A CEO who hated billboards lost Silicon Valley's favorite one
An employee went around her boss to sell the joke, a crash made a prime spot cheap, and a handshake deal let a rival take it.
Invest Like the Best with Patrick O'Shaughnessy · Christina Cacioppo - Building an Enduring Software Company in the Age of AI - [Invest Like the Best, EP.496]Sarah was out to dinner with a friend who works at another startup when the friend offered condolences. It was so sad, the friend said, that Sarah's company had given up its famous billboard spot. Sarah, a product marketing manager at the security company Vanta, had no idea what she was talking about.
Her boss did not, either, at least not at first. Christina Cacioppo, the co-founder and chief executive of Vanta, had built a business with about 16,000 customers and five products by helping other companies prove they handle data safely, and pass the security audits big customers demand. The company had become almost as well known in Silicon Valley for a joke on the side of Highway 101 as for its software.
Cacioppo had started out as firmly anti-billboard. Tracking was terrible, she thought, and billboards seemed like founder ego, a way to feel cool because your company name was big enough to see from a car.
In the summer of 2021, her marketing team wanted to try outdoor advertising around a big software conference. Cacioppo was skeptical but told them to try it. Sarah came up with the line, "Compliance that doesn't suck too much." Her head of marketing did not like it. Sarah believed in it so strongly that she went around her boss, something she did not normally do, and took it directly to Cacioppo.
Cacioppo loved it immediately. She texted Andrew Reed, an investor she trusted to have good internet meme taste, and he loved it, too. The company put the billboard up, tweeted a photo, and the tweet went viral. Cacioppo said it worked because it captured the company at its best, serious about the work but not about itself, and obscure enough that engineers who got the joke felt like they were in on a secret.
In 2022, when the market crashed, empty billboards lined Highway 101. Vanta grabbed a prime spot where Interstates 101 and 280 meet for what Cacioppo recalled as not that much money. On podcasts she joked that Vanta had the location secured for years to come. In reality, there was no long-term agreement.
Other startups kept asking Sarah how Vanta did billboards, and she referred them to the salesman who sold the space. He got millions of dollars of business from the referrals. What Vanta had was little more than a placement order, not a multiyear contract.
That was why Sarah was blindsided at dinner. The friend's startup had paid more and taken the spot. Cacioppo called the salesman, then called the other company's founder and offered to double the price to get it back. She described herself as an extremely inelastic buyer, willing to pay about $3 million for a spot she thought cost about $1.5 million. The founder said no. He said his company was cash-flow positive.
Vanta lost the sign. Cacioppo joked that the company had probably just lost a bit of market value, and that losing the billboard felt like a bad omen.
Questions people ask
What does Vanta actually do?
Vanta sells software that helps companies build security programs and prove it to customers. That usually means getting ready for audits like SOC 2, ISO 27001, and HIPAA, which are standard checks that a company handles data safely, plus answering security questionnaires and running what Vanta calls trust centers.
Why does a billboard on Highway 101 matter?
Highway 101 is the main commuting road through Silicon Valley, past San Francisco International Airport and the headquarters of many tech companies. A billboard where 101 meets Interstate 280 sits in front of tens of thousands of engineers, founders, and investors every day, which is why tech companies prize it.
How much does a billboard like that cost?
Prices vary widely by size, lighting, and traffic, but prime Bay Area highway boards can rent for tens of thousands of dollars a month, with annual contracts often running into six or seven figures. Advertisers usually sign placement orders for specific periods, and a higher bidder can take a spot if it was never locked up long term.