How to Apply to Grammarly

Key Takeaways

Run every piece of your application — resume, cover letter, and application question responses — through Grammarly's own product before submitting, then refine further for precision and impact. Applying with writing errors to a writing-improvement company is an immediate disqualifier.
Study Grammarly's product evolution from grammar checker to AI communication platform, and be prepared to discuss where you see the product going — interviewers want candidates who think about the product's trajectory, not just its current state.
Format your resume as a clean, single-column PDF optimized for Greenhouse parsing, using exact keywords from the job posting for technologies, methodologies, and skills mentioned in the role description.
Prepare 3-4 behavioral stories mapped to Grammarly's EAGER values (Ethical, Adaptable, Gritty, Empathetic, Remarkable), with specific examples of navigating ambiguity, showing persistence, and demonstrating empathy in professional settings.
Quantify your impact using product-led growth metrics wherever possible — user activation rates, retention improvements, conversion percentages, and engagement at scale all resonate deeply with Grammarly's data-driven culture.
Treat the application questions in Greenhouse as writing samples, not afterthoughts — craft concise, well-structured responses that demonstrate the communication clarity Grammarly values.
Research Grammarly's enterprise expansion and GrammarlyGO AI features so you can speak knowledgeably about how your role connects to the company's current strategic priorities during interviews.

About Grammarly

Grammarly is the world's leading AI-powered writing assistant, used by over 30 million people and 70,000 teams daily to communicate more effectively. Founded in 2009 by Max Lytvyn, Alex Shevchenko, and Dmytro Lider, the company has grown from a grammar-checking tool into a comprehensive AI communication platform that spans tone detection, generative AI writing with GrammarlyGO, and enterprise-grade solutions for organizations. Headquartered in San Francisco with additional hubs in Kyiv, New York, and Vancouver, Grammarly operates as a remote-first hybrid company — a deliberate cultural choice that shapes how teams collaborate asynchronously across time zones. Grammarly's culture centers on its EAGER values: Ethical, Adaptable, Gritty, Empathetic, and Remarkable. Employees consistently highlight a genuine commitment to the mission of improving lives by improving communication, which creates a product team deeply connected to user impact. The engineering culture is especially notable for its investment in AI and natural language processing at massive scale, making it one of the most technically challenging environments in the NLP space. With a valuation of approximately $13 billion following its 2021 funding round, Grammarly sits in a rare position: a profitable, product-led growth company that competes at the frontier of generative AI without the instability common to many startups. This financial stability, combined with ambitious product expansion into enterprise communication workflows, makes Grammarly particularly attractive to candidates seeking startup-level impact with the security of an established, revenue-generating business. The company currently lists approximately 76 open roles spanning AI engineering, product design, growth, enterprise sales, and customer experience.

Application Process

Explore Roles on Grammarly's Careers Page
Start at grammarly.com/careers, where roles are organized by team (Engineering, Product, Design, Business, etc.) and location. Grammarly clearly labels which positions are remote-first versus hub-specific, so filter carefully — some roles require proximity to San Francisco, New York, Kyiv, or Vancouver for periodic in-person collaboration. Read each job description thoroughly, as Grammarly tends to write unusually detailed postings that describe not just responsibilities but the specific team's mission and current challenges.
Submit Your Application Through Greenhouse
Grammarly uses Greenhouse as its applicant tracking system, so all applications flow through structured online forms. You'll upload your resume, provide contact details, and typically answer 2-4 role-specific questions — treat these as mini writing samples, since Grammarly's hiring teams reportedly pay close attention to how clearly and concisely you communicate in every written touchpoint. Some roles may also request a portfolio link, GitHub profile, or cover letter.
Recruiter Screen (30-45 Minutes)
If your application advances, a Grammarly recruiter will schedule an initial phone or video conversation. This screen typically covers your career motivations, interest in Grammarly's mission, and high-level experience alignment. Expect questions about why AI-powered communication excites you and how your background connects to the specific team's goals — recruiters at Grammarly are known for being well-briefed on the role's technical and strategic context.
Hiring Manager Interview
The next stage commonly involves a deeper conversation with the hiring manager, focused on your domain expertise and how you approach problems relevant to the role. For engineering positions, this may include architectural discussions or system design thinking. For product, design, and business roles, expect scenario-based questions tied to Grammarly's actual product challenges — such as how you'd approach activation metrics for a freemium product or design for a cross-platform writing assistant.
Skills Assessment or Take-Home Exercise
Many Grammarly roles include a practical assessment designed to simulate real work. Engineering candidates often complete a coding challenge or system design exercise, while product designers may receive a design prompt related to Grammarly's user experience. These assessments are typically time-boxed and evaluated not just on technical quality but on communication clarity — how well you explain your reasoning, tradeoffs, and decisions in accompanying write-ups.
Team Interview Panel (Virtual Onsite)
The virtual onsite typically consists of 3-5 back-to-back interviews with cross-functional team members. Given Grammarly's remote-first model, these are conducted over video. Sessions commonly include a deep technical or functional deep-dive, a collaboration and communication assessment, and a values-alignment conversation where interviewers evaluate how you embody EAGER values. Prepare for behavioral questions that probe empathy, adaptability, and grit specifically.
Offer and Reference Checks
Grammarly typically conducts reference checks before extending a formal offer. The offer process is known to be transparent, with recruiters walking candidates through total compensation including equity, benefits, and remote work stipends. Given the company's remote-first culture, offers commonly include details about home office setup support and expectations for periodic hub visits.

Resume Tips for Grammarly

Critical Lead with AI, NLP, or Communication Technology Impact

Grammarly sits at the intersection of artificial intelligence and human communication, so your resume should immediately signal relevance to this space. If you've worked with machine learning models, natural language processing, large language models, or any product that improves how people write or communicate, place that experience prominently. Even non-engineering candidates should frame their impact in terms of communication outcomes — for example, a marketing professional might highlight how they improved user engagement through content clarity.

Critical Quantify Product-Led Growth and Scale Metrics

Grammarly is one of the most successful product-led growth companies in tech, with tens of millions of daily users converting through a freemium model. Your resume gains significant traction when it includes metrics tied to user activation, retention, conversion, or engagement at scale. Instead of writing 'improved onboarding flow,' write 'redesigned onboarding flow that increased 7-day activation by 18% across 2M monthly signups.' Grammarly's hiring teams are steeped in growth metrics, so speak their language.

Critical Demonstrate Clear, Concise Writing Throughout Your Resume

This cannot be overstated: you are applying to a company whose entire product is built on making writing better. Every bullet point on your resume is a writing sample. Eliminate passive voice, cut unnecessary words, ensure grammatical perfection, and use precise language. Consider running your resume through Grammarly's own tool as a baseline — but go further by ensuring your writing demonstrates the tone and clarity the company champions. A resume with clumsy phrasing or typos will be disqualified faster here than at virtually any other company.

Optimize for Greenhouse ATS Parsing

Greenhouse parses resumes for structured data including job titles, company names, dates, and skills. Use a clean, single-column format with standard section headers (Experience, Education, Skills) to ensure accurate parsing. Avoid tables, multi-column layouts, headers/footers with critical information, and graphics that Greenhouse's parser may skip. Save your file as a PDF with selectable text — image-based PDFs will not parse correctly.

Mirror Grammarly's Job Description Language in Your Skills Section

Grammarly's job postings use specific terminology that reflects their technical stack and priorities. If a posting mentions 'distributed systems,' 'Kotlin,' 'TypeScript,' 'product experimentation,' or 'cross-platform development,' use those exact phrases in your resume where truthful. Greenhouse allows recruiters to search and filter by keywords, so alignment between your resume language and the job posting directly affects your visibility in candidate searches.

Highlight Cross-Functional and Remote Collaboration Experience

Grammarly's remote-first, hub-flexible model demands strong asynchronous collaboration skills. Dedicate resume space to experiences where you worked across teams, time zones, or functions — especially if you can show outcomes from that collaboration. Phrases like 'partnered with engineering and design teams across three time zones to ship...' resonate with Grammarly's operating model. If you've used async tools like Loom, Notion, or detailed written briefs to drive alignment, mention them.

Include a Concise Professional Summary Tied to Grammarly's Mission

A 2-3 sentence summary at the top of your resume that connects your career arc to Grammarly's mission of improving communication can set a strong first impression. Avoid generic summaries — instead, try something like: 'Product designer with 6 years of experience building AI-assisted tools that simplify complex workflows for millions of users. Passionate about making written communication more effective and inclusive.' This signals intentionality and mission alignment before the recruiter reads a single bullet point.

Showcase Enterprise or B2B Experience for Business-Side Roles

Grammarly has been aggressively expanding its enterprise product (Grammarly Business and Grammarly for Education), so candidates applying to engagement management, enterprise design, or sales roles should highlight B2B SaaS experience. Include details about deal sizes, enterprise deployment, change management, or customer success metrics. Demonstrating familiarity with how communication tools get adopted across large organizations is a meaningful differentiator.

ATS System: Greenhouse

Greenhouse is a structured hiring platform used by Grammarly to manage its entire recruitment pipeline, from application intake through offer. The system parses uploaded resumes to extract work history, education, and skills, which recruiters then search and filter using role-specific scorecards. Greenhouse also powers Grammarly's structured interview process, where each interviewer evaluates candidates against predefined criteria — meaning your application data directly populates the evaluation framework.

Use a single-column PDF format with selectable text — Greenhouse's parser struggles with multi-column layouts, tables, and image-based PDFs
Place your name, email, and phone number in the body of the document rather than in headers or footers, which Greenhouse may not read
Match keywords from the Grammarly job posting verbatim in your resume — Greenhouse enables keyword filtering, and recruiters commonly search for specific technologies and skills mentioned in the role
Use standard section titles like 'Experience,' 'Education,' and 'Skills' rather than creative alternatives like 'My Journey' — this helps Greenhouse categorize your information accurately
Complete every field in the Greenhouse application form, including optional ones — partially completed applications may rank lower in recruiter search results
If a role includes application questions, write polished, substantive responses — these are stored alongside your resume in Greenhouse and are often the first thing a reviewer reads
Avoid special characters, icons, or unusual fonts that may cause parsing errors — stick to standard fonts like Arial, Calibri, or Times New Roman

Complete Greenhouse Resume Guide

Interview Culture

Grammarly's interview process reflects its core identity: a company obsessed with clear communication and thoughtful collaboration. Expect a process that is structured, well-organized, and deliberately designed to assess both your functional expertise and your alignment with the EAGER values (Ethical, Adaptable, Gritty, Empathetic, Remarkable). The typical process spans 4-6 weeks and includes 4-5 distinct stages. After the recruiter screen and hiring manager conversation, most candidates complete a skills assessment followed by a virtual onsite consisting of 3-5 interviews. Engineering candidates commonly face system design discussions, pair programming or code review sessions, and architectural problem-solving — often with scenarios drawn from Grammarly's real technical challenges around NLP, distributed systems, or cross-platform architecture. Product and design candidates typically present a portfolio case study or complete a design exercise, with heavy emphasis on how you articulate your reasoning and handle feedback. What distinguishes Grammarly's interview culture is the weight placed on written and verbal communication quality. Multiple Glassdoor reviews note that interviewers pay attention to how clearly you explain complex concepts, how well you listen and respond to follow-up questions, and whether you can distill ambiguity into structured thinking. This is not incidental — at a company building a communication product, your communication skills are treated as a core competency regardless of role. The values-alignment interview is a dedicated round where you'll be assessed on behavioral examples demonstrating empathy, adaptability, and ethical decision-making. Prepare specific stories about navigating ambiguity, receiving difficult feedback, and making principled tradeoffs. Interviewers at Grammarly are trained to use structured scorecards through Greenhouse, which means every interview has predefined evaluation criteria — you'll rarely face unstructured or off-the-cuff conversations. Grammarly's remote-first culture means all interviews are typically conducted over video, even for candidates near a hub. Interviewers are reportedly respectful of candidates' time, often providing detailed agendas in advance and leaving space for candidate questions. The overall experience is frequently described as rigorous but humane — challenging without being adversarial.

What Grammarly Looks For

Exceptional written and verbal communication skills — this is non-negotiable at a company whose product is a writing assistant, and every interaction from your application to your final interview is evaluated on clarity
Deep alignment with the mission of improving lives through better communication, demonstrated through genuine enthusiasm for the product and thoughtful ideas about its potential impact
Comfort with ambiguity and adaptability in a fast-moving AI landscape — Grammarly is rapidly evolving from a grammar checker to a generative AI communication platform, and they seek people who thrive during transformation
Evidence of grit and follow-through on difficult, long-term projects — Grammarly values persistence in solving hard problems, especially when building AI features that must work reliably for millions of users
Empathy for users and teammates, demonstrated through collaborative work styles, user-centered design thinking, and the ability to give and receive feedback constructively
Technical depth combined with product intuition — even in pure engineering roles, Grammarly values candidates who think about how their work translates into user outcomes and product metrics
Experience operating in remote-first or distributed team environments, with strong asynchronous communication skills and comfort using written documentation to drive decisions
Curiosity about AI, NLP, and large language models — whether you're in engineering, design, or business development, understanding how AI technologies shape the product roadmap is increasingly expected

Frequently Asked Questions

How long does Grammarly's hiring process typically take from application to offer?

Based on candidate reports, Grammarly's hiring process commonly spans 4-6 weeks from initial application to offer, though this can vary by role and team. The recruiter screen typically occurs within 1-2 weeks of application if you're selected, followed by a hiring manager interview and skills assessment in subsequent weeks. The virtual onsite is usually the final major milestone before reference checks and offer discussions. Grammarly is generally regarded as communicative throughout the process, with recruiters providing timeline updates — but high-demand roles like AI engineering may move faster or slower depending on candidate volume.

Does Grammarly require a cover letter with applications?

Cover letters are not universally required across all Grammarly roles, but they are strongly recommended — especially given that Grammarly is fundamentally a communication company. A well-crafted cover letter serves as a live writing sample and an opportunity to articulate your connection to Grammarly's mission in ways a resume cannot. Focus your cover letter on why improving communication matters to you personally, how your specific experience connects to the role's challenges, and what excites you about Grammarly's evolution into generative AI. Keep it to one page, use clear structure, and ensure it's flawless — this is perhaps the highest-stakes writing sample you'll submit.

What format should my resume be in when applying through Grammarly's Greenhouse system?

Submit your resume as a PDF with selectable text, using a clean single-column layout. Greenhouse, Grammarly's ATS, parses resumes to extract structured data, and multi-column layouts, tables, infographics, and text embedded in images commonly cause parsing failures. Use standard section headers (Experience, Education, Skills), place your contact information in the document body rather than in headers or footers, and stick to widely supported fonts like Arial or Calibri. While creative formatting might seem appealing, accurate parsing ensures your qualifications are fully visible to recruiters when they search and filter candidates.

Does Grammarly offer remote work, and do I need to live near a hub?

Grammarly operates on a remote-first model, and many roles are open to candidates across multiple regions. However, some positions specify proximity to one of Grammarly's hubs — San Francisco, New York, Vancouver, or Kyiv — particularly for roles that involve periodic in-person collaboration. Each job posting on Grammarly's careers page clearly states the location requirements, so read these carefully before applying. Remote employees are commonly supported with home office stipends and equipment, and the company has invested heavily in asynchronous communication practices to ensure remote team members are fully integrated. Periodic hub gatherings for team bonding and strategic planning are typical.

What experience level does Grammarly look for — can I apply as an early-career candidate?

Grammarly hires across experience levels, from early career to senior leadership. The company runs an Early Career Program specifically designed for recent graduates and candidates with limited professional experience, which typically includes structured mentorship and onboarding support. For mid-level and senior roles, Grammarly generally expects demonstrated impact in relevant domains — particularly in AI/ML, product development, growth, or enterprise sales. If you're early in your career, focus your application on relevant internships, academic projects (especially in NLP, linguistics, or AI), and any evidence of strong communication skills and self-directed learning.

How should I prepare for Grammarly's technical interviews as an engineer?

Engineering interviews at Grammarly typically include system design discussions, coding exercises, and architectural problem-solving sessions. Given the company's focus on NLP and AI, familiarity with machine learning pipelines, distributed systems, and cross-platform architecture is particularly valuable for relevant roles. Prepare to discuss how you'd build features that serve millions of concurrent users with real-time feedback — this is the core technical challenge of Grammarly's product. Practice explaining your design decisions clearly and concisely, as communication quality during technical interviews carries significant weight. Review the specific technologies mentioned in your role's job posting (commonly Kotlin, TypeScript, Python, AWS, or Spark) and be ready to demonstrate depth in those areas.

What is Grammarly's interview culture like — is it collaborative or adversarial?

Grammarly's interview culture is widely described as rigorous but respectful. Interviewers use structured scorecards aligned with predefined evaluation criteria, which means conversations tend to be focused and purposeful rather than unpredictable. Candidates on Glassdoor frequently note that interviewers are genuinely curious about your thought process, ask thoughtful follow-up questions, and provide space for you to ask questions in return. The dedicated values interview assesses behavioral alignment with Grammarly's EAGER principles, so expect warm but probing questions about how you handle ethical dilemmas, demonstrate empathy, and persist through challenges. The overall tone is collaborative — interviewers want to see how you think and communicate, not whether you'll crack under pressure.

Should I use Grammarly's product before applying, and will they ask about it?

Absolutely — using Grammarly's product before applying is strongly recommended and could reasonably be considered essential. Interviewers commonly ask candidates about their experience with the product, what they'd improve, and how they see it evolving. Install the browser extension, try Grammarly Premium's tone and clarity features if possible, and explore GrammarlyGO's generative AI capabilities. Having firsthand experience allows you to speak authentically about the product's strengths and opportunities during interviews. Bonus: use the product to polish your actual application materials, which demonstrates both product familiarity and commitment to communication quality.

How important is mission alignment at Grammarly, and how do they assess it?

Mission alignment is a core evaluation criterion at Grammarly — this is a company where 'improving communication' isn't just marketing language but a deeply held organizational belief that shapes product decisions, hiring, and culture. Interviewers assess mission alignment through behavioral questions, your articulation of why you want to work at Grammarly specifically, and how you talk about the impact of effective communication in your own life and career. Generic answers about wanting to work at a tech company will fall flat. Prepare specific examples of how better communication made a difference in a project, team, or personal experience, and connect your career aspirations to Grammarly's vision of helping everyone communicate more effectively.

What should I do if I don't hear back after applying to Grammarly?

If you haven't heard back within 2-3 weeks, it's reasonable to follow up with a brief, polite email to the recruiter if you have their contact information, or through LinkedIn. Grammarly receives a high volume of applications — particularly for AI and engineering roles — so processing times can vary. If you applied through Greenhouse, you should receive automated status updates as your application progresses. While waiting, consider strengthening your candidacy by engaging with Grammarly's engineering blog, attending their public events or webinars, and connecting thoughtfully with team members on LinkedIn. If you're not selected for one role, many applicants report successfully reapplying to different positions after gaining additional relevant experience.

Sample Open Positions

Sources

Grammarly Careers — Open Positions and Company Culture — Grammarly
Grammarly Interview Reviews and Company Ratings — Glassdoor
Grammarly Blog — Company Culture, Values, and Team Insights — Grammarly
Greenhouse Recruiting — How ATS Parsing and Structured Hiring Works — Greenhouse Software
Grammarly's Approach to Remote-First Work — Grammarly