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In today's episode, Ryan Zauk is joined by Christina Cacioppo, Co-Founder & CEO of Vanta.

Ryan and Christina recorded this episode live at Newcomer's Breaking the Bank Summit in San Francisco.

The Summit was an invite-only, one-day summit for fintech founders, builders, and investors to explore the future of finance and technology. Breaking the Bank was a phenomenal event, with speakers including Jackie Reses, Zach Perret, Eric Glyman, Matt Harris, Josh Reeves, William Hockey, Annie Lamont, and many more.

Check out some pictures below and see if you can put a face to a name...

And if you're looking for more fintech events, check out Stablecon in NYC coming May 29th.

Now back to the episode...

Vanta has been a "center of the valley" company for years now, becoming one of the fastest companies to hit $100M ARR.

Christina has been at the heart of this great success story and was a phenomenal guest. She shared a lot of insight (and laughs) talking through lessons scaling from $0 to $100M ARR as well as how Vanta helps companies turn compliance into a competitive advantage.

Here were a few big takeaways:

1️⃣ Viewing compliance as a 'box-check' = leaving money on the table. Vanta has helped customers achieve a 526% ROI in their first 3 years through both faster revenue generation / sales cycles and streamlined operations

2️⃣ The best and worst part of software is that it's always What Are You Doing For Me Lately? You're only as good as your next release. This approach has given Vanta openings in the market, but leaves them equally vulnerable to the next great product, requiring constant adaptation

3️⃣ Her biggest advice for founders scaling to $100M? If you have PMF (you'll know), hire leaders before you need to. She famously disagreed with an early angel, who advised hiring an exec when she was just at a few million ARR. As the company went vertical, they scrambled to fill the void as the business was overwhelmed with demand

4️⃣ On navigating sales in today's environment? It's a human business. It will always be humans buying software, and in an era of AI BDRs, a human touch matters more than ever

5️⃣ "The Sweatshirt Test" - Perhaps the most enduring differentiation in the Age of AI is your brand, trust, and quality. You want to build a company that customers and partners would be proud to wear on a sweatshirt walking not just around the block but out at work or a conference (h/t Kyle Leahy)

6️⃣ Turn the mirror on your VCs. Your board members will be with you for the long haul - diligence them back. When Christina met Andrew Reed of Sequoia Capital, she put in the work to diligence him with both onsheet and offsheet references. And be sure to dig in on their working styles, how they disagree with founders, their principles, and more.

7️⃣ The most interesting app on her mind? Retro by Nathan Sharp and Ryan Olson

8️⃣ Christina is a proud Ohio native...Graeters > Jeni's and SF needs an artisan 'Midwest bake sale theme' shop

Episode Timeline

• 0:58 - What sparked her journey to technology and startups
• 4:03 - What exactly Vanta does, how it serves startups, and how they can quote a 526% ROI over 3 years for clients
• 10:13 - Why auditors, consultants, and lawyers can be friends instead of foe for Vanta
• 11:33 - Vanta's differentiation in a hot market
• 14:12 - Why shipping quickly is critical to staying relevant in software and the AI wave
• 16:43 - Vanta's in-house AI use and what her engineers love (and really don't love)
• 18:06 - Her top advice for founders facing hypergrowth and her views on Silicon Valley hyperscale lore
• 21:30 - The forever 'human' aspect of selling (and buying) software
• 22:38 - Hiring their first "Founder in Residence" and why it may be the new hottest job in the AI era
• 24:42 - Where differentiation will still exist in the AI era
• 26:45 - Raising from Sequoia and her advice to founders on how to vet your VCs (and why it's so critical to diligence them back) + the one thing founders really want from VCs at the early stage. It's simple, but not easy!
• 30:44 - A fun rapid fire round including the origin of the Vanta llama, favorites of her Ohio roots, their craziest marketing stunt attempt, her favorite books, a startup she's most excited about, and much more

Enjoy the show.

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Vanta is the leading trust management platform backed by Sequoia, Craft, YC and Crowdstrike Ventures. Over 10,000 companies, including Atlassian, Omni Hotels, Quora and ZoomInfo rely on Vanta to build, maintain and demonstrate their trust. All in a way that's real-time and transparent.

Christina Cacioppo is the Co-Founder & CEO of Vanta. Prior to founding Vanta, Christina led product management for Dropbox Paper and was a member of the investment team for Union Square Ventures. Christina received her B.A. in Economics and M.S. in Management Science and Engineering from Stanford University.

Ryan Zauk is the Host of the This Month in Fintech Podcast and Bay Area lead for the broader This Week in Fintech platform. In his day job, Ryan is an investor at OMERS Ventures, the direct investing arm of one of the world’s largest pension plans with $130Bn+ in net assets. OMERS Ventures focuses primarily on Series A through C direct investments in Software, Fintech, and AI. Prior to OMERS, he worked in Morgan Stanley’s Tech Investment Banking team focused on M&A and capital markets. He is based in the Bay Area. You can find him on Linkedin or Twitter.

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Transcript

[00:00:00] Ryan Zauk: The views expressed in this podcast are the speaker zone and are not the views of this weekend FinTech or any other person or entity. The content provided in this podcast is for informational purposes only and should not be construed as legal, business, tax, or investment advice or recommendation, solicitation endorsement, or offering by me or anyone else for the sale subscription or purchase of securities, or for investment advisory services of any kind.

Welcome to today's special edition of the This month in FinTech podcast recorded live at the newcomer Breaking the Bank Summit in San Francisco. You're in for a great conversation today with Christina Caspo, co-founder and CEO of Vanta, as she covers her founding story, how Vanta is transforming compliance lessons from hyper scaling to a hundred million A RR, hiring their first founder in residence, how founders should vet VCs and much more, including a fun rapid fire round.

Let's get started.

Well, Christina, welcome to this month's episode recorded live. In this kind of back office room at, uh, the newcomer breaking the Bank Summit out here in San Francisco.

It's wonderful to have you on the show today.

[00:01:07] Christina Cacioppo: Great to be here. Thank you so much.

[00:01:08] Ryan Zauk: Thank you. , Well, how are you doing? Where'd you come in from?

[00:01:11] Christina Cacioppo: Uh, we just got a new office in San Francisco. Oh, congratulations. Today was my first day in our brand new office, so I came over from there.

[00:01:18] Ryan Zauk: So Christina, you've been a long time tech tinkerer and curious mind from what I found online.

You used to flip Beanie Babies as a kid. What a throwback. Love microeconomics. And your website has shown dozens of things you've built, ranging from a prettier iPhone contact book, to crowdsource. Bitcoin use cases. Where did this love of learning and tech tinkering come from?

[00:01:39] Christina Cacioppo: Um, , probably my parents, uh, my parents are,, were. College professors and teachers, but primarily researchers. And, , the salient part of that for me that I just kind of grew up around and didn't think twice about was they loved their jobs and they loved their work. I didn't kind of realize like Sunday scaries wasn't, you know, a thing, but I like didn't even know that was like a, not just the words, but like the concept. Yeah. Yeah. Um. I think there was something that was like really affirming and wonderful about growing up around people who were, you know, wonderful parents and cared about my brother and I, but also like, loved their jobs and loved what they did .

[00:02:13] Ryan Zauk: I love it. And so clearly worked out. You started your career just after Stanford at Union Square Ventures? Mm-hmm. Dropped, dropped out, quote unquote Union Square ventures , ended up at Dropbox as an engineer and then Vanta.

[00:02:25] Christina Cacioppo: Yeah.

[00:02:26] Ryan Zauk: Can you just walk us through what was the founding story here in Decisioning framework for starting this company?

[00:02:31] Christina Cacioppo: Uh, everything makes sense in retrospect at the time. Oh

[00:02:34] Ryan Zauk: yeah. Feel free to revise. Yes. Yeah. Yeah. Great. Okay, so the revise

[00:02:37] Christina Cacioppo: version, which makes a ton of sense and is true just as stylized is, , at Dropbox as a product manager trying to launch what at the time was , a new product.

It was Dropbox Paper. It was like. Notion without the sidebar and most notions, magic is one way. Describe it. Um, and wanted to launch that. We had a handful of startups using it, but kind of no big Dropbox customers wanted to launch it to Dropbox customers and we're actually about to and thought, uh, thought we were all doing really well.

And then I. Realized we couldn't because all these Dropbox customers had these big contracts that had contractual obligations like SOC two and vulnerability monitoring and pen testing in them. And we mostly didn't even know how to spell those words. And sort of learned what it would take for Dropbox in 20 15, 20 16 and like the height of its Silicon Valley power to go and do those things. And that was. To like, give up your engineering team for a year, have them full screenshots, work with accountants, and you just kind of look at that and you're like, wait, what?

, And you think this will work, you know? Right. Um, but kind of went deeper and realized like, okay, there's a, there's a good thing here, which is go demonstrate your reasonable security practices to a trusted third party who writes up this comprehensive report. And then everybody trusts that.

Like, that process made sense. Um. It's just the way you kind of showed your security practices to that third party, which were screenshots from six months ago, felt very silly and antiquated. , And it felt like a, a problem that could be solved with technology and was worth solving with technology.

That's a very stylized like.

[00:04:03] Ryan Zauk: It was destined that it was written. Exactly. And now let's talk Vanta. You previewed it a little bit there, but probably the hardest question in Silicon Valley, what exactly does your company do?

[00:04:12] Christina Cacioppo: Yeah, we talk about it as the leading trust management platform, which is kind of a very Silicon Valley answer, but basically we more, what does that mean more helpfully?

We help companies either build out or understand or improve their security programs. And do all that work. And because that's a lot of real work to get prioritized, we help them do that because by using all that security work to get compliance certifications, answer security questionnaires, , demonstrate their security, build trust with big companies so that they can, um, open up new industries, sell to larger companies, like ultimately drive revenue for the business and tie that to security so they can continue to invest in building more secure software.

[00:04:51] Ryan Zauk: Got it. And who exactly , does this product serve? Is it new startups, fintechs, enterprise, software, government?

[00:04:57] Christina Cacioppo: Yeah, we're a little bit of all of the above right now, but we very much started with startups and I think it was 'cause in true Silicon Valley fashion, the MVP was good enough for a startup, but not good enough for literally anyone else.

Um, just startups that had no alternative. So that's where we started and probably we were best known, but today we have some of the world's largest banks. We have, um. Increasingly talking to government, uh, a bunch of healthcare. So kind of like truly like multi hundred thousand person organizations across the globe and highly regulated industries.

I. But it all started with startups.

[00:05:31] Ryan Zauk: That's awesome. And I actually was just speaking to a startup last week. Shout out Kato, KATO, that said they needed to get SOC to compliance to serve banks and was looking at using Vanta. Yeah, a nice customer plug here. Uh, and then I do have to quickly ask, since we are at the break breaking the bank summit, you mentioned you might work with.

Large banks, how exactly are you working with that big of an org? I can see the use case for a 10 person, 20 person company, but look at the Morgan Stanley's of the world.

[00:05:56] Christina Cacioppo: How does it work? Right. So our version of the classic land and expand is like we, you know, aspire to serve a large bank's full compliance program.

That is, that is a tall order. We are not quite there yet from a product maturity standpoint. Yes. Um, but where we are, there's a couple use cases. I think probably the easiest to understand is. These banks make acquisitions.

[00:06:15] Ryan Zauk: Yes.

[00:06:16] Christina Cacioppo: Right. And then, and they're often FinTech acquisitions and so they're bringing unknown technology into the bank parameter with bank customer data, and they wanna understand.

That security posture and then it to my, you know, old Dropbox story. Like that new technology then has to meet that bank standards. And so we, that is kind of our land is you can land on these things that maybe look more like startups, but they're within a bank parameter. Mm-hmm. And so they have to hit that really high bar.

Um, and that's, that's some of where we started. Got it.

[00:06:45] Ryan Zauk: Makes sense. And then I do want to dive a little deeper on the product, 'cause I get this one a lot. Soc two's certification doesn't necessarily guarantee compliance. Right. In the end. It is a framework that people try to wrap their businesses around and comply with.

Yep. What's the real value of having this SOC two certification and a platform like Vanta over the life cycle of a business?

[00:07:05] Christina Cacioppo: Yeah, so I think about Vanta, at least for engineers or folks who have kind of more experience with engineering as if you think about a observability tool like a Datadog or you just have a dashboard of like, here's how the system is performing.

Like compliance people don't have that, right? They have screenshots and when they wanna know if. You know, a control is performing. They go email an engineer and say, Hey, can you go, you know, pull me a screenshot out of AWS And it like, sounds like I'm making that up. But , that is the process today.

And so some of it was can we take all the, like engineering best practices of the last decade or two and bring them to compliance. This place that is still operating off of task trackers and screenshots. And so then they, uh, and this might be in our compliance team, a security team, a founder, a head of engineering.

They just understand, hey, , these are the commitments we made. We said. Data would already always be encrypted at rest. We said every employee would've two factor in their email. Right. You know, we said this, that and the other. Is it actually happening? Um, and here I have a dashboard I can pull up, I can see, uh, uh, what's in place and what's not, and then what I need to go to go fix things that aren't in place.

[00:08:07] Ryan Zauk: And then one stat that I saw on the website that really stood out was, , customers report a 526% ROI over three years . The ignorant mind, including myself. Compliance is often viewed as box checking software. Yep. And a flat a CV, you just get it to eliminate tail risk. Yep. Down the road of an audit or whatever else.

. What is the ROI that you're providing?

[00:08:28] Christina Cacioppo: Yeah, so I'm gonna get a little is truly was around in the founding days, but I think compliance is like deeply misunderstood, but it sounds as terrible box checking, like, I don't know, basement dwelling. Like why would you care about this like cost center, .

And I mean, two things. One, I think it can actually be a revenue driver to the, when you, you know, you're a startup and you get SOC two, the banks open up to you, there's a bunch of healthcare regulations. You know, there's all these European regulations that you're like, it's part of opening a new market, a new geography, a new segment.

So that piece, the other piece is once that's open, again, your customers kind of don't, they ask you for lots of features. They don't really ask you for the security feature. They ask you for compliance, right? And then they ha send security questionnaires, right? Which are these like loft and long spreadsheets or websites and forms of just hundreds of questions.

And in those are embedded, I would argue, like a bunch of feature requests. They're these security features and I think compliance is a great way to tie here's what a customer wants. Then maybe here's a like revenue figure associated with that customer to here's all the security work. Then maybe what we want to do, but it's hard to prioritize.

But when you can say, oh no, when we implement these five things, we get to close this bank, that contract is $2 million. Look at this ROI, right? Right. And it helps the security team point to like the value of their work in the, in terms the business understands. And I dunno, one things I've liked about that is, 'cause often security teams know their work is valuable, but kind of struggle to like communicate, uh, to your, you know.

Silly, CEO of like why it's important beside they wanna do it and it's fun work to do. And you can say, no, no, no. Here's a revenue figure. It's very big. Um, and the fundamental belief in Vanta is like, if you can do that, you're gonna get more security work done. Companies will be more secure.

[00:10:14] Ryan Zauk: No, it makes sense.

And then, uh, quick follow up on that. A lot of companies might be using auditors, big four consultants, lawyers, other service providers in this world. Do you view them as partners, competitors? Are you partnering with them? I know this might be a thorny question here. No,

[00:10:31] Christina Cacioppo: we, we partner with a lot of them. Um, I think the, uh, so every standard or framework is kind of written slightly differently and the audit works slightly differently, but generally there is a broad principle of, you probably shouldn't.

Audit your own work. Right. So historically there was this bifurcation of their sort of readiness consultants that would get someone ready and then there was an auditor who'd come in and do the work. And those were either not the same firm, or if they were, they were like different parts of the firm that wouldn't talk to each other.

We are much more similar to the readiness work, which for a small company we can kind of replace the consultant. But honestly for a small company, I'm definitely big ones. We end up augmenting that consultant with your, again, like they want the dashboard too, right? But like anyone who's built software knows building software when we have the battle and the second battle is maybe the second 90% is like getting someone to use your software.

Right. And there's still like so much organizational change management and like that's where consultants very much still have a role. Yeah. Is, you know, again, dashboard can tell you to do whatever it wants, but like how do you get that actually manifested in real life?

[00:11:34] Ryan Zauk: Got it. And then on the note of competition, it's like any massive market.

There's a slew of competitors out there. We don't have to name names. How do you ensure that Vanta is different? And where do you view Vanta ass differentiation over the medium term now?

[00:11:47] Christina Cacioppo: Yeah. So when we started, we were, there was no software. People thought this was a bad market. I kind of thought it was a bad market as well, to be clear.

Um, it was $10 million most selling soc twos, uh, that was wrong. Turns out, um. But kind of by the time we figured out it was wrong. So it was also deep covid and it was the time when everyone wanted to start startups. So a lot of AMTA doc offs got started. Mm-hmm. And that was a shift for us. 'cause I think we went from basically selling to startup founders.

Like do you wanna, you know, talk to a person or do you wanna talk to software And sort of, founders tend to like software more to like the slew of software providers. Um. The way we thought about it then, and still to some extent is like the blessing and curse of building software is you're only as good as your latest release and no one really cares if you made the space, nor should they.

Right? Uh, you know, no one really cares if you shipped something cool last year, like cool, but like that was last year. Like, what have you done for me lately? And that's kinda, again, being on the other side of it, it's wonderful and terrible both, but probably more wonderful than terrible. And so the thing we talk about more than anything else is shipping velocity.

Um, and it gets to kind of, I think one of my core beliefs about building things for at least myself, which is I very rarely build the right thing the first time. Hmm. But I can usually build it right the fifth time. And so you just wanna minimize like your iteration time to get to that fifth right. Cycle.

Exactly. And if you do that, you'll figure it out. Like if you just iterate and listen, you'll figure it out. But if you know, it takes you three months every cycle, like, well now you're 15 months later and you're just behind the market. Um, and so that's kind of, that's, I don't know, maybe slightly philosophical and slightly tactical.

The other answer is I think we've just tried to, um. Broaden what Vanta is and does. It's like we're known for SOC two for startups. We added on this whole alphabet soup of other standards. Great. Um. Now we feel like we've kind of earned the right to start building more security products and adjacent products and things that aren't audits, like security questionnaires, like trust centers and that like, you know, third party risk.

And that's been a very fun chapter 'cause it's something we talked about back in the early days. And then we just built compliance for a really like straight compliance automation for a very long time. Yeah. And there were definitely times when you kind of wondered like. Am I one of those crazy founders, like pitching this dream and then, you know, the real, like the, the Instagram reality is just like way too far apart.

Yeah. So that's been kind of rewarding

[00:14:13] Ryan Zauk: and so as you think about retaining companies, right? So in like the PEO HR software space, there's a big concept of startups graduating off of PEO or hr, HR software going up market after 10, employees, a hundred, and then a thousand. , It, it seems you're already thinking about that with that multi-product vision, but.

What do you see as the reason why people will stay on Vanta as they grow?

[00:14:33] Christina Cacioppo: . For like overly simplistic, but basically when you're a small company and you haven't done this before, you just want someone to tell you what to do, right? Right. You want TurboTax for your compliance. Yeah, it's push me through focus.

Exactly. Just tell me what to do and be super prescriptive. And that's what the MVP of Vanta was. , And it worked well for that audience. Then as your company grows and you hire a compliance or a security expert, they say, uh, you know, hey, my job as compliance person at this company is to figure out what our practices should be.

I don't want your standard ones. I don't want your outta the box ones. Right. They're not Right. Yeah. And so , our product challenge, but I think, I think we're rising to meeting, is saying, okay, yeah, you can have the TurboTax if you want it, or you can have something that's much more custom about customizable.

And so you, you know, , experienced security or compliance person, you can put in whatever controls you want and we will check them and we'll make the dashboards you want. And that's what we need to do to continue growing with our customers. .

[00:15:31] Ryan Zauk: And then earlier you talked about, it's all about what are you doing for me lately?

Are you building into the moment quick iteration cycles? No bigger moment of course, than AI and agentic workflows. How are you adapting your products? Let's, let's take it from the customer facing angle first. Yeah. What are you building to help these customers who all wanna ship AI products now be compliant

[00:15:51] Christina Cacioppo: on like folks building with ai? Yes, yes. So there is, okay, so this area, it's still kind of shaken out. Yeah. But . There are a handful of new AI regulations, right? Colorado and Texas I know had Colorado and Texas have them. Yeah. There's NIST, IRMF across the US there's ISO 40 2001, which is like more European, but not totally.

There's kind of a, there's a lot of these and right now a lot of flowers are blooming, so are tact at mans like we will just support all of these. Probably like grab, like the universe will settle around one of them, but rather than trying to pick that now, we'll just support them. Okay. I think what we're generally seeing in its very early days, so watch, this will sound really dumb in six months, but is more of the pressure on AI vendors who's coming from European.

Companies. Mm-hmm. European companies tend to like ISO standards. So like I had to pick a horse, it would be ISO 40 2001, but again, six months, this is gonna seem real dumb.

[00:16:43] Ryan Zauk: . Hey, no, that's a good bet. , And then now let's turn it inward.

AI use advanta. Where are you deploying it internally? What's surprised you to the upside and then maybe . Been a little lackluster in its adoption

[00:16:54] Christina Cacioppo: in the product or in op, like our internal operations, how we work.

[00:16:57] Ryan Zauk: Let's go internal operations.

[00:16:58] Christina Cacioppo: Oh, okay. Yeah, yeah, yeah. We are trying to do a lot here. .

Very broadly generalizing. There's two camps. There's the, like I am chay be everything in my life, you know, and I kind of forget how to communicate without it, not quite kind of, and then there's the like, get off my lawn. I don't want any of this. Right folks. Yeah, exactly. And I mean, there's a lot in the middle to clip, but like, you know, broadly there's that.

And I think, uh, we've seen actually a ton of adoption on the go-to-market side of the company, which I don't know if I would've guessed, would've been wrong because turns out so much of the go-to-market jobs are kind of tedious, like. I listened to a call. I thought about my notes. I put my notes in the format.

My manager wants them in Salesforce. I like take my notes. I put them in another format, which is like the email to the customer, right? Just there's like so much of a go to market role is stuff like that. Um, and so we've seen really, really great adoption there. I think on the engineering side, you know, all the stuff you'd expect.

Co-pilot cursor, like looking at tab completions, how many prs are automatically generated, right? We have some like, um, uh, a tool that's writing tests for us, uh, you know, and like some of that. So there's like a lot of playing around there too.

[00:18:06] Ryan Zauk: And anything that's been lackluster in adoption that you're more bullish on.

[00:18:11] Christina Cacioppo: Gemini shots fired. I don't know how much of it, yeah, I shouldn't have said that. Um, I don't dunno how much of it's like actually Gemini the product and how much like chat g PT just like, seems like the premium brand, you know? And so it's like, oh, you're gonna make me use the like free thing, like Right, right, right.

Um, that bias going in. Yeah, it was kinda like Chromebooks. Oh yeah. A couple years ago where it was like no one wanted a Chromebook, even though they were probably great. Exactly. It was just like everyone wanted the shiny MacBook. And then I guess we have not had, you know, the full stack Ai, BDR as much as the San Francisco, like one on 1 0 1 billboards.

Oh my God. We should all hire Ava, but like we haven't, we haven't, I dunno if we've actually tried that one in particular, but that concept we have not,

On that note, it doesn't seem to have slowed you down at all. You're now at over 10,000 customers and passed a hundred million a RR in under five years. What a journey. . But let's get started on some advice for founders. What was the secret to this kind of hypergrowth? And again, feel free to add some revisionist history if necessary.

[00:19:09] Christina Cacioppo: Um. I do think product market fit is very real and the like. If you wonder whether or not you have it, you definitely don't.

, Like all the tropes are so true and it just feel, and this is kind of true, even in the early days working on Vanta, just felt distinctly different than working on like literally kind of anything else I'd ever worked on. To that though, I think it is very, there's this wonderful.

Revisionist history that Silicon Valley writ large is very good at, which is like the kind of brilliant founder. Like I wrote, I went into my dorm room, I stayed up all night, I coded Facebook. It was the first thing I made. And like now, right? 4 billion people use it. And like that I think might actually be the story of Facebook.

It is basically not the story of like any other company ever. And it's certainly not the story of Vanta and I learned this actually when I worked at Early Stage vc and I kind of saw, you're like, oh, that's the public story. And then like, this is what I actually, this is what actually happened.

Yeah. And I found that like so humanizing and kind of encouraging mm-hmm. That this is one of my soap boxes. Um. I think more of these stories should be told so that being a founder doesn't, isn't like, oh, and I need an IQ of 272 and you know, like, go off into my room and like everything I touch turns to gold.

'cause like, that's not how it usually works. Um, and you don't have to be that person.

[00:20:27] Ryan Zauk: And then, what broke along the way what should founders be aware of if they're seeing that product market fit that you mentioned coming?

Oh

[00:20:34] Christina Cacioppo: my God. Hire much faster than you think you should. , And hire like leaders. Uh, I remember. This was just before the pandemic. We were probably 2 million in revenue. And uh, like kind of well-known angel investor who was very smart, uh, was like, oh, and Christina, you should start building out your leadership team.

And I literally laughed at him because I was like, leadership team. For what? It's not that we work around a kitchen table, but we like basically work around a kitchen table. Yeah. Like, what are you talking about? And I didn't. And then six months later we were at whatever, 8 million and like everything was breaking and everybody was very much including me.

We were in the biggest job of their lives and was like, well, it's going really well, but we're like really angsty and kind of unhappy and, you know, and then how do you, how do you think about that? Yeah. Um, you know, I, and then you start trying to like, hire people who've done some version of it, even at that scale.

And it, and you have to go sequentially and it, it just, it was brutal. And I should have started when that person told me to start, even though I thought that was. Some of the craziest advice I'd gotten up to that point.

[00:21:35] Ryan Zauk: I love it. And then what about selling, you mentioned selling to banks and some of these larger upscale institutions.

Selling to startups is one thing and there can be a lot of good word of mouth, PLG, right? Channel motions. When you're selling upstream to these customers, what's the advice you have to founders? 'cause I mean, there's more a ai K-Y-C-K-K-Y-B-G-R-C software that I've ever seen.

[00:21:56] Christina Cacioppo: Yeah. Right now. I think I was told, but I didn't appreciate almost more than a startup.

The world's largest companies buy from people and it's people who wanna buy from people. And I think I would've guessed, you know, oh, this is like a, you know, again, 300,000 person global financial institution. Like that's, that's a Borg, that's not a person. And yet there is in fact is a person there. Um, and they're, they wanna.

Bet on a founder and a technology and yeah, they want someone where they know where they live and they know their phone number and they can call 'em at 3:00 AM and like there's some of that. Yeah. But then there's, there's some of it that's like not that. Um, and again, I think I would've expected founders to have more of that, and founders do, but it's almost like the banks have more of it.

[00:22:38] Ryan Zauk: And then one of the big hires that you've been working on, you posted for a job title called Founder in Residence to Build an ai First Go To Market. Yeah. Back in April. What was the thinking and do you have any updates to share? We

[00:22:51] Christina Cacioppo: just hired someone. Yeah. Oh, I don't think we've changed LinkedIn yet, so I won't steal your thunder, but yes.

We just hired someone breaking news. Yeah. , Uh, I think the offer we accept was last week. . , , so the thinking there was kind of to your, you know, AI tool going through to 80 zero to 20, you know, like kind of, I would say like the companies don't really have go to markets or they have PLG, but Right.

But whatever they're gonna build from here on out is gonna look pretty different than what Vanta has and what we started building in 20 19, 20 20, depending on how you count and. We, we can't just blow up what we have. ' We have these, all these customers and all these people and all this pipeline, whatever.

It's like wonderful problems to have. But the go to market in NAIH is probably different. Yeah. And, but again, it's hard to ask all the people we have do, like keeping the plane flying to tear up the plane as they're doing it. And so the thinking of that role was bring someone in who is a builder. On the go to market side, give them some like small starter projects like, Hey, fix this workflow, take a couple hours out of this person's role.

Mm-hmm. And have them build intuition and wins honestly. And then have them be like, okay, cool. Now if you were gonna rebuild the airplane, like what are you

[00:23:57] Ryan Zauk: doing?

[00:23:58] Christina Cacioppo: Yeah. Um, and do it that way.

[00:24:00] Ryan Zauk: Got it. It's one of the best rebrands I've ever, or names of a title I've ever heard. I have a feeling found in residence is gonna be all over the place in a lot of high growth.

[00:24:09] Christina Cacioppo: Honestly, the other part of, there's a USV inspiration part of it, which was that job was time boxed. Right. And of course the secret with all time box jobs is their time box still or not. Right, right. Also, but I think, you know, like if you're good and they want you to stay and you wanna stay, you can probably stay.

Mm-hmm. Um, but you get a different applicant. And sort of the thinking was we want someone who is kind of angsty about not getting, like, taking a job and Yeah. Um, who wants to go start a startup but maybe doesn't have that idea. And like, largely, you know, I was this person at various points and .

probably should have worked at a company before I did. I was just angsty about it. And so how do you like attract that personality too?

[00:24:47] Ryan Zauk: Yeah, it's a tough fire. It's all that you're able to get them in the door. Yeah, I'm excited to see the announce. Uh, and then last question on, on this broader topic, let's say, you know, this found in residence goes and starts a new company.

Differentiation is getting harder and harder it seems by the day. In all tech. Yep. And growth software. , Taking a broader view on the ecosystem, where do you see differentiation still existing for high growth tech startups in the next few years?

[00:25:16] Christina Cacioppo: I think there is still differentiation and differentiation to be had in the product.

Again, I'm very biased and very like shipping velocity. Um. But I think that often, even if you have that it can get obscured. 'cause explaining that it's hard and I don't think it's always something we've nailed at Vanta. Certainly. Um, I mean even to this day, sometimes we're on a head-to-head, you know, we'll try to explain the difference and it won't really land.

And we say, cool, just trial our product and go trial our competitors and come back and our win rate goes through the roof, right? And so there's something there, but we don't actually not explain it. But anyway, , all to say, I think that skill of explaining what it is in, in the terms that customer understands is exceedingly valuable.

, You know, people talk a lot about community and I think, I think for good reason, I think that term does get, um, used in sort of a loosey goosey manner. Um, but the, there is something very real there. Uh, I actually love the, um. I dunno, I first heard it from Emily Weiss and Glossier the makeup brand. Oh yeah.

But is, uh, you wanna make a brand or you wanna make a company where someone would be glad to wear your wear its name on a sweatshirt. I'm like, I wear a Glossier sweatshirt, but like Right. It kinda worked on me, but like, I actually think that's a, you know, glossier aside, like a really clear framing. Yeah.

Um, and if you put a bunch of, you know, quote competitors' head to head, like, which, which sweatshirt do you wanna wear? Right. Um, and then whatever that is, like that is real.

[00:26:38] Ryan Zauk: That's a great point. I'd rather wear that cool. Like orangey anthropic sweatshirt, to be honest, as opposed to a black and white opening.

There

[00:26:44] Christina Cacioppo: you go. Right? Yeah. Yeah. Like what? You know that thing is real

[00:26:47] Ryan Zauk: thing. Yeah. And yeah, I remember Newbank had a customer who had literally tattooed their logo on their arm and I was like, that's the best that you could ever have. Exactly. Immovable mode. Yes. Um, well last question before we get to the rapid fire round, let's talk a little bit.

About, the fundraising process. You raised a massive round from Sequoia a few times now, and backed by Andrew Reed, who's one of the best tweeters out there. So good, hysterical. What stood out about Sequoia and the fundraise? I'm sure there were several investors knocking on their door.

[00:27:16] Christina Cacioppo: Yeah, I think at that first Andrew Round, um, the thing that was very surprising in a good way was that I didn't know him ahead of time, uh, and I did not think I'd go with someone I didn't know ahead of time.

Uh, just add to the list of things I didn't know, uh, or like messed up. Um, but he, so I like met him on Thursday, maybe that Thursday night or so. He emailed me intros to like four or five founders he'd backed Oh. Emailed them on Friday and said, Hey, talking to Andrew, like, would you mind getting on the phone?

They all got on the phone with me before Sunday afternoon. Wow. But these were like founders of like companies you would recognize. Yeah. Yeah. Um. And so it's not just like, oh, the founders he works with said nice things. It was like they got on a phone for him on a Saturday when they did not have to do that.

And then, you know, I, then I went and found the five founders he didn't introduce me to, and we emailed them. Right. And they actually all said nice things, you know, and, and got on the phone with me quickly. And so there was like, you know, again, I don't you like quite call that, but like mm-hmm.

Uh. Uh, that was, I think, quite persuasive. It's like, oh, these people actually like, like him and again, like him enough to take time outta their Saturdays and their families. Um, not just like, yeah, here's my EA and we can talk next Thursday at 9:00 AM you know?

[00:28:30] Ryan Zauk: What advice do you have for founders in picking investors?

What advice do you have for VCs that are. Trying to get in your inbox and you're cutting through the noise.

[00:28:38] Christina Cacioppo: Oh, okay. Yeah. For founders, picking investors, like, uh, getting someone off your board is one of the absolute hardest things to do in a company.

Like, harder than many other things, harder than parting ways with, , executives, co-founders in some ways. Um, and so like interview them, um. And yeah, do the chat GBT question and ask them you a question thing, but like, what if your company has a, we call it a principles interview, a principals interview, a values interview, a like mm-hmm.

You know, like do that on your prospective investors and you might have to be kind of polite about it so they don't totally feel like they're being interviewed. Yeah. Or not, uh, 20 style, but like, do that. 'cause again, this person will be around for years, whether or not you like it or not. Um, I do think though, like, yeah, do all the references they give you and then go find a bunch of references that they didn't give you and listen to people.

And it's not, you know, usually you won't get. Uh, people saying mean things or kind of this person was bad in these ways, but just kind of listen, one of the questions I usually ask is, how does this person disagree with you? That's a good, right? And you're not, you just wanna figure out like they're gonna do their thing.

You have your style. Yeah. Are they gonna match or are you gonna like run into each other? Um, so that on the founder side, on the investor side, I think, uh. All kind of, all founders want, quote unquote, is like more customers. And so, uh, we, and we did this in the early days, but we would just ask for, for customer intros.

My pitch back was like, look, this is great diligence. Like send someone one my way. Right? They're gonna talk to us, they're gonna get a demo, they're gonna buy or not buy, right? And then just like, go talk to them and that will, you will learn more about the company than I will ever tell you. Mm-hmm. And I was like, pretty high confidence.

We could close some and it would be a good sales tactic too, like if sales technique for all the investor. Right. But, um, I actually do think VCs should be more. Should kind of push more customers towards startups, both to get in the founder good graces, but also is just better diligence than like literally anything else.

Got

[00:30:45] Ryan Zauk: it. Awesome. Well, Christina, you've made it to the final round of the episode, which is the rapid fire, easier questions, hopefully than all of the last. Um, so we got a couple questions here. You know, max answer on a 10, 20, 30 seconds speech. First one we did talk a little bit about, you know, wearing a logo on a sweatshirt.

You have this very notable llama. Yeah, what's the story of the llama? And if the llama didn't exist, what would be vantis mascot?

[00:31:09] Christina Cacioppo: Uh, longer story with a short version is llama slash alpacas are guard animal and alpacas. It's, it's a llama, um, mostly llama, um, alpacas are guard animals and we wanted, you know, security company guardian normal, but not a guard dog.

That felt kind of basic. So this was like the hipster version of a guard dog? . Uh, my favorite animal, uh, is a red panda. I would not make that the company s thing, but we do have a handful of like really old legacy internal tools at Vanta called Red Panda and new people joined it. It was just like, what is going on?

[00:31:42] Ryan Zauk: That's always a fun one. Alright, you have the quote. Looking forward to the back half of the chessboard. I believe it's on your Twitter profile.

[00:31:48] Christina Cacioppo: Yeah.

[00:31:48] Ryan Zauk: What

[00:31:49] Christina Cacioppo: does that mean? Um. It's an old story. I think I first found it on like Mad Glacio, his blog maybe when I was blogging for slate to age myself.

But basically it's this idea where, uh, you take a chessboard and you put, you double, you put a stone on each, or like a stone on the first one. Two stones, four stones, eight stones, and you're like doubling the stone and like the back half of the trash board kind of falls over. Yeah. Right. And it's sort of this idea of like compounding is.

Uh, so important and kind of all that matters and like impossible to think through. Yeah. Um, I've always kind of liked the, the mental image of half the chess board just kind of falling over.

[00:32:24] Ryan Zauk: When I first saw it, it seemed like this, like back half of life almost. Mortality.

[00:32:28] Christina Cacioppo: Oh no,

[00:32:29] Ryan Zauk: the back.

[00:32:29] Christina Cacioppo: Yeah.

[00:32:30] Ryan Zauk: Nine.

[00:32:30] Christina Cacioppo: Yeah.

[00:32:31] Ryan Zauk: Uh, got it.

That's a much better

[00:32:32] Christina Cacioppo: Yeah.

[00:32:33] Ryan Zauk: Image then

[00:32:33] Christina Cacioppo: can't play chess. So sometimes people ask me, really?

[00:32:35] Ryan Zauk: Surprising. Yeah. Um, all right, next one. You have a Slack channel advanta called Wacky Ideas where employees get to throw some crazy stuff and see if it sticks. Yeah. What's been your favorite to date?

[00:32:46] Christina Cacioppo: Um. We, that's like truly wacky stuff we haven't done, but sometimes we get like, uh, you know, oh, RSA, it's big security conferences coming to San Francisco. Why don't we paint all the streets purple? Um, or like just get a bunch of llamas and walk them. Or like around Moscone. Yeah. Yeah. The city won't let you do that.

. We did taxis this year. Oh, that's surrounded it with purple taxis.

[00:33:09] Ryan Zauk: I really hope you can get the along. I know right. Streets next year. Yeah. Alright, next one. You're a very big book nerd. I saw an Nazi's gold, uh, Mumba plot about the Congo.

[00:33:19] Christina Cacioppo: Yeah.

[00:33:19] Ryan Zauk: You list a lot of books on your website. What are your top two most underrated books on the list? I think

[00:33:24] Christina Cacioppo: you mentioned it, but I think Lumumba plot was great. Uh, it was just, it was one of these, um, uh. Blogger who talks about this, but like I did just learn something on every page. Uh, it's a story of Patrice Womba who was sort of the first president of the Congo and then was, or first second, depending on how you really count it, but like, and then sort of murdered, um.

But in that you get, uh, uh, like colonialism in Africa, you get independence and the independence movement across the continent. You get the Cold War, um, you get the un, like you get so much out of that. Um, and so like it is a book about, you know, uh, uh, sort of folk hero, Congolese politician, um, but you like learn so much about the era and kind of the world and I really enjoyed that.

Um, fiction side. Do I really like lately, Claire Keegan is one of my go-tos. She's an Irish short story writer, so they are short stories, so they're easier, but they're well, easier in that they're shorter, not easy in that they're like emotionally gut-wrenching and decimating and like beautifully written.

Um, and when I read her stuff, it's, it's kind of this like, oh, I read a lot of text on the internet, but like nothing is written like this. You know, there is like a deep skill here that so few people possess, but I think she does.

[00:34:40] Ryan Zauk: Got it. Okay. Different part of your interest now you list running up hills as a big interest.

Mm-hmm. What's the go-to top hill to run, in essence? Not anymore of a

[00:34:47] Christina Cacioppo: Beal ses. Ooh. Used to live kind of near the foot of Beal and running up. That is brutal, but also kind of great. Yeah. My

[00:34:53] Ryan Zauk: God.

[00:34:53] Christina Cacioppo: Yeah.

[00:34:54] Ryan Zauk: Beast. Um, all right. You're an NBA fan. The fi, the Eastern Western Conference finals are kicking off. Who is your team?

Any playoff predictions?

[00:35:02] Christina Cacioppo: I don't know who my team is now, but like, okay. See.

I'm a LeBron fan. I can't tell you I'm a Lakers fan 'cause I still haven't reconciled that. But like big LeBron, big LeBron fan. .

[00:35:10] Ryan Zauk: Didn't have

[00:35:10] Christina Cacioppo: the season anyone wanted.

[00:35:12] Ryan Zauk: Definitely not early exit. Yeah. So let's talk about those Ohio roots then. What is, uh, you're from Columbus, .

[00:35:18] Christina Cacioppo: Mm-hmm.

[00:35:18] Ryan Zauk: And what is one Midwest staple you'd love to bring to sf and where would you open it?

[00:35:23] Christina Cacioppo: Um, I mean Western Bake sales in elementary school, these don't seem to be things as much here. So in elementary school it's just like your classic elementary school bake sale Parents and kids.

Yeah. Yes. But I don't know unless you make Buckeyes when you make like puppy chow. Do you know what puppy chow is? Yeah, yeah, yeah. Tex Mix, spit, block bag. Exactly. That's like pepper and powdered sugar and get you everywhere. Yeah. Which is just, I forget that. Well now I forget it exists ever once you see it, but like then you find people who haven't grown up with puppy chow

[00:35:48] Ryan Zauk: so we'll have this Midwestern bakery themed.

[00:35:51] Christina Cacioppo: Yeah. Oh, and not the like gas station check, like check fix now makes puppy chow. Not that you

[00:35:55] Ryan Zauk: do. Oh yeah.

[00:35:56] Christina Cacioppo: It's not as good. You gotta make it at home. Yes. Yeah. Have to. Okay. And where would you open it? Hate Valley. I don't know. Where do you put kit? The mission?

Tiny sliver space. $47 a egg. Yeah.

[00:36:07] Ryan Zauk: No. And then let's talk ice cream. Everyone's favorite. Yeah. Jen, these are graders.

[00:36:11] Christina Cacioppo: Okay, so this is kind of verboten, but like I am a grader's person. Jenny actually went to my high school though many years before me, but she didn't start till I graduated.

Okay. So like the Jenny's rise is. I was that. Yeah. Yeah. So graders was the, like, you take your report card, you get free scoops when you're in third grade, black, raspberry chip till the end

[00:36:31] Ryan Zauk: graders. Okay. And then a, a favorite Jenny's flavor though. I don't know. They have crazy flavors. It's hard.

[00:36:36] Christina Cacioppo: Are you supposed to say salted caramel to this?

[00:36:38] Ryan Zauk: Probably, yeah, probably. I'm not. I'm more of a s swen sim guy in San Francisco. Oh. That I haven't. Amazing. Okay. Really, really good. That's my recommendation. Um, alright. Last couple. You're a music person, so am I. What are your top three favorite artists?

[00:36:51] Christina Cacioppo: Oh God. Uh, I don't have a good answer that.

Uh, actually, , somehow it took me, I was last year, years old until I discovered Maggie Rogers.

[00:36:59] Ryan Zauk: Oh, she's so good.

She's so good. Have you not discovered that? I didn't

[00:37:03] Christina Cacioppo: know, but then I got to go down the rabbit hole and I, I did, I missed the Rell video when it first came out. People watched she at n nyu.

[00:37:09] Ryan Zauk: . And then last questions, uh, most exciting startup that you've come across recently that you're excited to shout out?

[00:37:16] Christina Cacioppo: Okay. Uh, I have a friend, Nate Sharp, who is building a social photo sharing app on mobile, uh, in, you know, the year 2025. How say? Yeah, yeah, yeah. In year 2025. I'm, he's paying you for this one? No, he's not. Uh, and part of it is I like, so he, like, he, he was the PM on Instagram stories, so he knows what he's doing.

Yeah, exactly. Um. He like deeply cares about this. The investor updates are so fun 'cause he walks through the growth strategy and it's just a very different way of thinking about product than I basically would ever do it. Yeah. And so I usually feel like I learned so much from them and just like, and he deeply cares about this thing that everyone else has decided, his passe and last decade's news and like I admire that a lot too.

[00:38:05] Ryan Zauk: What's the name of the app? Retro. Retro. Okay. And then who would you love to see as a next guest on the this month in FinTech podcast? Doesn't have to be FinTech.

[00:38:13] Christina Cacioppo: I mean, Matt Levine..

[00:38:14] Ryan Zauk: Oh, the absolute best. I was just listening to his podcast. I listen to the podcast too.

Yeah. Well, Christina, thank you so much for coming on this month's episode of the podcast. It was great to have you on live at the Breaking the Banks Newcomer Summit.

[00:38:25] Christina Cacioppo: Thank you. Thanks so much.