COMMAND DASHBOARD
Funding & investors: $43M Series A (April 2025) | Investors: a16z + OpenAI Fund (OpenAI’s first-ever cybersecurity investment) | Stage: Early, pre-revenue scale
Founders: Brian Long and Andrew Jones — repeat founders who built Attentive ($10B+ valuation) and TapCommerce (acquired by Twitter); this is not a first-time founding team.
Product: AI-powered cyberattack simulation — deepfake video, vishing (voice phishing), smishing — for enterprise security awareness training.
Market timing: AI-generated social engineering attacks increased 3,000%+ between 2022 and 2025; enterprise CISO budgets are actively reallocating toward AI-specific threat simulation.
No VP Sales has ever existed: The entire revenue function is being built from scratch.
Revenue target: Job posting language: "Clear runway to build a $100M+ ARR machine" — founders have stated this target explicitly.
Competitive context: KnowBe4 (market leader, human-phishing simulations), Proofpoint, and Cofense all lack AI-native deepfake/vishing simulation capability — Adaptive Security owns a meaningful product gap.

The security awareness training market is dominated by platforms built for the 2015 threat landscape: static phishing email simulations with checkbox compliance outcomes. Adaptive Security’s product is built for the 2026 threat landscape: AI-generated voice clones impersonating the CFO, deepfake video of the CEO authorizing a wire transfer, SMS smishing campaigns indistinguishable from real enterprise systems. No incumbent can build this fast enough to compete. The gap is not product — it is the absence of an enterprise sales motion capable of converting CISO urgency into signed contracts at scale. Building that motion from zero requires someone who has deployed AI-powered lead qualification infrastructure, understands multi-stakeholder enterprise sales cycles (CISO, CIO, legal, procurement), and can construct the team and processes to reach $10M ARR before the Series B is required.

Days 1–90Q1 — FOUNDATION
Days 91–180Q2 — BUILD
Days 181–270Q3 — SCALE
Days 271–365Q4 — OPTIMIZE
Conservative

$5M ARR (CISO buying cycles longer than modeled; government/defense vertical pushes to Year 2)

Target

$8M ARR (outbound motion producing 60% of pipeline; MSSP channel contributing 20%)

Stretch

$12M ARR (financial services vertical accelerates; 2 anchor enterprise deals close early; MSSP channel exceeds forecast)

Strategic Summary

Core Opportunity

Adaptive Security has $43M from a16z + OpenAI Fund, repeat founders who built Attentive ($10B+), and an AI-native deepfake/vishing simulation product that no incumbent (KnowBe4, Proofpoint, Cofense) can replicate. The entire revenue function is being built from scratch with a stated $100M ARR target.

Execution Thesis

Deploy AI-powered CISO intent scoring, automated deepfake demo generation, multi-agent engagement coordination, and MSSP channel development to build the revenue function from zero to $5M–$12M ARR — establishing the financial services vertical as the primary growth engine and delivering the Series B narrative within 12 months.

Production systems, not theory. Revenue captured, not demos given.