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Squarespace

Staff Red Team Engineer

Squarespace, New York, New York, us, 10261

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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 and strengthen our security posture. This position requires deep technical expertise, the ability to work independently on complex engagements, and 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 and work with the teams directly to address them. This position reports into the VP of Security and can be based remotely in the United States.

You’ll Get To…

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.

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, 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 & Perks

A choice between medical plans with an option for 100% covered premiums

Fertility and adoption benefits

Access to supplemental insurance plans for additional coverage

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

Pretax commuter benefit

Education reimbursement

Employee donation match to community organizations

8 Global Employee Resource Groups (ERGs)

Dog-friendly workplace

Free lunch and snacks

Private rooftop

Hack week twice per year

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, and 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 and businesses online. We empower millions of customers in more than 200 countries and territories with all the tools they need to create an online presence, build an audience, monetize, and scale their business. Our suite of products range from websites, domains, ecommerce, and marketing tools, as well as tools for scheduling with Acuity and creating and managing social media presence with Bio Sites and Unfold. Our team of more than 1,500 is headquartered in bustling New York City, with offices in Dublin, Ireland, Aveiro, Portugal, and coworking spaces in the UK, Netherlands, and 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 and experiences with the world. Not only do we embrace and 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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