Head of Grammarly Business Sales

Grammarly is excited to offer a remote-first hybrid working model. Team members work primarily remotely in the United States, Canada, Ukraine, Germany, or Poland. Certain roles have specific location requirements to facilitate collaboration at a particular Grammarly hub.

All roles have an in-person component: Conditions permitting, teams meet 2–4 weeks every quarter at one of Grammarly’s hubs in San Francisco, Kyiv, New York, Vancouver, and Berlin, or in a workspace in Kraków. This flexible approach gives team members the best of both worlds: plenty of focus time along with in-person collaboration that fosters trust and unlocks creativity.

Grammarly team members in this role must be based in the United States, and they must be able to collaborate in person 4 weeks per quarter, traveling if necessary to the hub(s) where the team is based.

The opportunity 

Grammarly is the world’s leading AI writing assistance company trusted by over 30 million people and 70,000 professional teams every day. From instantly creating a first draft to perfecting every message, Grammarly’s product offerings help people at 96% of the Fortune 500 get their point across—and get results. Grammarly has been profitable for over a decade because we’ve stayed true to our values and built an enterprise-grade product that’s secure, reliable, and helps people do their best work—without selling their data. We’re proud to be one of Inc.’s best workplaces, a Glassdoor Best Place to Work, one of TIME’s 100 Most Influential Companies, and one of Fast Company’s Most Innovative Companies in AI.

To achieve our ambitious goal, we are seeking a highly motivated and experienced Head of Sales to lead our growing team and drive revenue growth within the Grammarly Business segment. The ideal candidate will have a proven track record of success in sales leadership across SMB, mid-market, and enterprise segments, experience in the B2C+B selling motion, and will be responsible for developing and implementing sales strategies, managing sales activities, and ensuring the achievement of sales goals.

Your impact

As the Head of Sales, you will: 

• Develop and implement sales strategies to surpass revenue targets.
• Manage sales activities and monitor performance metrics to ensure sales goals are met.
• Build and lead a high-performing sales team as a second-line leader in the business.
• Develop and maintain strong relationships with key customers and stakeholders.
• Identify new business opportunities and develop strategies to capitalize on them.
• Analyze market trends and adjust sales strategies accordingly.
• Collaborate with other departments to ensure alignment of sales strategies with overall business objectives.
• Forecast sales revenue and manage budgets.

We’re looking for someone who

• Embodies our EAGER values—is ethical, adaptable, gritty, empathetic, and remarkable.
• Is inspired by our MOVE principles, which are the blueprint for how things get done at Grammarly: move fast and learn faster, obsess about creating customer value, value impact over activity, and embrace healthy disagreement rooted in trust
• Is able to collaborate in person 4 weeks per quarter, traveling if necessary to the hub where the team is based.
• Has a minimum of 10 years of sales leadership experience.
• Has a proven track record of success in achieving sales targets.
• Demonstrates strong leadership and team management skills, from hiring to performance management.
• Has excellent communication, interpersonal, and negotiation skills.
• Possesses strong business acumen and strategic thinking skills.
• Is experienced in selling to corporate or government institutions is a plus.
• Holds a Bachelor's degree in Business Administration, Marketing, or related field.

Support for you, professionally and personally

• Professional growth: We believe that autonomy and trust are key to empowering our team members to do their best, most innovative work in a way that aligns with their interests, talents, and well-being. We support professional development and advancement with training, coaching, and regular feedback.
• A connected team: Grammarly builds a product that helps people connect, and we apply this mindset to our own team. Our remote-first hybrid model enables a highly collaborative culture supported by our EAGER (ethical, adaptable, gritty, empathetic, and remarkable) values. We work to foster belonging am