Sr. Staff Offensive Security Operator- Eng

UKG

6d•$145,600 - $209,300•Remote

About The Position

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.

Requirements

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

Nice To Haves

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

Responsibilities

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

Benefits

UKG offers a comprehensive total rewards package including competitive base salary, annual bonus, equity, full medical/dental/vision, 401(k) match, unlimited PTO, and professional development budget.

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