Acquisitions Advisor

At Contrarian Thinking, we free minds and build bank accounts. We’re on a mission to help 1 million people become financially free and to create 100,000 small business owners—starting right here in our vibrant Contrarian Community. As our Acquisitions Advisor, you’ll combine strategic advisory chops with hands-on coaching to shape and scale our community’s deal-making mastery.

You will be the driving force behind our members’ breakthroughs—on Slack, on calls, and at live events. You’ll ensure the Community feels personal, not transactional, and that every member has the roadmap, resources, and confidence to source, negotiate, and close “boring businesses” that cash-flow.

• Strategic Coaching & Curriculum
  
  
  
  • Design and lead a full curriculum of group programs (e.g., weekly office hours, monthly deal review calls, etc.).
  
  
  • Partner with leadership to iterate on curriculum based on member feedback and performance metrics.
  
  
  
  


• High-Touch Member Engagement
  
  
  
  • Facilitate weekly structured, energizing group calls.
  
  
  • Host two AMA-style office‐hour sessions per month, providing real-time insight on individual deals.
  
  
  • Jump into Slack channels and 1:1 deal‐review threads to answer questions, give feedback, and spark “aha” moments.
  
  
  
  


• Community Activation & Events
  
  
  
  • Orchestrate quarterly flagship events for community dealmakers (three in-person, one virtual each year).
  
  
  • Drive community initiatives that surface member wins, celebrate progress, and foster peer collaboration.
  
  
  • Partner with marketing to craft program communications that boost enrollment, engagement, and referrals.
  
  
  
  


• Program Innovation & Growth
  
  
  
  • Track success metrics (deal close rates, retention, member satisfaction) and propose initiatives to improve outcomes.
  
  
  • Identify opportunities to expand service offerings (e.g., peer mastermind cohorts, live intensives, tool integrations).
  
  
  • Serve as a thought leader—publishing insights, case studies, and “lessons from the field” to elevate our brand.
  
  
  
  

• Deep Deal Expertise
  
  
  
  • You’ve bought, built, or sold businesses yourself—or you’re operating one now.
  
  
  • You understand deal sourcing, due diligence, negotiation tactics, financing structures, and post-acquisition ops.
  
  
  
  


• Executive-Level Coach & Facilitator
  
  
  
  • Proven track record coaching entrepreneurial audiences to achieve stretch outcomes.
  
  
  • Superior facilitation skills: you command the room, challenge conventional wisdom, and create a culture of accountability.
  
  
  
  


• Curriculum Architect & Strategist
  
  
  
  • Experience designing programs, workshops, or masterminds that move the needle on member success.
  
  
  • Analytical mindset: you measure impact, iterate based on data, and continually raise the bar.
  
  
  
  


• Community Builder
  
  
  
  • You believe in “people over platforms”—fostering authentic connection in Slack, live calls, and in-person events.
  
  
  • Skilled storyteller: you surface member stories to inspire, educate, and drive momentum.
  
  
  
  


• Contrarian Mindset
  
  
  
  • You challenge assumptions, embrace “boring businesses,” and find opportunities where others see obstacles.
  
  
  • You live by our Creed (e.g., “Less words, more meaning,” “We do the dirty work,” “We want your weird”).
  
  
  
  

• Warm, direct communication—whether on Zoom, Slack, or stage


• Tech-savvy with tools like Notion, Zoom, and community platforms


• Empathetic, curious, and relentlessly solution-focused


• Proactive, reliable, and driven by purpose

• Higher deal-close rates and faster member progress through our curriculum


• Buzzing Slack channels with insightful Q&A, peer support, and celebration of wins


• Outstanding feedback (NPS) on group sessions, office hours, and events


• Growth in program enrollment, retention, and member-driven referrals

• Salary: Based upon experience plus performance bonus


• Benefits: 100% company-paid health, dental & vision; unlimited PTO; 401(k) via Guardian


• Perks: VIP access to all Contrarian events; free ticket to Main Street Over Wall Street Summit; backstage entry to a network of 1,300+ dealmakers


• Community Access: 100% free access to our full suite of courses and Contrarian Community resources