Squarespace is seeking a Staff Red Team Engineer to join our Security team. In this role, you will act as a senior individual contributor, emulating real-world threats to test our defenses & strengthen our security posture. This position requires deep technical expertise, the ability to work independently on complex engagements, & a passion for finding innovative ways to bypass security controls. You will be a key contributor to the team's success, helping to mature our offensive security capabilities.  You will also need excellent communication skills to work with our internal teams to describe the vulnerabilities you find & work with the teams directly to address them. This position reports into the VP of Security & can be based remotely in the United States. 

You'll Get To...

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

Who We're Looking For

• 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, & cloud environments (AWS & GCP).
• Strong understanding of cybersecurity frameworks such as MITRE ATT&CK, NIST, & OWASP.
• Proficiency in scripting & programming languages, such as Python, Go, or Java.
• Demonstrated ability to think like an adversary & apply an adversarial mindset to complex systems.
• Excellent written & verbal communication skills, with the ability to articulate complex topics clearly & effectively.

Benefits & Perks

• A choice between medical plans with an option for 100% covered premiums including medical, dental, & vision
• Supplemental Life & Disability Insurance plans
• Health Savings Account with Squarespace funding
• Fertility & adoption benefits
• Headspace mindfulness app subscription
• Global Employee Assistance Program
• Retirement benefits with employer match
• Flexible paid time off
• 20 weeks for parental leave & 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)

Cash Compensation Range: $170,000 - $299,000 USD

The base salary for this position will vary based on job-related criteria including relevant skills, experience, & location, among other factors. 

In addition to the cash compensation above (which includes base salary and, where applicable for eligible roles, may include on-target commissions or overtime pay), Squarespace employees are eligible to be granted an option to purchase our common stock.

About Squarespace

Squarespace is a design-driven platform helping entrepreneurs build brands & businesses online. We empower millions of customers in more than 200 countries & territories with all the tools they need to create an online presence, build an audience, monetize, & scale their business. Our suite of products range from websites, domains, ecommerce, & marketing tools, as well as tools for scheduling with Acuity & creating & managing social media presence with Bio Sites & Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, & coworking spaces in the UK, Netherlands, & Australia. For more information about our company culture, visit https://www.squarespace.com/about/careers.

Our Commitment 

Today, more than a million people around the globe use Squarespace to share different perspectives & experiences with the world. Not only do we embrace & celebrate the diversity of our customers, but we also work toward the same in our employees. At Squarespace, we are committed to equal employment opportunity regardless of race, color, ethnicity, ancestry, religion, national origin, gender, sex, gender identity or expression, sexual orientation, age, citizenship, marital or parental status, disability, veteran status, or other class protected by applicable law. We are proud to be an equal opportunity workplace.

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