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Gray Swan

Real-time AI risk detection and protection

Head of Cyber Safety

Full-TimeUpdated on 10/23/2026
$230k - $280k/yr+ Performance-based bonus + Equity package
Expert
Remote in USA
RemoteRemote work is limited to the United States. U.S. only
CybersecurityOffensive Security & Testing
H1B Sponsorship Available

About the job

Requirements
  • Deep technical expertise in offensive cybersecurity, vulnerability research, exploit development, penetration testing, malware analysis, reverse engineering, or a closely related field through industry, research, or equivalent experience.
  • Significant experience assessing advanced cyber threats, offensive tooling, or AI-enabled cyber capabilities, especially in critical infrastructure domains.
  • Hands-on experience conducting adversarial evaluations, AI red-teaming, LLM security research, or building evaluation datasets for frontier AI systems.
  • Comfort operating at the intersection of cybersecurity research, AI safety, and machine learning engineering.
Responsibilities
  • Design and lead adversarial evaluations of frontier large language models for offensive cyber capabilities, including vulnerability discovery, exploit development, malware generation, privilege escalation, social engineering, persistence, and autonomous cyber operations across text, agentic, and multimodal systems.
  • Partner closely with machine learning engineers to translate cybersecurity expertise into scalable benchmarks, classifiers, guardrails, automated detection systems, and evaluation infrastructure for internal products and frontier AI lab deployments.
  • Develop and maintain Gray Swan’s catastrophic cyber harm taxonomy, continuously evolving cyber evaluation frameworks as frontier model capabilities advance.
  • Produce technical risk assessments and actionable recommendations for frontier AI labs, enterprise customers, and internal stakeholders to guide responsible model deployment and security mitigations.
  • Build, mentor, and lead a team of cybersecurity subject matter experts while establishing scalable evaluation processes, quality standards, and technical infrastructure.
  • Represent Gray Swan as the company's cybersecurity authority, collaborating with frontier AI labs, security researchers, government partners, and the broader AI safety and cybersecurity communities.
Desired Qualifications
  • Experience developing machine learning models, AI security classifiers, or automated cyber detection systems.
  • Hands-on experience red-teaming frontier language models, jailbreaking, prompt injection research, or agentic AI evaluations.
  • Experience working with frontier AI labs, national security organizations, or leading cybersecurity research teams.
  • Background in threat intelligence, autonomous cyber operations, AI agent security, or AI governance.
  • Strong software engineering experience in Python, Go, Rust, or other systems programming languages.

About the company

Gray Swan AI develops security solutions for AI deployments to identify, manage, and reduce risks in AI models. Core products include Cygnal, which filters inputs and outputs to prevent harmful or unintended model behavior; Shade, which analyzes models and simulates attacks to uncover weaknesses; and Cygnet, a safety-focused enterprise language model. The tools integrate with existing systems with minimal performance impact, providing real-time monitoring and protection across the AI deployment lifecycle. The goal is to help organizations deploy reliable, compliant, and safe AI by reducing the chances of harmful behavior and misuse.

Company Size

51-200

Company Stage

Series A

Total Funding

$40M

Headquarters

Pittsburgh, Pennsylvania

Founded

2023

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Simplify's Take

What believers are saying

  • May 28, 2026 Series A raised $40 million from Wing and Madrona.
  • August 2026 Arena challenge drew UK AISI, Google DeepMind, Meta, and Amazon sponsors.
  • Rob Jenks joined January 8, 2026, strengthening partnerships and enterprise go-to-market execution.

What critics are saying

  • OpenAI, Anthropic, and Meta can build native guardrails, compressing Gray Swan by 2027.
  • Cybercompanyprofiles lists only verified frontier-lab traction; public enterprise revenue remains undisclosed.
  • If Arena-driven data stops differentiating, Gray Swan becomes another crowded LLM guardrails vendor.

What makes Gray Swan unique

  • June 2026 Series A and Snowflake integration place Gray Swan inside enterprise AI stacks.
  • Gray Swan sits in 11 frontier-model system cards from Anthropic, OpenAI, and Meta.
  • Arena’s 15,000 researchers generate attack data that trains Cygnal and Shade.

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Benefits

  • Health Insurance
  • Dental Insurance
  • Vision Insurance
  • Paid Vacation
  • Paid Holidays
  • Flexible Work Hours
  • 401(k) Company Match
  • Meal Benefits

Growth & Insights and Company News

Headcount

6 month growth

46%

1 year growth

33%

2 year growth

46%
Fortune
Oct 21st, 2026
Gray Swan relaunches AI red-teaming Arena with $300K prize challenge for agents

Gray Swan, a Pittsburgh-based AI security startup that stress-tests models for Anthropic, OpenAI, and Google DeepMind, has relaunched its public red-teaming platform, Arena, for the era of AI agents. Alongside Arena 2.0, it is running its largest contest yet: Indirect Prompt Injection (IPI) Black, with $300,000 in prizes sponsored by Anthropic, Meta, Google DeepMind, and Reflection AI. New attack scenarios will be released weekly through November 2. In such attacks, hackers hide instructions in content an agent encounters, such as a web page, hoping to hijack it. Sandbox environments let participants test safely. When Arena launched in September 2024, most AI applications were chatbots that were easier to jailbreak. "It's not chatbots anymore," said chief executive officer Matt Fredrikson.

Fortune
Oct 20th, 2026
Gray Swan relaunches AI red-teaming Arena for agents with $300K prize contest

Gray Swan, a Pittsburgh-based AI security startup that stress-tests models for Anthropic, OpenAI, and Google DeepMind, has relaunched its public red-teaming Arena for the era of AI agents. Participants compete for prize money by trying to trick AI models into breaking their guardrails. Alongside Arena 2.0, the company is running its largest contest yet, Indirect Prompt Injection (IPI) Black, with $300,000 in prizes sponsored by Anthropic, Meta, Google DeepMind, and Reflection AI. New attack scenarios will be released weekly through November 2. Chief executive officer Matt Fredrikson said the work now needs more technical skill, as AI systems have moved from chatbots to agents. The new Arena adds beginner challenges, training certificates, and a route for top performers to join real-world testing work. In May, Gray Swan announced a $40 million Series A round co-led by Wing Venture Capital and Madrona. Staff grew from about 15 to 66 this year.

Alabama Cultural Times
Oct 20th, 2026
Gray Swan launches redesigned Arena platform with $300K challenge to find the next generation of AI Red teamers.

Gray Swan launches redesigned Arena platform with $300K challenge to find the next generation of AI Red teamers. New adversarial testing experience makes AI red teaming more accessible to people of all backgrounds as Gray Swan and leading AI labs offer largest-ever prize pool. PITTSBURGH, Oct. 20, 2026 (GLOBE NEWSWIRE) - Gray Swan, the leader in AI safety and security solutions, today launched new enhancements to the Arena, its global adversarial testing and red-teaming platform, making it easier for anyone, from experienced security researchers to first-time AI red teamers, to test the limits of the frontier labs' most advanced AI models. Gray Swan's Arena is the world's largest AI red-teaming community, comprised of more than 15,000 AI enthusiasts and practitioners from around the world who test AI systems to uncover new vulnerabilities and failure modes before nefarious actors can exploit them in the wild. Through competitive challenges, participants identify weaknesses in frontier AI models, helping developers build safer, more robust systems while earning prizes and building careers in AI security. Gray Swan closely partners with the largest frontier labs, including Anthropic, Google DeepMind, OpenAI, Meta, Amazon, UK AI Security Institute, and the National Institute of Standards and Technology's (NIST) Center for AI Standards and Innovation (CAISI), among other sponsors, to anonymously test models and ultimately improve AI safety. "Understanding the safety and security of AI systems is hugely important today, and it shouldn't be left to a small circle of specialists," said Matt Fredrikson, co-founder and CEO of Gray Swan. "Some of the most unexpected vulnerabilities are uncovered by people who don't fit the traditional security researcher mold. The Arena levels the playing field, opening the door for anyone to learn and compete while uncovering valuable insights into where AI systems fail so that we can all work towards deploying AI safely and securely." Opening AI Red-Teaming to a Broader Community The new Arena experience lowers the barrier to AI red-teaming through a more intuitive, game-like environment designed for participants across skill levels and backgrounds. Novice red teamers can learn and practice alongside experienced researchers, while people from creative and nontraditional backgrounds can bring new approaches to uncovering AI vulnerabilities that conventional security testing may miss. Additional opportunities and enhancements of the Arena include: * More ways to learn and compete: Beginner-friendly and ongoing challenges give participants opportunities to practice breaking AI systems even when major competitions aren't live. * Credentials to demonstrate skills: Training certificates allow participants to showcase their AI red-teaming capabilities as they build experience. * A path to professional red teaming: Top Arena performers may be invited to join Gray Swan's red-teaming community and support real-world AI testing engagements. * A global community: Participants can connect with more than 15,000 hackers, researchers, and AI security and safety practitioners through the Arena and Gray Swan's Discord community. Alongside the launch of its newly designed Arena, Gray Swan is announcing a competition - Indirect Prompt Injection (IPI) Black - its largest Arena challenge to date, with $300,000 in prizes sponsored by Anthropic, Meta, Google DeepMind, and Reflection AI. The competition will challenge participants to uncover indirect prompt injection (IPI) vulnerabilities across a series of new scenarios released each week. From Competition to AI Safety Research Findings from the Arena challenges also extend beyond the competitions themselves. Gray Swan uses data generated through the Arena to develop benchmarks and evaluations that help researchers understand emerging AI risks and assess the safety and security of new models. Gray Swan's research and benchmarks have been cited in new system cards and model launch materials from leading frontier AI labs. Insights from the Arena also power Gray Swan's enterprise AI security platform. Shade uses emerging attack techniques from the Arena to continuously test AI systems for vulnerabilities, while also generating its own multi-turn attack techniques based on insights from its training data. Cygnal uses those insights to detect and block attacks at runtime, enforcing policies that keep AI systems operating within defined boundaries. Together, the Arena, Shade and Cygnal create a continuous feedback loop between discovering vulnerabilities, testing enterprise AI systems against emerging threats and enforcing safe AI behavior in production, regardless of whether organizations deploy proprietary frontier models or open-weight models. Join the Arena Community Between October 15, 2026, and November 5, 2026, Gray Swan will run its IPI Black challenge, releasing a new wave of scenarios each week and giving participants repeated opportunities to anonymously test new models, uncover vulnerabilities, and compete for prizes. Participants must be 18 years of age or older. Additional eligibility requirements apply. For complete eligibility requirements and competition rules, visit https://app.grayswan.ai/arena/about. To participate in Gray Swan's latest IPI Black challenge, practice breaking AI models and join Gray Swan's global red-teaming community, please visit the Gray Swan Arena. About Gray Swan Gray Swan is empowering the world to use AI safely and securely. Founded by leading AI security researchers from Carnegie Mellon University, the company provides automated adversarial risk assessment, continuous red-teaming, and runtime AI security monitoring and protection. Gray Swan is trusted by the world's leading AI labs and enterprises to deploy AI with confidence. The company is headquartered in Pittsburgh, PA. Learn more at grayswan.ai. Legal Disclaimer: EIN Presswire provides this news content "as is" without warranty of any kind. Alabama Cultural Times do not accept any responsibility or liability for the accuracy, content, images, videos, licenses, completeness, legality, or reliability of the information contained in this article. If you have any complaints or copyright issues related to this article, kindly contact the author above.

AltaWorld
Jun 1st, 2026
Gray Swan secures $40M Series A to strengthen enterprise AI security.

Gray Swan secures $40M Series A to strengthen enterprise AI security. Published in: News Gray Swan, an AI security company emerging from Carnegie Mellon University's AI safety research programme, has raised $40m in a Series A funding round to expand its mission of delivering advanced security solutions for enterprise AI deployments. The funding round was co-led by Wing Venture Capital and Madrona, with participation from Obvious Ventures, Snowflake Ventures, Hudson River Trading, Samsung Next, and existing investor Magarac Venture Partners. The company plans to use the new capital to accelerate go-to-market initiatives, strengthen partnerships with leading AI laboratories, and expand its team to support organisations adopting AI at scale while maintaining robust security standards. Gray Swan has established itself as a prominent security evaluation provider for advanced AI models. The company has been referenced in 11 recent frontier-model system cards, including those released by Anthropic, OpenAI, and Meta. Its benchmarking capabilities are integrated into safety assessment processes used before public deployment of these models, reflecting a level of trust and access that the company says is unmatched across multiple frontier AI labs. The company was founded on the belief that every AI deployment should be treated as a potential attack surface until proven secure. As AI agents increasingly move from experimental environments into production systems - where they access enterprise data, automate workflows, and make autonomous decisions - security risks such as prompt injection, jailbreak attempts, and data exfiltration have become practical operational challenges. At the same time, evolving global regulations have increased the importance of implementing strong AI security controls before deployment. Gray Swan was founded by Matt Fredrikson and Zico Kolter, researchers who have spent more than a decade studying adversarial AI failures and methods for preventing them. As AI adoption expanded from academic research into enterprise infrastructure, they identified a significant gap between existing security research and commercially available solutions. Gray Swan was created to bridge that divide. Today, the company serves more than 20 customers, including frontier AI laboratories and global enterprises, and has formed a strategic partnership with Snowflake. Through this collaboration, Gray Swan's runtime AI protection capabilities are natively integrated into Snowflake's AI ecosystem, allowing organisations to incorporate security measures directly into the environments where they develop and scale AI applications. The Gray Swan platform consists of three core offerings. Cygnal delivers real-time monitoring and protection by enforcing organisation-specific security policies with minimal latency. Shade functions as an automated red-teaming solution, conducting adversarial testing across AI models and agents throughout pre-deployment and CI/CD workflows to identify vulnerabilities before production release. Arena, meanwhile, operates as a continuous global competition involving more than 15,000 researchers and security professionals who probe AI systems for weaknesses. Collectively, the platform generates over one million real-world attack trajectories, providing valuable training data that enhances the effectiveness of both Cygnal and Shade in detecting and mitigating emerging AI security threats.

FinTech Global
Jun 1st, 2026
Gray Swan raises $40m to secure AI at the frontier.

Gray Swan raises $40m to secure AI at the frontier. June 1, 2026 Gray Swan, an AI security company founded out of Carnegie Mellon University's AI safety research programme, has raised $40m in a Series A funding round as it moves to bring frontier-grade security to enterprise AI deployments. The round was co-led by Wing Venture Capital and Madrona, with additional backing from Obvious Ventures, Snowflake Ventures, Hudson River Trading, Samsung Next, and existing investor Magarac Venture Partners. The capital will be used to accelerate Gray Swan's go-to-market operations, deepen its relationships with leading AI labs, and grow the team supporting organisations seeking to deploy AI rapidly without undermining security. Gray Swan has positioned itself as the go-to security evaluator for the world's most advanced AI models, having been cited in 11 recent frontier model system cards, including those published by Anthropic, OpenAI, and Meta. Its benchmarks are embedded into safety evaluation processes for these models before they are released publicly - a level of access and trust the company says no other AI security provider holds across multiple leading frontier labs simultaneously. The business was built on the premise that every AI deployment represents an open attack surface until proven otherwise. As AI agents have moved from experimental tools into production environments - accessing enterprise data, executing workflows, and making decisions autonomously - threats such as prompt injection, jailbreaks, and data exfiltration have become operational concerns rather than theoretical ones. Tightening global regulation has further raised the cost of deploying AI without appropriate security measures in place. Gray Swan was founded by Matt Fredrikson and Zico Kolter, two researchers who spent more than a decade studying how AI systems fail under adversarial conditions and how those failures can be prevented. As AI adoption moved from the research environment into enterprise infrastructure, the pair identified a significant gap between what their research had uncovered and what was commercially available to address it. Gray Swan was built to close that gap. The company currently works with more than 20 customers spanning frontier labs and global enterprises, and has established a partnership with Snowflake. As part of that arrangement, Gray Swan's runtime AI protection is natively integrated into Snowflake's AI ecosystem, enabling enterprises to embed the company's security capabilities directly into the platform where they build and scale AI applications. Gray Swan's platform is built around three core components. Cygnal provides real-time monitoring and protection, enforcing custom policies tailored to the specific risks an organisation faces, and operates continuously with low latency. Shade is an automated red-teaming agent that runs adversarial tests against AI models and agents throughout the pre-deployment process and the CI/CD pipeline, surfacing vulnerabilities before they reach production. Arena is a continuous global competition drawing more than 15,000 researchers and security professionals who attack AI models to expose weaknesses. The platform generates more than one million real-world attack trajectories, which are used to train the models underpinning both Cygnal and Shade. Gray Swan chief scientist and co-founder Zico Kolter said, "AI applications are growing at an unprecedented rate, and at Gray Swan we want to ensure that these deployments can continue without sacrificing reliability and security. We have spent our careers conducting research into the safety of AI systems, and we are putting this into practice to ensure the companies can deploy AI with confidence." Gray Swan CEO and co-founder Matt Fredrikson said, "AI is moving faster than any technology we've seen, and security hasn't kept pace. Our mission is to empower the world to use AI safely and securely, and this funding lets us pursue the mission on pace with the frontier. Our partnership with Snowflake is a perfect example: bringing the same security trusted by frontier labs to the platform where enterprises are already building on their data." Enjoying the stories? Investors. The following investor(s) were tagged in this article.