1224: Building a Cybersecurity Leader for the AI Era | with Joe Iantosca, CFO, Cyera

0:00Support for CFO Thought Leader comes from OneStream, Trusted Data, Faster Decisions, and Salesforce. Explore new research on the future of finance and AI at Salesforce.com slash CFO Report. Hello, this is Sonowi Torero, CFO of Envoy, and you're listening to the CFO Thought Leader podcast. This is episode 1224. war.

0:29Joe Iantosca: What market do you operate in? Sire operates in like the global information security market. It's hundreds of billions growing over 10 % a year. And then it's, okay, what subsectors within that market do you have a unique right to win in? How big is that? What is your right to win? Who are your competitors in that market? What are the deals like in that market? Are they fast moving? What are the deal sizes? And I think this is the first place that finance has a seat at the table. Because it's how does that impact your growth goals? What new markets are you going to unlock? If you are a growth-oriented business, you have to keep thinking about what are the next products that are coming off of the conveyor belt and how does that serve your three, five, ten-year plan?

1:23Hi, it's Jack. On today's show, we speak with Joe Iantosca, CFO of SyAra.

1:34There's an interesting tension that comes with building a company in a market that's changing as quickly as the technology itself. You want people experimenting, trying new things, moving quickly. But at some point, those experiments become major investments. And someone has to ask whether the evidence supports the commitment. For CFOs, that's becoming an increasingly important judgment call. How much discipline is enough? And when does that discipline begin to slow the innovation you're trying to encourage? What's interesting about today's conversation is the idea that finance doesn't have to choose between the two.

2:18But knowing when to shift the gears may be the harder part. Our talk with CFO Joe Iantosca begins after this.

2:35What is a forward finance organization? Finance leaders are under pressure to move faster, adopt AI, and guide decisions across the business. But here's what most people miss. AI doesn't create value on its own. You need the right operating model behind it. That's what Ford Finance is. It's the blueprint for building trusted data with finance and IT actually aligned. And AI working right where decisions are made. OneStream brings this to life. As the AI operating system for modern finance, it's all in one platform. Your financial and operational data in one place with purpose-built AI embedded across planning, close reporting, and analysis.

3:29The result? Faster decisions, less busy work, stronger governance, and more value from AI. Explore the Forward Finance Blueprint at onestream.com. slash forward finance. And see how to turn AI ambition into real business value. Visit us at onestream.com slash forward finance. That's onestream.com slash forward finance.

4:06Hello, CFO Joe Ayantaska is with us. Joe began his career at Morgan Stanley before moving into finance at Palantir Technologies. At BetterCloud, his responsibilities expanded well beyond finance, eventually leading him to the COO role. Today, as CFO of Sierra, he brings that operating perspective to a fast-growing data security company where scaling the business and investing for growth and navigating an AI-driven market are all central priorities. Joe, welcome. Thanks for having me, Jack. It's great to be here. Joe, please take a look back for us. We always begin this way, but we always ask the guests to look back in time and try to identify some of the experiences they feel prepared them for a CFO role.

5:01What would come to mind for you?

5:06I think I still have so much left to be written, but if I reflect on, you know, to date,

5:16Joe Iantosca: growing up in New York, in the New York area, and going to school at St. John's, I always aspired to work at, you know, one of the big banks. And through college, I found my way into Morgan Stanley and then navigated the internship programs from the back office to the middle office to the front office. And when I think about pivotal moments in your life where you don't really know they're happening to you, I had a good friend who was a few years older than me that was a pretty early finance employee at Palantir. And he had told me, hey, we're going to hire our first out of college guy. I took a leap of faith and moved out to the Bay Area and got bit by the tech bug.

6:09Joe Iantosca: I think that early experience at Palantir where the company was a few 100 people growing quickly, tech was still cool and unique. You got to put your fingerprints on many different areas of the business really helped me understand not only just the spreadsheet of how a business operates, but how does the company organize itself? What matters? How do sales happen? What does the commercialization process look like? How do you take a company from a loss-making position to a position of great unit economics? And I think that foundational experience really helped me create perspective on not just what a CFO is, but how do you build a generational technology company?

6:58We always like to ask about the things, the decisions you might have wished you made differently or the career steps you would have taken in a different direction, perhaps. I don't know, but it's interesting. You did become a COO at BetterCloud and sort of jumped into operations instead of taking a more traditional finance route. How did that happen?

7:25Joe Iantosca: Well, I'm a big fan of things happen for a reason. If you put your head down, you work really hard. So in many ways, there's no changes that I would have made to decisions that I made. But at BetterCloud, I had amazing mentorship.

7:46Joe Iantosca: Early on there, the executive team, the founder were amazing mentors and I think gave me responsibility well beyond maybe what my resume deserved. And as a result, I would end up taking a finance slant and moving into many different areas of the business. Sales operations early on, customer success, how does the research and development team optimize hosting spend and bringing new products to market. And as a result, I ended up having a hodgepodge of different teams along the way. And as I got later into my journey there, I just had an honest conversation where I was like, hey, I feel like I'm ready for more.

8:39Joe Iantosca: I think I can add a lot more value than maybe my current job set allows for. and the CEO felt the same. And that was kind of where he formalized my expanded scope across post-sales, data, and other operations teams. When do you recall feeling like you had become a leader? Was that at BetterCloud, I would imagine? I mean, as you advanced into a COO role, certainly, but it happened earlier. Suddenly you looked around and there were people depending on you? Yeah, I would say that happened at BetterCloud. Were you prepared for it when it happened? I think that there's two things that come to mind when you ask this question.

9:27Joe Iantosca: The first is what's your leadership style? For me, I have a very simple framework, and it's company, team, self. So I think if you apply that framework anywhere there inside these companies. Whether you are a leader by title or chart or not, you will be perceived as a leader because it forces you to come to different business problems from a really first principles perspective of like, what is the thing that we can do here that will have the best outcome for the customer, for the company? And I think that through Osmosis, I picked that up at Palantir and then BetterCloud is where I really applied that.

10:14Joe Iantosca: And I think before even I was managing people there, I was perceived as a leader because it was a 100-person company where people were like, what's this young guy doing asking all these really interesting first principles questions? And then the second part of that is as they start to actually manage people, I would say I was very hands-on. How can I help? What are you working on? Here's where I think that you can do better. And I think those open and honest conversations have been really foundational to how my leadership style has developed. I'm extremely candid, but I'm also extremely empathetic.

10:57Joe Iantosca: And I think that's led to fairly strong followership. Let me ask if there's like a different approach to leadership. As you evolved as a leader, you had this experience in the customer facing realm. And then leading as a CFO, I wondered if that was different. If you look at it differently as a different leadership challenge. Yeah, I think every person in a way needs to be managed differently. And there's the obvious points of what the motivating factors are for the different groups across the organization, who's on variable compensation. But I think in general, when you apply the company, team, self-methodology, we're really looking for people who are mission-oriented and excited to take the hill every day.

11:55Joe Iantosca: And I think from that perspective, the leadership styles are actually quite similar. All right. Well, thank you. Some great insights there for us. We are going to ask you a few more career-related questions probably later, but right now we'd like to find out about Syaira. What does the company provide and who are its customers? Meanwhile, where's the opportunity here? Tell us about it. Yeah. Syaira is an AI security platform, and we are building the next generation cybersecurity company. We're focused on making sure that CISOs, Chief Information Security Officers can confidently say yes to the benefits of AI and really trust this agentic enterprise that we're finding ourselves in rapidly.

12:45Joe Iantosca: The origins of the business go back to data security. So we are the only company in the world that is able to provide visibility across the entire data estate from a security perspective. And we've used that data advantage to bring many new products to market over the last years. It's a five-year-old company. We bring products to market in both organic and inorganic ways. So we've done seven M &As to date. We're focused on the global 2000, so upmarket customers, and we operate across 15 different countries with 2000 employees. Now, Saira has attracted significant investment How has that capital shaped the company's growth priorities?

13:35Joe Iantosca: So I think that the thing about all the fundraising that you see is that it's really just recognition of the opportunity ahead. And the opportunity ahead for us is hundreds of billions of value realization across the cybersecurity landscape. and the funding in the simplest way is building and buying more products and market expansion. But when you think about it from a more tactical perspective, how that shows up is customer value. Like new products that allow CISOs to embrace AI, to enable their businesses for all these new challenges that they're facing and allowing their businesses to maintain a real competitive advantage.

14:29Help us understand how Syra makes money today. Is that more important story, customer acquisition expansion or how products are packaged or what part of that model matters most?

14:45Joe Iantosca: Yeah, new customer acquisition is the primary one. We're fortunate that we have super high NPS and wonderful retention. But we're still, as a five-year-old company, very focused on bringing new customers into the Saera ecosystem. You mentioned a number of acquisitions. Were they on your, and turn back the clock, you've been there a little over three years, I suppose. Were they on your watch, those acquisitions? Yeah, I think security is a bit unique, the security market. It's very fragmented. To pull up Gartner, IDC, what you see is a sea of acronyms. And there have been very few companies that have been able to truly consolidate across all of these acronyms.

15:45Joe Iantosca: And security teams, companies, are yearning for consolidation. CISOs work with over 200 vendors. and with AI, they have the potential for that to balloon and they would prefer to work with 20. And there's been very few companies that have been able to consolidate effectively. And Sierra's mission basically from the first dollar of revenue was to create a comprehensive security platform across many, many different verticals, all rooted in data. So while I can't say from day one all of these acquisitions were on the watch list, M &A has always been an important part of the puzzle given the dynamics of the security market.

16:38So we always like to talk about your lines of sight into the revenue in part. From customer commitments through deployment and billing, where does finance gain the clearest visibility into that future revenue? Sorry, how do you mean here? I'm just thinking that when you try to understand future revenue, what is it that you're looking at? Is it the customer commitments that have been made? Is it the deployment that's taking place and the billing? What are you looking at? Where does finance gain the visibility?

17:22Joe Iantosca: Well, I'd start with this a bit more meta and then get more specific. So the meta is, you know, what market do you operate in? Sire operates in like the global information security market. It's hundreds of billions of market, depending on who you ask, growing over 10 % a year. And then it's, okay, what subsectors within that market do you have a unique right to win in? How big is that? What is your right to win? Who are your competitors in that market? What are the deals like in that market? Are they fast moving? What are the deal sizes? And I think this is the first place that finance has a seat at the table because it's how does that impact your growth goals?

18:11Joe Iantosca: What new markets are you going to unlock? If you are a growth-oriented business, you have to keep thinking about what are the next products that are coming off of the conveyor belt and how does that serve your three, five, 10-year plan? So I think that's the first part of it. Then you get to customer acquisition. And for a company like Sayer, it's an enterprise sales motion. How does your sales process work? How many account executives do you have? What geographies are they in? What new geographies are you opening up? What new segments are you opening up? So really like the go-to-market part of the funnel.

18:50And then you win the customer.

18:55Joe Iantosca: And now you've got to get them happily deployed, get them to value, grow them. If you're a happy customer, it's a growing customer. Hopefully get them using more and more of these products that you're bringing to market. And I think this is another place that finances a seat in the table. And this whole go-to-market and customer lifecycle, you know, how does pricing and packaging work? How do you incentivize the workforce? how are you ensuring you have the right telemetry around customer utilization from a data perspective and we'll get into that a little later on like my perspectives on data and AI and then you have how does that all impact the P &L of the business and how do you make sure that you're selling these customers efficiently and growing them and building a wonderful generational company.

19:53Joe Iantosca: So I think in many ways, finance has a seat through the entire stage of the funnel from product ideation all the way through the whole customer lifecycle. We always like to try to understand sort of, we call them decision mechanics within the company. I mean, can you walk us through maybe a recent decision about where Syra should invest to support growth? Like, what's involved there? So I think Syra is a place that has extremely high agency and a high willingness to try new things. And the way that shows up is, you know, like, we're very focused on the security market. And within the security market, we're very focused on being the company that lets CISO say yes to AI.

20:55Joe Iantosca: So if you're within that framework, we probably have a high willingness for you to try something new, whether it's a new product, whether it's a new go-to-market motion, whether it's a new message. and I would say where the

21:12Joe Iantosca: where it becomes truly like a critical decision is, is this something we're going to go out to the masses with? Is this resulting in a potential acquisition of a new company or a potential major reallocation of resources in the company? And then that's where we need hard data. what have you tried? What has the customer feedback been? Who's been involved? What's the sponsorship internally? And it's not a company like we make decisions quickly. So it's not a company where you need to reach 100 % consensus. But if it's a big strategic change, there's a little bit more friction in the process to make sure that it's been fully thought through.

21:56Joe Iantosca: But even at the scale that we're at, around 2 ,000 employees, there's still a very high degree of agency and ability, again, to really try new things out. Wow. Interesting. With AI central to Syri's data security offering, where are customers seeing the most tangible value today?

22:25Joe Iantosca: So when the founders started a data security company, Many people thought that was a pretty bad idea. They've really not been a data security company of much relevance. And I think they had the very good insight that as a result of AI, data is becoming significantly more valuable. And our customers see the most value today in their AI deployments when they're actually using agents in production. Because that's where they have the confluence of critical data, making decisions based on context, and identities interacting with that data. And Syra helps secure that trifecta. And we enable them to do this securely, but in a way where they have the right controls and guardrails.

23:22Joe Iantosca: So we work with some of the most sensitive data across the world, with some of the world's most prestigious institutions, and we help secure their agentic AI deployments. Your experience, I want to just jump back to your past experience we talked a little about. Your experience running operations at BetterCloud gives you really an unusual perspective. We wonder how has that shaped your approach to Syaira's revenue engine? early on in my journey, I think where it really shaped my approach is getting in to the deals. I remember some of the early sales conversations where I was in and a lot of the leaders were like, this doesn't feel like the traditional finance guy because I was getting in there.

24:13Joe Iantosca: I understood that winning these customers is the most important thing to the business at this exact point in time. And what's going on in the deals? Where is the friction? How can we move resources around to make sure that the team has everything that they need to win? And then as we've grown, that's moved into how do we create programs around some of those things? How do we constantly interrogate our go-to-market motion? How do we ensure we have the right incentive structure in place? So it's given me much more empathy in how hard it is to win customers. But it's also allowed me to jump into some of the details in a way that I think, you know, a traditional financial operator wouldn't necessarily have the skill set to do.

25:10Inside Sayara's finance organization, where is AI making the biggest difference? I mean, you know, we hear about efficiency all the time, but maybe it's visibility. Maybe it's actual decisions. I don't know. Where is it making the biggest difference in your opinion?

25:27Joe Iantosca: Yeah, I think where we feel the most tangible impact is on like those mundane tasks that used to take forever, reconciliations, bringing data together from many different sources. But I'm starting to see, you know, and we're very advanced in how we're using AI internally. we have an entire internal AI team that goes around and supports non-technical teams. I would put finance in that bucket. You know, the traditional accountant or FBNA person isn't an engineer by trade. And basically it's like, what's the hardest thing that you're working on today and how do we use agents to help support that?

26:09Joe Iantosca: And what I'm seeing the potential over the next three to six months for is complete automation of processes that were previously extremely tedious. Accruals, recurring entries into the ERP. Reporting is something where we've been seeing the value for over a year with AI, and we'll jump into that in a bit. But I'm seeing the ability to automate with AI complete parts of the month-end close over the next three to six months. Wonderful. Yeah, we are up to what we like to refer to as our finance strategic moment. And again, this is where we say it might have happened last week, it might have happened 10 years ago.

26:58What comes to mind when we ask for a finance strategic moment?

27:04Joe Iantosca: I can think of a couple moments, but if you will allow me to tell a bit of a story here. And when I was thinking across each company that I've worked at, when I was at Palantir, and this was, you know, 15 years ago, the team that I was on helped to centralize a bunch of the business data into like a SQL data warehouse. and at the time you would go into different systems, the ERP, the CRM, the payroll system, the credit card system, the travel system, and you'd export a CSV and drop it into a tab in an Excel spreadsheet, write some formulas, and you'd create a consolidated analysis manually. And that's just how the world operated at this point in time.

27:58Joe Iantosca: and they set up what was called Cronjobs and brought it into a SQL database, wrote SQL and created a master template, if you will. And that felt transformational at the time. And it really, it was, it was like cutting edge and you would view it through a BI tool. And then when I got to BetterCloud, it was a bit of a shock to go back to having to do these things manually going into all these consoles and I was like whoa I can't live like this and technology had evolved a bit and I really took that like data background and I would say brought it to the next level with like an amazing counterpart.

28:53Joe Iantosca: And he really helped take data from everywhere, not just the business systems, but the product, external data sources, marketing data sources. And it really became the foundational infrastructure that we ran business intelligence and FP &A and all of that out of. And I would say for me, that was like two or three years into BetterCloud when I was starting to hear external people who would look at the business for fundraisers saying, hey, you have the best handle of data, the cleanest data, the most accessible data. I would say that was an aha moment for me. And then when I joined Syara, my first hire was that individual who was also my first hire at BetterCloud.

29:47Joe Iantosca: and I would say many people were scratching their head. They're like, hey, we hired a finance leader and he wants to hire a data engineer as his first hire. And when they asked why not hire an FP &A person, I said, well, I think the fastest way for you to lose trust in me is not having access to the data to make decisions and centralizing this into a snowflake database and bringing in data across the business will pay dividends not just for me, but for the company. And that's become the foundation that we run much of the internal AI infrastructure off of. So while it's not like one specific moment in time, I would say like thinking back on Palantir, it was like the aha moment of, oh my gosh, there's a different way to do this.

30:43Joe Iantosca: And then at BetterCloud, it was kind of bringing it to the next level and connecting in data beyond just things with dollars and cents. And now at Sayara, it's really become the brain that supports much of the decisions that we make and also has become foundational for how we use AI.

31:08AI is changing the finance function, but how much business value is it actually delivering? According to new research from Salesforce, 90 % of finance leaders using AI report a positive return on investment. And as AI agents enter the picture, finance leaders are seeing opportunities to improve productivity, reduce costs, and strengthen forecasting. But there's another side to the story. CFOs are also confronting growing revenue complexity with more subscription, consumption-based, and hybrid business models to manage. And that raises an important question. How can finance leaders gain the visibility they need to make better decisions while putting AI to work?

31:58Salesforce explores these challenges and the opportunities ahead in its latest CFO research. Discover what finance leaders are saying about AI, revenue complexity, and the evolving CFO role. Visit salesforce.com slash CFO report. That's salesforce.com slash CFO report. We want to know about, you know, three years ago as you entered this role. you thought you knew everything about it. You had been in a COO role before, but still there was something different about being a CFO, something if you could go back in time, you would tell yourself what. What is it that you'd tell yourself about that first 60 or 90 days in the role?

32:47What is it that you wish you knew?

32:51Joe Iantosca: Well, I think first, I still don't know anything about it. I'm learning every day. And I think in this crazy world we live in, if your mentality is you've got it all figured out, you're going to get clobbered in the head by a meteor.

33:10Joe Iantosca: And I think it's the same advice that I give people who are just starting out in their career. Like it's just as valid in your first day of work as it is on your 10 ,000th day of work, which is like, it's okay not to know. and really like I embrace mentorship and I've been lucky to have many, many, many, many, many amazing mentors. Even this morning I had breakfast with one of my mentors and I'm okay being vulnerable. Like I'm okay just saying, hey, sometimes I'm just like, hey, I'm going to say this out loud because I know I need to fix it and I don't really, I need to like work through how to articulate what the exact problem is.

33:52Joe Iantosca: but I know I have a problem in this area. So let's talk about it. And being grateful for a mentorship and always saying thank you for going out of the way, for helping me. And then also, karma is a thing. So always giving back. One of my mentors, the first time I met them, I probably didn't have business being on the phone with them, but I got connected through someone they respected. and they said, I said, you know, thank you for taking the time. Like, here's what I want to get out of it. I had sent them a pre-note, came super prepared, and they said, listen, like, the only, you always have to give it back now.

34:33Joe Iantosca: Whenever someone reaches out to you and asks for 30 minutes, it's important that you give it back. So I'm a big believer in that as well. Wow, a great, great anecdote for us. Hey, we always like to ask our guests to reflect a little on the personal side, Joe. So what is maybe your colleagues don't know about you? What's something from your past, an interest that you had, a pursuit, maybe a feat from the past? Probably my favorite hobby as a teenager was playing a lot of Halo. Like tens of hours a week, I became ranked in the world. At one point, spent a lot of time on Xbox, and I don't think many people know that.

35:18What did your parents make of it?

35:21Joe Iantosca: A lot of confusion, like their 12-year-old son screaming into a headset in their bedroom. They probably were very confused. I guess happy that I was in the house, though. What about a book or a resource for us? Something you, it could be something related to business or maybe not. Anything for us? I think the best book I've ever read was Shoe Dog, the memoir of Phil Knight. And I'm not a founder. I'm not sure I'll ever be a founder, but I feel like my job is to really help support founders and help them bring the vision of their company to life. And I think that journey of how hard it was for him to really take Nike into a company that he was literally hand-building shoes and selling them out of his trunk in Oregon to the company that we knew today is both inspirational, but also the life of a founder.

36:35And I think that it's really like an amazing, inspirational story.

36:43Joe Iantosca: But even though it's a retail company that was built tens of years ago, there's a lot of things that you can apply to technology. And building a business in this AI world, there's a lot of similarities if you look closely. Yep, great selection for us. Thank you for that. We're up to our final question. This is where we ask you to look forward finally. We're interested in your priorities for the coming 12 months as a CFO. What would those be?

37:17One, staying adaptable.

37:20Joe Iantosca: The world is crazy. There's many things changing, both in and out of our control, so making sure that we stay on the balls of our feet, listen to our customers. and continue with the innovation journey that we've been on. Two is discipline. In a company like Sarah where we're growing quickly, things are going well, it's important in my role to make sure that we have the financial discipline to grow into a generational company. And then three is commercialization of all the new products that we're bringing to market. and making sure that the value for our customers is there and that Sair is continuing to grow off of these amazing new products.

38:17Joe, I and Tasca, thank you for joining us on CFO Thought Leader. Thank you, Jack.

38:39Hello, we're benchmarking the CFO path. Join 500 finance leaders helping define how today's CFOs rise and lead. If you're a CFO or senior finance executive, contribute your experience. It takes just a few minutes and you'll receive early access to the findings. visit cfothoughtleader.com slash benchmarking.