Christina Cacioppo On Building A $1.6 Billion Business By Simplifying Cybersecurity Compliance

Christina Cacioppo has gone from academia to a VC firm to becoming an operator. Leveraging that breadth of experience, she has not only raised $200M for her own venture, but is also helping other software startups launch and accelerate themselves. The startup, Vanta, has attracted funding from top-tier investors like CrowdStrike, Y Combinator, Craft Ventures, and Diogo Monica.

In this episode, you will learn:

• How to maintain company culture as you expand internationally
• Fundraising for your startup
• Building a business that thrives in good and tough economic times
• Christina’s top advice for other aspiring entrepreneurs

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About Christina Cacioppo:

Born in the Midwest and based in Silicon Valley, Christina Cacioppo sits at the intersection of security, tech, and business. After starting her career in early-stage VC at Union Square Ventures, Christina went on to lead product management for Dropbox Paper, bringing the product to market. With Vanta, the Y Combinator alum is pioneering a continuous, automated approach to security monitoring.

Christina received her Masters in Management Science and Engineering from Stanford University and has taught Entrepreneurial Design courses at the School of Visual Arts in New York City. In her spare time, she reads books, runs with no destination, and cooks Sunday dinners for friends.

Connect with Christina Cacioppo:

• Crunchbase
• LinkedIn
• Twitter

Read the Full Transcription of the Interview:

Alejandro Cremades: Hello everyone and welcome to The Dealmakers Show. I’m very excited about the guest we have today. We’ll be talking about building and scaling businesses, and the incredible journey of this entrepreneur—from the investment side to becoming an operator. There are super inspiring stories ahead. Without further ado, let me welcome our guest, Christina Cacioppo. Welcome to the show, Christina! You were born in Iowa, but you moved around a bit. Could you walk us through your journey so the listeners can get to know you? What was life like growing up?

Christina Cacioppo: Thank you so much for having me! Growing up was good. I spent my early years in a Midwestern college town, Iowa City, and later moved to Columbus, Ohio. I still bleed scarlet and gray. My parents were both professors who really loved their work. I grew up thinking that’s what jobs were supposed to be like—something you were really excited about every day. It took me a while to realize that not every adult feels that way.

Alejandro Cremades: So, you were initially going to follow in their footsteps. What made you change direction?

Christina Cacioppo: Well, as I mentioned, my parents were both professors, and I really admired their passion for learning and their work. As a curious kid, academia felt familiar and accessible. I literally grew up running around the hallways of the psychology department at Ohio State. For a long time, I implicitly assumed I’d become a professor. It made sense to me.

I went to Stanford and studied economics. I loved it and even wrote an undergrad thesis. But by the time I was 21 and nearing the end of college, I started to realize there were other paths in life besides academia. I stayed at Stanford for a fifth year to get a master’s degree. During that time, I took a lot of product design classes, which introduced me to building things—not just with equations and theories but with my hands and pixels. It was so much fun and ultimately put me on a completely different path that I’m still on today.

Alejandro Cremades: At Stanford, you were surrounded by innovation. Many people there choose the entrepreneurial path, but you took some detours before starting your own company. You even went to Europe and New York. What took you so long to say, “Okay, it’s time”?

Christina Cacioppo: I think I felt like I had to accomplish a lot before I was ready to start a company. In retrospect, I’m not sure that was entirely true, but I had my hangups. For example, I couldn’t code, and I thought, “People who start software companies need to know how to code.” How can you make a product if you can’t actually build it? There was also a sense of imposter syndrome—like “people like me” don’t start companies.

Alejandro Cremades: What do you mean by “people like me”? You seem more than capable to me.

Christina Cacioppo: Thank you! For me, “people like me” meant not having a background in computer science—I only took a couple of classes in school—and not feeling like I knew an industry well enough. When you’re 21, what do you really know about industries, let alone how to navigate them? I also thought employing people sounded intense and scary. I just had this notion that I needed to have it all figured out before I could start a company.

Alejandro Cremades: So, you taught yourself to code. What motivated you to take that step? It sounds like quite the challenge.

Christina Cacioppo: It was a challenge! After graduating, I was lucky to work at Union Square Ventures, an early-stage venture capital firm in New York. Over two years, I met with hundreds of founders, which helped dispel some of my hangups. I saw that founders came from all sorts of backgrounds, and it became clear that I could potentially do it too.

But I still felt like I needed to know how to build a product. So, I took my bonus from working at Union Square Ventures and lived off it for two years, taking online coding classes. My first project was a blog I built during an online course. I turned it into a book website because I’ve always loved seeing people’s bookshelves. It was kind of like Goodreads but different. These projects weren’t meant to be businesses; they were just ways to teach myself how to build products.

Alejandro Cremades: During your time at Union Square Ventures, you met with 500 founders. That’s a lot of exposure! Working with legends like Fred Wilson and Albert Wenger must have been incredible. What did you learn about what it takes to succeed as a founder?

Christina Cacioppo: One key takeaway was that fundraising success doesn’t equate to company-building success. Raising money is often necessary but it’s just a means to an end. If you don’t have product-market fit or if you lose it, the money doesn’t matter. I’ve seen companies that raise money but struggle with slow decay over years. That made me very skeptical of ideas, including my own, unless I felt they were truly strong.

Another important lesson was the clarity of communication. Founders who could clearly explain what they were doing had an easier time raising money, recruiting talent, and building teams. Later-stage founders had this succinctness and clarity of thought that translated into better decision-making and leadership.

Alejandro Cremades: Let’s talk about Vanta. Ideas take time to marinate, so at what point did the idea for Vanta come to you? What sequence of events led to its creation?

Christina Cacioppo: While working at Dropbox as a product manager, I was tasked with launching Dropbox Paper. During this process, I ran into challenges with the legal team. They pointed out that our contracts with customers required compliance certifications like SOC 2, pen testing, and HIPAA compliance, which the product didn’t have. I didn’t even know what those terms meant at the time! But I quickly learned that these processes were necessary, manual, and time-consuming—a huge blocker for launching products.

After leaving Dropbox, I spent about a year exploring different ideas. I was particularly interested in security and how startups could build strong security programs. I spoke to founders who often admitted they didn’t have proper security practices in place, even though they knew they should. That’s when I came back to compliance. It was the bridge between showing you’re secure and meeting customer requirements.

For six months, I manually did what Vanta does now—helping companies achieve compliance—to see if it was viable. Over time, I built software around these processes, which eventually became Vanta.

Alejandro Cremades: For those listening, can you explain the business model of Vanta?

Christina Cacioppo: Absolutely!

Alejandro Cremades: Now, in your case, when we think about culture, you recently completed an acquisition. Most acquisitions fail because of integration challenges. So, when it came to integration, especially regarding culture, what kind of safety measures or strategies did you employ to ensure success?

Christina Cacioppo: That’s a great question, and we’re still working through it. Hopefully, this answer doesn’t sound terrible in six months if it turns out we were way off, but a few things come to mind.

Beforehand, we focused heavily on values alignment. This was a significant factor in the company we acquired deciding to sell to us. Many of my conversations with the founder of the other company weren’t just about Vanta. They were more personal—questions like, “What was your childhood like? How does that influence how you work at Vanta?” These conversations were serious but also a bit jokey. It was about understanding who we were as people and what we wanted on both sides to see if there was enough alignment.

From a product and vision standpoint, everything made sense—it was a clear fit. But we needed to ensure the cultural and personal alignment was there because that’s what makes the integration work.

As for the integration process itself, it all comes back to people. We’ve focused on maintaining consistent touchpoints and asking questions like, “How does this feel? Is anything off? On a scale of 1 to 10, how do you feel about this integration?” It’s about creating a space for honest feedback and addressing issues as they arise.

Alejandro Cremades: I think your team is fortunate, given the type of business you have with Vanta. The current macroeconomic environment is a bit scary—many companies are doing layoffs—but nothing seems to be stopping Vanta. What’s driving this resilience?

Christina Cacioppo: There’s a saying by Greg LeMond: “It doesn’t get easier, you just go faster.” That’s very true in startups.

Vanta’s resilience comes partly from the “painkiller” nature of our product. Good security isn’t optional—it’s critical. Hackers don’t care about the macroeconomic environment, and scrutiny around security is constant. Buyers need to know their data is safe, whether times are good or bad.

For B2B companies, especially those selling to larger organizations, what Vanta offers is essential. That doesn’t change based on federal interest rates or other economic factors.

Alejandro Cremades: Imagine you went to bed tonight and woke up in a world where Vanta’s vision is fully realized. What does that world look like?

Christina Cacioppo: In that world, the security of software is always verified. At a high level, we’d go back to trusting the software we use.

Today, when we encounter new software, there’s often skepticism: “Will they get breached? Is my information safe?” In Vanta’s vision, software would be both secure and trusted. We’d rigorously ensure security while allowing people to feel confident and optimistic about the tools they use.

Alejandro Cremades: Vanta has grown significantly—something like over 78% growth in headcount last year. When transitioning from early-stage to growth-stage, the challenges change drastically. What are some of the differences you’ve observed at this stage?

Christina Cacioppo: In the early days, it felt like we were plugging holes with as many fingers and toes as we could spare. It was chaotic but necessary to keep things running.

Now, the challenges are different. One of my biggest fears is that as Vanta grows, we might slow down. More people mean more communication overhead, more processes, and the risk of losing speed.

Another shift is in the type of work we do. Early on, you do everything yourself—often poorly but with your best effort. Now, we have experts in key roles, and my focus has shifted. I’m no longer trying to teach a sales leader how to sell—that would be a disaster. Instead, I provide context about Vanta, customers, and market trends to support their expertise.

Alejandro Cremades: Let’s reflect on the past for a moment. Imagine I put you in a time machine and brought you back to your days at Union Square Ventures when you were contemplating starting your own company. If you could give your younger self one piece of advice, what would it be and why?

Christina Cacioppo: I cringe thinking about this, but I’d probably tell my younger self to chill out a bit. Work hard, and things will happen—but don’t stress excessively over every detail.

I remember a moment at USV when I missed a meeting due to a calendar mix-up. I was mortified, but the other person was kind and said something like, “This happens. Just be nice to the next person who does this to you.” That stuck with me—the idea of playing the “universe karma game.”

Work hard, be kind, and don’t beat yourself up when things go wrong. You can’t control everything, but with enough persistence, something will work out.

Alejandro Cremades: For listeners who want to reach out and say hi, what’s the best way for them to connect with you?

Christina Cacioppo: Email is best: ch*******@va***.com.

Alejandro Cremades: Amazing! Christina, thank you so much for being on the Dealmakers Show. It’s been an honor to have you with us today.

Christina Cacioppo: Thank you for having me! I really appreciate it.

* * *
If you like the show, make sure that you hit that subscribe button. If you can leave a review as well, that would be fantastic. And if you got any value either from this episode or from the show itself, share it with a friend. Perhaps they will also appreciate it. Also, remember, if you need any help, whether it is with your fundraising efforts or with selling your business, you can reach me at al*******@pa**************.com

 

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