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How to Avoid Pressure to Achieve Short Term Results at the Sacrifice of Long Term Strategy in Cyber Security

Mike Krass • Friday, April 1, 2022 • 17 minutes to listen

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Welcome, everybody to what's the problem, the show that explores problems that practitioners, buyers, and cybersecurity professionals face in today's world. Today, we are very fortunate to have Dani Woolf join the show.


Mike Krass: Dani, say hello to our listeners.

Dani Woolf: Hello, hello, and thanks so much for having me on the show. I think this is show number two that you all have invited me to. So I'm super thrilled, and thank you for that.

Mike Krass: I know you are a longtime listener, a second-time caller. So we're excited to have you not just on Tea Time with Tech Marketing Leaders but also on What's the Problem. They get into not the problem yet. But our first question, as we know, is always Dani, why are you qualified to talk about security?

Dani Woolf: Wow, I'm not sure I'm qualified to talk about security. Totally, suffering from imposter syndrome right now. But I think, if anything, all first and foremost, I've been in security for about four years as a cybersecurity marketer, working on the vendor side. Secondly, if anything, I've dedicated the last I don't even know what better half know even better, like about a year to really trying to become as obsessed as possible with the buyer and get as close as I can with them. So that's me literally just taking the time to interview them to understand what makes the practitioner and the business decision-maker insecurity tick. What pisses them off is that vendors try to establish a genuine and authentic relationship with my audience. Because I think that's a huge differentiator as a marketer or a salesperson, if you're in sales, I really have a genuine curiosity to understand them to get as close as I can to them and become as literate as I can insecurity. I think it starts there. So my hope is that I'm qualified, I think I am, but I think you agree; otherwise, I wouldn't be here. So that's about it.

Mike Krass: Absolutely. And I think a little-known university named Stanford University also didn't give you earned a certificate from them. Not on the topic of cybersecurity; specifically, it's got within the world of human interaction and computer science.

Dani Woolf: Yeah. So, first of all, Stanford was my dream school. When I was in high school, I didn't get in. So it was my dream to have somehow a connection to Stanford, you know, I was raised in California, and I really wanted to go there. And about a decade ago, I stumbled upon the value of user experience as it ties back to technology. And it ties back to just general, you know, general customer, customer experiences, and the way we do things digitally as a marketer, and I noticed they had a certification program there. And I said, Yeah, I got to do that. I thought it was super valuable to me. I'd love to redo some form of that kind of certification because that was ten years ago, and things change so rapidly that some of the theories there, and the tactics are refreshed now.

Mike Krass: Awesome. You mentioned the word curiosity earlier, and I think my listeners and I are curious. Name a problem in the security world. Let's talk about getting curious.

Dani Woolf: Okay, so prepping for this call, by the way, I have a list of maybe 101 problems. So it was hard to pinpoint, but I'll dig into the main problem that I've experienced, and my hope is that to those listening, I hope this will help them; this is a big problem. I think many suffer from many marketers' sales to organizations. So, marketers and sales teams alike in the security space are pressured by the need to produce quick results to appease investor profits. So I think this need to demonstrate financial strength results in kind of shady and sometimes unethical business practices. And that really compromises the buyer experiences and sometimes the product quality in favor of short-term gains.

Mike Krass: So optimize product quality.

Dani Woolf: Go quick to market without validating the audience or go quick to market with a message that doesn't tie into the actual product right over promises under-delivering that's huge thing insecurity. And it just pisses off the practitioner and the business decision-maker in organizations. So my big H is this profit at all costs mindset in organizations versus the mission before money mindset, which is key to success in security organizations and vendors just in all industries. So if I take the alternative, if I take time to get to know my audience and apply insights to strategies and tactics and do things more authentically double down on the longer-term plays which down the line are going to provide exponential growth, it'll take a little bit time to take off, but it'll provide exponential growth versus the linear incremental growth. There's a fear of harming those short-term earnings if I do that or negatively affecting the investors' perspectives of the brand, which causes a lot of anxiety, and I suffer from it. I've been there many times, I still sometimes suffer from it because we're all funded by investors, and they invest a lot of money. They expect exponential growth like that. What happens then? Right? Marketers' salespeople fall into the comfort of the status quo. They fall into the comfort of just routines, day-to-day habits that after a while, don't feel like bad habits. They're just the way things are done, and marketers continue to talk to marketers about how things are done, and not many challenges that status quo. And so, we focus on these trivial tasks at the expense of the audience's experience. So my experience is why I'm doing what I'm doing and trying to become more customer-obsessed. In the past, I've suffered, and I've fallen into the trap of the law of triviality, and I didn't make time, or I was hesitant to approach customers or the audience and show a genuine curiosity to get to know them. And that pisses off buyers, right? Because we fall into those bad habits for quick results. It's a big issue and failure to get close to the practitioner or the business decision-maker and security in any industry. It causes blind spots in the organization, and we're working against what the investors and our managers want in the first place. Right? Blind spots, what are those? If anything, the biggest blind spot is just insight, lack of insight, and if anything, getting access to those insights is your differentiator. So, in the end, that just causes companies to lose touch with what really brings value to the organization, customer, and audience. To me, it’s a huge fundamental issue.

Mike Krass: I can imagine that on the product, and the engineering side, what you're seeing is probably being welcomed with like everyone's doing the wave, and they're jumping up and down. Because there's always this friction between sales and marketing to actually promote and sell the product, and not all organizations have this issue. But I've certainly spoken to some who have that issue around, like, sales and marketing are saying things that we can't do or that isn't possible, or two quarters away on our engineering roadmap, or whatever. I can imagine the experience you just shared by being authentic and understanding the buyer. The word honest and transparent also comes to mind; being honest and transparent around where we are today. Here's where we'd like to go, but you know that doesn't exist yet. I've never met a product leader or an engineering leader who loved it when sales and marketing promised something that wasn't quite ready or wouldn't be ready or fundamentally was going to change a roadmap that we on the marketing side didn't even make in the first place like, wow, this is probably being met with you know, like a Rochus-like cheer.

Dani Woolf: I hope. I was gonna say, you know, in my discussions with buyers and customers. Honesty and transparency are core themes that I hear across all of my conversations, and the expectation from them is that you cannot do everything. As a security vendor or a product, you cannot do anything, but you can solve an issue. If you really focus on that core competency, there will be a lot, and be honest about what you cannot solve. You will meet with arms wide open from a practitioner who understands your core competency and value. So, as a marketer, vendor, or security salesperson, I just think that you cannot be everything to that one person. And I feel like, you know, in my discussions is just validated that a lot of vendors over promise and under deliver. It's okay to admit that you cannot do everything.

Mike Krass: Yeah, before we get to our final and most fun question, I did want to reflect on one more thing. Based on the conversation you mentioned, I'm paraphrasing that you are getting these habits, which could be poor. And over time, those habits just become air quotes, the way things are done, or because we've always done it that way, you know, some semblance of that statement. And it really reminds me one of my hobbies is flying small airplanes, and you hear of pilots that have crashed; it's called safe that controlled flight into terrain. It's usually at night, or an increment or instrument weather, and what happens is you start turning the airplane very slowly from left to right. And talking about the way it's always been done, or those habits becoming like they feel normal. So you're turning the airplane to the left, let's say, you think you're flying straight ahead and you have fluid. All human beings have fluid in their ears, which tells you it's almost like a level you'd buy at the hardware store. And by staying in that left turn, if it's not too sharp, your brain actually that fluid, thinks oh, great like we're kind of level I might be off. But after a minute or two, we just go into over completely level. And then pilots, what happens is that turn to the left becomes a tighter and tighter turn. Suddenly, you start to notice, oh my gosh, my heading is going literally backward at this point, you know. From where I started, my speed is increasing, and my altitude is dropping like now you're in a tight, spiraling turn that will get tighter unless you get out of it. But your brain, until you know, happens with pilots until you look at your instruments. Your brain is sitting there, and it kind of lies to you, and that's kind of what I wanted to reflect back in this conversation of these habits that have over-promising and under-delivering or saying you can do something, we're not being transparent and saying you're not good at something, even if you can do it just saying, we can do that, but it's not really our strength, like, our strength lies over here. Those habits turn into the fluid in your ears, and all of a sudden, it just becomes normal. Like it's okay to behave this way because my ears are telling me it's fine.

Dani Woolf: Yeah, 100% While I have on LinkedIn a list of all those habits I've stuck to for years that have just wasted time and pulled me away from getting close to the customer and audience. Sometimes we just have to stop for a second. If you can't get access to customers, get access to the closest best thing, your ideal customer profile. Reach out to them, and build those authentic relationships because you'll be surprised after just a few conversations. After six to eight, you'll start understanding themes, and you'll start seeing similarities in what they're saying based on the questions you're asking. You'll be able to apply that to your strategy and tactics, which I can't even tell you how great that'll affect your results quickly too, so you're not only building relationships, you're also positively affecting what you're doing as a marketer within a short period of time.

Mike Krass: Yeah, absolutely. Well, Dani, we've arrived at question number three. It's the most fun and entertaining for our listeners. Tell us about your worst haircut.

Dani Woolf: Oh, yeah. Okay, so it's kind of a morbid story. But we're in 2022, so eight years ago, my grandmother passed away, and I don't know what I was thinking, but I said to myself, ‘’Okay, well, she passed away. Let's go get a haircut and color my hair to make myself feel a little bit better.’’ I don't know why I thought that would help. It made me feel worse because I didn't even know what I told him to do. At that time, I was kind of blonde. I was doing all these things, highlights in my hair. I had long hair. He chopped my hair off to a short haircut, and I still have a shorter haircut now. And he dyed it brown and blonde, and I literally went out looking like a skunk. And I looked like a skunk, and I had to go to the funeral like that, and I remember it was a very hot day in December, ironically, and I went with a skullcap, so I was sweating like crazy in crying and bawling at the funeral. It was just the worst experience ever. So I think it's a tie between that and shaving my head like ten months ago. I literally shaved everything, like I quit my job, shaved my head, and then started at cybersecurity skills, which was an interesting experience as well. So I'm pretty risky when it comes to haircuts. So I think that's the story, both are winners.

Mike Krass: Well, I appreciate you sharing both of those stories. That was a twofer right there. I wasn't expecting stories. Awesome, Dani. Well, again, thank you for joining us, and to all our listeners, thank you for listening What's the Problem, the show that explores problems that buyers, practitioners, and professionals in the cybersecurity space face in today's world.

Dani Woolf

Dani Woolf is a swimmer turned marketer. And she still has the same appetite to win (and eat!). Over the past 10 years, Dani has been applying lessons learned as a distance freestyler to B2B businesses in the cybersecurity and technology industries, specifically. You can connect with Dani on LinkedIn and listen to one (of her 2!) podcasts, Dr. Dark Web or Audience 1st.

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