Account Executive — High-Ticket Closer

Position Overview

We're looking for a proven closer to join Contrarian Thinking as a remote Account Executive. You'll help qualified members of our audience take the leap from interested observer to active business buyer.

You'll meet with prospective members of the Contrarian community who've engaged with our brand — through our content, virtual events, and in-person experiences — and consult them on the best next step toward business ownership. The majority of leads are warm, inbound, and often pre-qualified by a setter. Your job is to run world-class consultative sales conversations and enroll the right people into the right Contrarian program, community, or event.

If you've closed premium offers in the high-ticket or transactional space and have consistently been a top performer, this role could be for you.

Key Responsibilities

• Conduct discovery and consultation calls with qualified, inbound leads via phone and Zoom
• Close high-ticket enrollments ($5K–$25K offers) with a consultative, education-first approach
• Understand each client's goals, financial readiness, and desired outcomes
• Recommend the appropriate Contrarian Thinking program, event, or membership
• Own the full sales cycle from consultation to enrollment, with a focus on integrity and highlighting the value of our program
• Rigorously manage your pipeline and follow-up. No lead left behind
• Track performance, conversion rates, and feedback to continuously improve
• Partner with sales leadership and marketing to optimize messaging and lead flow
• Learn from deep, hands-on exposure to business acquisition, operational optimization, and scalable growth strategies

The Ideal Candidate

• 2+ years in a closing role for high-ticket offers or SMB transactional sales motions ($5K–$50K+ price points)
• Documented track record: close rates, marquee wins, and references you're proud to share
• Comfortable running 1-call and 2-call closes over Zoom and phone with inbound leads
• Strong ability to listen, empathize, and tailor solutions to client goals — you diagnose before you prescribe
• High emotional intelligence and professional communication
• Self-managed and disciplined in a remote environment: you show up, take calls, and work your pipeline without a manager over your shoulder
• Excitement for entrepreneurship, personal finance, and helping others take bold steps
• You think like a leader and excel in competitive environments
• Entrepreneurial spirit — you're comfortable in ambiguity and move fast

What Is Contrarian Thinking?

We are 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 in scaling to create enduring, profitable businesses they love to run, and that change the world.
2. Events & Community — We help business buyers and builders with live workshops, weekly calls, and annual events around the country. For Buyers: a vetted community using our curriculum and advisors to buy or invest in businesses. For Builders: a community and events helping 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.

Come build with us.

The Contrarian Creed

1. People who say it cannot be done should not interrupt those who are doing it.
2. Be a great f*cking human. Do what's right even when it hurts.
3. How you do anything is how you do everything.
4. We do the dirty work.
5. Your word is your contract.
6. We are Archimedes. Find your lever.
7. Winners want pressure.
8. We want your weird. Better weird than boring.
9. Your job isn't done until THE job is done. We work the problem.
10. Assumptions are for assholes. Find the truth.
11. Less words, more meaning.
12. Even our notes are worth stealing. Make every creation a mini-masterpiece.
13. Show me your results, not your intentions.

Crew Benefits

• 100% company-paid health, dental, and vision for all full-time Crew Members, with an option to add dependents
• Unlimited PTO policy (with approval from your Direct Support) + 8 paid US holidays
• On-time direct deposit pay 2x/month
• Option to enroll in a 401(k) plan via Vestwell with competitive match options
• Learn expert deal-making and how to buy businesses with 100% free access to all of our courses and our flagship Contrarian Community