Executive Assistant

About The Role

We are seeking a highly strategic, detail-oriented, and proactive Executive Assistant to serve as a key operational partner and force multiplier to our senior executive leadership team. Far beyond complex calendar orchestration and administrative workflows, you will protect executive time, anticipate organizational needs, and maintain seamless operational rhythm across high-stakes meetings, presentations, and cross-departmental projects. We are looking for an agile, highly discreet partner who thrives in ambiguity, commands operational rigor, and brings the poise, emotional intelligence, and business judgment required to operate at the C-suite level.

This role is based in SF with a minimum of two in-office work days at our SF Headquarters office.

What You Get To Do Every Day

Partner to your executives

• Own your executives' calendars end to end as their gatekeeper, fielding internal and external scheduling requests, weighing them against priorities, and recommending trade-offs, not just options
• Schedule and coordinate meetings across executives, teams, and external partners, handling rooms, video, agendas, and last-minute changes
• Look weeks ahead to flag conflicts, prep time, and decisions before they become urgent
• Prepare executives for key meetings, take clear and concise notes, and drive timely distribution and follow-up
• Handle confidential and sensitive information, including personnel, financial, and Board-related matters, with complete discretion
• Plan and coordinate domestic and international travel, including air and ground transportation, hotels, and detailed itineraries, and adjust quickly when plans change
• Process and reconcile expenses accurately and on time
• Schedule personal appointments for your executives that fall during the workday (less than 10% of the role)

Support the full leadership team

• Own at least one exec-wide workstream, such as all-hands, offsites, or internal events, including logistics and budget
• Plan meetings, presentations, and events across teams in creative formats, coordinating with fellow EAs and outside vendors
• Partner with the Chief of Staff to ensure consistency across decks and executive communications
• Help executives recognize and engage their teams to boost appreciation and morale
• Partner with Facilities and other teams to keep the office running well

Build better ways of working

• Build lightweight systems and documentation that improve executive workflows, using AI and modern tools to increase speed, quality, and reliability
• Manage contracts, NDAs, vendor paperwork, invoices, and secure document storage

What You Bring To The Role

Minimum Requirements:

• 7+ years supporting C-suite or senior executives, including multiple executives at once
• A track record of anticipating needs and solving problems before they surface
• Sound judgment: you weigh trade-offs and make clear recommendations
• Proven discretion with confidential and sensitive information, including personnel, financial, and executive matters
• Hands-on use of AI in your daily work, with examples of workflows you've built or improved
• Fluency with Google Workspace, Slack, and modern productivity tools, with curiosity to learn new technologies
• Excellent interpersonal and communication skills, high emotional intelligence, and a team-first approach to sharing work across an EA team
• A growth mindset: you seek feedback, learn quickly, and keep looking for better ways to work

Preferred Requirements:

• Public company experience, including board processes, SEC reporting timelines, or investor relations

Compensation, Benefits, + Perks

• Employee Stock Purchase Plan

• 401K with Company Match

• Medical, Dental & Vision Insurance

• Paid Parental Leave

• 9 Paid Company Holidays

• Flexible Time Off (With Manager Approval)

• Find out more about our Benefits here.

The expected salary range for this role is $120,000.00-$155,000.00. To determine starting pay we carefully consider a variety of factors, including primary work location and an evaluation of a candidate's skills, experience, market demands, and internal parity. Additionally, salary is just one component of TRR's total rewards package. Depending on role, employees may also be eligible for a bonus program, incentive pay and benefits.

The RealReal is the world's largest online marketplace for authenticated, resale luxury goods, with 40 million members. With a rigorous authentication process overseen by experts, The RealReal provides a safe and reliable platform for consumers to buy and sell their luxury items. We have hundreds of in-house gemologists, horologists, and brand authenticators who inspect thousands of items each day. As a sustainable company, we give new life to pieces by thousands of brands across numerous categories-including women's and men's fashion, fine jewelry and watches, art, and home-in support of the circular economy. We make selling effortless with free virtual appointments, in-home pickup, drop-off, and direct shipping. We handle all of the work for consignors, including authenticating, using AI and machine learning to determine optimal pricing, photographing and listing their items, as well as shipping and customer service.

The RealReal is committed to providing an equal employment opportunity regardless of race, color, ancestry, religion, sex, national origin, sexual orientation, age, citizenship, marital status, disability, gender identity or expression, or Veteran status. We will consider qualified applicants for a position regardless of arrest or conviction records. At TRR, People Come First. That's why diversity and inclusion are vital to our priorities as an equal opportunity employer. You can read about our Diversity Equity and Inclusion program here.

Reasonable accommodations may be made to enable individuals with disabilities to perform the essential functions. The employee is regularly required to sit; use hands to finger, handle, or feel and talk or hear. The employee is occasionally required to stand; walk; reach with hands and arms; climb or balance; stoop, kneel, crouch, or crawl; and taste or smell. The employee must occasionally lift and/or move up to 10 pounds. Specific vision abilities required by this job include close vision. The physical demands described here are representative of those that must be met by an employee to successfully perform the essential functions of this job.