Web Application Penetration Testing Cybersecurity Jobs

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Penetration Tester

Deloitte Cincinnati, OH

Cincinnati, OH

Today

Full time Ai/llm Security Api Penetration Testing Application Security

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Job Description

Deloitte offers an opportunity to support Global cyber services by delivering penetration testing work for member firms. You will combine hands-on testing with technology to help uncover risks across a wide range of application and infrastructure environments, including web, API, AI/LLM, network, mobile, and thick client targets.

This onsite role in Cincinnati, OH emphasizes practical impact: translating findings into clear, actionable guidance for customers while continuously improving testing methodologies and documentation. You will also use AI/LLM tools and prompt engineering to accelerate reconnaissance and improve testing scripts and automation.

Responsibilities

Provide penetration testing services as part of the Global cyber services organization for member firms, using a mix of technology and manual ingenuity.
Execute penetration testing engagements across:
- Web Application Penetration Testing
- Web Services / API Penetration Testing
- AI/LLM Penetration Testing
- Network Penetration Testing
- Mobile Application Penetration Testing
- Thick Client Penetration Testing
Deliver consultative guidance on findings in clear, actionable writing and verbally to customers.
Enhance and update testing methodologies, processes, and standards documentation.
Leverage AI and LLM-based tools and prompt engineering to accelerate reconnaissance and generate or refine testing scripts, using both established platforms and emerging frameworks.
Build, customize, and maintain AI-driven agents to automate recurring testing tasks.
Continuously validate the accuracy and reliability of self-developed AI tools, working to reduce hallucinations and false positives in vulnerability identification.
Evaluate and integrate emerging AI-assisted offensive security tooling into team methodology and playbooks.
Analyze and understand complex architecture designs.
Communicate the services and capabilities the group can facilitate to clients.

Requirements

Experience with Kali Linux or other dedicated penetration testing OS platform.
Working knowledge of common testing tools, including Burp Professional, AMASS, Metasploit, Postman, Swagger, NMAP, Qualys, SQL Map, and others.
Familiarity with OWASP Top 10 software security weaknesses and vulnerabilities.
Familiarity with AI models and frameworks from providers such as Anthropic and OpenAI, with experience configuring tools like Obsidian and Ollama as a plus.
Working knowledge of one scripting language and familiarity with at least one software programming language and framework.
Demonstrated experience working with diverse stakeholders, preferably in global multi-national environments.
Ability to manage concurrent initiatives using sound judgment for prioritization and time management.
Strong written and verbal communication skills.
Must be a US Citizen.

Technologies

Kali Linux
Burp Professional, AMASS, Metasploit, Postman, Swagger, NMAP, Qualys, SQL Map
OWASP Top 10
Anthropic, OpenAI, Obsidian, Ollama
OWASP Application Security Top 10, OWASP API Security Top 10, OWASP Thick Client Top 10, OWASP LLM Top 10
MITRE ATT&CK Framework
Static Application Software Testing (SAST), Dynamic Application Testing (DAST)

Preferred

Certified Ethical Hacker (CEH)
Offensive Certified Security Professional (OSCP)
Any GIAC certification (GSEC, GWAB, GPEN, GMOB, GCPN)
OWASP Application Security Top 10, OWASP API Security Top 10, OWASP Thick Client Top 10, OWASP LLM Top 10
MITRE ATT&CK Framework
Cloud service testing
Reverse Engineering
Experience with agentic development and its application to support penetration testing
Limited immigration sponsorship may be available

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