MEL #023 | From Paper Routes to Cloud Transformation through Grit and Growth with Giacomo Mascillaro

MASCILLARO (00:00)

Start by leading yourself. Before you can lead others, lead your time, your energy, your mindset. Actively work on building resilience by stepping out into the uncomfortable.

ADAMS (00:37)

In this episode, I speak with Giacomo Mascillaro, Vice President at Konversant, a technology-based professional services firm, where he advises organizations on leveraging AI to modernize operations, strengthen cybersecurity, and fuel business growth. Giacomo’s path started with a mechanical engineering degree, but evolved into IT consulting, cloud strategy, and cybersecurity leadership. He built his career on curiosity, adaptability, and a lifelong commitment to learning.

In our leadership segment, Giacomo talks about how six weeks into a new role, he was thrust into crisis leadership when a cybersecurity breach hit just before Christmas. Despite illness and limited resources, he led a rapid response and company-wide transformation through calm, strategic communication and adaptable leadership. Giacomo’s advice to aspiring engineering leaders, lead yourself before you lead others. Build habits, sharpen communication, stay curious, and prepare for change through reflection and resilience.

Giacomo stresses that great engineers build things. Great leaders build systems, people, and culture. Without further delay, here is my conversation with Giacomo Mascillaro.

ADAMS (01:42)

Hi, Giacomo. Welcome to Mastering Engineering Leadership.

MASCILLARO (01:45)

Hi Angelique, great to be here. Thank you for asking me to join your podcast.

ADAMS (01:50)

Thank you for being here. I’m excited to have you. Can you start by telling us how you got into engineering as a career path?

MASCILLARO (01:55)

Okay, sure. For me, engineering wasn’t just a career path. It was a natural evolution of who I had always been. I came to this country at the age of two. As a first generation immigrant, I was shaped early by hard work. I watched my parents work tirelessly at multiple jobs every day to provide a better future for us. At eight years old,

I happily got my first job delivering the New York Daily News. It might sound small, but it taught me powerful lessons. Show up consistently at 6.30 a.m., even on those days when it’s five degrees outside and windy. Do great work and people will trust you. I grew my little 18 customer base to more than 100 by just being reliable and going the extra mile.

That mindset stuck with me and I never stopped working. One of my proudest moments was being able to fund my entire family’s trip to return to Italy by the time that I was 11 years old. wow. I found myself naturally capable in math and science. It just made sense to me. I simply paid attention in class and did my homework. Nothing else as I was busily working on most days after school. With that level of effort, I graduated number seven out of nearly 500 in my class. It was my high school guidance counselor who pointed out the obvious, you should look into engineering. I didn’t know much about engineering, but mechanical engineering felt like something I could wrap my head around. I applied to three schools in the New York City vicinity and was offered full scholarships by all of them. I picked the one that gave me the most flexibility, just in case I wanted to pivot to something else. That decision led me to NYU’s engineering program, where I learned how to study and develop a discipline for solving problems methodically, thinking like an engineer. After college, I actually struggled a bit to land my first job. There was a recession at the time.

And although I had no problem getting interviews, it was much harder to land the role that I wanted. Wake up call for me. Not too many mechanical engineers worked in New York City at that time. ⁓ I finally accepted a role at General Dynamics in Southeastern Connecticut to work with nuclear submarines. I was building 3D computer models of engine room and nuclear reactor components to perform structural analysis using finite element analysis. After starting at General Dynamics, one problem kept bothering me. Why did it take so many interviews to land my role? Communication skills emerged as my answer. So I got to work. I took public speaking courses at the local community college and I joined Toastmasters. When I realized that growing my career, was not going to be happening at a pace that I could tolerate, I put my communication skills to the test. One of my visits back to Brooklyn, New York, I bumped into a college classmate at a local pizzeria. I shared with him that I was looking for a new job, and he introduced me to a CEO. This time, my communication skills were much better, and I got an offer on the spot.

This started my career in IT. I had no background in IT, but applied my engineering mindset and relentless grit to the role. I was immediately billing full-time for my consulting firm. In eight months, I was a certified systems engineer, and in less than a year, I had doubled my income. I was hooked and committed to becoming a lifelong learner across a broad spectrum of topics. I have never stopped reading the equivalent of at least a book per week. Within a few years, I set out to be an independent contractor before it was normal to do so. Over the next 15 years, I delivered large technology infrastructure projects for big brand names that you’ve probably heard of like Pfizer, Goldman Sachs, Credit Suisse, NBC, Fox, and the United Nations.

Eventually, one of my former clients recruited me into a leadership role at Fox. It was there, right after the Sony hack, that I dove headfirst into cybersecurity. After remediating 203 security audit points over two years, the security posture of the company was completely transformed. And that experience taught me how critical cybersecurity is to the future of every business.

While at Fox, I began my executive MBA at MIT. Juggling that work and family was no joke. Commuting bi-weekly from New Jersey to Cambridge and squeezing in 20 to 30 hours a week of coursework on top of a demanding 50-hour work week and leading a growing family. I not only survived, but I thrived. I was surrounded by amazing peers like you.

And was drinking from a fire hose and loving it. That experience taught me to think bigger and measure success by the impact that I create. Since then, I’ve led cloud and cybersecurity strategy at a top real estate firm, helped them to recover from a data breach, migrated legacy infrastructure to the cloud, and implemented systems that drove record performance.

I’ve earned multiple cybersecurity certifications and now sit on the board of the Society for Information Managers in New Jersey, leading both their communications and a passion project of mine helping members in transition maintain their identity and momentum after layoffs. I’m still that same hardworking and curious kid. Engineering was just my launchpad.

It gave me the mindset and discipline to grow into a leader, a builder, and a problem solver. To the students listening, and this is dear to me since I have two kids, 23 and 21, your degree is important, but your mindset, your drive, and your ability to learn and adapt will be what define you. That’s how you build a career that matters.

ADAMS (07:56)

Yeah, that’s great, Giacomo. Thank you for sharing your career trajectory with us. I think a couple of things came out to me that I want to double click on with you. You talked about going into engineering, mechanical, then pivoting into IT, and then pivoting again into cybersecurity, who people like me, I’m not in that space, but I know enough to know they’re not the same thing. my point being is, can you talk a little bit about your approach to sort of deciding to pivot, that’s part A, and then maybe part B is then learning about this new field that you have chosen to go into. Can you talk a little bit about your approach to both deciding and then learning because you had great success in all these pivots that you’ve had?

MASCILLARO (08:42)

Well, sure. One thing that fuels the ability to pivot like that is that insatiable learning drive. Since I’m reading the equivalent of a book a week, I’ve learned quite a bit about cybersecurity and other fields long before I needed it. And I’m constantly looking at the environment and what and reflecting upon the moves that I’ve made. So it’s important to do that. It’s important to check in and measure where you’ve been, where you’re going, and what the market looks like as well. There was a point in my career where I was consulting for 15 plus years, and my clients happened to be big big companies that had their own email infrastructure and compliance, I had to comply with SEC rules, SOX rules and all that kind of stuff. So I was helping them with those systems, but I saw that more and more companies were starting to evolve and go to the cloud. So instead of staying with that business, said, let me pivot here again.

Because I don’t want to be in a market where there are lots of resources and fewer jobs. So yeah, I’m constantly doing that, constantly looking at what’s next.

ADAMS (10:05)

Okay, that’s great. And then you also mentioned, you learned kind of early on that you had somehow self-identified that you needed to improve your communication skills. And so you went about Toastmasters, which by the way, I highly recommend myself, I’m a Toastmasters. I guess graduate’s not the right word, but I was in Toastmasters early in my career too and found it to be pivotal. I’m curious how you made that self-assessment that you needed to improve your communication skills.

What kind of inputs did you use to kind of say, you know what, I’m actually gonna proactively go after improving this. I think it’ll make a difference for myself. Yeah.

MASCILLARO (10:39)

Again, it was reflection. I started my career at General Dynamics. It was fine. was perfectly happy to be in a cubicle working, and nobody would bother me. And that was my job. But I wanted to grow. And I couldn’t stomach the fact that it took me 36 interviews to land my first job. I would get first and second interviews, no problem, because my resume was good, my career development office was solid, but something was missing. So I had to process that I had some really tough public speaking experiences in high school that actually traumatized me.

And I wanted to relearn the whole process. So taking a public speaking class at a community college actually made that wound come back to life because I actually froze in front of an entire group out there, my entire class. And I knew this was something I needed to develop. So I took to it with passion and every single week was going to, I was going to Toastmasters and working on it and improving and improving until I felt a whole lot more comfortable. What made the huge difference to me was when I realized that when we’re having communication, it’s not about me. It’s about my audience. It’s about making sure that I care about my audience and getting a message to them. When I saw that, it totally changed my ability to communicate. I still not completely over it. In fact, when I was at MIT, I knew this was a problem area. So I volunteered as often as I possibly could to speak on behalf of every team that I was a member of. know, as long as I obviously tried to be fair so that anybody could speak. if we were on the fence, I would jump in and volunteer, even though it still scared me.

ADAMS (12:48)

Yeah, think that’s really important. I think so many people will avoid, right? They’ll try to avoid these uncomfortable situations and try to, know, public speaking is a big thing for a lot of people, right? I think that’s the number one phobia. So a lot of people will try to avoid that. And I, like yourself and other leaders that I’ve had the privilege of interviewing, often will hear them say, I proactively put myself in these uncomfortable situations. And in many cases, that is the way through, is through the uncomfortableness. And so I appreciate you sharing that. The other thing you mentioned that I wanted to touch base on is, you talked about the importance of mindset in really having a meaningful career. And I’m curious your approach to mindset. Is it something that you proactively…

work on, work on strengthening. You I know you do a lot of reading. Are you reading books about mindset as well? Or is this something that is sort of naturally a part of who you are maybe because of how you grew up? I’m just curious your approach to strengthening your own mindset.

MASCILLARO (13:54)

None of this comes naturally. Okay. This is all learned behavior. And I read across a broad spectrum. So that includes books on personal development and mindset. Okay. I don’t leave it up to chance. I have routines that I work on to improve like, you know, our brains are designed 

to actually keep us safe. And I work actively to get out of my comfort zone and to actually be grateful for what I do have, which is not innate. It’s your mind left to its own will always look for problems. Where’s there a problem? Here is a problem here. There’s another problem there. So you have to instill that you have to build routines, morning routines, evening routines that and just check-ins regularly, where has my mindset been? I can’t emphasize enough the importance of the connection between physical and mental and emotional. If you take care of the physical health, you actually help your emotional responses too. And I will say, and it’s going to come a little bit in the next second question or two, but life is not all fun and games. And there are plenty of challenges coming your way. And one of the best things that you can do is take control of your mind and work on strengthening yourself in times when you don’t have to. 

Why?

Because there are going to be times when you’re put into positions that you need to overcome. And that training will be very valuable if you’ve already gotten yourself into uncomfortable positions on your own volition.

ADAMS (15:51)

All right, Giacomo, can you give us an example of when you had to use leadership skills in your work?

MASCILLARO (15:56)

Sure, absolutely. One of the most defining leadership moments for me happened at Varis Residential. That’s a real estate investment trust that I worked at recently, where I was brought in to lead their cloud technology transformation. I was six weeks into my role and deep into a major cloud migration initiative, modernizing legacy infrastructure when everything changed. It was 4 p.m., two days before Christmas.

I was at home, sick with COVID, that I probably got at our company holiday party the week before, and I had already been clocking more than 10 hours daily of work in my state of uninterrupted isolation. When the call came in, I believe we’ve been fished, said my general counsel. I gathered all the details that I could and proceeded to work through the night. At 7 a.m.

I had the entire leadership team of the company on a call and I took them through a journey of my preliminary forensic investigation. This fishing expedition had begun months before I joined the company and I could prove it. In an instant, my priorities had to shift. The cloud migration, while still important, had to take a backseat. We needed to respond quickly, strategically and transparently.

And this wasn’t just a technology issue. It was a leadership moment. The first thing I did was rally the executive team, our board, the legal team, and our insurance carrier. I laid out the situation clearly, what we knew, what we didn’t, and what our immediate next steps needed to be. I didn’t sugarcoat anything, but I also made sure we didn’t panic. Calm is contagious.

I brought in external counsel that was intimately familiar with cybersecurity incidents and selected a forensic team to help lead the formal investigation. I led the response from my organization’s perspectives. I just wish there had been a mention during my interviews just a few weeks earlier that I was the acting CISO, the Chief Information Security Officer, no matter. From that day forward,

I took full responsibility for the incident response, communicating as transparently as possible with the board and with each of our stakeholders. I launched a comprehensive security transformation, multi-factor authentication, security awareness program, decommissioning of compromised systems, single sign-on, a security audit, et cetera, et cetera. In a matter of months, we implemented new controls, addressed audit points, strengthened our cloud architecture and built a cybersecurity posture that our auditors would later describe as a model for our industry. It was a textbook case of adaptive leadership. I had to pivot quickly, inspire confidence during uncertainty, and keep the entire organization aligned while shifting from offense to defense. That moment taught me that leadership isn’t about sticking to your original plan. It’s about knowing when to change the plan and getting everyone aligned around that new direction with urgency and purpose.

ADAMS (19:08)

All right, that is an excellent example and so much I want to dive into. Maybe just picking up on the last thing we talked about in the previous segment about mindset. So here’s a perfect example of what you’re talking about, You were thrust into a situation that probably challenged your mindset. So I could imagine, and you alluded to it, but I could imagine one, there’s frustration on your part because you’re like, I didn’t sign up for this, maybe. But also, there is true concern and panic around, know, with the people around you and these are really important and potentially devastating situations that can happen in an organization. So maybe can you start just by talking about how you manage your own mindset, like when you got the call and had to quickly figure out what you were gonna do. Like what was kind of going through your mind and how were you thinking, okay, I’ve got to be cool, calm and collected, because I might be the only one in this organization right now who is.

MASCILLARO (20:02)

Yes. I realized that there was no cybersecurity department. There was no one that could be responsible in this situation. And fortunately, I had some cybersecurity experience from my time at Fox. basically, knew that I was it. I’m comfortable taking leadership when that’s the situation. And I knew that the biggest thing I could do at that moment in time was to have been still calm, to do everything that was in my power to control, yet not panic about what I couldn’t control. I brought in people that had that kind of experience from a legal perspective, from a forensic perspective. But I tried diligently to actually keep calm and keep everyone calm. It comes natural to me to stay calm. That’s something that is part of who I am. And as an engineer, you tend to be more logical. And that was… one of the times that actually my engineering discipline came out.

ADAMS (21:13)

Yeah, well, that’s great. The other thing that I wanted to ask you about is communication. So when there’s a crisis situation, lots of people are asking all different questions. I could imagine that you had different people coming at you, all different frequencies, different, so there’s just a lot. But as you said, of managing the situation and keeping people calm is being very intentional about how you’re communicating, what you’re saying, how frequently you’re talking, those sorts of things. So can you just talk about your communication strategy during this crisis?

MASCILLARO (21:45)

Sure. The immediate instinct was to take control of the communication component. as much as I may have been tired and sick and wanting to go to bed, I stayed up all night the night that the incident was brought out.

Did my own forensic investigation, learned everything I could, detailed it all into a very detailed PowerPoint presentation, got my CEO, COO, chief marketing officer, chief public relations, legal team, everyone on a single call, and then proceeded to, at 7 a.m., proceeded to walk them through. Okay, this is what happened. This is…

how it started. This is what they did next. They knocked at the door, tried to get in, failed. Tried again here, failed. Tried again here, succeeded. Okay, this is what I was able to progressively show to all the leaders and then basically worked with the head of public relations to put together a a strategy to communicate. immediately afterwards, within like a week of that, I also presented similar message to the entire board of directors so that they could understand and ask me whatever questions that they needed. And then I proactively on a quarterly basis was briefing the board and the audit committee on where we stand, how we’re progressing.

Where our cybersecurity program is. And I would proactively also send messages to the entire community of our organization about the incident, cybersecurity changes that are coming up, how that will affect them, because we could not stay status quo. I had to make changes, and not everyone’s going to like the fact that their username’s not on their computer when they go to log in. We need to be better. Maybe not everyone’s going to be OK that every time they try to log in, they’re going to need their cell phone to be able to multi-factor authenticate. So I got in front of that and got support from all the organization.

ADAMS (24:01)

Yeah, that’s great. And I appreciate you sharing. you share really a very effective managing up strategy, Getting all the key stakeholders early on, explaining to them what happened, and then working with the PR firm because maybe you had your own internal PR folks because you probably had some external communications that you needed to make that were effective. then communicating to the board on a regular cadence and getting their buy-in on the changes that you need to make.

Can you also talk a little bit about the downward communication meaning and you started to allude to it, but I could imagine that the team, the people that are either in your organization or other organizations were also panicked when they heard this, is they knew this was bad, this probably shouldn’t have happened, there are some holes there, people can maybe feel like they might be seen as at fault. So you’ve got that component. And then of course you also have the component of just managing change, because absolutely I’m sure you implemented several things, if not many, many things to make sure that this kind of thing doesn’t recur. So can you talk a little bit about the downward communication that took place during this crisis?

MASCILLARO (25:07)

Yeah, and it was further complicated by the fact that I was at the company six weeks. The previous CIO was gone. The previous director of IT, gone. The several other members of the team were all gone. So I was the only technology leader in the organization and my team was panicked. They had been panicked about the whole cloud migration and now this incident comes up and they were panicked. So I lent them my call. Okay, that was something, we got into this, we’re a team, we are where we are. And we will journey to, we will take steps to tighten up security, to do the most important things first. Almost immediately we changed everyone’s passwords. Almost immediately we implemented multi-factor authentication, using the cell phone to authenticate whenever you’re logging in. And then shortly we took steps and I involved the team. I involved everyone in the whole process. Okay. This is what I’m thinking we should do next. I think this would have the greatest impact.

After multi-factor authentication, our ERP system was not protected. Let’s protect that under multi-factor authentication as well. So how do we do that? Well, okay, well, let’s do single sign-on. Single sign-on now, it’s simpler for our users because now they don’t have to remember seven passwords. They only have to remember one. So I sold it to the organization as, yeah, I’m simplifying your log and you only have to you have to use your phone now, but you only have to remember one password. And so I took them on a journey and said, you know, we’re all in this together. If you understand, if you see an opportunity, if you have ideas for improving our security, by all means, let’s discuss it. I don’t try to be authoritative downwards. I want involvement. I want to use the brains of of my teams. So that’s how I did it.

ADAMS (27:18)

Giacomo, you’re an avid reader. Is there one book in particular that you’d recommend for our audience?

MASCILLARO (27:23)

Sure. I think one of the books that actually made an impact on me was the book Atomic Habits by James Clear. The premise of the book is to not try to go and make gargantuan changes in one shot, to actually try to seek out 1 % changes and just consistently do incremental little changes on different fronts that before you know it, they compound and you come out completely different. We underestimate what we can accomplish in a year, yet we actually overestimate what we can accomplish in one year. And we underestimate what a decade of doing something like that, what the long-term effect could be of these changes. Start small and just keep at it.

ADAMS (28:09)

Yeah, that’s a great book.

All right, Giacomo, as we wrap up, what advice would you give to engineers who want to pursue leadership roles?

MASCILLARO (28:16)

Well, I want you to start by leading yourself. Before you can lead others, lead your time, your energy, your mindset. Actively work on building resilience by stepping out into the uncomfortable. Life has a way of throwing challenges your way. The best way to prepare is to throw yourself your own challenges that grow you each day.

Do more than what’s expected when you actually work or in life and develop a reputation for delivering excellence, even when no one’s watching. Leadership begins with consistency and character. Second, I want you to invest in your communication skills. Meaningful work requires interaction with others. You can be the smartest person in the room, but if you can’t communicate clearly and build trust your impact will be limited. Communication isn’t about you. It’s about reaching your audience, learning to listen well, translate complexity into simple steps that can be executed upon, and speak the language of your customers. Third, stay relentlessly curious, but pair it with reflection. Don’t just consume knowledge. Pause and ask yourself,

What does this mean for me, for my team, for the future I want to create? That’s how you turn learning into leadership. Fourth,

Build resilience and be ready to pivot. The future will unfold faster than the past. Disruption, especially from AI and factors beyond our knowledge today, won’t just affect your job. They’ll redefine your industry. Don’t fear change. Embrace it. Learn how to harness its power to solve real problems and create meaningful value.

The engineers who thrive will be those who adapt early, think strategically and move with purpose. And finally, remember great engineers build things, great leaders build people, systems and culture. So if you want to lead, start now, show up fully, stay humble, stay hungry, and most of all, lead with impact.

ADAMS (30:23)

Thank you so much, Giacomo, for your insights.

MASCILLARO (30:25)

This was fun.