Executive Assistant to VP, Strategy & Operations

The Rundown AI, Inc.; San Francisco (CA); On-site; USD 158,000 - 180,000; Full time

Job summary

A leading AI writing assistance company seeks an Executive Assistant for the VP of Strategy & Operations in San Francisco. This role involves managing logistics, maintaining systems for clarity, and fostering team connections, emphasizing operational excellence and strong communication skills to succeed in a dynamic environment.

Benefits

Excellent health care

Disability and life insurance options

401(k) matching

Paid parental leave

Generous paid time off

Annual professional development budget

Qualifications

• 3+ years of experience supporting senior leaders.
• Ability to communicate with clarity and empathy.
• Experience simplifying complexity through effective tools.

Responsibilities

• Manage complex calendar and travel logistics for the VP.
• Prepare for meetings by drafting materials and tracking action items.
• Support the leadership team with projects and initiatives.

Skills

Operational excellence

Emotional intelligence

Communication

Problem-solving

Resourcefulness

Job description

Grammarly team members in this role must be based in San Francisco, and they must be able to collaborate in person two to three days per week.

About Grammarly

Grammarly is the world’s leading AI writing assistance company trusted by over 40 million people and 50,000 organizations. From instantly creating a first draft to perfecting every message, Grammarly helps people at 96% of theFortune 500 and teams at companies like Atlassian, Databricks, and Zoom get their point across—and get results—with best-in-class security practices that keep data private and protected. Founded in 2009, Grammarly is No. 14 on the Forbes Cloud 100, one of TIME’s 100 Most Influential Companies, one of Fast Company’s Most Innovative Companies in AI, and one of Inc.’s Best Workplaces.

The Opportunity

We’re looking for an Executive Assistant to support our VP, Strategy & Operations, and help move some of Grammarly’s most cross-functional, high-impact initiatives forward. This role is based in our San Francisco hub and requires in-office presence 2–3 times per week.

As Molly's Executive Assistant, you’ll be a strategic and operational partner—not just managing logistics but helping her stay focused, prepared, and connected to what matters most. You’ll work at the intersection of company-wide priorities and functional execution, gaining exposure to executive-level strategy, operations, and decision-making.

In this role, you will:

• Own and optimize the daily workflow by managing a complex and dynamic calendar, coordinating travel logistics, organizing the inbox, submitting expenses, and ensuring seamless day-to-day execution.
• Design and maintain systems that foster clarity and efficiency, including streamlined Coda docs, polished Google Slides decks, and team communications that align stakeholders and drive momentum.
• Partner closely with the VP to prepare for key internal meetings by drafting talking points, curating briefing materials, and ensuring she’s equipped to engage with insight and confidence.
• Track and manage cross-functional action items to ensure follow-ups are completed and nothing slips through the cracks. Keep initiatives moving forward with thoughtful attention to detail and accountability.
• Provide support to the broader leadership team, stepping in to assist with projects, meetings, or org-wide initiatives that benefit from your logistical or strategic support.
• Help the VP stay connected with her team by identifying and facilitating moments of recognition, celebration, and personal connection, reinforcing a strong, engaged team culture.
• Collaborate closely with the Strategy & Operations team to improve internal workflows, team all hands, facilitate cross-functional planning, and ensure effective communication throughout the organization.
• Handle sensitive information with a high degree of professionalism, discretion, and emotional intelligence, maintaining trust and integrity at all times.

Qualifications

We are looking for a highly capable and forward-thinking Executive Assistant who thrives in fast-paced, ever-evolving environments. The ideal candidate brings a unique combination of operational excellence, strategic acumen, and emotional intelligence to support the VP, Strategy & Operations in achieving maximum impact.

Success in this role will come naturally if you:

• Think in systems and enjoy simplifying complexity — with the ability to build intuitive, effective tools (like a well-crafted Coda doc) that drive clarity and alignment.
• Act as a true force multiplier for executives — anticipating needs, managing details, and creating leverage in every interaction.
• Remain calm, resourceful, and solution-oriented in the face of ambiguity or rapid change, always bringing a steady, thoughtful approach to problem-solving.
• Communicate with clarity and empathy, both in writing and in person, helping to refine and elevate the COO’s voice in internal documents and presentations.
• Bring 3+ years of experience supporting senior leaders, ideally in fast-paced, high-growth, or cross-functional environments.
• Care deeply about people and team culture, and are energized by helping high-performing teams stay connected, aligned, and effective.
• Embodies our EAGER values — is ethical, adaptable, gritty, empathetic, and remarkable.
• Is inspired by our MOVE principles: move fast and learn faster; obsess about creating customer value; value impact over activity; and embrace healthy disagreement rooted in trust.

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
• 20 days of paid time off per year, 12 days of paid holidays per year, two floating holidays per year, and flexible sick time
• Generous stipends (including those for caregiving, pet care, wellness, your home office, and more)
• Annual professional development budget and opportunities

Grammarly takes a market-based approach to compensation, which means base pay may vary depending on your location. Our US locations are categorized into two compensation zones based on proximity to our hub locations.

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.

Zone 1: $158,000 – $180,000/year (USD)

We encourage you to apply

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