Senior Staff Offensive Security Engineer

Why choose UKG? Your work here truly matters. The code you write, the decisions you make, and the care you show our customers culminate in a significant impact. Millions of workers rely on our workforce operating platform daily, helping them manage pay, advance in their careers, and shape the future of their industries.

At UKG, we are dedicated to continuous learning and pushing boundaries. We value flexibility, offer reliable benefits, and foster a collaborative team environment. Your contributions at UKG are valued, and so are you.

About the Team

The Security Research & Innovation (SRI) team, part of Global Security, is a dynamic, automation-focused security group dedicated to vulnerability management, security research, and red team operations. This team's outstanding automation culture empowers every member to build solutions that scale and eliminate manual tasks.

The Red Team engages in a variety of external or assume breach exercises, purple teaming, and offensive security research to identify potential risks before they become threats. Successful engagements yield actionable insights that lead to executive-level discussions, driving immediate response actions across the organization.

Role Overview

We are looking for a Senior Staff Offensive Security Engineer to spearhead red team operations within UKG's extensive multi-cloud environment. This position merges profound offensive security expertise with a strong focus on AI-driven automation and scalable attack simulations. You will design and implement intricate threat scenarios, develop AI-augmented offensive tools, and present findings that lead to meaningful risk mitigation across the organization.

Key Responsibilities

Offensive Operations (30%) • Devise and implement full-scope red team operations (network, application, cloud, social engineering) targeting UKG's production and corporate environments. • Conduct assume-breach exercises to assess cross-tenant isolation and the ability to resist breakout in multi-tenant infrastructures. • Perform adversary emulation aligned with the MITRE ATT&CK framework, simulating relevant nation-state and criminal threat actor tactics, techniques, and procedures (TTPs). • Engage in purple team exercises with the SOC to test detection effectiveness and response capabilities. • Conduct security evaluations for mergers and acquisitions involving newly acquired entities and their integrations. • Create executive-level presentations and technical reports that effectively communicate offensive findings in terms of business risk.

AI-Powered Offensive Automation (40%) • Design, develop, and maintain autonomous security testing frameworks utilizing AI/ML for vulnerability discovery, exploit chain formation, and attack path analysis. • Create AI-assisted reconnaissance and target enumeration tools using LLMs (like Claude) for comprehensive attack surface evaluation. • Establish and manage continuous automated red team pipelines for testing UKG's defenses without manual intervention. • Engineer AI-driven command and control frameworks, payload generators, and evasion tools that adapt to defensive measures in real time. • Integrate offensive tools with Claude, MCP servers, and enterprise AI systems to enhance security operations. • Develop automation processes that produce findings, generate tickets, and monitor remediation efforts to close the gap between discovery and resolution.

Strategic Leadership (20%) • Steer the red team's technical strategy and roadmap, pinpointing high-value targets and emerging attack vectors (products, custom AI, and cloud-native services). • Mentorship and development of junior offensive security engineers, enhancing team proficiency in AI-augmented offensive strategies. • Represent the red team in cross-functional security initiatives, architecture evaluations, and incident responses requiring offensive insights. • Stay informed on emerging threats, zero-day vulnerabilities, and adversary tactics pertinent to UKG's technology stack.

Research & Knowledge Sharing (10%) • Publish internal research on innovative attack strategies, AI-assisted exploitation techniques, and cloud security assessment methods. • Contribute to the team's skills store and shared automation libraries focused on Claude Code. • Develop and maintain red team infrastructure (honeypots, command and control, phishing platforms) using infrastructure-as-code methodologies. • Remain current with the latest findings and techniques presented at offensive security conferences.

Required Qualifications • Over 8 years of experience in offensive security, red teaming, or penetration testing within enterprise settings. • More than 5 years executing red team operations in cloud environments, particularly with multi-tenant architectures. • In-depth expertise in at least three domains: network exploitation, web application security, Active Directory attacks, cloud infrastructure exploitation, social engineering, and physical security. • Strong coding skills in AI, Python, Go, or C/C++ for developing offensive tools and automation scripts. • Proven ability to construct automated security testing tools and frameworks. • Experience with Kubernetes, container security, and techniques for cloud-native attacks. • Familiarity with command and control frameworks and adversary simulation platforms. • Knowledge of the MITRE ATT&CK framework and adversary emulation practices. • Hands-on experience in AI/ML security including attacking AI systems and building AI-powered offensive tools. • Experience developing autonomous security testing agents using large language models. • Exceptional written and verbal communication skills to effectively translate technical findings into business terms for executive groups. • Bachelor's degree in Computer Science, Cybersecurity, or related field, or equivalent experience.

Preferred Qualifications • Published CVEs, security research publications, or speaking engagements at well-known conferences (DEF CON, Black Hat, etc.). • Experience in SaaS/multi-tenant environments that handle sensitive data (HCM, payroll, healthcare, financial). • Certifications such as OSCP, OSCE, OSEP, CRTO, GXPN, or equivalent offensive security credentials. • Familiar with .NET, Java/Kotlin, and assessments of legacy application security. • Experience with infrastructure-as-code creation (Terraform, Pulumi) for red team activities. • Prior history in a Senior Staff or Principal role with technical leadership across teams.

What Makes This Opportunity Unique

This role is not a conventional red team position. We are redefining the future of offensive security with AI-augmented automation. Here you will: • Collaborate within a team that emphasizes production automation - it's an engineering-first security team. • Access enterprise AI resources to develop next-generation offensive capabilities. • Work to secure one of the largest HCM/payroll platforms worldwide, safeguarding a vast network of customer organizations. • Have a meaningful influence - your findings will help prevent security issues for UKG's entire clientele. • Lead the incorporation of AI into offensive security practices, creating scalable red team methodologies.

Compensation & Benefits

UKG offers a thorough total rewards package that includes a competitive base salary, annual bonuses, equity, comprehensive medical/dental/vision plans, a 401(k) match, unlimited PTO, and funds for professional development. This role can be carried out remotely from anywhere in the US.

Company Overview:

UKG is the leading Workforce Operating Platform, focused on turning workforce insights into actionable strategies. With the world's largest collection of workforce data, we provide unparalleled ability to build trust, enhance productivity, and empower talent. Our insights enable customers to address challenges across various industries by leveraging their workforce as a competitive advantage.

Equal Opportunity Employer

UKG values equality and applies fair hiring practices regardless of race, color, disability, religion, sex, age, national origin, veteran status, genetic information, or other protected categories.

Disability Accommodation

For individuals requiring assistance during the application and interview phases due to disabilities, please contact UKGCareers@ukg.com.

The salary range for this position is $145,600 to $209,300, varying based on skills, experience, job-related knowledge, and work location. In addition to base pay, there may also be performance-based bonus opportunities and restricted stock units as part of total compensation.