As a Security Engineer at Grammarly, you will join a highly sophisticated security organization dedicated to protecting the data of over 30 million active daily users and thousands of enterprise customers. Because Grammarly acts as a real-time writing assistant integrated across web browsers, desktop applications, mobile devices, and enterprise workflows, the data processed is highly sensitive, personal, and business-critical. Security is not just a supporting function here; it is a core product value and a foundational pillar of customer trust.

In this role, you will be responsible for designing, building, and maintaining robust security systems that scale with Grammarly's rapid growth. Depending on your specialization, you will work on safeguarding cloud infrastructure, securing application codebases, implementing proactive threat-detection pipelines, or orchestrating incident response protocols. You will collaborate closely with product engineers, platform teams, and executive leadership to ensure that security is baked into every phase of the software development lifecycle.

The work is both technically challenging and strategically impactful. You will solve complex security problems at a massive scale—such as securing large-scale cloud deployments, managing high-throughput data pipelines, and architecting zero-trust environments. Successfully navigating this role requires a deep technical foundation, a strong risk-management mindset, and the ability to advocate effectively for security best practices across cross-functional engineering teams.

The interview questions you will encounter at Grammarly are designed to evaluate both the breadth and depth of your technical expertise, as well as your behavioral alignment with the company’s values. These questions are representative of actual interview experiences and are grouped below into core categories to help you identify patterns and structure your preparation.

Application & Product Security

These questions assess your ability to identify vulnerabilities, conduct threat modeling, and ensure secure coding practices across the software development lifecycle.

• How do you integrate security tooling, such as SAST, DAST, and dependency scanners, into a modern CI/CD pipeline without slowing down development?
• Walk me through your approach to conducting a penetration test on a newly developed web application.

Preparing for a Security Engineer interview at Grammarly requires a balanced approach. You must demonstrate deep domain expertise while showing that you can collaborate effectively with non-security teams. The evaluation process is rigorous, looking for candidates who can think critically under pressure and articulate their technical decisions clearly.

Grammarly assesses candidates across several core criteria:

Role-Related Knowledge – You must demonstrate a deep, foundational understanding of security principles, network protocols, cryptography, and modern attack vectors. Interviewers look for hands-on experience with security tools, cloud architectures, and secure development methodologies rather than just theoretical knowledge.

Problem-Solving & Systems Thinking – You will be evaluated on how you approach ambiguous, complex security challenges. Interviewers want to see how you analyze a system, identify potential threat vectors, prioritize risks, and design robust, scalable mitigation strategies.

Collaboration & Influence – Security at Grammarly is a shared responsibility. You need to show that you can build strong relationships with product and platform teams, influence engineering roadmaps, and advocate for security without being dogmatic or creating unnecessary friction.

Cultural Alignment – Grammarly highly values empathy, adaptation, and continuous learning. You should be prepared to discuss how you handle feedback, navigate organizational changes, and maintain a constructive, growth-oriented mindset even during high-pressure security incidents.

The interview process for a Security Engineer at Grammarly is highly thorough and designed to test both your technical depth and your cultural fit. The entire process typically spans two to four weeks, depending on scheduling and candidate availability. It is structured to give both you and the hiring team a comprehensive understanding of whether there is a mutual match.

The journey begins with an initial recruiter screen, which is a conversational call to discuss your background, your career goals, and your interest in Grammarly. Following this, you will transition into the technical screening phase. This stage often involves a technical screen and a deep-dive subject matter interview, which may cover core security concepts, incident response scenarios, or practical coding and scripting exercises.

If you pass the initial screens, you will move to the virtual onsite loop. This loop is comprehensive, consisting of four to five technical rounds and two non-technical rounds. The technical rounds focus heavily on systems design, cloud security architecture, and deep-dives into your specific domain of expertise (such as Application Security or SecOps). The non-technical rounds include behavioral interviews and a final chat with an executive or senior director to assess your leadership, communication style, and cultural alignment. To keep the process manageable, Grammarly often splits these onsite interviews over multiple days.

The timeline above outlines the typical progression of the Grammarly interview loop. Candidates should use this visual structure to pace their preparation, focusing first on core security fundamentals for the initial screens before diving deeply into complex system design and behavioral scenarios for the multi-day onsite rounds.

To succeed in the Grammarly interview loop, you must perform consistently well across several distinct technical and behavioral dimensions. Understanding what interviewers look for in each area will allow you to tailor your preparation effectively.

Cloud & Infrastructure Security

This area evaluates your ability to secure large-scale, modern cloud infrastructure. Grammarly relies heavily on cloud-native technologies, and your interviewers will expect you to possess a deep understanding of cloud security mechanisms that goes far beyond basic DevOps configurations.

Be ready to go over:

• IAM and Least Privilege – Designing granular IAM policies, role-based access control (RBAC), and cross-account access strategies.
• Container and Orchestration Security – Securing Kubernetes clusters, container runtime security, and scanning container images.
• Network Security in the Cloud – Implementing VPC security groups, network ACLs, transit gateways, and secure service meshes.
• Advanced concepts – Securing serverless architectures, managing secrets at scale (e.g., HashiCorp Vault, AWS Secrets Manager), and implementing automated cloud security posture management (CSPM).

Example scenarios:

• "Design a secure, multi-tenant AWS environment for an application that processes highly sensitive customer data."
• "How would you detect and mitigate a lateral movement attempt within a Kubernetes cluster?"

Application Security & Secure Coding

Application security is critical at Grammarly because the application code interacts directly with user input. Interviewers will assess your ability to identify vulnerabilities in code, conduct secure code reviews, and build automated guardrails for developers.

Be ready to go over:

• OWASP Top 10 – Deep understanding of common web vulnerabilities (XSS, SQLi, SSRF, CSRF) and their remediation.
• Threat Modeling – Methodologies like STRIDE to analyze application architectures and identify potential design flaws.
• Secure SDLC Integration – Automating security checks within the CI/CD pipeline using SAST, DAST, and Software Composition Analysis (SCA).
• Advanced concepts – Securing modern API frameworks (GraphQL, gRPC), implementing robust input validation and output encoding libraries, and managing third-party dependency risks.

Example scenarios:

• "Review this block of code, identify the security vulnerability, and write a secure patch to fix it."
• "How would you design a developer-friendly threat modeling process for a fast-moving product team?"

Incident Response & Threat Detection

This evaluation area focuses on your tactical readiness to handle active security compromises and your ability to build proactive detection mechanisms.

Be ready to go over:

• Incident Response Lifecycle – Preparation, identification, containment, eradication, recovery, and lessons learned.
• Log Analysis and SIEM – Writing detection rules, aggregating logs from disparate sources, and reducing false positives.
• Host and Network Forensics – Analyzing system memory, disk images, and network traffic to trace attacker activity.
• Advanced concepts – Building automated incident response playbooks (SOAR), hunting for advanced persistent threats (APTs), and securing endpoints in a remote-first corporate environment.

Example scenarios:

• "You discover that an unknown IP address is making unauthorized API calls using an engineer's credentials. Walk me through your immediate containment and investigation steps."
• "How would you build a detection rule to identify potential data exfiltration via DNS tunneling?"

Security Systems Design

This round tests your ability to architect large-scale, highly available security systems. You will need to balance security requirements with scalability, performance, and reliability.

Be ready to go over:

• Data Pipeline Security – Securing high-throughput data ingestion pipelines (e.g., Kafka, Kinesis) and ensuring data at rest and in transit is encrypted.
• Zero-Trust Architecture – Implementing identity-aware proxies, device posture checking, and continuous authentication.
• Scalable Cryptography – Designing key management systems, envelope encryption, and secure cryptographic storage.
• Advanced concepts – Implementing hardware security modules (HSMs), designing secure multi-party computation, or securing AI/LLM-based features.

Example scenarios:

• "Design a secure, high-throughput centralized logging system that can handle terabytes of data per day while ensuring log integrity and restricted access."
• "Architect a secure authentication and authorization system for a suite of desktop, mobile, and web applications."