Senior Offensive Security Engineer

Job Description: - Plan, design, and execute red (and purple) team engagements to simulate advanced adversarial tactics and techniques

- Perform in-depth penetration tests on web applications, endpoint agents, internal systems, and our people

- Utilize a mix of traditional scripting and generative AI platforms to rapidly prototype tools, replicate sophisticated cyber threats, and automate repetitive workflows during live engagements

- Conduct social engineering campaigns to evaluate human vulnerabilities

- Collaborate closely with the Security Operations Center and CSIRT teams to enhance detection and response capabilities

- Stay informed on emerging threats and update red teaming methodologies

- Partner with Product Security to prioritize testing efforts for new releases

- Analyze and exploit vulnerabilities through detailed operational logging, leveraging strong documentation and communication skills to translate complex technical findings into actionable remediation guidance that directly hardens the organization's security

- Develop and deliver detailed technical and executive-level reports post-engagement

- Integrate red team tools, techniques, and processes into a broader security strategy

- Lead or participate in after-action reviews to identify lessons learned

- Assist in designing and implementing security controls based on red team findings

Requirements: - 3+ years of experience as an offensive security professional

- A documentation-first mindset

- Deep knowledge of adversarial tradecraft

- Expert knowledge of cloud computing platforms (AWS, Azure)

- Skills in scripting languages

- Experience communicating findings that inform defenses

- A pragmatic approach to problem solving

- Experience working in a primarily macOS environment is a significant asset

Benefits: - 100% remote work environment - since our founding in 2015

- Generous paid time off policy, including vacation, sick time, and paid holidays

- 12 weeks of paid parental leave

- Highly competitive and comprehensive medical, dental, and vision benefits plans

- 401(k) with a 5% contribution regardless of employee contribution

- Life and Disability insurance plans

- Stock options for all full-time employees

- One-time $500 reimbursement for building/upgrading home office

- Annual allowance for education and professional development assistance

- $75 USD/month digital reimbursement

- Access to the BetterUp platform for coaching, personal, and professional growth