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About the Role

As a member of the Cyber Security team, an AVP Penetration Tester of Offensive Security will be responsible for helping with the scheduling, scoping, and execution of internal penetration testing with a strong focus on Large Language Model (LLM), agentic built applications, and supporting API penetration testing. This role will perform, at advanced levels, manual penetration testing to validate the security of resources across the company as assigned. Candidates will perform hands-on testing as well as serve as the point of contact for the assigned penetration testing activities as a part of their regular duties. The ideal candidate must possess a highly technical skill set, the ability to collaborate with stakeholders across the company to help recommend, as well as test mitigation strategies for challenging, systemic issues, across LPL applications. Offensive Security is a top area of focus at LPL. This is an exciting time to join the Information Security team as we look for highly skilled people to help expand the current program.

Responsibilities

Partner with product stakeholders to drive end-to-end pentesting activities, including working with Security Architects during the SDLC processes for LLM / AI to make recommendations and offer our ability to identify security weaknesses in applications prior to production deployment.
Conduct tactical security penetration test assessments to validate the security of company applications (LLM, agentic built applications, and supporting APIs) against OWASP Top 10 threats.
Work with the Application Security team to provide feedback and recommendations to increase automated capabilities, including AI-assisted tooling.
Think creatively and strategically to circumvent security guardrails, identify vulnerabilities, and develop effective mitigation strategies for AI.
Stay informed on ever-emerging and fast-changing TTPs, zero-days, and remediation strategies for Agentic developed applications, systems, and their supporting infrastructure.
Develop/modify custom tooling to solve new needs with the use of models such as Claude.
Document and formally report testing initiatives, test findings, justified risk ratings, remediation recommendations, and validation results in a clear and concise manner.
Partnering with technology teams to present security testing results, highlight the threat presented, and consult on remediation guidance in a way that is easy for IT stakeholders to understand.
Perform assessments of internal/external networks, infrastructure, cloud environments, along with a wide array of internally developed and commercial products.
Help develop and maintain tools or scripts used in agentic penetration testing.
Lead the execution of assigned Ai/LLM penetration testing initiatives to communicate status to leadership.
Oversee communication and reporting of findings identified during testing activities and performing retesting to validate successful closure of previously identified findings.
Develop tooling for agentic assisted LLM pentesting.

Requirements

5+ years’ experience conducting application/API and network-based penetration-testing engagements.
5+ year’ troubleshooting tools, manually finding issues in code, and rewriting code to remove bugs.
3+ years’ experience leading penetration testing engagements end-to-end.
2+ years' experience pentesting AI/LLM/GenAI applications.
2+ years' experience using AI Models such as Claude to rapidly develop tooling.
Advanced level of knowledge with security assessment tools and frameworks, including Burp Suite, Promptfoo, HexStrike, Claude, CAI, Garak, Pyrit, Kali Linux, Nessus, Metasploit, Cobalt Strike, Mitre Atlas, OWASP Top 10 for LLM, and similar.
At least one industry certification such as OSCP, OSAI, OSCE, OSWE, GPEN, GCIH, GWAPT, or GXPN.
Excellent communication skills and ability to collaborate with all stakeholders, internal and external, finding, advising, and implementing the best solutions.
Strong organizational skills.
Insatiable curiosity for tinkering with and circumventing security features and controls.
Bachelor’s Degree or equivalent in Information Security, Engineering, or Computer Science.
Advanced understanding of OWASP, the MITRE ATT&CK framework, Atlas, and the software development lifecycle (SDLC).
Advanced knowledge and experience penetration testing AI/LLM systems including MCP servers, Models, and Chatbots.
Advanced understanding of tool development with the use of AI such as Claude Code.
Advanced knowledge in programming languages (.NET, JavaScript, Python, Java, PowerShell, Perl, Ruby, Bash, C#, Golang, or similar).
Advanced level knowledge of Linux/Mac/Windows operating systems, AWS/Azure cloud environments, and cloud-native resources (ex. Containers, Kubernetes, microservices, serverless functions).
Breadth and depth of knowledge in security of LLM systems such as MCP servers, models, tooling, and infrastructures.
Must have valid U.S. work authorization that does not require employer sponsorship.

Skills

Penetration Testing
LLM Security
API Security
OWASP Top 10
AI Assisted Tooling
Tool Development
Claude
Burp Suite
Promptfoo
HexStrike
CAI
Garak
Pyrit
Kali Linux
Nessus
Metasploit
Cobalt Strike
Mitre Atlas
OWASP Top 10 for LLM
OSCP
OSAI
OSCE
OSWE
GPEN
GCIH
GWAPT
GXPN
Communication
Collaboration
Organizational Skills
Programming Languages (.NET, JavaScript, Python, Java, PowerShell, Perl, Ruby, Bash, C#, Golang)
Linux/Mac/Windows Operating Systems
AWS/Azure Cloud Environments
Cloud-Native Resources (Containers, Kubernetes, Microservices, Serverless Functions)

Location

Hybrid

Work Type

Hybrid
Full-time

Experience Level

AVP
5+ years’ experience conducting application/API and network-based penetration-testing engagements
5+ year’ troubleshooting tools, manually finding issues in code, and rewriting code to remove bugs
3+ years’ experience leading penetration testing engagements end-to-end
2+ years' experience pentesting AI/LLM/GenAI applications
2+ years' experience using AI Models such as Claude to rapidly develop tooling

Education Level

Bachelor’s Degree or equivalent in Information Security, Engineering, or Computer Science

Salary/Compensations

$128,647.00 - $214,343.00

Benefits

401K matching
Health benefits
Employee stock options
Paid time off
Volunteer time off

About the Company

LPL Financial Holdings Inc. (Nasdaq: LPLA) is among the fastest growing wealth management firms in the U.S. As a leader in the financial advisor-mediated marketplace(6) , LPL supports over 32,000 financial advisors and the wealth management practices of approximately 1,100 financial institutions, servicing and custodying approximately $2.3 trillion in brokerage and advisory assets on behalf of approximately 8 million Americans. The firm provides a wide range of advisor affiliation models, investment solutions, fintech tools and practice management services, ensuring that advisors and institutions have the flexibility to choose the business model, services, and technology resources they need to run thriving businesses. For further information about LPL, please visit www.lpl.com.
At LPL, independence means that advisors and institution leaders have the freedom they deserve to choose the business model, services, and technology resources that allow them to run a thriving business. They have the flexibility to do business their way. And they have the freedom to manage their client relationships, because they know their clients best. Simply put, we take care of our advisors and institutions, so they can take care of their clients.
For further information about LPL, please visit www.lpl.com.
Join the LPL team and help us make a difference by turning life’s aspirations into financial realities.

Equal Opportunity

Principals only. EOE.