Building a Successful Cybersecurity Company | Joe Aurilia, SVP of Operations Cyware (Podcast 356)

Firing the bottom performers and firing the, you know, cultural misfits, etc. Covering the cultural cancers in your organization. Jim Collins talks about getting the right people on the bus, the wrong people off the bus. What do you think point? I've never even asked this question before, but what do you think shows us where a functional head like the leader of a business area is the wrong person? What are the things that we should be on on the lookout for to know whether it's the head of a business area is causing the problems? And it's not necessarily the 5 or 50 or 500 people below them that we have to get rid of, but it's the leader. We had a really great episode in discussion just now with Joe Orillo who is the SVP Ops for Cyware. He joined the company about five years ago and was the first employee in North America. They've now got about 250 employees spread over seven countries. He reports into the CEO and he talks about what the different transition points have been like for the company as they've gone from raising a seed round when he joined to now a series C, they raised just over $70 million. Talks about some of the growth challenges. Talks about how to build collaboration and consensus and great culture when you're working with people and teams in all these different countries. Talks a lot about his ideas around hiring and interviewing key talent and also how do you even fire or when to fire some of the core senior people on the team that might actually be causing problems that and how to be aware of those. Talks about breaking down some of the silos. Just some really, really great insights around building a scaled company like this, how to go through the different due diligence rounds. I think you'll love this episode. You also want to check it out on our Second in Command podcast YouTube channel. We'll see you on the inside. This is definitely an episode you're going to want to share as well. Joe, welcome to the Second in Command podcast.

Thank you very much for having me here, Cameron. I'm super happy to have the conversation.

Yeah, looking forward to chatting with you today. I would love to even start off with just kind of doing a deep dive on the company that you're running today. I think it kind of makes sense where the space that you're in to start there and then we'll kind of go backwards into your career as well. So why don't you tell us a little bit about the company that you're running, Cyware, how you got involved with the organization and really what Cyware does today.

Sounds terrific. So Cyware is a cybersecurity company. We are now recently series C funded. The team has done a phenomenal job to get there. We focus in the threat intelligence space, essentially cyberfusion, collective defense where a combination of what you consider, you know, your sort of IR merged together into a single pane of glass. And allowing very large organizations with internal security teams to reduce silos, eliminate risk and collaborate through a combination of human and machine intelligence. We're really trying to push the industry forward and be on that offensive from threats and try to protect more and spread the protection across the industries. For myself, I joined here back in 2019. They had just got their seed funding and were looking for the first US employee here. I had one owner here in the US and one owner in India. And I had a team of India knocking out the product and kind of building out those first versions. And the ask was obviously vague. I think most operations folks receive the vague ask. We'd like you to build something. We don't know exactly what it is, but something just, just go out and build something. I know I need something. I know I need help to sort of to your book. You know every, every operations person is a bit different. They're kind of trying to fill in that missing puzzle piece of the owner, how to provide that set in half. The ask was there. It was very interesting. They sound like they had a lot of pre work done that would have been beneficial to build upon. I said yes. Not knowing Covid was coming, that made things a little bit more challenging from the hiring perspective. But the goal was simple. The goal was please build the operational framework to be as strong as possible to allow us to scale. So go find the best tools, the best processes, the best people, put them together, marry them and make them work. And a hefty ask. But it was fun. You know, we started to interview like crazy at one point we had about 100 recs open which laughable at just how many folks you were trying to fill in. The various different disciplines partnered with many different organizations. The team worked incredibly hard internally. They actually were able to receive their A and their B funding about six months apart in the heat of COVID during lockdown. They still think it's phenomenal from a team point of view. And they've been growing and scaling since then from two countries to seven countries hired individuals in more ways than it was physically possible in the beginning. Beginning scale to over, you know, 250 individuals procure over 170 apps from a procurement Point of view, full security compliance, ISO, SOC2, FedRAMP ready, all the bells and whistles. So we've been touching and prodding and trying to mature things ever since and just trying to keep that vision of trying to create excellence wherever we can.

If I was to ask somebody to please give me like an overview of their company in two minutes, you just crushed it. This is like the format that I want every guest going forward to use. We've had about 330 guests on our Second Command podcast. I think that was literally the most succinct. But also there I kept writing down questions and you just kept giving me the answers to each of the questions. It was like perfectly done. One of the things that you mentioned, you know, being the first employee in the United States and then a big team in India begs the question, where is the company based? Where is the leadership team or the head office of the organization?

We have leadership in both countries, but primarily would be considered a US Company that has an Indian subsidiary. But we do have executive leadership on both sides, which actually helps, I think in terms of guiding and preparing the mission and ensuring that there is less dangling parts and some other relationships might sort of create an environmental situation.

And you said an Indian subsidiary or Canadian subsidiary?

Indian.

Indian. Okay, but was the team originally out of India that hired you in the United States or was the team a US Company, but you were the first employee post the founders.

Yeah. So the US Company, the owner here in the United States hired me. So I was the first U.S. employee. Post him in the U.S. got it.

Okay. So now operating in seven countries, I really want to talk to you about the whole team in India component, because years ago, lots of companies seemed to be outsourcing to India. It seemed to be really the first big place where people tended to mostly outsource to. And now it's become a lot in Eastern Europe, a lot in the Philippines. The trend in the last five years has almost been now down into Latin America as well. What is it that makes it work with the teams in India? How do you most successfully work with the people over there in the tech roles, in the support roles, and even in like the leadership roles? Because there's some brilliant individuals there are.

And obviously, you know, the amount of technical excellence and capabilities and just the sheer quantity of people who want to be in that field is just ungodly. Right. So it's a great resource to have. I think the difference between this and, let's say past lives I've had is that you have a leadership on both sides. So the communication gets sharp. You don't have to have this laborious, overburdensome emails back and forth and kind of random things. Kind of keep things in line. So when person A here talks to person B there, they understand the mission, the vision, the alignment. It's one team. It's not that there's this outsourced arm that just does tech stuff. It's that there's one team. They just happen to do most of the engineering. We might do some other stuff here. So it's really sort of just twisting the script. They're not treating it as, hey, there's this tech arm, whereas we're one team. We might have different timelines, we might have different operating hours, but we're still focused on running on the same particular mission. I think that's sort of the differentiating factor. I've seen this in the past. More of A There's these 500 folks. They're out there, they're doing stuff, but they're not part of the conversation. If you're not a part of the conversation, you kind of missing half the mojo.

Yeah. Okay, so you just touched on, I think, one of the most critical parts of the business. You didn't even use the term, but it's around culture. Right. When you really have that strong company culture, everything emerges from there. So what's the secret on the kind of. How do you get tactical about keeping it as one team? What are the specific things you do to make them feel both sides. That we're on the same team. How do you do that?

Yeah, I mean, for me, I mean, I think certainly being table stakes, being cognizant of time zones, cultural differences, ways of communication, certain norms, that's sort of just out the gate. You have to have that. The second is paralleling your communication efforts. So let's have those important team sharing meetings in the morning. Let's provide the tooling and process to facilitate communication in an asynchronous manner, depending on the type of teams. So affording the different teams, the advances that we have in technology and process to allow them to work as one team even when the time zones are disjointed. In addition, I like the. We use the open door policy. I think it's kind of like lossless lust from a naming point of view. But just allow people to talk to someone, right? If you talk to Nancy or Bob or Prakash or Sue, just slap them and have a conversation. Don't ask my permission, don't ask if it's okay. Just have the what is the bad thing that can happen? Two humans talking, you know, if anything you made a friend or you know what they do and don't do, right? So just go out, talk, hunt, search. Especially in a startup, you can't be handheld. You have to be able to find the resources you need, understand what they are and if they're missing, go create them yourself, put your name on it, say thank you, add to the pile.

I like that a lot. Okay, so on the connecting with people and I think this is not even so much us, India or US over seven countries, but virtually every company today has become a hybrid. Some people in office, some are remote. And then obviously, clearly with post Covid, it's just blown the doors off this concept. How do you build the relationships with people when we are so remote? Because you guys, you know, operating in seven countries, you have to do that and your mindset is to do that is slack enough. Do you fly people in to meet with each other? Do you get together on zoom and run fun events together? What are the things that you do there?

I think certainly it depends on the country. I think there's always room for improvement. So I'll say what I believe. I think there's always ways to still make it better. It also depends on the number of people. Only one person in the country. It's really hard to ensure that you have that alignment sometimes. In the US we're remote from about 30 something different states. So we do the whole zoom, the sessions, the games, all that kind of stuff. Very hard to fly people from seven countries or even from 30 states. And that would be a tremendous budget right there. But you try to have the events online, you try to have the communication in terms of, you know, newsletters that goes out, information about different teams, celebrating wins, unit with the small wins, you know, having that channel collaboration, you know, sharing the mission, ensuring that that communication kind of brings everyone, right? It's not like it's this country versus that country. It's we're all working together and then in certain instances bringing the different countries together for those joint meetings, whether it's a fireside chat or it's a holiday celebration trying to mix and match. But I'll be honest, I mean the way we communicate and the way we have meetings, we never really think about it in different countries. The biggest rub is probably just the times of where is this person with times of view when you get in the call, you're just solving the business problem, right? It doesn't matter where you are, you're all together to solve that particular problem. So the country part does, I think, fade away a little bit.

Yeah, I think I've been living globally now for the last 26 months. We've been in 41 countries in the last 26 months, largely in Asia as well in Europe. I think everyone outside of North America is very used to working in lots of time zones in America. They're starting to get used to it now. Right. Time Scroller is my like go to app. I just, I'm using it constantly to figure out, you know, what time is it really when I want to be talking to people. You spoke about the ways of communication and I think you're talking there about just the way that different cultures communicate and different countries communicate. Can you give us a couple of secrets? Just things that you learned over the years as to how to work with people. And what other countries do you work in with Cyber?

Yeah, I mean for us, we primarily in the United States and India. We also do have Canada, we have the Middle East, Dubai, we have Singapore, Australia, uk. So really to kind of get around from that, from the time zone point of view, my best practice, again, I can't say it's followed 100% of the time, but I like to ensure that meetings have a purpose. You know, why are we actually talking? And when you walk away, what are people going to actually do from that conversation? And I think that's key. In certain cultures you might just say X, Y and Z and it's done. Sometimes it might be a little confusion or it might be a yes. It doesn't mean a yes or no. That doesn't mean a no. So it's best to just be clear for everybody. We came in to answer these five things. We walked out. We've got these 10 things. These 10 things are assigned to these people. These are the dates. Let's go knock it down and get these things over with. I think that's General. Whether in one country or for 100 countries, people talk, we have meetings, we converse, we have conversations, but there's no point to it or there's no net result of it. How much do we just spend? I mean I've seen meetings of looking at people's average headcount fully in. I'm like a $20,000 meeting that accomplished nothing. Was it worth it? Can we translate? And actually saw in the news a few months ago, some company actually built their own little Google widget that they add onto the calendar and they back into that which the fully weighted cost of individual this meeting Will cost you X. Do you really want to have it? We should all have that. That is a phenomenal point to just kind of bring home the monetary portion of is this meeting worth it and do we actually accomplish something from it?

Yep. Years ago, I wrote a book called Meetings Suck. And it was a book that every employee at every company is supposed to read to teach them how to unsuck meetings and teaches you how to run meetings, but also how to show up and participate in meetings as an attendee. And it was about 20 years ago when I was the COO at 1-800-got junk. We had about 2,000 employees system wide at the time. We only had about 200 at our head office. And I had a team meeting like a town hall and I pulled all the employees together and I did it in the wrong way, but I kind of gave everybody showed them on a whiteboard how much our meetings were costing us right down to our daily huddle. We had a seven minute all company meeting and I just showed them the cost of that seven minutes. And it wasn't in a we're wasting time. It was, let's take this seven minutes seriously. Like, we're investing a lot of money. When you take that seven minutes over 220 operating days, times the number of people there, times the two minutes on each side to stop what you're doing and walk to the meeting and come back, there's a lot of time invested and I wish companies would kind of understand that more. Funny how you mentioned the communication. The first time I ever realized that countries and cultures communicate differently was in 1991 in India. And I asked this woman, I was standing on a street and I kind of pointed in a certain direction. I said, is this where, you know, XYZ is? And she just kind of nodded her head and she just didn't want to be seen as not knowing or as stupid. So she just nodded for me. And then an Indian later told me, no, you just ask the question, but you keep your hands in your pocket. Then you say, which way is it to the place? And if they don't answer, then then you know the answer. I was like, gosh, I've never seen that in Canada.

And there are certain cultures that you know, are just purposely naturally nicer. Right. They always want to have the positive reply. And some of the business, you need the yes or the no. Right. So kind of creates a challenge at some points.

So you just touched on something there that I want to ask about as well is I think one of the core roles of the COO or the second in command is to be able to say no to the CEO. It is to be able to say I disagree or we're making a mistake or I think you are doing something wrong and to somehow do it in a safe way. Like it's like the emperor's new suit, right? Everyone knows the king is naked, but it was only the three year old boy that said, but the king has no clothes. How do you artfully say no or tell the CEO they're making a mistake? Do you have a way that you do that?

You know, I've used this description before, but I kind of want to go with it like this. You know, we all probably do some scouts in our days, maybe even just some door knocking, right? Door knock is pretty rough. You get a lot of doors slammed on your face, your nose gets a little smaller. I think sometimes you have to go into the conversation pretending like you have the door knocker. Right. You might get the world's worst reply. But you know, you did the right thing. You had to say it. I think it's similar to that. You want to share, you want to be respectful, you want to include, you know, what the other party may or may not be thinking and how they think. But sometimes you have to just say, this doesn't smell right for these reasons. More so I think as you mature in your role from our side, you have to also understand that you may go down a path that you don't agree with. You may take a path that you know is going to wind up in a giant fireball at the end. You aren't. You've documented and you've tried to elicit all the reasons, but at least you shared that ahead of time and you had the opportunity to have that conversation. You don't always get to win it, but just sharing it.

Yeah, you've got some really good insights around this stuff. I want to know what some insights you can share around some of your growth. Because, you know, coming from a company where you were very early, I mean, you said first employee in North America, so I'm guessing you were in the first dozen or 15 employees globally, or was it, you know, we did have.

A team about 50 or so in India making the product and that was the first year on the U.S. yeah.

Okay, so even from 50 to 250 employees globally now, what's been some of the change that you've seen over the years and how have you had to adapt as a leader?

Yes. I mean, in the beginning, you know, having had you Know, no one else here on the US side. You're just flipping your role hat every 10 minutes, right? You're going from it to finance to ops to sales. I mean, it's kind of, you know, all over the map. And you're constantly building. You're rolling out. There's this constant new things added over the time. You know, when you get past, let's say one and three, quarter, two and a quarter, give or take, you start to move into. Okay, let's slow down for a second. How do we ensure the process correct? Is a process kind of going throughout the right people? Is there a communication involved? Are all the right parties part of the table for the conversation? How is a collaboration going? And I think that you move into less the building so much and more as what I enjoy, I think is more of that glue. So I consider ourselves as super listeners, right? We're involved in all these conversations that may not even make sense for us. And we just kind of collect all this random information we had, like just massive, you know, database. And then we go into a conversation. We're pulling out all these tidbits that most people don't correlate together. So you realize Sam from finance said he wants to go golfing. Mike from sales said he wants to go to the movies. And you realize both of them actually mean they want to go have a burger, but they can't say it to each other. They have no way to communicate. And we step in and say, hey, guys. Hey, girls. This is what you meant. This is what you said. Did you mean this? And like, oh, yeah, we did. So you kind of that kind of integrator and communicator and kind of glue that brings people together. And then from the culture and collaboration part, not in a placated way, but I think ops folks need to be everyone's friend. You know, you need to be able to just have a nice conversation, be able to go along things in a smooth way. So that way, when something negative does happen, you have that mutual respect where you can say, this was absolutely wrong. Right? This was a problem. And you're not trying to be mean to the person, but you have the respect of each other to say, I got to call you out on this. You know, we have a situation here. Let's try to resolve this.

So you just touched on something. I covered this in my book. My newest book is called the Second in Command. And when I wrote the book, one of the sections that I honed in on was the core role, or a real core role. Of every second in command is to be the person who can integrate all the different functional areas in the silos, to break down the silos. Right as. And even if there's not turf wars, even if everybody's getting along, we often have these silos happening in the company where the head of finance is obsessed with finance, the head of marketing is obsessed with marketing, and the role of the second in command is for us to be obsessed with the company and to get all of those different functional heads talking and communicating and collaborating and kind of the forming, storming, norming, performing model. Do you have any secrets on getting these different functional areas to communicate better, to communicate proactively, to debate in a really good, healthy way for the good of the organization. Can you walk us through some things? There are some thoughts.

Yeah, I'll take it from two parts. I think one is from the operator's part and then two is from trying to do the people change. From the operator's part. I think that we have to consistently reframe our story in the way that would be best received by the listening party. So, you know, you all want to get to X, right? You all have the same mission, you all want to get to the same place. But how finance wants to get there might be different than marketing or sales or cs. You know, you have to kind of have a different path. So you're constantly sort of putting on your sales and marketing internally and reselling that vision, that process change, that modification, that collaboration, alteration. So each party understands it from their point of view and says yes. At the end of the day, we're all getting to the same point, but we got there for different reasons and that's okay. And that's part of just people. We all have different desires. As you said. Some people focus on one versus the other. How do you bring them all to the same place at the end? From getting people to collaborate more, there's always going to be those individuals who don't, those that just kind of want to rub the wrong way. But I think I was trying to be sort of the nice kid in the sandbox, sharing, maybe some hints. Hey, so and so from this team, you know that so and so from that team is thinking of it this way. So have you considered that maybe not. Okay, so maybe we can approach it this way. Okay, so we might be involved in all these backdoor conversations that never see the light of day. It might even look like we're not doing anything. We're just kind of like having these chats, kind of having these Situations to try to solve the mission. At the end of the day, like you said, we're not focused on one team. We're focused on the business. Is the business doing better? Are we moving things forward? We're not looking to be told that, hey, you did a great job. You moved it forward. We're looking to kind of move the pieces in the back, to allow that to occur in whatever machination that happens to be.

I like that a lot. So in the role that you're in and in operations in general, companies talk a lot about firing the bottom performers and firing cultural misfits, et cetera, hiring the cultural cancers in your organization. Jim Collins talks about getting the right people on the bus, the wrong people off the bus. What do you think shows us where a functional head, like the leader of a business area is the wrong person? What are the things that we should be on the lookout for to know whether it's the head of a business area is causing the problems? And it's not necessarily the 5 or 50 or 500 people below them that we have to get rid of, but it's the leader.

There's several things I think most important is to not make the judgment so quick. You have to take a moment and step back, maybe in private, maybe in silence, and just kind of consider the situation. Right. So I think, you know, in our. In the early days, maybe we're all kind of wanting to say, oh, all right, we have the answer. You know, kind of spit the answer out and kind of move forward. I think as you get older and you do this more, you sit back and say, I might just pass on this one. Right. I'm not going to say, come. Yeah, I'm going to go back, let the juices flow. Maybe I'm going to sleep on it. I'm going to come back and kind of weave those pieces together to kind of see what that larger story is, what is actually happening? What is the root cause? I think that's an important part. Is it the people, the technology, the process? Is it the individual? I think some signs, though, that the individual may not be correct. I mean, again, if you see the entire team having the same issues, from a performance point of view, from a conversational point of view, you constantly hear this name kind of being uttered. You know, you want to stop it before let's say the cancer spreads through the organization, in my opinion, one wrong person at the right point in the hierarchy could absolutely crush an organization of almost any size. Right. Because it propagates and it's almost Endless. And that is palpable. Right. Especially if you look at teams that, let's say revenue facing, they seal that information, they know the dirty laundry, they know how things are going. It's very easy to understand where those handoffs between different departments, between different heads have more friction and identifying sort of maybe what individual or process gap happens to be causing it.

Love that. All right, now, at the very beginning when you were telling me a little bit about Cyware and I want to ask this question and I'll come back into more around the day to day operations, but did I hear you write that something about your software or your product helps companies break down silos?

Yes. So from a communication point of view, and I'll kind of go a little more technical here, threat data comes in the form of feeds information out there. That is something a company should be paying attention from a threat point of view. That data can then be bidirectionally enhanced in the platform or they add other data to it to make it for a turn from data to intelligence. Imagine that was sent through email, right. What would your team, your security do with another thousand emails per day? It's just a thousand emails. They can't really sort it. So this is focused just on the threat aspect, allowing teams, networks, vendors, partners, all throughout the network of networks to collaborate and share this threat data to make that entire network stronger. So you're not just making your organization stronger, you're making the teams within your organization stronger. They're sharing that same information of bidirectionally enhancing it and then also being able to share that information within a network of networks. So it's both a, hey, my entity is getting better and then the opportunity for other entities or other sharing organizations to get better together. All in the premise of being more secure.

You've now done three rounds of funding since then to a series C if you can disclose that how much has the company raised and then what have been some of the changes and challenges that funding has raised? I mean there's obviously the good stuff. You got more cash, you can hire more people. But what are some of the challenges that come with going through those funding rounds?

Yes, I mean, haven't personally done the due diligence aspects here. We all know the amount of pain and fun those thousand questions can be. So we did three rounds after the seed, that combined with the seed and that is, you know, online public information. That would be a total of 73 million total. From a funding point of view, I think certain challenges always that expectation. Right. There's an Expectation of those who provided the funds, the expectation of the board, expectation of leaders, also the expectation of your employees. You know, are you managing the expectations properly across those spectrum of stakeholders where all their expectations may not always be congruent? And that comes down to the communication, the vision, the strategy, the sharing, and also the truthful execution. Right. You can have the best vision and strategy and presentation, but then if your day to day actions are divergent to what you just said in that pretty slide deck, it's meaningless. So you have to bring it all together. Because humans are smart, right? We're hiring very smart people. They're doing very technical, challenging positions. You have to be truthful in those conversations and be able to bring people in together to that shared understanding of why they're spending their time in this activity. They can spend the time in any activity, right? There's lots of things that people can do. Why do they want to do this thing?

Can you speak a little bit to the due diligence side? When the investors are asking for more and I mean, they just seem to keep asking, it's like, God, it's like this never ending, like where do you come up with all these questions of things that you need? Do you artfully push back or do we just surrender to it and keep getting more and more and more and giving more and more and more until they stop asking? Or do we bury them with information so they don't want any more from us?

I think that kind of goes back to sort of an operations team, sort of data collection mechanism. Right. So in this particular entity, besides other things, I also, all of contracts and all of legal, so very involved in all those particular parts of the business. So learning from the first one, at least here, you know, capturing that metadata is very key. So taking the time during each particular step of an agreement or a relationship to extract the things that might be needed later on to extract that from a contract point of view, from a relationship point of view, from a salesforce point of view, and having that data there and using that data not only just internally to flow throughout the systems, but allowing it to be reportable. So I can see measurable results between let's say A, B and C for how the data was collected. What was the actual pain for myself for my teams to be able to generate those replies? And as you get more mature and if you build on a framework where we're always audit ready, we're always able to have that data available, those cycles become less painful. I mean, granted, yes, there's a lot of questions there could be need to explain something. Six different ways to get to the same concept, that's part of the game. But if you can prepare your data, I think the data is really key. If you have to make the data up later by not make up, I mean if you have to go in and hunt for the data, right. And kind of produce it in a tabilized form is too late. Right. You have to have that ahead of time.

So if you're a small company, let's say that you're a 20 person company and you know that over the next three to five years you're going to start embarking on raising money or positioning the company to sell, etc. What are some of the systems you would put in place to make your life easier down the road?

It does make sense. I mean, you know, I certainly, I think my reply is going to be polarizing. Depend on the person, right? Some will say look, I don't need this right now. So that spend people are tooling is not needed. But then there's a future version of them that will say hey, you know, I really wished I knew that spend. I think it comes down to the relationship. Do they trust our advice? Do they trust our analysis and what will save them in the future and how that overall will be, you know, a lower cost for the company. I obviously strongly believe in tooling. We have a tremendous amount of tooling. There's a tremendous amount of tooling in my professional life. Stay away from loose files, Excel docs, you know, things that are not able to be tangibly stored, archived, reportable, you know, invest in a solid CRM, invest in a solid clm, invest in solid, you know, expense management and finance tools, those tools will naturally cost you more out of the gate. Right? You will spend more money. But if you count the amount of time you saved from the physical headcount having those conversations, the checks and balances, the back and forth, you saved multiples every single day over the course of the tooling. So I think just anywhere where you have a gap that the company would need to be concerned about, that's where to start. So customer data, CRM, financial data, expense management, get your, you know, your necessary system in place. All of those things help to, let's say chokehold the level of risk the company has by instantiating tooling that will maintain that data in an organized way and start to have those processes, you know, sort of tie in together to, to create that sort of puzzle pattern.

Yeah, two, two very like kind of obvious examples of this one would be, you know, if we had all of our processes documented in Google Docs or Google Sheets. That's one way. But if we also had processes in a software called Process street and they can just log in and see every single process in one platform. Oh, okay, we got it. And then secondly, I remember when I was running my first company Back in 1990, 1989, I had 12 employees. I was 20 years old. All of my accounting was just a bunch of receipts in, in envelopes. You know, I had receipts for, for like every, every category was a different envelope. And that was fine, that worked. My bookkeeper could work from that. All right, so I want to talk a little bit about the job wrecks you mentioned. At one point you had 100 different job recs out there.

Yeah.

What are some of your best recruiting, hiring and onboarding systems in those three areas? How do you get lots of applications for these job recs? How do you interview and select people? And then once you've got them, do you have any systems for onboarding?

Yes, I think I'll start with just saying it's hard. It's not an easy thing, you know, in any company it's hard. But you know, for startup you sort of need to strike that goal every single time. Right. The opportunity for error becomes much less because the impact is much greater. So it's much more challenging to kind of bring that person in. Tooling aside, I think you need to have some internal thought beforehand. Right. Take a moment. What do you need the person to do? What do you need to do over that? 30, 60, 90, who will they work with? Do they actually have a home here? Do they actually have a reason being not that you had a knee check idea, I need this particular role tomorrow, but do you really need this person to come in and do you have a place? Do they have a vision? Do they have a way to be productive here? Pass that bar first. I think it's also important that my personal favorite is I would give my team, now that we had a team in the early days, we didn't just simple audio recording. I'll talk for 10, 20 minutes about what I like and don't like about a particular role. What companies I think will be great, what companies I think would not be great, what background, what type of person, what type of attitude, what type of experience. And they can keep listening to that. So it's much better than some stacked email. A few hundred words and you're done. They now hear the person, the hiring manager, and physically saying what all the characteristics they desire. And now each recruiter can go in their head, listen to it at their own time, gel at whatever way works best for them. It doesn't really matter to me. And have a much better interpretation of what you want that person to do. I think that part of the communication is key. Tooling. Yes. You need an ats. I can't say I'm entirely sold on ATS making the decision making for you. We're not there yet. I think that it's still a human aspect involved, understanding if that person is a good fit, especially for a complicated role. But you want to be able to also ensure that keeping friends throughout the process. Right. Let people know if they're not accepted, if they're not moving forward. Let people know how the conversation is going because that will come back and bite you at the end. Right. Whether it's a negative review or potentially negative employee experience, from the minute you meet somebody, they could be a potential employee. Let's start that conversation cleanly. Let's start in a friendly fashion. Let's have good communication, let's have solid clarity, let's be clear what we want, what you want, what I want, what the company wants. It's a very people skill, heavy personalization type of activity that personally I've not seen any kind of significant automation yet. Right. You can, you can absolutely automate lots of things. But if you have to get those right people right now and you cannot make a mistake, it's still a very heavy effort from a manual point of view.

I like that a lot. You mentioned something and no one's ever said this on 330 episodes that I can recall. And I've been obsessed with this concept probably my whole life is do we even need to hire them? Like it blows me away that a company will spend a full two or three hours debating $100,000 marketing campaign and yet this mid level manager comes in and says, oh, we need to hire another person X and we go, okay, go do it. I mean that was a 12 second decision on a hundred thousand dollar expense for the next three or four years. You shouldn't be making decisions that quickly. And sadly most mid level managers solution to every problem is hire more people. And that's often never the solution. How do you artfully say no, we don't need to hire? Or how do you get the managers and leaders to know we don't need to even come in with a request to hire this person?

I think you have to ask questions. You know, we kind of become that sort of the counselor, right, you bring in the black couch, let's have a chat. What's bothering you? How can we get to a remedy here? This comes down to communication, you know, trying to understand. Okay, that's great. You need, let's say you need a solution architect. What are they going to do? Who are they going to work with? What kind of skills are they clients? Internal, external? Are they going to work on this current team? Who do they report to? Because it could be a heavy management structure if you got to keep adding people to the same person. Can they even be managed properly? Let it just be a black hole and sit in the corner, try to flesh out again operations folks. We try to be sort of think of this world of questions, all the things that can go wrong, all the different things that something is going to be touched by a particular action. Trying to just have a conversation around, let's say our own thoughts coming from the point of view of maybe we don't understand the situation properly. Maybe please educate us. Let's kind of understand the thought patterns in your head and then we can share the thought patterns in our head and maybe we would open up concepts that maybe they didn't think about. Oh, I didn't think about this part. Or maybe that's right, they wouldn't have anyone to report to. Or we don't even have the tooling to be operational. It would be the 3/4 till we even could have that person do the job we want. Those kind of things can nicely make the conversation be all good sometimes.

Super interesting. You've really got some solid skills. I mean it's obvious when we listen to you and you got some of the questions. We've started an organization about six years ago called the COO Alliance. We have a network of second in commands from 17 countries that are members and they're always working on growing their skills and their confidence. What have you done over the years to grow your skill sets as a leader and as a second in command?

I am a huge opponent. Thinking that you should constantly be learning stuff, right? You know, you have to not that whole like education, always be learning but just, just be curious. Your job's going to change, the world is going to change, things going to be different. I personally just read a lot of random stuff. I'll be honest, it's not any particular thing. I am part of way too many communities, way too many email lists. I try to keep them down to be as humanly possible. But if something strikes me, I see a white paper or a PDF in some Community that seems attractive. That's interesting. I will speed read it, I'll look at it. I'll find webinars and videos that are interesting and I can listen to it at 2x 2.5x, cut down the time, get the gist of the information, have random conversations with people, people who I don't even know if we really have anything in common. And you tend to just kind of pick up these things. So they use this tool in that way, they did this that way, they had this thing. And you come back with these thoughts and these patterns and you're trying to manipulate things together that you honestly would not have done if you just sat there doing a job. Right. Like yes, you did your job, that is today's job, but you may be entirely useless tomorrow. You won't be able to grow and to bring any innovation into the company if you're just doing this. So you did a great job on your current job. Pat yourself in the back is great, but can you innovate for what that job will be tomorrow, for the company needs you to do tomorrow? And for that I think you have to go out and hunt and get new information.

I love that you just touched on something that I think is a core behavioral trait that we need to hire more leaders who have this. And that's the ability to be curious and the desire to stay curious. Because they become self driven learners. They're not waiting for a quarterly personal development plan for somebody to teach them what they have to go learn. They're always learning. They're showing up learning. It's kind of like when you're green, you're growing, when you're ripe, you're rotting. They just, they're just hungry to keep just because it's kind of fun to learn. Right. Which is great.

Yes. And today, I mean, these days, I mean, let's be honest, there's practically probably nothing that you want to learn that isn't out there in some form for free. Even if it's not the best resource, you could probably find everything, whether it's an online learning, a community, a white paper, a PDF, a YouTube video. I mean, there's just so much information out there to say that I can't learn something or I don't have the resources. As long as you have an Internet connection, you can probably figure out a way to, to understand that information to a point to pass the full test.

Well, and that's why, why so many students these days are getting kind of disillusioned with university is it doesn't make a whole lot of financial sense if they understand basic math. The ROI of going to university for four years and coming up with all this debt when all the information is free online and they can condense the amount of time they're learning. It's going to be interesting to see what happens with post secondary education for people in the arts and business. I wanted to go back to the 21, 22 year old Joe and give yourself some advice. What advice would you give the younger you that you know to be true today, but you wish you'd know when you're 21 or 22?

Certainly. I think in an early version of me I was a computer science major, right? So I'm a hardcore tech from the start. So I was doing development, enterprise architecture, all kind of fun stuff. In that world, you don't talk with people, you talk with your teammates. You don't have Like a conversation like this would have never happened, right? A networking event would have never happened. And as you move past that into other forms of business, this becomes incredibly necessary for growth, both for the company and for yourself professionally. I think for a younger version I would have said to get out there more, have more conversations, meet more people, network more and kind of build that professional community around you. I think it's easier these days. There's a lot more professional community, a lot more knowledge around the concept. If I went back to an earlier day, I think that would have been one of the things that would have been important.

I love that. Joe Rollo, the SVP of Ops for Cyware. Thanks very much for sharing with us on the second Command podcast.

Thank you very much for having me here, Cameron. It was great.

Appreciate it.

Don't be so mean. There's a reason why I'm in the role that I do. I very organized and like things a certain way. As I've gotten older, I've realized that that stuff doesn't work so well in long term. It does a lot of damage and you have to do a lot of undoing to rebuild trust with people and get what you really want out of them.