TrojAI Raises US$5.75M, Names Rapid7 Vet CEO, and Opens in Boston

TrojAI announced a US$5.75 million (~C$7.75 million) additional seed round on April 3, 2024 — and with it a new CEO and a Boston office — as the Saint John company pushes enterprise buyers who want AI models tested before they ship and protected after they do.

The round and the leadership shift

Existing investor Flying Fish led, with returning capital from Build Ventures and Techstars, plus new cheques from Alteryx Ventures and Flybridge Capital Partners. Flybridge co-founder Chip Hazard joined the board.

Co-founder James Stewart moves from CEO to CTO. Incoming CEO Lee Weiner spent 11 years as a senior executive at Boston cybersecurity firm Rapid7 — product, engineering, and innovation through a scale-up from roughly $40 million to over $750 million in revenue, per the company — with earlier stops at LogMeIn, Symantec, and Netegrity.

Stewart’s framing was blunt: the company had the product thesis; it needed someone who had already run the growth playbook. “As we enter a new growth phase, it’s the right time to add a seasoned leader to our executive team that has experience with rapidly scaling businesses.”

What TrojAI sells

TrojAI’s platform red-teams AI models at build time (poisoning, evasion, Trojan-style attacks on training data and models) and defends applications at runtime. Hazard’s board comment pointed to production deployments that include “one of the largest financial services companies in the world” — the kind of reference enterprise security buyers actually care about.

BetaKit places the company in a 2019 Saint John founding, a prior ~$3 million seed in 2022, Vector Institute’s AI startups-to-watch list, and Google’s 2023 Canadian startup accelerator. The new money is earmarked for product, sales, marketing, and the U.S. beachhead.

Why Saint John still matters

New Brunswick’s cybersecurity story is usually told as a Fredericton tale — Q1 Labs, UNB’s institute, the cluster that followed. TrojAI is the Saint John counterweight: UNB Saint John roots, a judo-mat founding partnership between Stewart and co-founder Stephen Goddard, and a product category (securing models, not just networks) that did not exist when the last generation of NB security exits happened.

Raising with U.S. and national funds while keeping HQ in the port city is the bet. The next milestone to watch is whether Boston sales capacity converts that financial-services logo into a broader enterprise roster — without hollowing out the team that built the product here.

Sources

• TrojAI Raises $5.75M in Seed Funding to Secure AI in the Enterprise — company CNW release (investors, Weiner bio, Stewart quote, Boston office)
• With $7.75 million CAD, new CEO, Boston office, TrojAI looks to expand — BetaKit (CAD conversion; prior seed; Vector/Google context)
• Saint John Region Headquartered AI Security Company Continues to Expand — Envision Saint John (founders, local footprint)