Join our companies in their quest to drive powerful, positive, change that endures.

Director of People Ops and Compliance, North America



People & HR, Legal, Operations
Sterling, VA, USA
Posted on Friday, June 7, 2024

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 up to a maximum of 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 goals, we’re looking for a strong leader for our People Operations and Global Compliance teams to join our People team and drive initiatives that will allow Grammarly to continue scaling.

Your impact

As the Director of People Operations and Compliance at Grammarly, you will be responsible for leading Grammarly’s Global Mobility & Immigration, Contingent Workforce, and North America People Ops teams. Additionally, you will play a critical role in developing M&A integration and international expansion capabilities and the HR compliance function for our rapidly growing multinational company. Your experience and expertise will be instrumental in creating and implementing effective cross-functional solutions that align with Grammarly’s short- and long-term strategic objectives.

In this role, you will:

  • Build strong relationships with stakeholders across HR, Legal, Finance, and Business teams to drive forward cross-functional, company-building initiatives and influence change as the company matures and grows.
  • Determine, drive, and operationalize a comprehensive global HR compliance strategy that aligns with organizational goals, public company readiness, and legal requirements with support.
  • Set up Grammarly’s People Ops team to scale, partnering with Systems and IT teams on thoughtful tooling and automation that leverages the latest AI technology capabilities while keeping employee experience design as a priority.
  • Own relationships with our Finance, Payroll, and Equity Administration teams and consult with them to determine and implement appropriate policies and protocols to address global mobility considerations.
  • Be responsible for a comprehensive contingent workforce strategy that provides short-term talent solutions to the Business and will be an influential change agent to drive adoption across the Company.
  • Partner with Legal, People Ops, Total Rewards, Finance, and other internal stakeholders to build employment capabilities in new jurisdictions, support merger and acquisition activities, and drive other key strategic People projects to completion.
  • Select and oversee external vendors, as needed, to ensure scaled programs and exceptional service to team members.

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 up to 4 weeks per quarter, traveling if necessary to the hub where the team is based.
  • Demonstrates experience leading operational People teams at a high-growth and innovative technology company and a track record of driving alignment and delivering results while managing, developing, and empowering teams to be greater than the sum of their parts.
  • Is comfortable with ambiguity and has a proactive affinity for breaking down complex problems and proposing operationally excellent solutions that balance risk, speed, employee experience, and resource considerations to drive the business forward.
  • Has significant experience working cross-functionally with internal stakeholders in Finance, IT, Recruiting, Legal, and other areas in a fast-paced, high-growth startup environment.
  • Can influence peers and senior leadership through deep subject-matter expertise, relationship-building abilities, and demonstrated strategic business acumen.
  • Has familiarity with global employment considerations across multiple markets and knows how to work with outside advisors and in-house experts to drive the best solution for the company.
  • Communicates clearly, influentially, and empathetically both face-to-face and in writing.
  • Ideally, has 10+ years in one or more areas of oversight — Global Mobility, People Operations, Contingent Workforce, HR Compliance, M&A Integration, and International Expansion. A combination of private and public company experience is preferred.

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 options
  • 401(k) and RRSP matching
  • 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, please refer to this page. If a location of interest is not listed, please speak with a recruiter for additional information.

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.

United States:
Zone 1: $273,000 - $334,000/year (USD)
Zone 2: $246,000 - $301,000/year (USD)

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.



All team members meeting in person for official Grammarly business or working from a hub location are strongly encouraged to be vaccinated against COVID-19.