Lead Executive Assistant

From Fivetran’s founding until now, our mission has remained the same: to make access to data as simple and reliable as electricity. With Fivetran, customer data arrives in their warehouses, canonical and ready to query, with no engineering or maintenance required. We’re proud that more organizations continue to leverage our technology every day to become truly data-driven. About the Role Fivetran is building data pipelines to power the modern data stack for thousands of companies. We’re looking for a Lead Executive Assistant to provide high-impact support to our Chief Legal Officer. This role goes well beyond traditional calendar and inbox management, you’ll serve as a strategic partner to your executive, owning complex operational workflows, driving cross-functional coordination, and ensuring the legal department runs smoothly behind the scenes. This is a high-visibility role that touches executive operations, event planning, team culture, and legal operations. The ideal candidate thrives in ambiguity, takes initiative without being asked, and brings strong judgment about when to act independently and when to escalate. This is a full-time, hybrid position 2 days per week in our Denver, CO, Oakland, CA or NYC, NY offices. Our hybrid work model offers a blend of remote flexibility and in-person collaboration, including two days in the office each week to connect and build as a team. Technologies You’ll Use Google Workspace (Gmail, Calendar, Drive, Docs, Sheets, Slides) Slack Workday Navan (travel and expense management) Greenhouse (recruiting) Slab (internal documentation) AI tools (e.g., Claude, ChatGPT) What You’ll Do Executive Support Calendar Management: Keep the CLO’s calendar organized and conflict-free. Field and prioritize scheduling requests in alignment with executive priorities, adapting swiftly to changing circumstances. Meeting Support: Schedule meetings, prepare agendas and briefing materials, and take notes with actionable summaries. Travel Logistics: Coordinate complex domestic and international travel, including flights, accommodations, ground transportation, and travel documentation, with attention to preferences, policies, and cost-efficiency. Inbox Management: Triage and organize email inboxes, draft responses, and surface priority items on behalf of the CLO. Departmental Support Document Creation & Editing: Draft, edit, and enhance documents and presentations with clear language and visual appeal. Expense Reporting: Manage expense submissions, prompt timely receipt gathering from the CLO, and submit reports accurately and on time. Internal Communications: Draft correspondence, team announcements, and Slack messages on behalf of Legal leadership. Ad Hoc Tasks: Handle one-off administrative requests such as document retrieval, research, meeting setup, and presentation preparation. Project & Program Management Task and Workflow Management: Use task management tools to track follow-ups, share updates, and keep work flowing across executive priorities. Legal Operations Partnership: Support cross-functional projects such as process improvements and operational tracking in coordination with Legal Ops. SOPs and Playbooks: Create and maintain standard operating procedures and playbooks for repeatable processes to ensure continuity and scalability. Team & Culture Building Offsites and Events: Plan and execute department-wide offsites and events end-to-end, including venue sourcing, contract negotiation, agendas, travel, meals, logistics, and on-the-ground coordination. Team Engagement: Organize team events, gifting moments, and employee recognition initiatives that foster connection and positivity within the Legal org. All-Hands Production: Own and produce monthly Legal All-Hands meetings, including agenda creation, deck management, host recruitment, and post-meeting recaps. Culture Champion: Monitor organizational health, surface engagement issues, and coordinate milestone celebrations. Skills We’re Looking For 7+ years of experience supporting C-suite or VP-level executives, preferably in a high-growth tech environment Strong project management instincts—you build systems, document processes, and think about scalability without being asked Excellent written communication skills, including experience drafting executive correspondence and internal comms Demonstrated comfort with ambiguity and a bias toward action; you figure things out and propose solutions rather than waiting for direction Familiarity with AI tools and a willingness to adopt new technologies to improve workflows and efficiency #LI-HYBRID #LI-SR1 The compensation range displayed on this job posting reflects the minimum and maximum target for new hire compensation for the target position and level, and may include sales incentives or target bonuses depending on the role. Our compensation ranges are determined by role, level, and location. Our job titles may span more than one career level. Within the range, individual compensation is determined by additional factors, including job-related skills, experience, relevant education or training, business need, market demands. The compensation range is subject to change and may be modified in the future. Your recruiter can share more about the specific compensation range for your location during the hiring process. New York Pay Range $151,072—$188,840 USD Perks and Benefits 100% employer-paid medical insurance* Generous paid time-off policy (PTO), plus paid sick time, inclusive parental leave policy, holidays, and volunteer days off RSU stock grants* Professional development and training opportunities Company virtual happy hours, free food, and fun team-building activities Monthly cell phone stipend Access to an innovative mental health support platform that offers personalized care and resources in areas such as: therapy, coaching, and self-guided mindfulness exercises for all covered employees and their covered dependents. *May vary by country and worker type - please reach out to your recruiter for more information Click here to learn more about Fivetran's Benefits by Region. We’re honored to be valued at over $5.6 billion, but more importantly, we’re proud of our core values of Get Stuck In, Do the Right Thing, and One Team, One Dream. Read about us in Forbes. Fivetran brings together high-quality talent across the globe to make data access as easy and reliable as electricity for our customers. We value and recognize that our customers benefit from having innovative teams made of people from many backgrounds, experiences, and identities. Fivetran promotes diversity, equity, inclusion & belonging through attracting, recruiting, developing, and retaining a diverse workforce, not only because it is the right thing to do, but because it helps us build a world-class company to better serve our customers, our people and our communities. To learn more about Fivetran’s culture and what it’s like to be part of the team, click here and enjoy our video. To learn more about our candidate privacy policy, you can read our statement here. We are committed to ensuring that all candidates have an equal opportunity to participate in our interview process. If you require accommodations at any stage of the process due to a disability, medical condition, or any other circumstance, please don't hesitate to submit your request by filling out this form. We will work with you to provide reasonable accommodations to facilitate your participation and ensure a fair and accessible interview experience. Your request and any information provided will be kept confidential and will not impact your candidacy. We look forward to hearing from you and accommodating your needs to the best of our ability.