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Software Is Eating the World

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HAA

a16z portfolio company

Executive Assistant / Chief of Staff

Location
San Francisco, California, United States
Work arrangement
On-site
Job type
Full-time

About the role

Posted Sep 20, 2026

Read the overview on our job board page before you apply: https://jobs.ashbyhq.com/theacademysf

I'm looking for a right hand operator who loves checklists, operations, and wrangling people. Fully in-person in San Francisco.

Over my last two companies, I've had an Executive Assistant at each. I rely heavily on them for both personal and professional life management. In turn, I'm an active coach, thought partner, and career champion.

The last EA I had (Audrey Bannon) is now Head of People at my last company, Maven. Over the years, I taught her everything I could about business, comms, and operations. She had access to my inbox and my take on every person I interfaced with - and as a result, she got to see exactly how a company operates at every level. And of course, along the way, her scope grew every day, and her compensation grew accordingly. By the end, she was doing the day-to-day operations for almost every non-core function - she ran our offsites, managed my email, built our internal company culture, handled our taxes, managed vendor contracts, etc.

What makes these relationships special is the following:

  • I am doing a million things at once. You keep things organized.

  • I am hard-charging and provide frequent feedback. You are calm under pressure.

  • I never remember anything. You remember everything.

  • I am deeply involved in everything at the company. You love learning new things and are excited to help in every aspect.

  • I have high standards on experience design and hospitality. You are naturally excellent with people and have good taste.

  • HAA is an AI-native school. You have Claude projects for everything in your life.

  • I am constantly interfacing with hundreds of people, including celebrities and 16-year-olds. You know how to write and communicate differently with each.

I truly believe this is an amazing opportunity for the right person. It is very likely the right person has never been an EA before, or has ambitions to learn the ropes and grow into a Chief of Staff. As long as you're willing to do the work for at least 2 years, then I'm open-minded.

Here's the work:

  • Managing my email. AI-assisted for organization but human-written for any critical communication.

  • Managing my calendar, travel, etc. Use Calendly for most people, but for the right people it'll be completely manual. The hardest part here will be picking hotels, restaurants, etc.

  • Creating a CRM for the company. Just look at the Academy's website - we already have a massive list of partners and relationships to manage, and it will grow.

  • Running the office. You'll make sure the office is stocked, set up workstations, onboard employees, etc.

  • Legal, HR, Finance, Accounting. You can know none of this when you arrive, but you must be excited to learn. Over time you will learn these skills and be able to review vendor contracts (especially with AI's assistance), onboard/recruit employees, manage billpay, etc.

  • Managing my personal life. You'll mostly prioritize my work life, but there will be some personal stuff such as managing my finances or interfacing with vendors at my house.

  • Implementing the company's culture. By working super closely with me, you'll learn to become a steward of my views on how the company should operate and you'll do your best to help create that culture within the company.

Prior work experience is not super relevant to me, but I've had success with former teachers and former operations managers in the hospitality industry.

Explore what’s next at HAA.

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At a glance

Location
San Francisco · San Francisco, California, United States
Workplace
On-site
Employment
Full-time
Team
Operations
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The company

HAA

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