Head of Sales Operations

Remote (Canada)

Grammarly empowers people to thrive and connect, whenever and wherever they communicate. Every day, 30 million people and 30,000 teams around the world use our AI-powered writing assistant. All of this begins with our team collaborating in a values-driven and learning-oriented environment. 


To achieve our ambitious goals, we’re looking for a Head of Sales Operationsto join our Revenue Operations team, which is responsible for our lead-to-close strategy and the planning and processes for our organizations-revenue line of business (business-to-business, education, and Grammarly for Developers). The person in this role will manage the day-to-day pre- and post-sale operations across all of our go-to-market motions, as well as build the foundations for how we optimize our self-serve new-business acquisition (in partnership with the Self-Serve Program Manager and Growth team) and transition high-value self-serve accounts to our Sales team—the foundations for product-led growth. In addition to overseeing traditional operations, such as strategy, process, and planning, you will oversee and build the team running our deal desk, territory planning, and commission management.


Your impact

As Head of SalesOps, you will directly contribute to our vision to help English writers around the world communicate more effectively. In addition to individuals, we want to empower businesses to be as effective as they can be by supporting their employees globally. You will have a crucial role in growing all segments via scalable and sustainable strategies. You will drive the development of an organizations-revenue SalesOps function and define its long-term capabilities and capacity roadmap.

  • Within your first 30 days, you will complete your general onboarding and meet the team; study and internalize Grammarly’s business models and our go-to-market motions; and begin to build relationships with key stakeholders across the business.
  • By month three, you will establish a framework for measuring performance and managing our business to assist revenue leaders in setting and tracking their progress toward revenue goals. You will also develop and begin to execute a hiring plan for your team.
  • By month six, you will hire and onboard at least two new members to your team.
  • By year one, you will have built the foundations of a multidiscipline SalesOps team to support all the needs of the Organizations Revenue team.


We’re looking for someone who

  • Embodies our EAGER values—is ethical, adaptable, gritty, empathetic, and remarkable.
  • Is able to collaborate in person 2–4 weeks per quarter, traveling if necessary to the hub where the team is based.
  • Has a history of building and managing high-performing SalesOps teams that drive real bookings growth and operational excellence in a software business.
  • Is an analytical problem-solver who can find coherent patterns in incoherent data sets.
  • Is passionate about business-to-business SaaS companies and the metrics that drive them forward. 
  • Has a clear communication and collaboration style that enables them to act on their strategic ideas.
  • Is comfortable moving others to action from an executive-level downwards.
  • Has—as a plus—prior management-consulting experience.


Support for you, professionally and personally

  • Professional growth: We hire people we trust, and we give team members autonomy to do their best work. We also support professional development 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. We have a highly collaborative culture supported by our EAGER values. We also take time to celebrate our colleagues and accomplishments with global, local, and team-specific events and programs.
  • Comprehensive benefits: Grammarly offers all team members competitive pay along with a benefits package encompassing superior health care (including mental health benefits). We also offer support to set up a home office, ample and defined time off, gym and recreation stipends, admission discounts, and more.


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 ancestry, race, place of origin, political belief, religion, marital status, family status, physical or mental disability, sex, sexual orientation, gender identity or expression, age, or any other characteristic protected by law. Grammarly is an equal opportunity employer and abides by the Employment Equity Act.


Grammarly currently supports the long-term work of team members in the following Canadian provinces: British Columbia, Ontario 


Grammarly currently supports the long-term work of team members in the following US states: Arizona, California, Colorado, Florida, Georgia, Illinois, Maine, Massachusetts, Minnesota, Nevada, New Jersey, New York, North Carolina, Oregon, Pennsylvania (Kennett Township, New London Township, Pittsburgh City, Shaler Township), South Carolina, Texas, Utah, Virginia, and Washington, as well as the District of Columbia


Please note that Grammarly’s COVID-19 vaccination policy requires that all team members in North America be vaccinated against COVID-19 to meet in person for Grammarly business or to work from a North America hub location. It is expected that this will be a requirement for this role. Qualified candidates in North America who cannot be vaccinated for medical reasons or because of a sincerely held religious belief may request a reasonable accommodation to this policy. For Europe, this policy requires team members to be vaccinated or produce a daily negative COVID-19 test administered on-site to work from the hub or attend in-person meetings.

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