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.

About Grammarly

Grammarly is the world’s leading AI writing assistance company trusted by over 30 million people and 70,000 teams. From instantly creating a first draft to perfecting every message, Grammarly helps people at 96% of the Fortune 500 and teams at companies like Atlassian, Databricks, and Zoom get their point across—and get results—with best-in-class security practices that keep data private and protected. Founded in 2009, Grammarly is No. 14 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.

The Opportunity

To achieve our ambitious goals, we are seeking a skilled and motivated Sales Enablement Segment Manager to drive impactful enablement initiatives across our global Revenue team. We are looking for a proactive, results-oriented enablement professional with a track record of success in sales enablement, specifically for Account Executives and Key Account Principals. This role will be essential in shaping and executing scalable enablement programs that foster skill-building, collaboration, and strategic alignment. 

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 the Sales Enablement Segment Manager, you’ll use a builder’s mindset to develop transformative sales training, resources, and programs that boost sales performance. You'll work directly with stakeholders across organizational levels to identify needs, develop tailored solutions, and influence key training initiatives, equipping our teams to thrive in a competitive, fast-growing B2B environment.

In this role, you will:

• Design and implement high-impact Sales Enablement programs that increase sales effectiveness and drive measurable results. 
• Collaborate closely with Account Executives, frontline managers, and cross-functional teams to pinpoint gaps and develop strategic, scalable enablement solutions focused on revenue impact.
• Implement a data-driven approach to continuously refine programs, ensuring alignment with core business objectives and improved performance outcomes. 
• Foster a coaching culture by leveraging data and technology to deliver meaningful insights and support sales and business growth.
• Incorporate feedback actively to maintain an engaging, interactive learning environment that addresses key KPIs. 
• Promote the adoption of methodologies, tools, and best practices, continuously innovating delivery, adoption, and reporting to optimize results. 

Qualifications

• 2+ years of top-performing, quota-carrying AE experience, demonstrating a deep understanding of sales challenges and opportunities. 
• 2+ years of Sales Enablement experience, demonstrating an ability to build foundational B2B SaaS learning programs for Account Executives across an organization.
• Excellent communication and simplification skills to make complex concepts engaging and accessible for all learners. 
• Metrics-focused mindset to develop and iterate training content aligned with business goals and learning outcomes. 
• Experience building scalable, repeatable coaching programs for individual contributors and teams. 
• Strong familiarity with SaaS tech stacks and a knack for optimizing workflows to enhance productivity and growth. 
• Proven sales coach with 1:1 and group training expertise in a high-growth SaaS setting, with a track record of driving coaching culture. 
• Knowledge of sales and adult learning methodologies and evaluation methods to ensure training effectiveness and engagement. 
• Strategic thinker with experience establishing performance benchmarks and standards for measuring success. 
• 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.

Compensation and Benefits

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. In Canada, all locations where we support employment are considered “Zone 1”. 

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. 

For more information about our compensation zones and locations where we currently support employment, please refer to this page. If a location of interest is not listed, please speak with a recruiter for additional information. 

We encourage you to apply

At Grammarly, we value our differences, and we encourage all to apply—especially those whose identities are traditionally underrepresented in tech organizations. We do not discriminate on the basis of race, religion, color, gender expression or identity, sexual orientation, ancestry, national origin, citizenship, age, marital status, veteran status, disability status, political belief, or any other characteristic protected by law. Grammarly is an equal opportunity employer and a participant in the US federal E-Verify program (US). We also abide by the Employment Equity Act (Canada).

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