Assistant for Contrarian Thinking

This is not a traditional Executive Assistant role. And it’s not a junior admin job either.

You are the in-person execution arm for the CEO of Contrarian Thinking. You will be embedded directly within her existing assistant team to ensure that her travel, scheduling, and day-to-day operations run flawlessly across all her ventures.

Your job is simple in theory and complex in practice: Keep the CEO focused on decisions, strategy, and growth—not logistics.

You will work in lockstep with the CEO’s broader support team, acting as the physical 'boots on the ground' extension of the office. If you are obsessive about logistics, calm under pressure, and think three steps ahead without being asked, this role fits.

Contrarian Thinking is an investment and advisory firm powered by media and led by veterans of Wall Street, Private Equity, and operators of Main Street businesses. We help owners BUY, SCALE, and SELL businesses.

Our Ecosystem:

1. Capital & Investment Company - We invest millions annually in businesses, and support our portfolio businesses in scaling to create enduring, profitable businesses they love to run, but also change the world.
2. Events & Community - We help business buyers and builders with live workshops, weekly calls, and annual events around the country. We have two types of communities: 1) For Buyers - a vetted community of buyers who utilize our campus, curriculum, and advisors to buy or invest in businesses, and 2) For Builders - a community and events where we help builders use our proven scaling systems, advisors, and curriculum to grow profitable, enduring businesses.
3. Media & Content - We aim to be the biggest and most trusted business media company in the world - through podcasts, YouTube, books, and online education. We aim to make business and finance content better than any University degree.

Come build with us.

Travel & Logistics (Core Responsibility)

• Full ownership of all CEO travel
• Flights, hotels, ground transportation, itineraries, contingencies
• Domestic and international, often multi-city, often changing quickly
• Real-time problem solving during delays, cancellations, reroutes
• Vendor relationships with airlines, hotels, and car services
• Travel expense tracking and reconciliation

If travel breaks, you fix it before it becomes a problem.

Calendar & Meeting Execution

• Manage the CEO’s calendar with judgment and authority
• Coordinate investor meetings, podcast recordings, internal sessions, and events
• Handle reschedules and last-minute pivots calmly
• Prepare meeting briefs, agendas, and logistics
• Track follow-ups and ensure nothing drops

You are not just booking time — you are protecting it.

CEO Team Coordination

• Work in lockstep with the CEO’s assistant team to ensure seamless coverage
• Communicate proactively when priorities shift
• Prevent duplication or gaps in support
• Maintain alignment across personal and professional commitments

This role requires low ego and high communication.

Operational Support

• Assist with meeting notes, action items, and execution follow-through
• Maintain organization across Notion and internal systems
• Support light operations projects as trust grows
• Help create systems that improve efficiency over time

This role begins execution-heavy and expands with capability and judgment.

This role is:

• In-person and hands-on
• Travel-first and logistics-heavy
• High-trust and high-judgment
• Fast-moving, sometimes chaotic
• Direct, high-feedback environment

This role is not:

• A passive admin position
• Remote or hybrid
• A rigid 9–5
• Pure calendar babysitting

This is a front-row seat to how a CEO operates across media, investments, and growth.

If your goal is to level up quickly, sharpen judgment, and build operational muscle at a high level, this is a strong foundation.

• 3–5+ years supporting a senior executive or founder
• Deep experience managing complex, high-stakes travel
• Based in Austin, TX and available in person
• Exceptionally organized with strong follow-through
• Clear, concise communicator
• Comfortable operating within a team of assistants
• Fluent in Notion, Slack, Zoom, and modern tools
• High discretion with sensitive information
• Comfortable with direct feedback and rapid change

• Austin, TX
• Full-time, in-office
• Travel required as needed

• 100% company-paid health, dental, and vision
• Unlimited PTO + 8 paid US holidays
• 401k via Vestwell
• Free access to all Contrarian Thinking courses and flagship community

• Tell us about a time you saved an executive from a travel or logistics disaster.
• Bonus points if it involved rebooking something that absolutely should not have been salvageable.