The future is already here.
It's just not evenly distributed yet.

Grammarly team members in this role will collaborate in person 4 weeks per quarter, traveling if necessary to different hubs. They are required to live within a commutable distance of their home hub of San Francisco. Grammarly may provide relocation assistance.

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 goals, we’re looking for a Head of Commercial to join our Legal team to manage and scale a world-class commercial function at Grammarly. This Commercial Counsel will work closely with our Sales, Customer Success, Revenue Operations, Compliance, Support, and Privacy leaders to build best-in-class systems and processes to set up Grammarly's B2B business for continued success across all channels. As a foundational member of the Grammarly Legal team, this person will also help develop the culture of the Legal team by exemplifying care for their craft, care for others, and a commitment to finding solutions to complex questions.

Your impact

As Grammarly’s Head of Commercial Legal, you will leverage your experience and expertise to support and accelerate Grammarly's next era of growth as a B2C and B2B business. This role reports to Grammarly’s General Counsel and will be a crucial partner to Grammarly’s executive team. You and your team will draft, analyze, negotiate, and close a wide range of complex commercial transactions with Grammarly’s strategic partners and customers, including channel partnerships, revenue-generating agreements with enterprises, governments, and educational institutions, and vendor agreements that power our daily operations and are critical to Grammarly’s growth. The Grammarly commercial team works cross-functionally with our finance, tax, revenue, communications, sales, marketing, and compliance teams to provide strategic and tactical guidance on growing and protecting Grammarly’s revenue. The team collaborates with product teams to achieve key business objectives, deliver strategic, business-minded, and solutions-focused guidance, and drive varied projects to scale operations in a fast-paced, high-growth environment. In this role, you will:

• Manage, influence, evolve, and scale Grammarly's inbound and outbound commercial contracting function, including operational aspects, to drive excellence in contracting.
• Lead, manage, mentor, motivate, and grow a high-performing team of attorneys and legal analysts, engaging personally in complex deals and working collaboratively with various company teams.
• Define and manage success metrics to gauge team success and reporting across Grammarly.
• Build templates, playbooks, and fall-back positions to help the broader team move more quickly in its negotiations. Regularly considering and adapting to shifts in the commercial landscape and legal standard terms to ensure that Grammarly is easy to do business with while balancing the appropriate level of risk tolerance.
• Inspire action through data-driven insights and drive teams to execute with operational rigor and efficiency.
• Be a cross-functional leader and ensure our work is cohesive, thoughtfully crafted, and executed.

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.
• Can manage multiple projects, stakeholders, priorities, and deadlines.
• Can lead and structure a deal and optimal deal flows, negotiate effectively, and have ideas about optimal negotiation and deal management, with demonstrated past effectiveness in scaling tech enterprise/B2B-focused legal teams.
• Is comfortable working with cross-functional teams at all levels across the company and advising senior leaders on risk mitigation to ensure we take the optimal path.
• Communicates clearly and empathetically both face-to-face and in writing.
• Has 10+ years of experience in a demanding and time-sensitive legal role that involved advising high-growth companies on commercial matters and scaling a commercial function, with a minimum of 4+ years as a manager. In-house and SaaS experience is a plus.
• Holds a JD (required) and has been admitted to the bar, with a license to practice law in at least one US state.

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 among team members in a variety of ways. This includes our employee resource groups, Grammarly Circles, which promote connection among those with shared identities, such as BIPOC and LGBTQIA+ team members, women, and parents. We also celebrate our colleagues and accomplishments with global, local, and team-specific programs.

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 options401(k) matching (US only)
• Paid parental leave
• Twenty days of paid time off per year, eleven days of paid holidays per year, and unlimited sick days
• Home office stipends
• Caregiver and pet care stipends
• Wellness stipends
• Admission discounts
• Learning and development opportunities

Grammarly takes a market-based approach to compensation, which means base pay may vary depending on your location. Our US and Canada locations are categorized into compensation zones based on each geographic region’s cost of labor index. For more information about our compensation zones and locations where we currently support employment, please refer to this page.

Base pay may vary considerably depending on job-related knowledge, skills, and experience. The expected salary ranges for this San Francisco-based position are outlined below and may be modified in the future.

We encourage you to apply

At Grammarly, we value our differences, and we encourage all—especially those whose identities are traditionally underrepresented in tech organizations—to apply. 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).

Please note that EEOC is optional and specific to US-based candidates.

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