[Remote] Staff Red Team Engineer

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Note: The job is a remote job and is open to candidates in USA. Squarespace is a design-driven platform helping entrepreneurs build brands and businesses online. They are seeking a Staff Red Team Engineer to act as a senior individual contributor, emulating real-world threats to test their defenses and strengthen their security posture.


Responsibilities

  • Execute Red Team Operations: Plan, scope, and execute sophisticated red team engagements to test the effectiveness of our security controls and incident response capabilities.
  • Technical Expertise: Conduct advanced penetration testing, exploit development, and research to identify and exploit vulnerabilities in our systems, applications, and infrastructure.
  • Cross-Functional Collaboration: Partner with the Engineering, Product, and other stakeholders to provide actionable insights and recommendations for improving our security posture.
  • Tooling and Automation: Develop and maintain custom tooling and scripts to automate attack techniques and enhance operational efficiency.
  • Reporting and Communication: Write detailed reports on operation goals, outcomes, and findings. Clearly and concisely communicate complex technical information to various stakeholders.
  • Stay Ahead of Threats: Stay current on the latest tactics, techniques, and procedures (TTPs) used by adversaries and integrate this knowledge into our red team exercises.

Skills

  • A minimum of 8+ years of experience in cybersecurity, with a strong focus on offensive security roles such as red teaming, penetration testing, or vulnerability research.
  • Expertise in exploiting vulnerabilities in web applications, networks, and cloud environments (AWS and GCP).
  • Strong understanding of cybersecurity frameworks such as MITRE ATT&CK, NIST, and OWASP.
  • Proficiency in scripting and programming languages, such as Python, Go, or Java.
  • Demonstrated ability to think like an adversary and apply an adversarial mindset to complex systems.
  • Excellent written and verbal communication skills, with the ability to articulate complex topics clearly and effectively.

Benefits

  • A choice between medical plans with an option for 100% covered premiums including medical, dental, and vision
  • Supplemental Life and Disability Insurance plans
  • Health Savings Account with Squarespace funding
  • Fertility and adoption benefits
  • Headspace mindfulness app subscription
  • Global Employee Assistance Program
  • Retirement benefits with employer match
  • Flexible paid time off
  • 20 weeks for parental leave and up to 12 weeks to care for an ill family member
  • $100 per month remote Stipend
  • Education reimbursement
  • Employee donation match to community organizations
  • 8 Global Employee Resource Groups (ERGs)

Company Overview

  • Squarespace is a website building and hosting platform that helps users create websites without needing advanced technical skills. It was founded in 2003, and is headquartered in New York, New York, USA, with a workforce of 1001-5000 employees. Its website is http://www.squarespace.com.

    • Company H1B Sponsorship

  • Squarespace has a track record of offering H1B sponsorships, with 23 in 2025, 13 in 2024, 11 in 2023, 21 in 2022, 36 in 2021, 22 in 2020. Please note that this does not guarantee sponsorship for this specific role.

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