Community Architect

At Contrarian Thinking, we’re on a mission to help people achieve financial freedom by acquiring and scaling businesses. We’ve built two thriving communities — Contrarian Academy, focused on business acquisitions, and Growth Boardroom, focused on scaling existing companies. Together, they’re filled with ambitious entrepreneurs chasing freedom on their own terms.

Your job? Architect the experience. Not just manage a community — but design the strategy, team, and systems 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.

You’ll lead the team that powers the heartbeat of our communities. That means:

Community Strategy & Outcomes

• Build and own the community strategy across Contrarian Academy and Growth Boardroom.

• Align community initiatives with business outcomes: deals closed, business growth, retention, referrals, and brand impact.

• Define community goals, KPIs, and quarterly plans in partnership with the Head of Product & Experience.

• Continuously evaluate performance and member feedback to ensure the community drives measurable results.

• Collaborate closely with the Product & Experience, Growth, and Events teams to ensure community strategy aligns with the broader member journey.

Member Experience & Engagement

• Partner with the Head of Product & Experience and Growth team to design and refine the member journey — from onboarding to long-term engagement.

• Create rituals, challenges, and magic moments that foster belonging, accountability, and measurable member success.

• Maintain a visible presence in both communities to model connection and culture.

• Empower the Community Coordinator and Concierges to deliver exceptional daily member interactions.

• Ensure communications across Slack, email, and events feel personal, intentional, and aligned with our brand voice.

Volunteer Leadership & Member-Driven Programs

• Strengthen and expand our volunteer ecosystem, including Ambassadors, local chapter heads, and superusers.

• Own the strategy, recognition systems, and success metrics for volunteer leaders.

• Collaborate with the Community Coordinator on day-to-day communication, scheduling, and logistics for these programs.

• Manage a budget for community recognition, micro-grants, and member-led initiatives.

• Partner with Events to ensure strong community participation in major events and empower members to run local meetups.

Team Leadership & Development

• Lead and grow the community team (currently a Community Coordinator and Concierge team of seven).

• Build out team structure, roles, and performance expectations.

• Hire, onboard, and develop new team members; create a culture of ownership, collaboration, and excellence.

• Provide mentorship, feedback, and accountability to drive team success.

Operations, Delivery & Collaboration

• Co-own with the Community Coordinator the delivery of all virtual community experiences — ensuring smooth logistics, attendance, and follow-up.

• Partner with Product & Experience operations to ensure accurate reporting and insights that inform strategy.

• Collaborate with Growth and Events to align community activities with larger company initiatives.

• Produce a Monthly Community Insights Brief highlighting member wins, key learnings, and opportunities for improvement.

• Maintain documentation and SOPs that make our community scalable and reliable.

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

• More members closing deals and growing profitable businesses.

• Activation, engagement, and retention rates consistently improving.

• The community team operates smoothly, on time, and at a high standard.

• Member satisfaction (CMFS) remains world-class.

• Community becomes a key driver of retention, referrals, and brand growth.

• You’ve built or scaled communities before (7+ years in community management, member experience, or related leadership roles).

• You’re as comfortable designing strategy as you are jumping into Slack to connect with members.

• You get fired up about creating systems, experiences, and culture that drive measurable impact.

• You thrive in fast-paced, entrepreneurial environments where freedom + accountability 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 community programs or events.

• Leading volunteer ecosystems like Ambassadors or superuser programs.

• The chance to lead and design two of the most dynamic business communities in the world.

• A front-row seat to watch thousands of members 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 dedicated team of Community Coordinator + Concierges to help you execute.

• 7+ years of experience in community management, member experience, or related leadership roles

• Proven ability to build and lead community teams that deliver measurable outcomes

• Experience designing and executing strategies that connect community engagement to business results

• Strong facilitation and hosting skills for virtual calls, workshops, and live events

• Excellent written and verbal communication skills; able to spark conversations and build culture in digital spaces (Slack, forums, etc.)

• Skilled at identifying, training, and motivating ambassadors, superusers, or volunteers

• Comfortable analyzing community metrics and translating insights into action

• Strong organizational and operational skills to manage workflows, calendars, and reporting

• Creative mindset for designing experiences that feel personal, high-impact, and scalable

• 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

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 portfolio companies in scaling to create enduring, profitable companies that change the world.

• Events & Community – We help business buyers and builders through live workshops, weekly calls, and annual events around the country. We have two types of communities:

  1. For Buyers (Contrarian Academy): a vetted community of buyers who use our campus, curriculum, and advisors to acquire or invest in businesses.

  2. For Builders (Growth Boardroom): a community and event ecosystem where we help business owners use our proven systems and advisors to grow enduring, profitable companies.

• Media & Content – We aim to be the biggest and most trusted business media company in the world through podcasts, YouTube, books, and education that make business content better than any university degree.

Come build with us.

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:

Austin, TX — Full-time, in-office

Full-Time

• 100% company-paid health, dental, and vision for all full-time Crew Members (option to add dependents)

• Unlimited PTO (with approval from your Direct Support) + 8 paid US holidays

• On-time direct deposit pay twice per month

• Option to enroll in a 401(k) via Guardian

• Free access to all Contrarian Thinking courses and community programs to learn expert deal-making and business buying