Head of Cybersecurity Assurance Testing

Join Guardian Life as the Head of Cybersecurity Assurance Testing and lead the charge in safeguarding our organization's digital assets. This pivotal people management and hands-on leadership role drives the evolution and measurable success of Guardian's application security testing, ethical hacking/red team programs, and third-party testing initiatives. Based in New York, United States, you'll deliver impactful results through strategic team leadership, tactical planning, expert-level hands-on testing, cross-functional collaboration, and comprehensive program ownership.

Why Join Guardian Life?

At Guardian Life, we're more than an insurance leader—we're a protector of futures. For over 160 years, we've empowered individuals, families, and businesses with innovative financial security solutions. As a Fortune 500 company, we invest heavily in our people, fostering a culture of innovation, inclusivity, and excellence. Join our cybersecurity team in New York and contribute to a mission that protects millions while advancing your career in a hybrid work environment at our state-of-the-art Hudson Yards office. Enjoy competitive pay, comprehensive benefits, and opportunities for professional growth in a collaborative, high-impact setting. Guardian Life is committed to diversity, equity, and inclusion, offering a supportive workplace where your expertise in cybersecurity assurance testing can thrive.

Role Description

The Head of Cybersecurity Assurance Testing oversees two US-based full-time employees (FTEs) while collaborating closely with India-based counterparts, cyber defense stakeholders, and application owners. You'll ensure all offensive security efforts are risk-aligned, actionable, and focused on driving meaningful risk reduction. This role demands on-site presence an average of three days per week at our Hudson Yards, NY or Bethlehem, PA offices. Expect to manage staff development, plan and execute red team missions, coordinate penetration testing and third-party adversarial exercises, and spearhead collaborative purple teaming through head-to-head exercises with the blue team. If you're passionate about ethical hacking, red team operations, and application security in a financial services powerhouse, this is your opportunity to lead transformative cybersecurity initiatives at Guardian Life.

Detailed Responsibilities

Program Leadership & Accountability

• Develop and own the roadmap, backlog, and quarterly planning for Application Security Testing, Red Teaming, and Purple Teaming programs.
• Lead red team missions, conduct hands-on application security tests, and coordinate third-party adversarial exercises.
• Ensure exceptional team performance, resource planning, and program outcomes; deliver results both directly and through your team.
• Oversee project delivery, capability expansion, and alignment with enterprise risk priorities.

Cross-Functional Collaboration

• Plan, execute, and report on Purple Team (offense/defense) exercises to enhance detection and response capabilities.
• Partner with Cyber Defense teams to improve resilience and actionable insights.
• Deliver comprehensive readouts, lessons learned, and remediation recommendations to stakeholders.
• Align with Vulnerability Management, Threat Intelligence specialists, and peer teams for strategic red team planning.

People Leadership & Team Development

• Manage, coach, and develop a high-performing team of engineers; set goals, provide feedback, and support career growth through conferences, hands-on learning, capture-the-flag exercises, and certifications.
• Foster an innovative, accountable culture with optimal resource utilization.

Strategic Collaboration & Innovation

• Partner with application owners, global teams, and security stakeholders to prioritize high-risk areas and ensure finding closure.
• Translate technical findings into business insights and recommend defense improvements.
• Influence offensive security and application testing standards, policies, and integrate new technologies like AI-driven tools.
• Promote automated testing in CI/CD pipelines and encourage continuous experimentation.

Governance & Reporting

• Define, track, and report KPIs on coverage, risk reduction, remediation rates, and automation maturity.
• Produce executive-ready reports that translate technical findings to business risk language.
• Ensure timely remediation or risk acceptance of all findings.

Required Skills

Guardian Life seeks a cybersecurity leader with proven expertise. Key skills include penetration testing, red team operations, purple teaming, application security testing, team management, stakeholder communication, automation scripting, and secure SDLC integration.

Education & Experience

Required Qualifications

• 5+ years in offensive security, ethical hacking, or application security leadership.
• Hands-on experience with penetration tests, red team ops, app sec testing, and purple team exercises.
• Team management experience delivering results through others.
• Proficiency in tools like Burp Suite, ZAP, Cobalt Strike, and automation frameworks.
• Strong knowledge of secure SDLC, threat modeling, adversarial simulation, CI/CD security.
• Excellent communication and stakeholder skills.
• Bachelor’s in cybersecurity or related; equivalent certs (OSCP, OSWE, GWAPT, CISM).
• Proven ability to drive urgent responses and automate processes.

Preferred Qualifications

• Financial services or enterprise experience.
• AI-driven security testing and automation.
• Cloud/container security testing.
• Global team leadership.

Compensation Overview

Salary range: $118,980 - $195,465 annually, based on experience. This competitive package reflects New York market rates for senior cybersecurity roles.

Benefits

Guardian Life offers top-tier benefits including health, dental, vision coverage; 401(k) match; generous PTO; professional development stipends; hybrid work flexibility; wellness programs; and tuition reimbursement. Protect your future while building ours.