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David Cross

CISO, Atlassian · 1 appearance on the record.

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executiveinvestorengineerLinkedIn ↗raincap.vc ↗

David B. Cross serves as CISO at Atlassian and Venture Partner at Rain Capital, following senior cloud security leadership roles at Oracle SaaS Cloud, Google Cloud, and Microsoft. A U.S. Navy electronic warfare veteran holding more than 30 security patents, he actively invests in and advises early-stage enterprise cybersecurity startups.

9statements → 4claims → 4claims resolved → 100%fully supported → 3.78/5average certainty → 2.11/5average debate potential → ≈4.0/5argument clarity, estimated →

4 supported 0 partly supported 0 contradicted how the 4 claims stand · each chip opens the sources

2 predictions · 2 assertions · 5 insights · every statement was checked. The predictions and assertions are the 4 claims: statements the public record can support or contradict. 4 are resolved. Everything else (opinions, insights, what ifs, disclosures) can never be settled by the record, so it carries no assessment.

The record, in short

What the tape says about how David argues and how the claims held up. Everything they said, and everything said about them, is in the tabs below.

Their most notable supported claim

Assertion Supported
Cross: No evidence yet of adversaries using AI for complex attacks
“We haven't seen really any, I say evidence, right? Or of cases that are occurring now where that they're using AI to do very complex or compound attacks and surveys. We haven't seen that yet.”
David Cross Dec 10, 2024 ▶ 5:14 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross

Expressed certainty vs assessment result

none yet certainty 1
none yet certainty 2
100% certainty 3
100% certainty 4
none yet certainty 5

weighted support: a fully supported claim counts one, a partly supported claim counts half. Each filled bar is clickable and opens exactly those claims; "none yet" means nothing said at that certainty level has resolved yet

How they sound: not measured why? →

We measure speaking style by listening to the audio itself, and a fair number needs at least 2,000 words from one person on tape we have measured. There is too little of David Cross on measured tape to publish a rate. This says nothing about how they speak.

Everything David Cross said on Innovators & Investors that made the record, most notable first. Filter by type, assessment or year in the ledger →

Insight
David Cross: Founders should send pitch decks upfront instead of teasing calls
“For me personally, is an element is like, you send me the deck as the pre-read opening versus get on a call, right, is I say, be proactive. If you really have something that good, and you'll send me the deck right up front, and it's that good, I'm going to wan…”
David Cross Dec 10, 2024 ▶ 16:21 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: Seed VCs and founders should pursue fast $20M-$50M exits over unicorns
“I think there's a ton of opportunities that you think about of smaller companies, that 20 to fifty million dollar is that some people call it the aqua hire, but right, it's like a founder can come in, your founders can come in, in 18 months, take a couple mill…”
David Cross Dec 10, 2024 ▶ 20:21 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Assertion Supported
Cross: No evidence yet of adversaries using AI for complex attacks
“We haven't seen really any, I say evidence, right? Or of cases that are occurring now where that they're using AI to do very complex or compound attacks and surveys. We haven't seen that yet.”
David Cross Dec 10, 2024 ▶ 5:14 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Prediction Held up
Cross: Adversaries will eventually use AI to find zero-days in code
“Is that saying that we're going to use AI to find zero days in source code? We just haven't seen quite the evidence of yet, but we should still be very suspect that it will occur in the future.”
David Cross Dec 10, 2024 ▶ 6:02 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Assertion Supported
Cross: Ransomware is shifting from encryption to data extortion
“Ransomware now is not going so much after encrypting everything. It's more of a great grab the data, breach, pull it out, and then hold it for extortion, right?”
David Cross Dec 10, 2024 ▶ 7:25 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: Founders often get trapped keeping early executives who cannot scale
“You may hire someone at the very start when five people, they're the chief marketing officer, but now you're 200 people. Are they really still ready to be the chief marketing officer for that next stage? And it's hard sometimes as founders, it's hard as early,…”
David Cross Dec 10, 2024 ▶ 15:13 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: Founders who hide data and claim secrecy have zero chance
“If there's no data, red flag, right? Is if you'd say, oh, it's secret. Oh, we're behind the scenes. We know what we're doing, right? Red flag, right? If you can't be open and transparent, open in the kimono, no chance.”
David Cross Dec 10, 2024 ▶ 18:31 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Prediction Held up
Cross: AI-powered targeted spear phishing is occurring and will increase
“AI, is they're collecting data and public and public information to do very targeted spear phishing, right? And email and things like that. And that is occurring. And it's, or we say that it's very clear that AI is helping those attackers in those cases. So I …”
David Cross Dec 10, 2024 ▶ 5:40 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross
Insight
Cross: New venture investors should assume they will lose their capital
“The first, the best piece of advice I think is, I think the best piece of advice I got is that I, when I started from the very beginning, as soon as you get in venture capital, assume you're always going to lose. And it's going to Las Vegas. You put the money …”
David Cross Dec 10, 2024 ▶ 22:39 10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Capital Partner David Cross

Appearances (1)

EpisodeDateSpeaking time
10 - Investing in Early-Stage Cybersecurity and Enterprise Software Startups with Rain Cap Dec 10, 2024 13m
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