Episode 005 – Breaking into Cybersecurity PreSales Roles with Damian Tommasino

Summary

Let's talk PreSales within Cybersecurity!

On this episode of Path to PreSales, we explore key learning considerations for breaking into tech and presales with a cybersecurity focus.

Our guest, Damian Tommasino, is Principal Security Sales Engineer at Feroot Security and founder of Cyber Informants: a unique content hub, education platform, and community that is on a mission to redefine pre-sales within the cybersecurity industry. 

Join us as we dive into Damian's path to PreSales within cybersecurity, and discuss many excellent resources that he's working on to help you find your own path within cybersecurity! 

Hit play and subscribe to get more great episodes like this every Friday! 

Resources Discussed

Check out these great resources from Damian's company, Cyber Informants, today!


PLEASE NOTE: I use an AI-based service for episode transcriptions, so please forgive any transcription typos found below!

[00:00:00] Matt Madden: All right. Hey everyone, this is Matt Madden and today I'm here with Damien Tommasino. So Damien, is the principal security sales engineer at Feroot Security. he is been there for going on two years, correct me if I'm wrong, Damien. Uh, but also the founder of Cyber Informants, which I'm really excited to talk about today and how that's aiming to help many different pre-sales professionals and people looking to break into the role.

Damien, I just wanna say thanks for coming on the show.

[00:00:25] Damian Tommasino: Yeah. Thanks for having Matt. I'm uh, excited to be here. I definitely wanna talk and dive into all things pre-sales cause I think there's so much we.

[00:00:33] Matt Madden: Absolutely. Well, let's get right to it. Would you mind just taking a moment to give a high level overview of what you're focused on today and your current role and with cyber informants, and we can certainly dive deeper from there.

[00:00:46] Damian Tommasino: Yeah, absolutely. So, uh, during the day, as they say, I uh, worked for a Canadian startup called Feroot. So I'm the principal security engineer over there. So I actually have the, uh, privilege as they say, of covering both pre and post sales. So I see both sides of the equation, which as you know, has, uh, some pros and cons to it.

And then I also have cyber informants, uh, that I had started and. You know, I had started it with a friend. We wanted to do something that really focused on not just pre-sales, but specific for the cybersecurity community because we're our own beast and we have all these, you know, unique challenges associated to cyber as well.

And as we've been building up that, you know, bit by bit, we kind of broke it down into three pieces and it's. helping people break into pre-sales in general. Building a community specifically for cybersecurity, pre-sales, kinda like a support mechanism. And as you'll hear, launching leg hopefully next week, which is all about training and education for those that are in the pre-sales role.

Cause I'm, I'm sure you know, once you get into this role, it's kind of, you're on your own, you're doing your own thing. So

[00:02:00] Matt Madden: That's right.

[00:02:00] Damian Tommasino: you need, you need a sports system.

[00:02:02] Matt Madden: Oh man. I'm so excited to dive into that. And you're right. I mean there's, thankfully, there's been some amazing communities and organizations and resources that have come together, including what we're gonna talk about today with cyber informants and the work you're doing there. but there's.

Still a, a lot of room for, filling knowledge gaps in niche ways within the industry, within specific verticals where pre-sales roles are absolutely necessary. And, you know, learning by doing is so much of the job, but it certainly helps when there's great resources. So I'm excited to hear what you're working on there.

[00:02:36] Damian Tommasino: Yeah, absolutely.

[00:02:38] Matt Madden: One thing I like to. Before we really start to unpack that in, in what you're doing in your current role, um, as well as within cyber informants is, would you mind taking us back to where you first found out about pre-sales, uh, and your first role in tech? they don't have to be connected, but if they are, that's great, but just would love to hear your story there.

[00:03:00] Damian Tommasino: God, they're gonna make me age myself by telling you this story.

[00:03:04] Matt Madden: Sorry, David.

[00:03:06] Damian Tommasino: I, I, I've always been into tech. I went to college for Comp Sci and business double majored, so it was something that I always knew that I wanted to break into, and I actually started. Long time ago on the practitioner side, so did a Windows admin for a while, was a network engineer for a little bit.

And I knew that I wanted to go into security, but I had been taking different roles, trying to build up experience to break in. Cause even back then you needed a lot of experience to break into cyber. And this one company I was working for in downtown Manhattan,they had this one guy who was in charge of.

Cybersecurity for the organization. And I would like constantly pester him, trying to be like, how can I help? What can I do? Can I work on projects with you? And he was just like not having it. And I tried finding other avenues within the organization to try and get involved in cyber. And we ended up working with this reseller who was like, you know, saw firewalls and endpoint security and other things.

And I ended up having some really good conversations with them and they actually needed. A sales engineer because they didn't have one and they were growing really rapidly and I had no clue what a sales engineer was. That was something I'd never heard of before, but couple conversations with them turned into offer.

Um, uh, you know, I didn't really take it because it was a pre-sales role. I took it more because I'd have access to like all these different technologies and I, I found out once I got in the role that, you know, being in pre-sales, you get to see all these different things by not only talking to customers, but then translating that into solutions.

And it was something I had such interest in and it kinda just evolved from there.

[00:04:47] Matt Madden: Amazing. You came from this journey of not necessarily having, I would say, pure customer facing experience from what it sounds like. Um, Right out of the gate. And I think that's really interesting and I'd be curious to know, I know that's the path for many that started more on the direct engineering side of the house, um, before and transitioned into sales engineering, pre-sales roles and so on.

I'm just curious to know, I've met folks who are very successful sales engineers that. Struggled to make that jump for a while because they were intimidated by the customer facing element of it. Is that something that you struggled with

[00:05:29] Damian Tommasino: Yeah, that's a good question. And I, I think a lot of it really comes back to self-awareness, right? So I knew going into it, it was very customer facing and like I'd be meeting a lot of people. And I do love that element of the role, and honestly we could talk about later, but it's one of the reasons I've actually keep coming back out of a management position because I love the IC side of the house when you're just engaging with people at that contributor level.

Um, but going into pre. I am an introverted extrovert, so it's like I have that I want to connect to people. I love having those conversations. I love hearing about what they're working on, but I also know that the energy I expend doing that is limited in nature and like once it, once that energy is, it's spent, I need to like be alone in a dark corner for four hours to recharge.

It's like, as long as you know, you know how you approach the situation and the impact it's gonna have on you. You'll be fine. Then it's really just a matter of imposter syndrome that's in the way. Nothing more.

[00:06:33] Matt Madden: Great advice. Yeah, and that makes total sense. Uh, just having that self-awareness and. being confident enough to know, getting out of your comfort zone in an area where you want to grow, uh, is going to be a good thing. Even if it hurts in the moment, as you get through it, it'll get better each time and so on.

And so that makes a ton of sense. Well, one thing I think it makes sense to dive into next then is, you know, let's say someone came to you today and They're interested in breaking into pre-sales. It could be specifically within cybersecurity. Um, I, I would like to have you answer the question in two ways.

One, if somebody was just in general, Interested in a sales engineering or a solutions engineering role, what advice would you give them or tell them to focus on to successfully land that? If it's just more general? And then if you wouldn't mind answering the question. for somebody who's like, I want to work in cybersecurity, I want, I wanna be in pre-sales, if is, what are the extra things?

If there's anything specific there that you would also.

[00:07:35] Damian Tommasino: Yeah, absolutely. the first thing I always tell everybody is to not read the job descriptions, which I know sounds insane, but hear me out on this. Most job descriptions for pre-sales roles. Are written for technical people, which is quite possibly the dumbest thing that I've ever heard.

I know why it exists that way cuz like 30 years, you know, sales engineers or systems engineers used to come in and like, you know, have all this physical equipment and they'd be very technical in nature. They literally were engineers. The world doesn't work that way anymore, right? With the rise of cloud, the rise of all this data going everywhere and just so much content that can be consumed by buyers on the internet.

You don't need super technical people anymore to a degree. You need some technical knowledge, but you don't need to be the expert on everything from a technical perspective. And since most job descriptions are poorly written in that manner, If I'm somebody looking to break in and I read a job description, the first thing I'm gonna see is like, you know, must know, uh, AWS or must be familiar with APIs and, and no Python and all these other really technical things.

But at the heart of it, you know, pre-sales solution consultants, your job is to uncover pain points. That customers have, right? And how you compare a solution with those pain points takes a lot more than just technical aptitude. So I always tell folks that are looking to break in to actually go and if they haven't done one already, like you can take them online for free.

Take a skills assessment that evaluates your soft. Right. Are you a good communicator? Are you a public speaker? Do you critical think in a really good manner? Like look at all of those skills because yes, they may not be the first thing that gets you the job, right? Because again, job descriptions are just written so poorly, but it will be the thing that helps you make yourself once you've broke into that role, right?

So that's, that's general. You know, anybody who wants to break into pre-sales, the only spin I would put on that for cyber. You kind of have to work both muscles at the same time, right? There is just a natural, certain level of technical aptitude you need for cyber, given how complex the world really is when it comes to securing systems and networks and devices.

So again, I don't feel like job descriptions really do a good job sharing what the role really needs when it comes to cyber and you. Employers in general in cyber are really, really, really bad hiring associate level. And I, and you know, that's something I hope to fix one day and get more associate level roles built out in some of these big organizations because you know, it's easier to bring somebody in at an associate level and help shape them to what you need them to be.

Then just to wait for that one really good senior resource to open up and then have 50 people competing for them.

[00:10:39] Matt Madden: Hmm. That makes a ton of sense. I think that's gonna be so helpful for people to hear when they are in that situation you were talking about, they're reading the job description for a cybersecurity role, or specifically a pre-sales role within a cybersecurity organization, and they see some of those bullets like you described, and it's just like, wow.

I am. Miles away from that, or it feels that way in terms of, you know, just feeling underqualified and the imposter syndrome sets in. you know, regardless of where you're in your journey, it seems like that's a common trend, unfortunately, with job posts. So I think that's a good call out just for anybody to keep in mind.

And I'd love to unpack, you mentioned, a comment around, you are personally, and I know this just from a lot of the great content that you share on LinkedIn, you're personally invested in trying to help people land that associate role through, as we mentioned before, cyber informants. I just would love to learn a little more about some of the things you're working on within that, to, to really help people on that journey.

Specifically for cybersecurity, presales.

[00:11:42] Damian Tommasino: Yeah, so there's one piece of this called Scout that we have that's online, and Scout was, you know, Literally like helping people scout out their first job in pre-sales. Like, that was the, the vision behind it. And there's, it's all free content. It's all out there, you know, nobody can read through it. And the way it works is I broke it down in terms of like, here's all the things you need to break into pre-sales in general.

Not cyber specific, but just pre-sales in general, and then. I laid it out in a manner with, you can kind of build up different areas. So one is around like soft skills, one's around technical skills, one's on like how do you survive the interview. There is another piece on like the ultimate guide to pre-sales compensation, which you wouldn't think it's complicated, but that's probably, I wanna say it's one of the longest pieces I've written so far.

It's about 5,000 words just on that one post. So it's, it's a huge guide. Because there's just so much to consider from that lens. Um, and then I also wrote, um, we were actually talking right before the show too, a couple of transition guides. So I've talked to a whole bunch of people from other professions, like, teachers, a lawyer, um, a couple of doctors.

there are several people who are like in the construction business who wanna break into presales. And what I did was I actually listened to their stories and asked them a lot of questions, and I wrote this like, you know, transitioning. Insert your profession here into presales, and I kind of mapped out like, these are all the things that you probably don't even think about that would apply directly to presales.

So they can learn to tell their own story based on the experiences they already have. So like that's all this content that I put out there for Scout, trying to help people break in. Cause we really do need more people in pre-sales in general. We need a whole lot more diversity. You know, it's a, a huge thing for us right now.

Um, and then just kind of as a value add for Scout, for those that are wanting to break into cyber specifically. Um, part of Scout is, I run a job board there, so I track. Probably four or 500 jobs, uh, or companies with jobs and job openings every month and write up report once month on, like hiring trends and who's.

[00:13:57] Matt Madden: That's amazing. Well, for everyone listening. Go check out Scout, and I'm gonna provide links in the show notes to various things we talk about today related to cyber informants. So including a direct link to that job board that Damian just mentioned, as well as to the scout resources. So, I mean, that's amazing, just the.

The free content that you have there, I, I know it's gonna be so helpful for people to go check out. Um, especially those that I know who are wanting to break into cybersecurity and are open to different roles and they're just learning about pre-sales, as a function within cybersecurity software organizations, um, which is certainly the case.

And, you know, your e. And yeah, and just in general, the fact that regardless of where you're at, even if you're not necessarily heartset on cybersecurity, but you want to work in pre-sales, now that you're learning about the role, the fact that you're, you have a lot of content that just in general will help there, uh, is exciting.

So, yeah, looking forward to having people check that out and you guys should get, get in touch and follow up with Damien if you're alright with that. Damien, I don't want to flood your,

[00:14:58] Damian Tommasino: Yeah, no abs.

[00:14:59] Matt Madden: but,

[00:15:00] Damian Tommasino: It's all good. I, I love dms on LinkedIn. Reach out, say hi, ask questions. I mean, I, a lot of the content that I produce is based on really good conversations with people reaching out. Looking for advice, looking for ways to break in. So like, you know, the more folks that I get to have conversations with the, just the better the content becomes.

[00:15:20] Matt Madden: One thing that I saw as well when I was on cyber informants is your buyer experience framework, and it aligned with a lot of what I've learned on my journey thus far in continuing to learn and improve that every day in my current role. As a sales engineer, but, um, I wanna make sure I got the core tenants right, but starting with build, um, and then connect, engage and close.

And just would love to have you speak for, you know, a few minutes on that. And how somebody who's, if they're looking at cyber informants and they see that in, they're still at the stage of wanting to break into pre-sales, how they should start thinking about that as they're learning and upskilling and trying to even transition.

[00:16:05] Damian Tommasino: Yeah, so the buyer experience framework was something that I developed probably over the last couple of years, honestly, and there's about a decade's worth of knowledge that I poured into that when I started writing it. And really the foundation before it was. You know, buying has changed. I don't think anybody can really deny that anymore, right?

Most of the information, the content, the timelines, it's all in the hands of the buyer right now. All they have to do to find out about a solution, go google it, right? Ask some questions, hop into a peer community and ask a friend. Uh, you know, the, the control is really in the hands of the buyer these days.

But for some reason organizations refuse to acknowledge that and they're still running these, you know, sales playbooks from 5, 7, 10 years ago that just aren't working anymore. And like you can see that in organizations that struggle to get off the ground or don't connect really well with their audience.

So I ended up writing this framework. Right to help folks who want to kind of think about sales in a very different way, especially for pre-sales, because of how plugged in we are to all these different areas of the business. You've got the sales side, the delivery side, the product side, the working with marketing, right?

You get to touch all these different areas of the business, and you have all this knowledge from talking to customers. This framework was meant as a way to help kind of guide those conversations. To almost turn pre-sales individuals into their own little, you know, demand gen engines essentially within the, the bigger confines of an organization.

So the, the way it was written, you, you kinda touched on them a little bit, um, it starts with build and build is all about, like, how do you craft a story. Now, usually when you walk into an organization, you know, as part of the onboarding process, they tell you like, Here's why the founders started this and here's their vision and here's where we're going.

And it's like, how do you take that story and like make it your own so that you can tell it as passionately as the CEO or the founders and, and relate to that? Because I think people really pick up on the fact that like, if you don't believe what you're selling, they're gonna smell that a mile. So knowing the stories is, is kind of the, the first part of it.

And then moving on to connect. And I think this is where we kind of see a lot of people fall into the wrong trap. Um, if you've ever been on LinkedIn, connect with somebody and like immediately they try and pitch you on some sort of service, call it a pitch slap, right? Everybody hates the pitch slap. Um, Right, that that is just like the old school way of thinking about sales.

It's like you just shoot out emails, shoot out cold phone calls, you pitch slap people looking to see who's gonna bite. And the idea behind this is the connect phase of this framework is more about establishing actual connections and relationships with people with no ulterior motive. Which, if you're in sales sounds counterintuitive, but it's really about building relationships, not necessarily trying to sell something.

So the the simplest way I can explain it is stop selling, right? And start telling a story. Instead, start talking about the problem. Why do you exist as a company? Right. And that will resonate with people cuz they're, hopefully, if you have product market fit, there are people who have this problem and talking about the problem in different ways, different lights, different angles, different pains will resonate with folks and they'll want to learn more naturally, just purely outta curiosity.

But let them take the lead. And I think that's the big part of it is, you know, when knowing when to ask. To move to the next step versus letting them ask to move to the next step. When they do, that's where you transition from connecting with someone to engaging with them. And the engaging part is all about, you know, the traditional pre-sales activities, doing demos, POCs answering questions, you know, building internal champions.

It's really all like that engagement between them. And then the last piece is around close. And the reason that close actually gets its own stage of the framework is because closing a deal is actually more complicated than you would think because a lot of people think it goes on autopilot, right? So you get to this point where it's like, all right, customer's gonna buy.

Built an order form. You put together a proposal, you sent it over, you haggle back and forth on a negotiation. Procurement beats the crap outta you, and you eventually, you know, come to this point where someone signs the deal and you, you've won the business. And there's a lot that can go wrong along the way when you're going through the procurement process.

But if you think about it, if you actually brought all the right data points and business cases to the table, To beat procurement to the punch, you actually have the ability to close much faster at a higher price point. And that's why close has its own face. And like the most realistic example I give is every time Apple releases a new phone, you know, it's not selling for less than a thousand dollars yet people are lining up down the block, right, waiting to get into the store to get a new.

Because they've built such a premium service and you, they just have like such a brand recognition. And that's the thing, like if you're really delivering value and you really have a premium service, and what I mean by service is like how you've built the relationship and how you've established connection with that person.

And built champions as an internal stakeholders, you shouldn't be fighting in negotiation war. You should be closing based on the premium value that you've delivered today.

[00:21:46] Matt Madden: Absolutely. So well said. And if we could just for a moment, for folks that are learning about the role, who maybe aren't familiar with, what is a pilot typically in the context of a solutions engineering role or who is a champion?

Would you mind just kind of giving your definition of, common pilot formats that you see within cybersecurity or just in general?

And then also, the importance of. Building that relationship with the champion. I mean, we talked about the importance there, but who is the champion and how that fits into what you just shared around relationship building.

[00:22:20] Damian Tommasino: Yeah, for sure. So I, I think when it comes to champions, um, perhaps like, let's zoom out a little bit, right? you typically have two different sales motions, whether you're selling downstream into more like the SMB or the mid-market, right? So it's a, it's a faster sales cycle. Less people are involved, less people required to sign off on buying a deal.

You still wanna build what we call champion. It's like someone think of it this way, it's like, what do people say about you when you're not in the. If it's good things that you're building a champion because they're remembering and it's resonating with them, they're saying bad things. Well, it's no longer a champion.

It's somebody who's gonna detract from the deal itself. Right? That's probably the best way to it when you're selling in mid-market. You probably have a single stakeholder, right? And that's the person you work with most. And they're also the decision maker. As you go upstream though, and start selling into the enterprise, whether it's small enterprise or you know, all the way up to Fortune 500, you're talking large, complex deals, multiple months if not years in, in the making.

And rarely does one person have like full sign off authority to make these types of purchases. Cause we're talking. Six to seven figure type deals the way you wanna enable yourself to do better, have a better chance of closing and, and really bring value to the table, is actually working with different people along the way.

And having them make the case to buy whatever it is you're selling, not just you saying, Hey, you know, sign my, my piece of paper. So in, in the example that I was giving about the whole, you know, close phase of the framework, it's like if you've actually built a relationship with somebody in the procurement department, right?

You may not be selling to procurement, but when it comes time to close the deal, if you've got that relationship, You kind of already know what they need to get their job done. So you've built a champion in them to help move the deal along faster than it normally would.

[00:24:21] Matt Madden: Absolutely. It's so key and something I continue to learn more and more every day, uh, working within presales is that importance of buyer enablement that you mentioned earlier and how that ties into what we're talking about on, on champion building and like you said, everybody. Can hop on Google and very quickly inform themselves and prefer to educate themselves.

There's a lot of good, you know, data to support that before they even get into that first conversation. And so that's being aware of the current state of how people, uh, buy. And, there are, some really good books that I've been digging into this year I'll link to. that speaks specifically to just the importance of buyer enablement and specifically within my own role, I've had the.

Good fortune of being able to test different platforms that help in that regard. Um, there's of course a lot of platforms that people are working in pre-sales may be familiar with that I'm referring to. I won't name any specifically, but I'll provide some links there today, because it's just really helpful to have something that can help the buyer.

Let's say do a self-service demo, on your website or that maybe the. Business development representatives, you know, the inside sales function within the software company could include a link to, and really help give the buyer something more than just a PDF or, you know, a case study and so on. That they probably would go and find that themselves if they wanted it.

But if you can give them an experience that really helps educate them, how could that accelerate the overall sales cycle if they've seen what they needed to see in terms of the value from just that little snippet there. So that's, that's something I'm actively kind of working on and testing right now in my current role.

But, um, it speaks to the buyer enablement side.

[00:26:02] Damian Tommasino: Yeah. And yeah, I think the term buyer enablement, you're kind of hitting the nail in the head. Like I'll, I'll ask a question back to you. So for any of the pre-sales roles that you've been in just, or sales in general, have you ever been through like a sales enablement program internally at an organization?

[00:26:18] Matt Madden: I, I have in terms of training, um, if that's which, like a kind of one to two day training and it's, and, and I, I might know where you're, where you're heading with that in terms of just the fade from the training, while even with the training being really good, um, you know, I, I felt like I, you know, you're fired up in there and you're learning it, and then it's, it can be hard to kind of really keep the application of what you were taught moving forward. So,

[00:26:44] Damian Tommasino: Not only that, but if you kind of stop and zoom out and think about what kind of training you get, most sales enablement is actually centered around the company you work for, right? The use cases, the customers, the product, the solution, the 1000 different features and functions that is offered as part of the product.

But if you think about it, none of which you learn in sales enablement. Is actually centered around the buyer. It's centered around the company you work for in the product. And that is the disconnect of sales enablement versus buyer enablement. So when you just said, you know, buyer enablement is really what.

I don't wanna call it like hip right now. Sounds ridiculous, but that that's really where everything is trending right now because so many buyers are in control of the deal of the sales motion right now. So it's like you can know everything there is to know about your solution and your product, but if you don't understand how the buyer thinks, you are just almost working against yourself from that sales motion perspective.

[00:27:50] Matt Madden: Absolutely. One thing I found so helpful, uh, on that journey I mentioned that I recently went on in testing various demo automation platforms that are available for pre-sales organizations. Was being in the shoes of the, the person really evaluating it as a buyer, even though, you know, I didn't have the ultimate decision making.

I was the one building the business case internally on my side. And that was really helpful perspective. I mean, because just. When let's say you are on the side of the house participating in the interview, you know, interviewing the candidate and the perspective that gives you, like the next time perhaps you're sitting down and, uh, trying to go through the interview process for a role that you want, that, that extra layer of just knowing what it's like to be in the shoes of the person on the other side of the table is so helpful.

So I would encourage everybody out there, If you have that opportunity, even if it's not within pre-sales, but to get involved in the interview process, at your current company if you haven't been already, or you know, just make it known that you're interested in that. I, I think that would be helpful.

Anything you would add to that, Damien, for those that are trying to break in,

[00:28:56] Damian Tommasino: Yeah, so I'll give you a real world example of, of something that I do. Is once you understand, let, let's say you find a company that you wanna go work for, or at least within an industry, right? Who they sell to is gonna be public knowledge, right? You can look it up, you can see who their customers are, what space they're in, the types of roles that they have.

So I'll give you an example from fruit,

[00:29:18] Matt Madden: Mm-hmm.

[00:29:19] Damian Tommasino: In working for fruit, we sell to security teams. And one of the things specifically application security, and it's about right two halves of the equation. It's either helping them understand where they have vulnerabilities or risk inside the application. And then the other half of it is understanding how the application is impacted by privacy concerns, right?

Like, are you sending data to Facebook or TikTok? You know, some of these other things that we've seen in the, the media really recently. Instead of just saying that, right. Those two things. Okay. I, I know who I should talk to and who I should understand, but the core of it is really who's building the actual application, because that's the person who's really not necessarily responsible for securing it, but they're the ones who are in it and day in and day out.

So when you think of it from like, all right, well the developers are the ones that actually, you know, work with the product team and build these applications. So instead of me just saying, Let's build a demo environment at Farru and you know, we can demo that to customers. I actually sat down and wrote our demo environment, like from scratch through different coding languages.

So that I could put myself in the shoes of the customer and really understand, well, you know, what do they go through when they build product specs and how do you bring that to life in an application? How do you publish that to an environment? And it's like, I knew what I was getting to. You know, my end state right is having a functioning application that works with my product that I can show a demo, but it's not just showing a demo.

It's showing a demo of what my buyers are going through every single day. And the more you can put yourself in the shoes of your buyer, so to speak, the easier it is to speak the language that they understand and connect with them.

[00:31:12] Matt Madden: I love that example, and I think it tees up something that really anyone could do at home right now if you're trying to break in and transition is, thankfully we live in a day and age where, A lot of software organizations you may want to go work for, have a self-registration process where you can sign up for a developer account perhaps and really get hands on and take it on.

If you think about it like a project that you would have in a portfolio almost, where you're putting yourself in the shoes of the customer, who's leveraging their platform, the thing that you would. Get well educated on, or, you know, hopefully should, should educate yourself on going into the interview process so you can really speak to the space and the value that, you know, they're bringing the pains that you know they're solving.

But you have that opportunity, I think, to go sign up for something like, you know, um, let's just say a API heavy company like I, I'll just say Twilio for example, and go in there and start digging in and understanding their ecosystem, different products they have and you know, not recommending that everybody necessarily go.

Put a bunch of money into account that you might have to spend, um, whatever you might sign up for. But if you have a, a little bit of education budget that you can kind of put to that to say, you know what, I'm gonna put 20 bucks here so I can cover the cost of whatever the service may be. It could be within aws, um, for example, and going through that.

So I think there's just a lot of opportunities where people can get creative there. And would love to know if you have any specific recommendations within cybersecurity, pre-sales projects like that people should consider.

[00:32:41] Damian Tommasino: Oh, I mean, you're, it's spot on cyber or not, there's just so many SaaS services out there right now that you can just sign up for. I think the, the best way to look at it though is as part of the interview process, you're always gonna want to try and work in like, here's what I think a 30, 60, 90 day plan looks like.

Right? And, and hence show how you could be successful in a role. It, it's a pretty common topic in interview. Instead of just saying, you know, you're gonna learn the product and be able to, jump on sales calls at the end of 30 days or 60 days, think about how even the product you are, you're talking about right for the company, you are potentially gonna go work for you, work that into the 30, 60, 90 day plan, not as the stellar, but as the actual user.

Right. So, uh, a good example would be, um, if we're familiar with Asana, the project management software,

[00:33:33] Matt Madden: Yep.

[00:33:34] Damian Tommasino: right? So let's say I want to go work for Asana in the interview, I wouldn't actually talk about like how I would sell Asana. I'd actually cut, pull up like on my screen and show them, Hey, I built my 30, 60, 90 day program in Asana and here's how I mapped my dependencies and put timelines and owners to it.

And the thing is, I'm not telling them how to sell it. Right? That's what I'm being evaluated on. I'm telling them how I would use it and showing them how I use it is a clear connection to, I thought of this from the, the lens of the. Or the buyer, right? Not necessarily knowing how to sell it, but it's like, you know what adoption and you know what good looks like and it just, it brings more credibility to you in the interview process.

[00:34:20] Matt Madden: Absolutely. That's a great idea. And there's just, I get fired up when I think about the different opportunities like that where you can. Dive in and think about, your transferrable skills as well, which you brought up earlier, and how you can plug that in creatively. and, and really just keep that top of mind because it, it does hold a lot of weight, especially when you're going into specific domains.

If we think about, your background, it could be, in a specific vertical where you've worked as, um, you know, a practitioner, non-technical role, but you have domain expertise there that is, Relevant to, I would bet there are software companies that are servicing that space that you could, you could go and find and find a pre-sales role within.

And it's gonna be very valuable there. there may very well be people that are on the pre-sales team that are great solutions consultants, engineers, but they didn't have that background and. While they can help you get up to speed, uh, you can certainly help them get up to speed on what's the current state, how do things really work in this space for people who might ultimately be buying our product.

[00:35:23] Damian Tommasino: Yep. Absolutely. And it's, it is very common. Both inside and outside cyber, you'll often find that a lot of people who are on like the board of advisors for a lot of companies are often heavy users of products in their very, very early days. And the reason they end up on the board of advisors is because they not only understand the market, but they understand how the product better fits inside the market.

[00:35:51] Matt Madden: Absolutely. That makes sense. Well, this has been a great conversation so far. I wanted to just ask you a couple questions before we wrap up. Um, specifically I wanted to unpack something we were talking about a little bit before we started recording, which is, mentioned on LinkedIn recently that there's something coming within cyber informants and I'd love for you to just take the opportunity to share, um, whatever you'd like for the audience today on that and just, you know, help, help them get up to speed cuz I'm really excited for it.

[00:36:23] Damian Tommasino: Yeah, absolutely. And I appreciate that. So we were definitely talking about, um, another piece of cyber formats that's come into life next week as a, as a launch date for us. And really the LinkedIn Post started off with, you know, a very simple statement, right? You can't go to school for presales, can't go to school for sales at all, really.

Right? There's different facets of it. You can learn. You know, almost everybody who's in sales knows that you learn most of what you need on the job, and especially for pre-sales, where you kinda, again, have your hands in so many different areas of the business, it's very hard to have like a single guide or a single resource that can help you along the way, and you kind of just learn as you go on the top.

So this is one of the areas that I'm trying to. Really make an impact in, and as part of what we're calling campus, which is gonna go live next week, it's really kind of like a, a digital or online school, if you will, but, uh, very self-served, focused, right? So you can sign in. There's a whole bunch of courses that are all focused on helping pre-sales.

And you can either jump around, look at any topics you want, you know, consume bits and pieces as you need, or if you're new in pre-sales role. We actually have learning paths laid out where like, this is the suggested order in which you consume this content so that it makes sense. Like for example, the first semester is all about ramping up into a job.

And then from there, once you've got some experience and you've ramped up, then it's about building experience, mastering your craft, and then potentially going into leading teams or, you know, a management role. Um, not that that's the only role there, but the idea is we just wanted to pull together this singular.

Hub, if you will, that has all of this content where people can have resources. Um, we've got a lot of templates and tools. Uh, been doing this a very long time, so trying to help people not reinvent the wheel, uh, by putting some of this content out there. So yeah, it's, uh, something we're going live with next week.

I'm super excited about it. There's been a lot of positive responses. Got a lot of dms, uh, on LinkedIn about it. So, uh, more to share next week when we go.

[00:38:33] Matt Madden: That's amazing. Uh, I can't wait, and I do know. Correct me if I'm wrong, but people can go check out and get a quick preview of what's to come on@campus.cyberinformants.com. there's links from within the site. We can go and start checking out some of the things that you spoke to, and I think it's just such a great way to lay it out when you think about having a path that.

Breaks it down into a more realistic vision of here's where I want to go and here's what I need to learn in a, in an order that you're curating for them, I think is excellent. And I'm just so excited to hear about what you're working on there.

So I think it's gonna be just a great resource and I'll definitely link to that, uh, in the show notes once I publish those.

[00:39:14] Damian Tommasino: I appreciate that. Yeah, I'm, I'm excited too. I, I think it's, uh, you know, again, you, the more people you can impact and, and touch their lives and, and help them move into something that's new and exciting. I think that's really why we wanted to do this is. I've just, I've been in either, you know, the first pre-sale resource into an organization or one among, hundreds, inside of our organization.

There's always a unique challenge or unique, just having community and resources to back on makes difference.

[00:39:47] Matt Madden: Absolutely. Well, I believe if I saw right, you have a community element. Um, within cyber informants, is that correct?

[00:39:55] Damian Tommasino: Yeah, we do. So, um, a little different from some of the others out there. Like I, I love pre-Sales Academy, pre-sales collective, what James, uh, is doing over there. Great, great community. And I'm a part of that too. Um, I did start one up more specifically for cybersecurity pre-sales, right? It's, again, it's very different space, very, uh, specific needs within cyber and it's a, a chance for us to kinda.

You know, talk about vendors and challenges and, and different things that we work through on a day-to-day basis specific to cybersecurity. So yeah, communities there, um, you know, for those that are in cybersecurity already, we'd love to have you in there. But we are very strict about, you know, only allowing folks in who are either in cybersecurity, presales, or like breaking into their first cybersecurity pre-sales role to, to keep the quality high.

[00:40:44] Matt Madden: Awesome. That makes sense and that's why I wanted to clarify, so I'm really glad you said that. For folks that are specifically wanting to break into cybersecurity, presales, it sounds like it could. A good resource, so. Awesome, Damian. Well, I have lots more questions. I feel like I could ask you your wealth of knowledge here, but I want to be respectful of your time, so I'll just ask you one more, uh, is there anything I didn't ask you that you think would be good for people to know or you wanna share before we, we stop recording?

[00:41:12] Damian Tommasino: Yeah. So one thing that I did wanna mention too, um, just in, in the spirit of, you know, the path into pre-sales right? Is a, is a big focus for this conversation. I think one thing, and in the, the guide that I wrote around the, the ultimate compensation, right? For pre-sales, one of the things that I talk about is when you're trying to break.

Always know what you're optimizing for. Right. And what I mean by that is if you're trying to break in, are you trying to optimize for salary? Are you trying to optimize for title? Are you trying to optimize for landing your first role? Cause you're trying to transition out, everyone will have something different, right?

And it's, it's personal to them and something that you really need to be aware of. And you need to stay true to that whenever you're trying to break in, because if you keep focused on that, you'll find a role that's a really good fit for you, and you'll know that it's a good fit for you because it's what you're trying to achieve.

And like as an example, when I broke into pre-sales, right? I was optimizing for. Money because I was really young. I was trying to, you know, do do more with my salary and the role itself. So for me, it's like I was willing to take a lower salary, although still higher than what I made, um, because I wanted to break into that type of role.

Now, 13 years later, I'm no longer optimizing for, you know, a title or seniority. I'm optimizing to maximize equity in companies that I go work for. Right? So it's, it's a good example of like, I, as time goes on, you'll always change in what you're optimizing for as you take each new role. But it, it always is going to change.

But when you're first starting to break into presales, know what's most important to. And always optimize for that.

[00:43:06] Matt Madden: Uh, I love that ending advice And if you need some guidance questions, recommendations on optimizing for where you're at in your journey, reach out to Damien. Reach out to me. If I don't know, I'll reach out to folks in my network, see if I can help. and. I ventured about that.

Damien would, love to hear from you as well

[00:43:26] Damian Tommasino: Absolutely.

[00:43:27] Matt Madden: and the cyber informants and their community as well. So, yeah Damien, this has been amazing. So just wanna thank you again for coming on the show and, look forward to following up and catching up again soon.

[00:43:39] Damian Tommasino: Thanks.


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