Episode summary
How AI Is Repricing Every Software Company
Invest Like the Best
· · Hosts: Patrick O'Shaughnessy · Guests: Christina Cacioppo
Summary
Christina Cacioppo argues that AI is forcing software companies to rethink both product and pricing, and that Vanta is responding by rebuilding around agents rather than treating AI as a feature add-on. She says customers are too smart to accept token-based markups: if a company simply passes through or inflates Claude tokens, users will compare directly against the model and push back. Vanta is therefore eating token costs for now and focusing on usage, retention, and better workflows instead of trying to force a new pricing scheme too early.
She frames the broader market as a “SaaSpocalypse,” where the valuation multiples for high-growth, high-margin software businesses have compressed even when the business fundamentals have not changed. In her view, investors now reward AI-native, lower-margin, faster-growing companies more aggressively, which creates cognitive dissonance for founders building durable software. She thinks the right response is to keep shipping, stay honest about the business, and avoid overpromising.
Cacioppo also says Vanta is becoming more of a security platform, using its trust graph and agentic workflows to automate work like offboarding and compliance tasks. She sees the biggest underappreciated advantage as company context: people who know the customer, the product, and the domain often outperform generic specialists in this AI era.
Key takeaways
- Christina Cacioppo says token-based pricing is a trap because customers can compare directly against Claude and will reject markups.
- Vanta is currently absorbing token costs and prioritizing usage and retention over near-term margin optimization.
- Cacioppo thinks the market now rewards AI-native growth more than traditional high-margin software, even when the old model still looks economically sound.
- She believes Vanta’s edge is its trust graph and integrations, which power agentic workflows across hundreds of tools.
- Cacioppo says company context is being undervalued relative to pure functional skill, especially in AI-era hiring.
Notable quotes
“if you try to charge them based on tokens they are very quick to say oh you've just marked up a claude token forex are you forex as good as claude”
“you're only as good as the last thing you shipped”
“the multiple for a business like yours is a third of what it used to be or quarter of what it used to be”
“If you're trying to mark up at all, users are very smart and you will lose on that comparison”
“We're eating the token cost right now”
How the episode opens
We have talked to our customers a lot about token based pricing and I think what we've generally heard people are real smart but actually and so if you try to charge them based on tokens they are very quick to say oh you've just marked up a claude token forex are you forex as good as claude I don't know let me go try it out you actually put yourselves in a competitive position against the models and so what we've seen on token pricing is like if If you're trying to mark up at all, users are very smart and you will lose on that comparison.
So, Christina, I've been so excited to do this with you. I think it's been five years since we last did it. So, a lot a lot has happened a lifetime ago. — Uh you've been very successful in the intervening 5 years. So, so I'm excited to catch up. Can you give us like the one minute history of Vanta? I know we've done this before, but just to level set for people when you started it, why, what it did then, how it's evolved, what it does now. Just like a quick quick overview.
Started Vanta about 8 years ago, which was about 8,000. Yeah, exactly. You're like in 17 centuries ago with the premise of can we help companies build and earn trust?
and build trust is like start security programs and compliance programs or mature them and then go go get credit for their customers through audits like a sock 2 or ISO 270 and HIPPA etc questionnaires trust centers but basically this idea of can we build a security company by helping companies implement security because it's what their customer is asking for and so we're initially known for sock 2 we had a billboard we do have a billboard on the 101 that We're mostly known for making billboards, I joke, but it started like very compliance, very audit centric.
From the episode’s captions: roughly the first two minutes, lightly cleaned. Keep watching on YouTube →
Topics
- ai repricing software companies
- saas valuation multiples
- ai pricing tokens
- ai agents in software
- cybersecurity and trust
Companies and tickers mentioned
- Vanta
Watch the episode
Watch “How AI Is Repricing Every Software Company” on YouTube
Summary, takeaways and quote selection by Octagon. Quotes are short excerpts; the full conversation is in the episode.
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