Sr. Customer Success Manager, Grammarly Business

Grammarly offers a dynamic hybrid model, and candidates in this role can be based remotely. You may be expected to travel to meet in person during your team’s scheduled collaboration weeks. Managers will determine in-person time according to business needs.

This hybrid approach helps foster trust, innovation, and a strong team culture, with the flexibility of working from home, whenever you need focus time.

Grammarly is the trusted AI assistant for communication and productivity, helping over 40 million people and 50,000 organizations do their best work. Companies like Atlassian, Databricks, and Zoom rely on Grammarly to brainstorm, compose, and enhance communication that moves work forward. Grammarly works where you work, integrating seamlessly with over 500,000 applications and websites. Founded in 2009, Grammarly is No. 7 on the Forbes Cloud 100, one of TIME’s 100 Most Influential Companies, one of Fast Company’s Most Innovative Companies in AI, and one of Inc.’s Best Workplaces.

To achieve our ambitious goals, we’re looking for a Senior Customer Success Manager to join our Enterprise Customer Success team. This role will be responsible for cultivating and maintaining strong relationships with their assigned enterprise accounts, ensuring high levels of value for our customers, and executing successful contract renewals.

Grammarly’s go-to-market teams are shaping the future of workplace communication. As a member of our team, you will be crucial in expanding the use of our innovative, trustworthy AI writing tools. We strive to ensure that every organization can communicate effectively and efficiently. If you are passionate about transforming the way professionals connect and collaborate, we would love to hear from you.

As a member of the Grammarly team, your role as a Senior Customer Success Manager will be pivotal in integrating our product into enterprise organizations to help solve some of their toughest challenges. You will be instrumental in creating a customer success engine that aims to maximize Grammarly's value for our customers.

In this role, you will:

• Own the full post-sales customer lifecycle for your assigned enterprise accounts, ensuring seamless onboarding, activation, and long-term success.
• Lead renewal strategies end-to-end, including pricing proposals and contract negotiations, to drive retention and account growth.
• Partner cross-functionally with Sales and Key Accounts teams to identify and execute on expansion and cross-sell opportunities.
• Deliver high-impact enablement experiences by deeply understanding customer goals, training users on Grammarly’s products and features, and aligning product capabilities with organizational goals and objectives.
• Conduct strategic account reviews, providing tailored insights and performance metrics to reinforce value, deepen engagement, and align on success plans.
• Drive adoption and product usage through thoughtful engagement strategies, champion development, and customer education.
• Leverage customer engagement data and trends to identify risks, uncover opportunities, and take proactive, data-informed actions that exceed performance targets.
• Act as a consultative partner and trusted advisor, aligning Grammarly’s AI-powered solutions with each customer’s business strategy and communication goals.
• Apply knowledge of AI and Large Language Models (LLMs) to help customers stay ahead of industry trends and maximize value from Grammarly’s offerings.
• Build and grow strategic relationships through multithreading, identifying and nurturing champions and influencers across departments and seniority levels.
• Lead effective, executive-ready customer meetings, crafting clear agendas, surfacing strategic insights, and facilitating collaborative decision-making.
• Gather and synthesize customer feedback, creating meaningful feedback loops to influence Grammarly’s product roadmap and innovation priorities.
• Contribute to continuous improvement initiatives by identifying gaps, streamlining processes, and supporting team-wide content and operational enhancements.
• Mentor peers and share best practices, serving as a trusted resource and collaborator across the Customer Success team and broader organization.

• 5+ years of experience in Customer Success, Account Management, or a related client-facing role with enterprise SaaS customers.
• Proven success managing large, strategic accounts—owning renewals, driving adoption, and exceeding retention and revenue goals.
• Strong communicator with exceptional relationship-building skills and a consultative, customer-centric approach.
• Comfortable working with C-level stakeholders and navigating complex organizational structures through strategic multithreading.
• Analytical mindset with the ability to interpret both quantitative and qualitative data, identify trends, and act decisively.
• Experience influencing cross-functional partners, including product, marketing, and engineering, to advocate for customer needs and business outcomes.
• Operational excellence in tools like CRM (e.g., Salesforce) for tracking activities, pipeline, and project milestones.
• Solid understanding of subscription models, including freemium, pilots, upsells, and customer lifecycle strategies.
• Demonstrated fluency in English—both written and spoken—with polished communication and presentation skills.
• Familiarity with the AI landscape, especially Large Language Models (LLMs), and a strong ability to translate technical concepts into business value.
• Has a demonstrated ability to work independently with minimal guidance, proactively manages tasks and priorities across multiple projects, analyzes and executes work efficiently, collaborates effectively with cross-functional teams, and thrives in fast-paced, results-driven environments.
• Embodies our EAGER values—is ethical, adaptable, gritty, empathetic, and remarkable.
• Is inspired by our MOVE principles: move fast and learn faster; obsess about creating customer value; value impact over activity; and embrace healthy disagreement rooted in trust.

Grammarly offers all team members competitive pay along with a benefits package encompassing the following and more: 

• Excellent health care (including a wide range of medical, dental, vision, mental health, and fertility benefits)
• Disability and life insurance options
• 401(k) and RRSP matching 
• Paid parental leave
• 20 days of paid time off per year, 12 days of paid holidays per year, two floating holidays per year, and flexible sick time
• Generous stipends (including those for caregiving, pet care, wellness, your home office, and more)
• Annual professional development budget and opportunities

Grammarly takes a market-based approach to compensation, which means base pay may vary depending on your location. Our US locations are categorized into two compensation zones based on proximity to our hub locations.

Base pay may vary considerably depending on job-related knowledge, skills, and experience. The expected salary ranges for this position are outlined below by compensation zone and may be modified in the future. The expected “On Target Earnings” (OTE) for this role are outlined below and may be modified in the future.