Sr. Staff Offensive Security Operator- Eng

Why UKG?

At UKG, the work you do matters. The code you ship, the decisions you make, and the care you show a customer all add up to real impact. Today, tens of millions of workers start and end their days with our workforce operating platform. Helping people get paid, grow in their careers, and shape the future of their industries. That's what we do.

We never stop learning. We never stop challenging the norm. We push for better, and we celebrate the wins along the way. Here, you'll get flexibility that's real, benefits you can count on, and a team that succeeds together. Because at UKG, your work matters-and so do you.

About the Team

The Security Research & Innovation (SRI) team within Global Security is a high-impact, automation-first security organization responsible for vulnerability management, security research, and red team operations. This team has an exceptional automation culture - all team members build production automation that eliminates manual work at scale.

The Red Team conducts various styles of external or assume breach exercises, purple team engagements, and offensive security research to identify systemic risks before attackers do. Successful engagements deliver results that lead to executive-level engagement to drive immediate remediation across the enterprise.

Role Summary

We are seeking a Sr. Staff Offensive Security Operator to lead and execute red team engagements across UKG's multi-cloud enterprise environment. This role combines deep technical expertise in offensive security with a strong emphasis on AI-powered automation, autonomous testing frameworks, and scalable attack simulation. You will design and execute complex attack scenarios, develop AI-enhanced offensive tooling, and deliver findings that drive measurable risk reduction across the organization.

Key Responsibilities

Offensive Operations (30%)

• Plan and execute full-scope red team engagements (network, application, cloud, social engineering) against UKG's production and corporate environments
• Conduct assume-breach exercises targeting multi-tenant infrastructure to validate cross-tenant isolation and breakout resistance
• Perform adversary emulation aligned with MITRE ATT&CK framework, simulating nation-state and criminal threat actor TTPs relevant to the HCM/payroll industry
• Execute purple team exercises with the SOC to validate detection coverage and response capabilities
• Conduct M&A security assessments for newly acquired companies and integrations
• Deliver executive-level readouts and technical reports that translate offensive findings into business risk language

• Design, build, and maintain autonomous security testing frameworks that leverage AI/ML for vulnerability discovery, exploit chain generation, and attack path analysis
• Develop AI-assisted reconnaissance and target enumeration tools using LLMs (Claude) and custom agents for scalable attack surface analysis
• Build and operate continuous automated red teaming pipelines that test UKG's defenses without manual intervention
• Create AI-powered C2 frameworks, payload generators, and evasion tools that adapt to defensive controls in real-time
• Integrate offensive tooling with Claude, MCP servers, and enterprise AI infrastructure for AI-assisted security operations
• Develop automation that generates findings, routes tickets, and tracks remediation - reducing the gap between discovery and fix

• Drive the red team's technical strategy and roadmap, identifying high-value targets and emerging attack surfaces (Product, Custom AI, and cloud-native services)
• Mentor and develop junior offensive security operators, building team capability in AI-augmented offensive techniques
• Represent the red team in cross-functional security initiatives, architecture reviews, and incident response when offensive expertise is needed
• Maintain awareness of emerging threats, zero-day vulnerabilities, and adversary tradecraft relevant to UKG's technology stack

• Publish internal research on novel attack techniques, AI-assisted exploitation, and cloud security assessment methodology
• Contribute to the team's Claude Code skills store and shared automation repositories
• Develop and maintain red team infrastructure (honeypots, C2, phishing platforms) using infrastructure-as-code
• Stay current on offensive security conferences, findings, etc - and incorporate new techniques into operations

• 8+ years of experience in offensive security, red teaming, or penetration testing in enterprise environments
• 5+ years conducting red team engagements against cloud environments including multi-tenant architectures
• Deep expertise in at least 3: network exploitation, web application security, Active Directory attacks, cloud infrastructure attacks, social engineering, physical security
• Strong proficiency in AI, Python, Go, or C/C++ for offensive tool development and automation
• Demonstrated experience building automated security testing tools, frameworks, or pipelines
• Experience with Kubernetes, container security, and cloud-native attack techniques
• Experience with C2 frameworks and adversary simulation platforms
• Knowledge of MITRE ATT&CK framework and adversary emulation methodology
• Experience with AI/ML security - attacking AI systems, prompt injection, model poisoning, or building AI-powered offensive tools
• Experience developing autonomous security testing agents using LLMs
• Excellent written and verbal communication skills - ability to translate technical findings into business risk for executive audiences
• Bachelor's degree in Computer Science, Cybersecurity, or equivalent experience

• Published CVEs, security research papers, or conference presentations (DEF CON, Black Hat, etc.)
• Experience in SaaS/multi-tenant environments processing sensitive data (HCM, payroll, healthcare, financial)
• OSCP, OSCE, OSEP, CRTO, GXPN, or equivalent offensive security certifications
• Familiarity with .NET, Java/Kotlin, and legacy application security assessment
• Experience building infrastructure-as-code (Terraform, Pulumi) for red team operations
• Prior experience in a Sr. Staff / Principal level role with cross-team technical leadership

• Work on a team where all of members build production automation - this is an engineering-first security team
• Have access to enterprise AI infrastructure to build next-generation offensive tools
• Operate against one of the largest HCM/payroll platforms in the world - protecting tens of thousands of customer organizations
• Have direct impact - your findings directly prevent issues across UKG's entire customer base
• Lead the integration of AI into offensive security operations, pioneering techniques that scale red team impact beyond headcount