Community Manager + Architect at Contrarian Thinking

🚀 Why This Role Matters

At Contrarian Thinking, we’re on a mission to help people achieve financial freedom through acquiring and scaling businesses. We’ve built two thriving communities: one focused on business acquisitions, the other on growing and scaling. Together, they’re filled with ambitious people chasing freedom on their own terms.

Your job? Architect the experience. Not just manage a community — but design the systems, rituals, and moments that turn thousands of members into engaged, empowered business owners.

If you’ve ever wanted to wake up knowing your work directly helps people quit their jobs, buy companies, and change their lives forever — this is it.

🌎 What You’ll Do

You’ll own the heartbeat of our communities. That means:

Community Strategy & Design

• Build and execute the strategy that makes our communities world-class.
• Design onboarding and activation experiences so new members hit their first wins in 30 days.
• Create rituals, challenges, and magic moments that keep people coming back for more.

Daily Engagement & Culture

• Be a visible leader in Slack: connect members, spark conversations, and keep the vibe alive.
• Ensure 95%+ of member posts/questions get a response within 24 hours (with support from our concierge team + ambassadors).
• Celebrate wins and elevate the best member stories.

Programming & Events

• Architect a calendar of calls, workshops, and events that deliver massive value.
• Host community calls, prep speakers, and make sure sessions spark continued conversations.
• Track event engagement → action (e.g. how many attendees post deals or take next steps).

Superusers & Ambassadors

• Lead and expand our Ambassador program: recognition, perks, micro-grants, and backstage access.
• Coach and support ambassadors, deal coaches, and volunteer leaders so they shine.
• Empower members to run local meetups and member-led events.

Operations & Insights

• Partner with our concierge + assistant community manager to keep everything humming.
• Use HubSpot, Common Room, and Slack analytics to measure activation, engagement, and retention.
• Publish a Monthly Community Insights Brief to leadership with member needs, wins, and opportunities.

📈 What Success Looks Like

Your North Star is member success and engagement. Concretely, that means:

• 75%+ of new members activated in their first 30 days.
• 65%+ monthly engagement rate.
• Weekly Active Users at 50%.
• 2 new deals reported every week.
• 95% of posts/questions answered within 24h.
• Community-Member-Fit Score (CMFS) 85+.

🧩 Who You Are

• You’ve built or scaled communities before (5+ years in community management, member experience, or related roles).
• You’re as comfortable designing strategy as you are jumping into Slack to welcome a new member.
• You get fired up about creating rituals, experiences, and systems that drive engagement.
• You thrive in fast-paced, entrepreneurial environments where freedom + responsibility are the norm.
• You believe in financial freedom, ownership, and doing work that actually changes lives.

Bonus points if you’ve worked in:

• Business, startups, entrepreneurship, or acquisition communities.
• Both online and in-person event programming.
• Leading volunteers, superusers, or ambassador programs.

🙌 What You’ll Get

• The chance to lead and design two of the most dynamic communities in business.
• A front-row seat to watch hundreds of people buy, grow, and scale businesses.
• A culture that lives by our Contrarian Creed: winners want pressure, we value weird over boring, and results beat intentions.
• The resources and budget to experiment, create, and delight.
• A team of concierge + assistant CM + deal coaches to support you.

Necessary Skills and Qualifications

• 5+ years of experience in community management, member experience, or related roles
• Proven ability to design and execute community engagement strategies that drive measurable outcomes (activation, retention, engagement)
• Strong facilitation and hosting skills for virtual calls, workshops, and events
• Excellent written and verbal communication skills; able to spark conversations and build culture in digital spaces (Slack, forums, etc.)
• Experience designing onboarding and activation flows that help members achieve quick wins
• Skilled at identifying, training, and motivating ambassadors, superusers, or volunteers
• Comfortable analyzing community metrics and turning data into actionable insights (experience with tools like HubSpot, Common Room, Slack analytics a plus)
• Strong organizational and operational skills to manage programming calendars, workflows, and reporting
• Creative mindset for designing rituals, challenges, and member experiences that feel unique and high-impact
• Ability to thrive in a fast-paced, entrepreneurial environment with high autonomy and responsibility
• Passion for entrepreneurship, business growth, and the mission of helping people achieve financial freedom

What is Contrarian Thinking and what do we do?

We aim to make Main Street > Wall Street.

Who are we: We are an investment firm and media company led by veterans of Wall Street, Private Equity, and operators of Main Street businesses. We help owners BUY, SCALE, and SELL businesses.

Our Ecosystem:

• 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.
• 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.
• 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.

The Contrarian Creed

These are the words we stand by, live by and define what it means to be a Contrarian.

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.

You ready to become an official Contrarian? Awesome, here are the details:

Location

Austin, TX - Full time in office.

Type of Employment

Full-Time

Crew Benefits

• 100% Company-paid health, dental, and vision for all full-time Crew Members with an option to add any 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 401K via Guardian
• Learn expert deal-making and how to buy businesses with 100% free access to all of our courses and our flagship Contrarian Community