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Grammarly team members in this role will collaborate in person 3 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 Chief of Staff to provide strategic and operational support for our people organization. The person in this role will drive integrated people planning, establish the team's business rhythm, and ensure programs are aligned with strategic objectives. This person will act as a strategic amplifier and extension of the Chief People Officer, driving operational excellence and measurable outcomes aligned with Grammarly’s growth strategy. This person will be essential in threading together people programs to drive company success, working with people leadership and cross-functional partners for comprehensive people strategy activation. 

The ideal candidate has a proven track record of transforming PMO capabilities and program performance. This person must be a flexible and cross-functional team player who can cultivate relationships and credibility with senior leadership and key stakeholders and is comfortable in a fast-paced and scaling environment and AI's rapidly developing macro environment.

Furthermore, the person in this role will develop and implement standardized program management methodologies, policies, procedures, tools, and templates across the organization to ensure consistent project delivery, enhanced visibility, and continuous improvement of program management practices to help Grammarly achieve its long-range plans. 

Your impact

As the Chief of Staff for People, you will corral siloed efforts into integrated work streams with shared objectives, timelines, and deliverables. Reporting to Grammarly's Chief People Officer, you'll be a valuable thought partner and significantly impact the company's growth and success.  This involves developing a deeper understanding of the business and industry, collaborating with cross-functional teams, and playing a pivotal role in strategic planning and execution. 

In this role, you will:

  • Establish business rhythms for people that create opportunities for strategic collaboration and intentional integration while empowering leaders and functions to drive action and make decisions. 
  • Build and manage an integrated people roadmap to maximize the impact of programs while responsibly managing team capacity.
  • Develop and maintain a user-friendly project management framework for people that provides a consistent way to scope, track, and evaluate projects. 
  • Serve as the main point of contact and driver for a matrixed set of program managers.
  • Quickly get up to speed on the business, key metrics, and must-dos to meet financial objectives.
  • Form project teams with precise deliverable rhythms and meeting cadences in a way that establishes camaraderie and ignites energy for completing high-stake programs.
  • Identify key decision points and resource needs and package them up for effective discussion and decision-making.
  • Provide visible leadership and subject matter expertise in program management principles and disciplines within the people domain.
  • Drive process improvements by analyzing project data patterns and leveraging lessons learned.

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 in San Francisco and potentially other hubs 3 weeks per quarter.
  • Has 10+ years’ experience in project/program management, specifically within a people domain.
  • Has a proven track record transforming PMO capabilities and program delivery performance.
  • Is experienced working in similar high-growth companies (bonus if it’s in the high-tech, security, or AI space).
  • Is a strategic and analytical thinker who can link projects and programs to business priorities.
  • Is comfortable with ambiguity an can take an idea with little to no direction, run with it, and see it through to impeccable execution. 
  • Has executive presence and strong communication skills. 
  • Operates with a high level of discretion. 
  • Builds trust within teams and holds teams accountable to commitments and outcomes. 
  • Demonstrates expert knowledge of PMO best practices and program management methodologies.
  • Has a strong leadership presence and can influence at an executive level.
  • Nice to have: Holds a PMP/PgMP certification.

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. 

San Francisco:
Zone 1: $273,000 – $334,000/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).


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