Adaptive Security Raises $81 Million In Series B Funding Round

Adaptive Security raised $81 million in a Series B round, bringing the company’s total funding to approximately $146.5 million. The round was led by Bain Capital Ventures, with significant participation from NVentures (NVIDIA’s venture arm), alongside Capital One Ventures and Citi Ventures.

Adaptive Security’s $81 million Series B round represents a significant milestone for the New York-based cybersecurity firm, specializing in preventing AI enabled social engineering attacks. The funding comes at a time when organizations face escalating risks from deepfakes, generative AI phishing, and multi channel scams, with the company emphasizing tools like interactive training modules, personalized simulations, and human risk monitoring. CEO Brian Long, a serial entrepreneur with a prior $10 billion exit from Attentive, highlighted the need to outpace AI attackers by expanding engineering teams and enhancing platform capabilities.

The investor lineup combines tech giants and financial institutions, signaling confidence in Adaptive Security’s approach to blending AI offense and defense. Bain Capital Ventures, as the lead, brings expertise in enterprise software scaling, while NVentures underscores NVIDIA’s interest in AI security applications. Capital One Ventures and Citi Ventures add financial sector insights, likely drawn to the platform’s relevance for protecting against impersonation in banking and payments. Returning investors like OpenAI Startup Fund, marking their first cybersecurity bet, and a16z provide continuity from the Series A, where OpenAI’s involvement highlighted synergies in countering AI misuse.

This round could enable Adaptive Security to expand its customer base, which already includes firms like Podium, NerdWallet, Lennar, Plaid, and Ramp, by investing in features such as custom AI deepfake personas and tailored phishing fail pages. In a broader sense, it highlights the cybersecurity market’s shift toward proactive, AI augmented defenses, with potential for increased valuations in similar startups amid debates over AI’s dual role in threats and solutions. While exact valuation details remain undisclosed, the funding suggests strong growth momentum, though challenges like evolving threat landscapes may require ongoing innovation.

Adaptive Security, a New York City-headquartered cybersecurity firm founded by CEO Brian Long, has solidified its position in the emerging field of AI powered threat prevention with its recent $81 million Series B funding round. This investment builds on the company’s prior fundraising efforts and underscores the escalating demand for solutions that address human vulnerabilities in an era dominated by generative AI and deepfake technologies. Long, who previously founded and scaled Attentive to over $500 million in annual revenue and a $10 billion valuation before its acquisition, brings proven entrepreneurial experience to Adaptive Security, focusing on tools that train employees to recognize and mitigate sophisticated social engineering attacks.

The Series B was led by Bain Capital Ventures (BCV), a firm renowned for backing transformative enterprise software companies, and featured new strategic investors including NVentures, the venture capital arm of NVIDIA, as well as Capital One Ventures and Citi Ventures. These additions complement the ongoing participation from earlier backers such as the OpenAI Startup Fund, Andreessen Horowitz (a16z), and Abstract Ventures, creating a robust syndicate that blends AI expertise, financial acumen, and venture scaling know-how. With this infusion, Adaptive Security’s total capital raised now stands at around $146.5 million, positioning it to accelerate product innovation and market expansion in a cybersecurity landscape increasingly threatened by AI driven impersonation and phishing schemes.

Company Background and Product Evolution

Established to combat the rise of AI fueled cyber threats, Adaptive Security offers a suite of next generation security awareness tools designed to fortify organizational defenses at the human level. Core offerings include interactive training modules on security, compliance, and AI specific risks; hyper realistic phishing simulations across email, phone, and SMS channels; and dynamic human risk monitoring with personalized remediation. Recent releases, such as custom AI deepfake personas and customizable phish fail pages, demonstrate the company’s agility in adapting to evolving threats like voice cloning and generative AI content creation. By leveraging open source intelligence (OSINT) and AI personas, the platform delivers role specific, hyper personalized experiences that go beyond traditional security training, aiming to build lasting behavioral changes among employees.

The company’s trajectory began with a Series A round in April 2025, initially raising $43 million co-led by a16z and Abstract Ventures, which was later extended to $55 million with additional investment from the OpenAI Startup Fund, marking OpenAI’s inaugural foray into cybersecurity. This earlier funding fueled initial scaling, including engineering hires and platform enhancements, setting the stage for the Series B. Adaptive Security’s customer roster, featuring high profile names like Plaid, Ramp, and Lennar, illustrates its appeal to tech forward enterprises grappling with AI risks.

Funding History and Capital Allocation

Adaptive Security’s funding progression reflects rapid growth in investor confidence amid a booming cybersecurity market projected to exceed $200 billion globally by 2025, with AI related segments expanding even faster. The Series B proceeds are earmarked for expanding the engineering team, enhancing AI driven features, and broadening market reach to counter threats like deepfake executive impersonations and multi vector social engineering. CEO Long emphasized using the capital to “move faster” in staying ahead of adversaries who increasingly weaponize AI tools for attacks.

This table captures the company’s fundraising milestones, though early seed details, if any, are not publicly detailed in available sources. The escalation from Series A to B in under a year suggests strong performance metrics, such as customer adoption and revenue growth, though specific financials like annual recurring revenue (ARR) remain undisclosed.

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Investor Syndicate Analysis

The investor group assembled for this round combines strategic and financial firepower, potentially unlocking partnerships and technological synergies. Bain Capital Ventures, with its track record in cybersecurity (e.g., investments in similar human focused security firms), provides operational guidance for scaling enterprise sales. NVentures’ involvement aligns with NVIDIA’s push into AI applications, offering access to advanced GPU resources for training deepfake detection models. Financial backers like Capital One and Citi Ventures bring domain expertise in fraud prevention, where AI impersonation poses acute risks to banking operations.

Returning investors add continuity: OpenAI’s Startup Fund, having led the Series A extension, signals belief in Adaptive’s role in mitigating AI harms, such as those from tools like ChatGPT in phishing campaigns. a16z and Abstract Ventures, early supporters, have a history with Long from his Attentive days, fostering long term alignment.

This table outlines the syndicate’s composition, emphasizing how each investor could contribute beyond capital.

The funding arrives amid heightened awareness of AI’s dual edged impact on cybersecurity: while tools like deepfakes enable sophisticated attacks, they also power defenses. Industry reports indicate social engineering accounts for over 90% of successful breaches, with AI amplifying scale and realism, e.g., cloned voices tricking employees into unauthorized actions. Adaptive Security differentiates through its AI Content Creator for rapid module customization and multi channel simulations, contrasting with legacy players focused on basic phishing tests.

Comparatively, peers like Oleria Security ($8 million seed in 2023 for adaptive access) or Bonfy.AI ($9.5 million seed in 2025 for content security) have raised smaller amounts, suggesting Adaptive’s larger rounds reflect its traction. Broader trends show cybersecurity funding surging, with firms like Illumio ($100 million Series C in 2015 at $1 billion valuation) and Snyk ($200 million in 2020) paving the way for AI centric innovators. However, debates persist on AI’s net effect, some argue it democratizes attacks, while others see it as a force multiplier for defenses, with Adaptive leaning toward the latter through ethical AI use.

Looking ahead, the funding could propel Adaptive Security toward greater market share, potentially through acquisitions or international expansion, as global regulations like those on deepfakes tighten. Challenges include keeping pace with AI advancements (e.g., models passing Turing tests at 73% efficacy) and addressing ethical concerns around OSINT usage in training. Long’s advice to delete voicemails to prevent cloning exemplifies practical, immediate strategies the company promotes. Overall, this round positions Adaptive Security at the forefront of a critical intersection between AI innovation and security resilience, with potential for substantial returns if it navigates the complex threat environment effectively.

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