5 Things Vanta Got Right and 5 They Got Wrong getting to the first $10m ARR
When Christina Cacioppo co-founded Vanta in 2017, security compliance was an afterthought for most startups. Fast forward to 2025, and Vanta is valued at $2.45 billion with over 8,000 customers worldwide, having fundamentally transformed how companies think about trust and compliance.
Key metrics:
- Valuation: $2.45B (July 2024 Series C)
- ARR: $100M+ (reached in January 2024)
- Customers: 8,000+ globally (75% of current YC cohort uses Vanta)
- Total funding: $354M across seed through Series C
- Team: 500+ employees across North America, UK, Germany, and Australia
- Lead investor: Sequoia Capital (led all three institutional rounds)
Vanta has evolved from a simple SOC 2 automation tool to “the leading trust management platform,” using AI-powered questionnaire automation, real-time security monitoring, and 300+ integrations to help companies turn compliance into a competitive advantage rather than just a checkbox exercise.
But Vanta’s journey to becoming a $2.45 billion trust management platform wasn’t a straight line. In fact, some of their biggest wins came from learning quickly from spectacular mistakes.
Based on Christina’s candid reflections from SaaStr presentations in SF and London, here’s an honest look at what Vanta got right—and what they got painfully wrong—on their path from $0 to the first $10M ARR.
5 Things Vanta Got Right
1. Created an Ultra-Minimal Viable Product to Test Real Customer Workflow
Most founders talk to customers. Christina Cacioppo moved into their office.
When validating Vanta’s initial concept, Christina didn’t just conduct interviews or send surveys. She and her co-founder literally set up desks at Segment’s office for weeks, eating chocolate-covered pretzels while reading dozens of SOC 2 reports.
Their “V0” product? A color-coded spreadsheet. Not software. Not a fancy prototype. Just a simple spreadsheet that listed everything Segment needed to do for SOC 2 compliance, with red/yellow/green status indicators.
“This was literally Vanta’s V0,” Christina recalls. “We handed this over to Segment and then asked them three questions: What did I give you? Would you use it? Would you pay for it?”
This approach gave them insights no amount of customer development interviews could provide. They understood the actual workflow, the real pain points, and the specific language customers used. When they finally built software, it solved actual problems rather than theoretical ones.
2. Simplified Pricing to Annual-Only Early
Vanta initially offered both monthly and annual pricing options, following the standard SaaS playbook. Then their first salesperson did something that terrified the founders: he stopped offering the monthly option entirely.
“We were pretty shocked and pretty scared,” Christina remembers. “But he came back and said, ‘You guys are creating security automation as a category for startups… That’s hard enough. Then you’re creating all this other uncertainty in how to buy.'”
The results were immediate: deals closed faster with fewer decision points. More importantly, customers on annual contracts used Vanta continuously rather than just for audit preparation, fundamentally changing how they thought about the product.
This taught them a crucial lesson: in a category-creation business, every point of friction matters. Removing pricing complexity actually helped customers make decisions faster.
3. Built Category-Defining Creative Marketing
In a space known for dry, enterprise messaging, Vanta chose humor and creativity. Their first viral moment came in 2021 with a Highway 101 billboard before SaaStr that simply said: “Compliance that doesn’t SOC 2 much.”
“That campaign got a ton of attention and was one of the first moments where we really leaned into creative marketing,” Christina noted.
But it wasn’t just about clever wordplay. They invested heavily in podcast marketing with attribution pixels showing significant ROI. “We hear it all the time—people saying, ‘Oh, I first heard about Vanta on a podcast,'” their marketing team reports.
This creative approach helped them stand out in a crowded field and made compliance feel approachable rather than intimidating—crucial for their startup customer base.
4. Integrated AI Early and Iterated Continuously
While many companies rushed to add AI features in 2023-2024, Vanta had been quietly integrating AI into their compliance tools for years.
“At Vanta, we integrated AI into our product early on—and we’ve been iterating ever since,” Christina explains. “Our AI-powered tools help accelerate compliance, assess risk, and automate previously manual processes.”
This early investment allowed them to build genuinely useful AI features rather than tacking on chatbots for marketing purposes. Their AI-powered questionnaire automation tool now achieves 80% immediate acceptance rates from human reviewers, and the company has built over 200 integrations with security tools in-house, plus another 100+ built by partners. As Christina puts it: “If you can give people credit — which really means revenue — for showing off all the good security work they’ve done, they will do more good security work.”
5. Waited to Fundraise Until They Had Conviction
Perhaps Vanta’s most unconventional decision was waiting until $10M ARR to raise their Series A, running the business on just their seed funding for three years.
“We were operating at basically cash flow break-even,” Christina recalls. “We didn’t need to go fundraise, felt really clear-eyed about the opportunity in front of us.”
This patience gave them several advantages: they understood their unit economics, had proven product-market fit, and could negotiate from a position of strength. When they finally raised their $50M Series A from Sequoia in 2021, it was on their terms.
5 Things Vanta Got Wrong
1. Over-Engineered Early Hiring and Created “Unicorn” Roles
In their early days, Vanta convinced themselves they were so special that standard SaaS roles didn’t apply to them. Instead of hiring a customer success manager, they created bespoke roles that mashed together different functions.
“We were so convinced that Vanta was really special… that normal jobs at a SaaS company like customer success manager operations didn’t apply,” Christina admits. “We had special versions of those jobs.”
This led to mismatched expectations and roles that simply didn’t work in practice. The “unicorn” employees they hired expected something very different from what the business actually needed.
The lesson? Save your differentiation for your product, not your org chart.
2. Paused Revenue Generation to Focus Solely on Hiring
After graduating from Y Combinator, Vanta made a near-fatal mistake: they stopped selling to focus on hiring engineers.
“We’d hit our revenue milestones, raised a seed round, and were so confident that we paused all sales so we could go try to hire our first engineers,” Christina explains.
Months later, a YC partner pulled Christina into their office with sobering news: “Most of your peers in the batch had gone out, kept building their businesses, also been able to recruit somehow at the same time, hit a million dollars in ARR, and were driving up and down Sand Hill Road. And we hadn’t.”
The mistake nearly killed their momentum during a critical growth phase. The lesson: you can’t pause business development for team building—you have to do both simultaneously.
3. Underestimated the Competitive Landscape Shift
When Vanta started, Christina thought compliance automation was “a bad market”—and she was initially right. But by the time they proved it wasn’t, the landscape had completely changed.
“It was deep Covid and it was the time when everyone wanted to start startups. So a lot of [competitive] docs got started,” Christina notes. “That was a shift for us, ’cause I think we went from basically selling to startup founders… to like the slew of software providers.”
They had to quickly adapt their messaging from “person vs. software” to competing against numerous well-funded competitors. While they ultimately succeeded, better competitive intelligence earlier could have helped them prepare for this shift.
4. Initially Offered Too Many Pricing Options
Before their salesperson simplified things, Vanta offered multiple pricing tiers and billing options. This created decision fatigue for customers who were already anxious about compliance.
“We were creating this product that was meant to relieve a bunch of anxiety… And then we were creating a bunch of anxiety in how you buy it,” Christina realizes in retrospect.
In a space where customers are already overwhelmed, every additional choice point creates friction. Sometimes the best customer experience is fewer options, not more.
5. Took Too Long to Recognize They Were Behind Benchmarks
Vanta’s founders were so focused on building that they lost sight of external benchmarks. It took a YC partner’s intervention to realize they were “way off track” compared to their batch peers.
“I left this partner’s office really freaked out, probably appropriately freaked out,” Christina recalls. “I didn’t want to pitch Vanta then. I didn’t want to pitch it without the full confidence that it deserved.”
While this wake-up call ultimately led to better focus and eventual success, better self-awareness and peer tracking could have prevented the crisis in the first place.
The Meta-Lesson: Mistakes Are Features, Not Bugs
What’s remarkable about Vanta’s story isn’t that they avoided mistakes—it’s how quickly they learned from them. Every major error became a competitive advantage:
- Over-engineered hiring led to a disciplined approach to standard roles
- Pausing sales taught them to balance growth and team building
- Competitive blindness forced better market awareness
- Pricing complexity drove them toward elegant simplicity
- External feedback created internal accountability systems
Today, Vanta has evolved far beyond their original SOC 2 automation roots. They’ve built what Christina calls a comprehensive trust management platform, with AI-powered questionnaire automation achieving 80% acceptance rates, over 300 security tool integrations, and customers ranging from startups to enterprise companies like Omni Hotels.
Their $150M Series C in July 2024, led again by Sequoia Capital, valued the company at $2.45 billion—up from $1.6 billion just two years earlier. With over 8,000 customers globally and 25% of revenue coming from outside the US, Vanta has proven that turning compliance into a competitive advantage creates massive value.
Their journey from a color-coded spreadsheet in Segment’s office to a $2.45 billion platform serving 8,000+ customers proves a crucial point: in startups, learning faster matters more than being right initially.
As Christina puts it: “Product market fit is very real and… if you wonder whether or not you have it, you definitely don’t. It just feels distinctly different than working on literally anything else you’ve ever worked on.”
The companies that reach $100m+ ARR aren’t the ones that make fewer mistakes—they’re the ones that turn their mistakes into rocket fuel.
