Role Description The Senior Application Security Tester & AI Red Team Subject Matter Expert is a senior-level offensive security role for a tester who has mastered modern web and API security and is now defining how Evolve Security tests AI-enabled applications, large language models, and agentic systems. This role wears two hats: - Hands-on senior application penetration tester for our most complex client engagements. - Firm-wide subject matter expert who builds, scales, and represents Evolve Security’s AI red team practice. The senior tester executes assessments with full autonomy, owns the technical relationship with client security and engineering leadership, mentors mid-level engineers and OSOC analysts, and is the recognized internal authority on offensive AI/ML testing methodology, tooling, and threat modeling. Qualifications - 5–8+ years of offensive security experience with a deep concentration in web application and API penetration testing. - Demonstrable hands-on work testing AI/ML systems — LLM-backed applications, RAG pipelines, fine-tuned models, multi-agent systems, or production ML inference. - A track record of dozens of completed assessments, published research, conference talks, CVEs, or open-source contributions. Requirements - Mastery of web application and API security beyond the OWASP Top 10. - Fluency in OWASP Top 10 for LLM Applications and OWASP ML Top 10. - Expert with the modern offensive toolchain — Burp Suite Pro, OWASP ZAP, Nuclei, Postman, Nmap, Metasploit, BloodHound. - Strong scripting and small-tool development in Python, with working knowledge of JavaScript / TypeScript, Bash, and PowerShell. - Excellent written and verbal communication skills. - Preferred certifications: OSWE, OSCP, OSEP, GWAPT, GXPN, Burp Suite Certified Practitioner. Benefits - Healthcare Benefits - 401(k) Match - Parental Leave - Flexible Paid Time Off - Annual vacation reimbursement Company Description Evolve Security is a cybersecurity services firm headquartered in Chicago, IL. We are dedicated to improving our client’s security posture by providing continuous penetration testing, training services, and talent solutions. - Offers a cybersecurity bootcamp, “Evolve Academy”, currently ranked the #1 cybersecurity bootcamp in the world. - Provides immersive training, giving students the concrete and practical skills needed on the job. - Students gain real work experience through live security assessment work that they perform on not-for-profit companies. - Passionate about directly improving our customers’ security posture and training others to help meet the need for qualified cybersecurity talent.

• Ensono is building a new portfolio of Managed AI Services, and we need a Product Architect to design the technical foundation. This is a senior, hands-on role where you'll architect how our AI services are built, integrated, and delivered to enterprise clients. • You'll work at the intersection of cloud platforms, AI/ML technologies, and managed services operations—designing solutions that integrate third-party AI capabilities (Azure OpenAI, AWS Bedrock, etc.) into scalable, secure, enterprise-grade managed offerings. • This isn't about building AI models from scratch; it's about architecting the infrastructure, integrations, and operational frameworks that allow Ensono to deliver AI services reliably to clients. • This is not a client-facing role, but at times you'll engage with customers to understand their needs, translate those into technical architectures, and collaborate closely with Security, the CTO office, and Operations to ensure our services are production-ready.

• Design and curate upper-undergraduate and graduate-level Biology problems with clear, fully worked solutions. • Create challenging, realistic tasks that expose failure modes in frontier AI systems. • Convert diagram-heavy or multi-part biology questions into self-contained, text-only problems with definitive answers. • Write rigorous explanations and verify scientific accuracy throughout the problem and solution. • Evaluate AI-generated responses, diagnose errors, and refine questions to meet difficulty targets. • Review Biology tasks created by others and improve clarity, correctness, and realism. • Collaborate with cross-functional teams to maintain consistent standards across large task batches.

• Design and solve challenging Maths problems to probe the limitations of large language models. • Create clear, high-quality, step-by-step solutions with well-articulated reasoning. • Collaborate with LLM researchers to align problems with evaluation goals, especially in areas where models struggle (e.g., abstraction, multi-step reasoning, symbolic manipulation). • Help define new evaluation benchmarks based on Mathematics curricula spanning early undergraduate to PhD-level topics.