Evolve Security

• Serve as the primary point of contact for assigned clients throughout active engagements, ensuring clients feel informed, supported, and confident in the delivery process. • Manage client expectations, project scope, communication cadence, timelines, and deliverables in alignment with the Statement of Work. • Own the client communication rhythm, including kickoff calls, status updates, project meetings, follow-ups, closeout conversations, and escalation communication. • Partner closely with security engineers and delivery leaders to help ensure projects are delivered on time, within scope, and with a high-quality client experience. • Build lasting relationships with client stakeholders by learning their business, communication preferences, priorities, and goals. • Identify and escalate risks related to scope, schedule, responsiveness, client satisfaction, delivery expectations, or renewal health. • Support client onboarding and project readiness by ensuring required information, access, documentation, and stakeholder alignment are in place. • Support Quarterly Security Reviews, client check-ins, renewal preparation, and other client success activities as assigned. • Identify opportunities to improve client satisfaction, deepen relationships, and strengthen the overall client journey. • Recognize potential expansion, renewal, or additional service opportunities and communicate those insights to the appropriate internal stakeholders. • Help improve internal processes, communication standards, project quality, and delivery consistency.

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, and the 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.

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.

• Review eASM dashboard daily to monitor for any anomalies or security incidents. • Conduct testing and validation of vulnerabilities identified by the ASM system, providing evidence of validation to support remediation efforts. • Investigate eASM vulnerabilities thoroughly, analyzing potential impact and root causes. • Conduct various types of penetration testing, including scanning and password attacks, to identify potential weaknesses in the system. • Perform technical vulnerability scans and validate remediation efforts to ensure effective security posture. • Escalate identified vulnerabilities and security incidents to appropriate client or internal team members for resolution. • Engage with clients during project kick-off meetings to understand their specific security requirements and objectives. • Assist in maturing eASM Evolve Security processes, procedures, templates, and methodologies to enhance overall effectiveness. • Take on other duties as assigned to support the growth and expansion of enterprise and academy initiatives, contributing to the overall success of the security program.

Role Description Evolve Security is looking for an OSOC Security Analyst to join our growing team. This position will assist with the overall successful delivery of various application vulnerability assessments, continuous internal / external penetration assessments, incident response and detection assessments, and other types of security strategy and architecture reviews. - Review eASM dashboard daily to monitor for any anomalies or security incidents. - Conduct testing and validation of vulnerabilities identified by the ASM system, providing evidence of validation to support remediation efforts. - Investigate eASM vulnerabilities thoroughly, analyzing potential impact and root causes. - Conduct various types of penetration testing, including scanning and password attacks, to identify potential weaknesses in the system. - Perform technical vulnerability scans and validate remediation efforts to ensure effective security posture. - Escalate identified vulnerabilities and security incidents to appropriate client or internal team members for resolution. - Engage with clients during project kick-off meetings to understand their specific security requirements and objectives. - Assist in maturing eASM Evolve Security processes, procedures, templates, and methodologies to enhance overall effectiveness. - Take on other duties as assigned to support the growth and expansion of enterprise and academy initiatives, contributing to the overall success of the security program. - Passionate about cybersecurity with a curiosity to learn. Qualifications - 0-1 years of information technology experience, ideally with a focus on information security. - 0-1 years penetration testing, application and vulnerability management experience through education or security/consulting firm. - Knowledge of multiple operating systems and associated command-line administration tools (Bash / PowerShell). - Knowledge of the application stack including web. - Scripting experience in one or more of: Ruby, Python, Perl, Bash. - ESCP, Security+ certifications. - A desire to tinker and understand how things work. - Ability to interface with clients, utilizing consulting and negotiating skills. - Strongly self-motivated and able to work independently towards team objectives. - Strong communication skills (oral and written) and ability to work as part of a team. 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. - In addition to our professional cybersecurity service offerings, Evolve Security offers a cybersecurity bootcamp, “Evolve Academy”, currently ranked the #1 cybersecurity bootcamp in the world. - The Cybersecurity Bootcamp in Chicago 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. - We are passionate about directly improving our customers’ security posture, and we proudly train others to help meet the need for qualified cybersecurity talent.

• Work under the guidance of more experienced team members • Deliver network and cloud assessments • Build core skills, learn methodologies, tools, and reporting standards • Utilize system administration skills for vulnerability scanning, configuration assessments, and testing infrastructure improvements • Develop skills necessary to become a penetration tester

• The Penetration Testing Engineer – Application Security is a mid-level role for a tester who has grown beyond the basics and can independently execute penetration tests within a primary domain of expertise. • Engineers are offensive security subject matter experts – conducting full assessments with minimal supervision, contributing to methodology improvements, and acting as a point of contact for clients during engagements. • By this stage, they are capable of scoping and planning a test in their domain, executing tests, and producing and communicating detailed reports with practical remediation advice. • Mid-level testers act as the technical client focal within engagements, leading technical execution for assigned projects.

• Execute internal and external network penetration tests • Perform port scanning, service enumeration, and network mapping • Identify and validate security misconfigurations • Assess cloud and on-prem network architectures • Conduct red team and purple team operations • Support social engineering campaigns • Draft technical reports and executive summaries