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 a new type of investment and advisory firm supported by highly leveraged media.

Led by Codie Sanchez, 15+ year veteran of private equity and operator of a portfolio of Main Street businesses, we help owners BUY, SCALE, SELL. We buy businesses, teach our partners how to do acquisitions, and then we help them scale to create enduring businesses they love to run.

We build tools like BizScout (one of the largest business acquisition marketplaces in the world), Growth Boardroom (an operating system and community for business owners over $1M+), and Contrarian Thinking Capital (a venture capital firm investing in innovation for the next generation of businesses).

In less than 5 years, we have:

• Rallied ~11 million followers
• Turned 9-to-5ers into owners, helping thousands ditch the corporate hamster wheel
• Bought into dozens of real-world businesses through our Main Street holding company
• Launched an investment fund that backs some of the world’s fastest-growing companies

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.