I’d say constantly learning about my audience. Regularly as a swimmer, I was a distance swimmer, so I would also study my competition. Not just my audience but my competition. Is this a video podcast, by the way?

Chris: No, it’s only audio.

Dani Woolf: Dogs and kids and wives coming in and out. So constantly learning my competition in my audience so that I understand how I can beat them. You have to do strenuous things out of your comfort zone to build stamina and growth. So not only swimming your event but doing things and tactics that are physically strenuous, like swimming the 200 butterfly and then right after doing the 100 free sprints or swimming the 500 free, which my was my event, and then the 200 breaststroke. I was the worst breaststroker ever. I would just-

Chris: I was the worst butterflyer… My coach would let me swim two laps, and then he would say, “Okay, that’s enough, Chris, you’re done.” Because I just looked like a drowning something.

Dani Woolf: Yeah, no, no. I would just pop up and down in one place. It was never forward. And it’s so hard. And I think it’s also in terms of form, body position, rotation, and breathing patterns. It doesn’t have to be pretty or comfortable. It has to be accurate and move you forward for maximum propulsion. And the same way for my career. Things don’t have to look pretty. They have to move you forward.

Chris: Exactly.

Dani Woolf: So there are a lot of things. Thinking about it now. Wow. It makes me miss swimming.

Chris: Me too. What was your stroke? What was your main stroke?

Dani Woolf: The Main was long-distance free. And I would also do the 200 butterfly.

Chris: I was long-distance free, and then I was the 200 in the backstroke and the medley relay.

Dani Woolf: Nice. Yeah, backstroke was not my forte, either. But yeah, I got good at sprint fly and sprint butterfly towards the end of my collegiate career. And that was fun because I got really strong because we did a lot of weight lifting, and that was the best shape I’ve been in. Holy moly. I still have the appetite of a swimmer, just not the same at metabolism, unfortunately.

Chris: Yeah, me too. I miss it the most. Okay. So you know what? We’ve been talking about building trust with the customers. When a customer trusts a vendor, what type of investment do you think they’re willing to make? For example, doing references and public speaking. What are some of the benefits you’ve seen from customers and building these relationships that can really resonate with marketers besides-

Dani Woolf: I definitely think public and private referrals. Lots of private referrals. CISOs and other execs have their circle of trust, their networks, and their Slack channels and Discords. And so referrals, for sure. I mean, it’s just, hello, expansion on deals. Your direct customer will give you more money.

Chris: Exactly.

Dani Woolf: If they trust you. So that’s what it’s about. And I think those programs like advisory boards, speaking opportunities, and dinners are our fuel for those expansion deals. They want to feel they’re contributing; they want to feel they’re learning. And so I think that’s a great way for vendors to build customer trust. And I want to know, again, I’m going to throw one more question back at you, Chris, why do you think cybersecurity vendor firms are not investing in these kinds of customer engagement programs earlier in their growth? Are they doing it much later or not at all?

Chris: Well, in the beginning, we don’t have any customers, and we have a few, and they’re usually spread pretty thin. I’ve always worked at companies where we had a few big-name customers, so we were really careful around them. And then there’s this massive push for leads. I mean, RSA, you’ll get some great conversations at RSA. Every RSA I’ve been to, we always get that we shouldn’t do RSA anymore. That’s not true. I was there in 2016, and I was with the CMO, and I was consulting with them, and one of the new customers came by, and he’s like, we were in the small booth side, and he’s like, “I don’t go over to that side.” He’s like, “I don’t need any of that crap to bring home to my kids, but I want to come over here and see what’s new and exciting.”

And it was really interesting to hear that. And we spend so much time scanning everybody when there are probably only ten people a day. We should be scanning because we’re going to close a deal with those people, and the rest are just tchotchke grabbers. Maybe they’re there to get an education, but there’s so much push on the number of leads, filling the funnel with leads, and making sure the inside sales team has enough leads to call on. And we need to change that because it’s not working. It’s just not working. And I’m sure you heard the same thing.

Dani Woolf: I think there’s a stat out there. I think I saw in a Forester article that you’re likely to get five to 25X more revenue when you nurture your existing customers than on net new customer acquisition and doing nothing with your existing customers.

Chris: And I think it just comes from the VCs. They want to see that revenue hockey stick so they can get out and sell the company. I mean, I’ve been through four or five acquisitions, and you get to that 3X revenue, and that’s when things shift, and you get acquired.

Dani Woolf: 100%. Well, again, I’m still trying to tap into how to change that mindset from an organizational standpoint. It’s hard inside.

Chris: I’ve seen big companies, so there’s a big security company, and they probably have a product for every security need you have, and they don’t have a strong customer base. They didn’t have a lot of relationships there. It was all transactional, which was depressing because they have all these fricking products. If they had a good relationship, they could probably cut out everybody else because wouldn’t you want to buy from one vendor? I mean, all of your stacks integrate, then. So even the big companies aren’t paying attention to it.

Dani Woolf: I particularly, I think, you take a look at some of the… I get inbound emails from security practitioners in CISOs who send me emails from some. I won’t name names, but some well-established vendors. And I’m like, “How are you leading in this industry?” I know how, but it’s made a lot of brand visibility. But it’s like, seriously? This vendor? And it’s not just one rep. It’s a bunch of reps from the same vendor. They’re starting to get called out on LinkedIn, unfortunately. It’s a sad story.

Chris: So I’m going to ask you one last question, and I’ll end it. So what advice would you give your younger self or those starting?

Dani Woolf: You’ll control your career, get close to your customers, hands down, be curious, ask for help, and continue self-learning. I would say don’t be afraid to make trade-offs and bets. Be strategic much earlier in your career than later. Don’t be too tactical. There are trade-offs between strategy and tactics, but think of how to be strategic earlier in your career. I’d say those. And don’t sell your soul to organizations because of fear of not making money or making money. Do things that make you happy and wholesome in your career.

Chris: I 100% agree. Yeah. That’s the scariest part. I’ve been to many startups because we get acquired, and I’m not happy when we’re part of a big company or it’s just not a good fit anymore. And I quit, and I just wait. And my husband’s like, “I can’t believe you can do that.” And I’m like, “No, because something always better comes up. Always.”

Dani Woolf: Yeah, yeah. I mean, look at me. I quit my job and made a company scary. It’s scary, but I believe in it. One of my guests on the Audience First podcast, Evan Francen, said, “If you focus on the mission, you’ll make money.” So I’m focusing on the mission, taking that risk and doubling down and making that bet, listening to what I would’ve told my younger self, and hoping it’s going to work out.

Chris: Well, it sounds like you’re doing great, and I have 100% faith in you. And I’ve been consulting on my own for nine years, and it’s always worked out.

Dani Woolf: Thank you. Yeah.

Chris: Okay, so let’s do a shameless plug. Give us your podcast and any other things you want to share with our audience that they should check out.

Dani Woolf: So definitely check out Audience First for any cybersecurity marketers, salespeople, founders, or even practitioners. Every week, I interview security executives and professionals on why and how they buy. I also highlight the things vendors do that piss them off and the alternative, which I think is really important. The buildup, not just the teardown. I’m also launching a new podcast with Chris Roberts, CISO at Boom Supersonic. It’s called… Can I curse on this website?

Chris: Sure, absolutely.

Dani Woolf: So I’m launching a new podcast with Chris Roberts. It’s called, What the Fuck Did I Just Read? Tech Sales and Marketing Edition. And we’re unveiling the inside of his inbox, his email inbox, and we’re going to tear down the worst marketing and sales messages. But again, more importantly, we’re going to build it up and show the audience what and how they should reach out to CSOs and build relationships with them. It’s going to be a live podcast, so we’ll open the floor for any questions and feedback. So it’s a great way to validate quickly. So if anybody is interested, happily, please join. Yeah. And if you want to hang out and chat, you can find me on LinkedIn. My name’s Dani Woolf. Again, always on LinkedIn. That’s my go-to. Yeah.

Chris: Awesome. Well, your podcast would be useful for anyone trying to sell or do marketing in pretty much any industry because we’re all trying to sell up.

Dani Woolf: 100%.

Chris: I mean, the CISO’s pain point is going to be the same as the CTO’s pain point, probably as far as sales marketing goes.

Dani Woolf: The C Suite, for sure.

Chris: It has been a pleasure speaking with you. Thank you so much for joining us.

Dani Woolf: Thank you.

Chris: Thank you, everybody, for tuning in, and be sure to check out our next podcast. You can stop recording, Suzanne.