Investing in Adaptive Security to safeguard against deepfakes and new threats

Nick Sands

Director, Citi Ventures

Max Mailman

Assistant Vice President, Citi Ventures

Adaptive Security Logo

Key Highlights

  • Citi Ventures is investing in Adaptive Security, a cutting-edge platform using employee training and phishing simulations to safeguard organizations against emerging AI-driven cyber threats like deepfakes.
  • With deepfake attacks costing organizations over $105,000 on average, Adaptive Security mitigates significant financial and reputational risks posed by new AI-generated threats.
  • Founded in 2024, Adaptive Security already serves over 500 clients, including PayPal, Xerox and the National Hockey League, and recently launched new voice and video deepfake phishing simulation modules.

AI agents have the power to dramatically change how we interact with the world. With commercial and consumer use cases that range from banking to shopping, we could be entering a new era of innovation where many of our day-to-day activities are touched by an agent. However, this same technology can be used by bad actors to generate sophisticated threats. Enter the dark world of deepfakes. With LLMs, data on an individual can be collected faster than ever before and synthesized into compelling deepfakes.

At the heart of this agentic paradigm is Adaptive Security, a cutting-edge security awareness training and phishing simulation platform. Founded in 2024, Adaptive Security equips organizations with a sophisticated toolkit to train employees to identify and act against this next wave of AI-related cyber threats.

The rise of AI threats and Adaptive Security's proactive defense

Digital transformation and the widespread adoption of AI have led to an explosion of proprietary corporate data and new attack vectors. Since ChatGPT's release, phishing attacks have surged, with the average deepfake attack costing organizations over $105,000.

AI deepfakes fully emerged in 2024, with one notable attack costing a design and engineering firm $25 million. Since then, deepfakes have extended into the voice and text messages realm, with AI agents authoring posts to mimic government officials including U.S. Secretary of State Marco Rubio.

It has never been more urgent for companies to train employees on how to identify deepfakes, which is why we are so excited about our investment in Adaptive Security.

Adaptive Security’s product suite

Adaptive Security takes a three-pronged approach to help organizations deal with this new threat: security awareness training; voice, SMS and email phishing simulations; as well as automated risk scoring and threat remediation.

For training, the company offers more than 200 interactive security demonstrations, delivered via the Adaptive web application, or directly to an organization’s Learning Management System (LMS). The modules are customizable using multi-modal language modules so each training can be tailored to the organization’s business processes.

For phishing simulations, the platform has the capability of launching smishing (text/SMS phishing), email spear phishing, voice and video agents. These channels offer two benefits: identifying weak areas in enterprise defenses and training employees to better identify deepfakes.

Visionary leadership team

Adaptive Security is led by an experienced and successful team. CEO Brian Long and CPO Andrew Jones previously co-founded Attentive, scaling it to a $7 billion valuation with more than $500 million in recurring revenue. Twitter acquired the duo’s first startup, TapCommerce, for approximately $100 million.

Overall, the Adaptive Security team brings extensive go-to-market experience from building Attentive. Brian has nearly two decades of sales experience in media and technology. Since its founding in 2024, Adaptive has quickly and steadily built its fully functional training development platform of security and compliance modules and integrations. They also recently launched modules for voice and video deepfake phishing simulations.

The company counts PayPal, Xerox, Bose, the National Hockey League, the Professional Golfers’ Association, Figma, Ramp, Vimeo, TaylorMade Golf and Perplexity, among others, as customers. Adaptive Security currently has more than 500 customers.

The road ahead

We are excited about the future for Adaptive Security. The company’s remarkable momentum in product innovation, product development and customer acquisition underscores its vital role in securing enterprises in the AI era.

For more information, email Nick Sands at nick.sands@citi.com or Max Mailman at max.mailman@citi.com.

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