Lead Offensive AI Security

Plain Concepts Group; United States; Remote; USD 150,000 - 210,000; Full time

Benefits offered by this job

Remote work option

Health insurance (full)

Education budget

Microsoft certifications

English lessons

Birthday day off

Home utility allowance

Gym discount

Annual team-building event

Employee discount portal

Job summary

Plain Concepts Group is seeking a Lead Offensive AI Security to shape the future of AI-powered penetration testing, application security, and secure software development. This role blends technical leadership, hands-on expertise, and innovation while guiding a growing team.

You will design services, assess web apps, APIs, cloud environments, and AI-enabled systems; evaluate LLMS and agents; drive Secure SDLC and DevSecOps, and build tooling to accelerate engagements while advising CISOs and

Qualifications

• 7+ years of experience in Offensive Security, Application Security, Adversarial Testing, or Penetration Testing.
• Experience leading technical teams or complex security engagements.
• Strong hands-on experience with web application and API security assessments.
• Solid understanding of authentication, authorization, business logic vulnerabilities, and exploit validation.
• Experience implementing or improving Secure SDLC practices, including threat modeling, secure code reviews, vulnerability management, and remediation workflows.
• Hands-on experience using LLMs, AI agents, or AI-powered security tools to enhance testing and automation activities.
• Experience integrating security into CI/CD pipelines and modern cloud environments.
• Knowledge of application security tooling, including SAST, DAST, Software Composition Analysis, and Secrets Scanning.
• Strong programming or scripting skills, preferably Python or PowerShell.
• Experience with offensive security tools such as BurpSuite, Nmap, or similar technologies.
• Understanding of AI application security risks, including prompt injection, data leakage, retrieval access controls, and unsafe tool execution.
• Excellent communication skills, with the ability to explain technical findings to technical and non-technical audiences.
• Fluent Spanish and English.

Responsibilities

• Lead AI-powered penetration testing initiatives, combining traditional offensive security techniques with AI-assisted capabilities.
• Design and evolve offensive security services, methodologies, assessment frameworks, and delivery models.
• Assess web applications, APIs, cloud environments, and AI-enabled systems to identify vulnerabilities and security risks.
• Evaluate the security of LLM-based applications and AI agents, including prompt injection, data leakage, excessive permissions, and insecure tool execution.
• Help organizations transform their pentesting programs, increasing assessment capacity and reducing delivery times without compromising quality.
• Drive Secure SDLC and DevSecOps initiatives, integrating security controls into engineering workflows and CI/CD pipelines.
• Build automation, tooling, and prototypes that improve efficiency and can be reused across multiple engagements.
• Act as a trusted advisor for CISOs, architects, engineering teams, and security leaders.
• Mentor and develop a multidisciplinary team of offensive security, application security, and DevSecOps specialists.

Skills

Lead AI pentesting

Offensive security

Security leadership

CI/CD integration

Cloud security

Secure SDLC

AI security tooling

Web app security

API security

LLM security

Automation

Scripting/Python

Tools

BurpSuite

Nmap

LLMs/AI agents

Job description

AtPlainSecurityStudios,we'reredefininghoworganizationscombineOffensiveSecurity,AI,andDevSecOpstobuildmoresecureapplications.

We'relookingforaLeadOffensiveAISecuritytohelpshapethefutureofAIpoweredpenetrationtesting,applicationsecurity,andsecuresoftwaredevelopment.

Thisisauniqueopportunitytocombinetechnicalleadership,hands-onsecurityexpertise,andinnovation,whileleadingagrowingteamofspecialistsandworkingwithclientsoncutting-edgesecuritychallenges.

KeyResponsibilities

• LeadAI-poweredpenetrationtestinginitiatives,combiningtraditionaloffensivesecuritytechniqueswithAI-assistedcapabilities.
• Designandevolveoffensivesecurityservices,methodologies,assessmentframeworks,anddeliverymodels.
• Assesswebapplications,APIs,cloudenvironments,andAIenabledsystemstoidentifyvulnerabilitiesandsecurityrisks.
• EvaluatethesecurityofLLM-basedapplicationsandAIagents,includingpromptinjection,dataleakage,excessivepermissions,andinsecuretoolexecution.
• Helporganizationstransformtheirpentestingprograms,increasingassessmentcapacityandreducingdeliverytimeswithoutcompromisingquality.
• DriveSecureSDLCandDevSecOpsinitiatives,integratingsecuritycontrolsintoengineeringworkflowsandCI/CDpipelines.
• Buildautomation,tooling,andprototypesthatimproveefficiencyandcanbereusedacrossmultipleengagements.
• ActasatrustedadvisorforCISOs,architects,engineeringteams,andsecurityleaders.
• Mentoranddevelopamultidisciplinaryteamofoffensivesecurity,applicationsecurity,andDevSecOpsspecialists.

• 7+yearsofexperienceinOffensiveSecurity,ApplicationSecurity,AdversarialTesting,orPenetrationTesting.
• Experienceleadingtechnicalteamsorcomplexsecurityengagements.
• Stronghands-onexperiencewithwebapplicationandAPIsecurityassessments.
• Solidunderstandingofauthentication,authorization,businesslogicvulnerabilities,andexploitvalidation.
• ExperienceimplementingorimprovingSecureSDLCpractices,includingthreatmodeling,securecodereviews,vulnerabilitymanagement,andremediationworkflows.
• Hands-onexperienceusingLLMs,AIagents,orAI-poweredsecuritytoolstoenhancetestingandautomationactivities.
• ExperienceintegratingsecurityintoCI/CDpipelinesandmoderncloudenvironments.
• Knowledgeofapplicationsecuritytooling,includingSAST,DAST,SoftwareCompositionAnalysis,andSecretsScanning.
• Strongprogrammingorscriptingskills,preferablywithPythonorPowerShell.
• ExperiencewithoffensivesecuritytoolssuchasBurpSuite,Nmap,orsimilartechnologies.
• UnderstandingofAIapplicationsecurityrisks,includingpromptinjection,dataleakage,retrievalaccesscontrols,andunsafetoolexecution.
• Excellentcommunicationskills,withtheabilitytoexplaintechnicalfindingstobothtechnicalandnon-technicalaudiences.
• FluentSpanishandEnglish.

NicetoHave:

• OSCP,OSWE,CRTO,orGIACcertifications.
• Experiencebuildingsecuritymethodologies,frameworks,orinternalsecurityservices.
• Backgroundinconsultingorclient-facingsecurityengagements.
• Experienceleadingsecuritytransformationinitiatives.
• KnowledgeofAzureandGitHubsecurityecosystems.

• Salary determined by the market and your experience

• Flexible schedule 35 Hours / Week
• Fully remote work (optional)
• Flexible compensation (restaurant, transport, and childcare)
• Fully free health insurance, with a co-payment for dental services
• Individual budget for training or equipment and free Microsoft certifications
• English lessons
• Birthday day off
• Monthly bonus for electricity and Internet expenses at home
• Discount on gym plan and sports activities
• Plain Camp (annual team-building event)
• Extra perks: events attendance and speakers, welcome pack, baby basket, Christmas basket, discount portal for employees The pleasure of always working with the latest technological tools!

Will you let us know you better?

The selection process: Simple, just 3 steps.

• Phone screen
• 2 interviews with the team

What is Plain Concepts?

Plain Concepts is a global company of over 500 people passionate about technology and innovation. Since our founding, we have grown through technical proficiency and confidence in ideas that others might consider risky, creating custom solutions for our clients. With offices in more than 6 countries, our mission is to continue to drive cuttingedge projects around the world.

We are highly committed to technical excellence. We are known for developing highly customized projects, offering specialized technical consultancy and training.

Thanks to the great work of our technicians, we have been recognized for our ability to lead innovative projects that generate value, from artificial intelligence to blockchain, driving solutions that help companies optimize their performance.

What we do at Plain Concepts?

We pride ourselves on being a 100% technical team, dedicated to crafting custom projects from scratch, offering expert technical consultancy, and providing top-tier training.

• Our approach goes beyond traditional outsourcing; we focus on creating value together with our clients.
• Our teams are diverse and multidisciplinary, operating in a flat, collaborative structure.
• We live and breathe AGILE principles, ensuring flexibility and efficiency in everything we do.
• Knowledge-sharing is at our core: from supporting each other internally to contributing to the broader tech community through conferences, events, and talks.
• Innovation drives us — even the boldest ideas are welcome here.
• Transparency underpins all our relationships, fostering trust and long-term partnerships.

Want to learn more?

Check out our website! https://www.plainconcepts.com/

At Plain Concepts, we certainly seek to provide equal opportunities. We want diverse applicants regardless of race, colour, gender, religion, national origin, citizenship, disability, age, sexual orientation, or any other characteristic protected by law.