Executive Assistant — Silicon Valley Family Office

Hire5; San Francisco (CA); Remote; USD 90,000 - 150,000; Full time

Benefits offered by this job

Remote work

Growth opportunities

Salary discussed during interview

Job summary

Hire5, a Silicon Valley–based family office, is seeking an Executive Assistant to support senior founders and investors across scheduling, travel, and operations. This role emphasizes ownership, discretion, and navigating high-trust environments.

You will manage complex calendars, coordinate international travel, handle communications, oversee household vendors, and help scale streamlined processes as the portfolio grows. Long-term growth potential is clear.

Qualifications

• 3+ years supporting an executive directly — pace and responsibility of an exec's right hand.
• Experience supporting US-based executives, working US hours.
• Confident, professional written and spoken English with clarity.
• Strong judgment, discretion, and comfort handling sensitive information.
• Highly independent, proactive, and systems-oriented.
• Comfortable juggling business and personal responsibilities.
• Active daily use of AI tools (e.g. ChatGPT, Gemini, DeepSeek) to work efficiently.

Responsibilities

• Manage complex calendars and scheduling with senior stakeholders (investors, fund partners, portfolio founders).
• Handle professional communication on behalf of principals.
• Coordinate domestic and international travel.
• Support expense review and coordination with bookkeepers.
• Build and maintain operational systems (intake forms, trackers, workflows).
• Research and book restaurants, meeting spaces, and conference rooms (US & Europe).
• Maintain strict confidentiality and information hygiene.
• Proactively identify gaps, inefficiencies, and process improvements.
• Coordinate household vendors and manage end-to-end contractor relationships.
• Manage household logistics and urgent requests.
• Support onboarding and oversight of household staff.
• Help scale household operations as needs grow.

Skills

Calendar management

Communication

Discretion

Independent / proactive

AI tools

US hours alignment

Tools

Google Workspace

Airtable

Notion

Job description

Founder details will be shared during the interview process, in alignment with privacy and confidentiality requirements.

A Silicon Valley–based family office supports early-stage investing, operating companies, and personal ventures, and has been recognized as a top early-stage investor. The Executive Assistant provides direct support to the principals across scheduling, communications, travel and logistics, vendor coordination, and day-to-day execution.

This role requires excellent judgment, clear and precise communication, and strong calendar and logistics management, along with comfort operating in a high-trust, high-context environment. The Executive Assistant works closely with senior leaders, founders, investors, and their executive assistants, serving as a thoughtful filter and force multiplier for the principals' time.

This is not a traditional EA role. It is designed for someone who wants ownership, complexity, and long-term growth in a fast-moving, execution-focused environment.

The principals are serial entrepreneurs and investors with deep experience building and scaling venture-backed companies, including businesses backed by leading Silicon Valley investors. Together, they manage a family office, oversee multiple operating companies, and continue to launch new ventures across technology and healthcare.

Responsibilities

Business & Operations (≈70%)

• Manage complex calendars and scheduling with senior stakeholders (investors, fund partners, portfolio founders)
• Handle professional communication on behalf of principals
• Coordinate domestic and international travel
• Support expense review, categorization, and coordination with bookkeepers
• Build and maintain operational systems (intake forms, trackers, workflows)
• Research and book restaurants, meeting spaces, and conference rooms (US & Europe)
• Maintain strict confidentiality and information hygiene
• Proactively identify gaps, inefficiencies, and process improvements

Personal & Household Operations (≈30%)

• Coordinate household vendors (housekeeping, plumbers, gardeners, contractors) — owning contractor relationships end to end, not just scheduling them
• Manage household logistics and urgent requests
• Support onboarding and oversight of household staff
• Help scale household operations as needs grow (e.g. new vendors, childcare support)

This role is not a fit if you

• Want a strictly 9-5 role
• Prefer narrowly defined EA tasks
• Need constant direction for standard workflows
• Are uncomfortable supporting both business and personal operations

What We're Looking For

Required

• 3+ years supporting an executive directly — operating at the pace and responsibility of an exec's right hand (Chief of Staff, startup ops, or senior EA roles with real ownership all count)
• Experience supporting US-based executives, working US hours
• Confident, professional written and spoken English — strong enough to comprehend and respond in your own words in real time (accent is fine; clarity and fluency are what matter)
• Strong judgment, discretion, and comfort handling sensitive information
• Highly independent, proactive, and systems-oriented
• Comfortable juggling business and personal responsibilities
• Active daily use of AI tools (e.g. ChatGPT, Gemini, DeepSeek, etc.) to work efficiently — using AI to amplify your own thinking, not replace it

What separates the right hire

• Operates unsupervised — once something is handed over, it's off the principal's mind
• Proactive: flags problems early, arrives with solutions, closes loops alone
• Absorbs feedback once; the same error doesn't recur
• Sound judgment on what to handle, what to elevate, and what to shield the principal from
• Full-scope comfort across business, household, property, vendors, and personal logistics
• Discretion by reflex with sensitive financial and personal information
• Detail-oriented and calm under pressure

Tools

• Google Workspace (required)
• Ability to quickly learn and use Airtable
• Familiarity with Notion or similar tools is a plus

Working Hours

• 8:00 AM-5:00 PM Pacific, weekdays
• Occasional weekend responsiveness (30-60 minutes) when something time sensitive breaks — a cancelled flight, an event falling through. This won't happen every weekend, but stepping in when it does should feel obvious, not like an imposition
• Flexibility required during international travel (short-term Europe coverage)

Growth Opportunity

This role has no fixed ceiling. Over time, it can grow into broader operations leadership, Chief of Staff–level ownership, or expanded responsibility across new ventures.

What We Offer

• Full-time role. We won't consider candidates planning to combine this job with another one.
• Remote work. You may be located in almost any country — you'll just need a good internet connection, a computer, and the ability to adjust your schedule to overlap with the team.
• Growth opportunities to learn and grow inside the family business.
• Salary discussed during the interview. Paid in USD.
• Application deadline: ASAP. The later you apply, the more compressed your selection process will be (e.g. less time for the test assignment).