About Gray Swan

Gray Swan is on a mission to empower the world to use AI safely and securely. We evaluate AI models for the leading frontier labs while building real-time threat detection and adaptive adversarial red teaming agents for teams deploying AI.

We’re a team of approximately 50 people, well-funded, and growing quickly. Our work directly influences how the world deploys AI agents and systems at scale.

Learn more about how we work

The Role

We’re looking for a Senior Technical Recruiter to own recruiting across Gray Swan’s technical organization, spanning Software Engineering, Infrastructure, AI/ML, Security, Research, and other emerging technical functions.

This is a high-ownership role for someone who can operate as both a strategic talent partner and hands-on technical recruiter. You’ll work closely with engineering and technical leadership to define what great looks like, develop hiring strategies, map highly competitive talent markets, and personally execute searches from first outreach through close.

We’re looking for someone who is a doer. You’ll source, screen, build pipelines, close candidates, analyze recruiting data, and solve problems when searches aren’t working. You should be equally comfortable partnering with an engineering leader on a difficult hiring decision and spending the afternoon personally sourcing exceptional engineers.

What You’ll Do

• Own full-cycle technical recruiting from role definition and talent mapping through sourcing, assessment, offer strategy, and close.

• Partner with engineering and technical leadership as a trusted talent advisor, helping define profiles, understand the market, calibrate on talent, and make better hiring decisions.

• Recruit across highly technical functions including Software Engineering, Infrastructure, AI/ML, Security, Research, and technical customer-facing roles.

• Build exceptional passive talent pipelines through creative sourcing, market research, networking, targeted outreach, and referrals.

• Develop a deep understanding of technical talent markets and proactively identify candidates who may not be actively looking.

• Recruit and close highly sought-after technical candidates, developing compelling pitches, understanding candidate motivations, navigating objections, and competing effectively for top talent.

• Coach and challenge hiring teams on technical profiles, interview processes, candidate calibration, and hiring decisions.

• Partner with engineering leaders to improve technical interview design, scorecards, calibration, and debrief processes.

• Use recruiting data and market intelligence to understand pipeline health, conversion rates, sourcing effectiveness, time-to-fill, and offer acceptance, and adjust strategy accordingly.

• Manage multiple high-priority technical searches simultaneously while maintaining a high bar for candidate quality and experience.

• Deliver an exceptional candidate experience that is thoughtful, responsive, rigorous, and highly personal.

• Help build recruiting infrastructure and processes that can scale as Gray Swan grows.

Who You Are

• 5+ years of full-cycle recruiting experience, with significant experience recruiting technical talent.

• A strong track record recruiting software engineers and other highly technical candidates in competitive markets.

• Experience recruiting for a high-growth startup, ideally at an early-stage or pre-IPO company.

• Experience partnering directly with engineering leaders, technical executives, and hiring managers.

• Strong technical sourcing instincts—you enjoy the hunt and know how to identify exceptional engineers beyond the obvious candidate pools.

• The ability to understand technical roles well enough to effectively source, assess, calibrate, and sell candidates, without needing to be an engineer yourself.

• A track record of identifying, engaging, and closing passive technical candidates.

• The confidence and judgment to coach hiring teams and push back when a profile, process, or hiring decision needs to change.

• High ownership and the ability to make decisions and move work forward without waiting for direction.

• Strong operational discipline and comfort managing multiple high-priority searches simultaneously.

• A data-driven approach to recruiting and the ability to diagnose why a search isn’t working and adjust quickly.

• A builder mentality. You’re energized by creating and improving recruiting processes rather than simply operating within established ones.

• Curiosity about AI and AI security. You don’t need to be an AI expert, but you should be excited to learn about our technology, understand our technical teams, and become fluent in the markets we recruit from.

Bonus Points If You Have

• Experience recruiting technical talent at an early-stage or rapidly scaling startup, where you helped build the recruiting function while actively hiring.

• Experience recruiting within AI, cybersecurity, developer tools, enterprise software, infrastructure, or another highly technical market.

• Experience hiring across a range of technical profiles, from software engineers and infrastructure engineers to security engineers, ML/AI engineers, and research-oriented technical talent.

• Experience recruiting for highly competitive or niche technical talent markets.

• Experience using AI and recruiting technology to improve sourcing, market mapping, candidate engagement, or recruiting operations.

• Experience building technical recruiting strategies from scratch, including talent mapping, sourcing strategy, interview processes, and recruiting metrics.

If you don’t have 100% of these, you should still seriously consider applying. We care more about what you can do than your credentials.

You’ll Thrive Here If You

• You’re an owner and a doer. You can advise an engineering leader on talent strategy in the morning and spend the afternoon personally sourcing the engineers you believe they should meet.

• You have a point of view and aren’t afraid to use it. You’ll challenge an unrealistic technical profile, push for a faster decision, or recommend changing course when the market tells us something isn’t working.

• You move with urgency, hold a high bar, and care more about building an exceptional technical team than simply filling roles.

• You’re excited by difficult searches. When the obvious candidates have already been contacted, you want to figure out where the next great candidate is hiding.

• If you want meaningful ownership over how Gray Swan builds its technical organization, we’d love to meet you.

What We Offer

We offer a competitive compensation package designed to reward impact and incentivize growth. Our compensation philosophy is informed by our current valuation and recent industry data. Compensation: $122,500 - $185,000 plus performance-based bonus and meaningful equity package

Benefits:

• 401k with up to 4% matching

• 28 days annual leave (vacation + holidays)

• Health, dental, and vision coverage

• Catered lunches (Pittsburgh office)

• Flexible work arrangements

• Visa sponsorship available for exceptional candidates\

Interview Process

🔎 Application Review — We read everything and will respond within 10 days.

🗣 Recruiter Screen — We learn about you; you learn about us.

🧑‍💻 Hiring Manager Screen — Meet with the hiring manager and dive deeper into your technical recruiting experience.

🗣 Virtual Onsite Interview — Meet members of the team and learn more about how we work.

😇 Reference Checks — We’ll reach out to 3–5 references that you provide.

📃 Offer — If it’s mutual, we move fast.