Director of Strategy & Growth: SMB Boardroom

Position Overview

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 thriving small business owners—starting right here in our vibrant Contrarian Community.

As a Director of Strategy & Growth, you’ll blend strategic advisory skills with hands-on coaching to help business owners grow, systemize, and scale. You’ll empower our members with frameworks, accountability, and clarity to transform their businesses from stuck to scalable. You’ve built businesses, worked with founders, operated in finance companies or been a consultant or advisor.

Why This Role Matters

You will be the driving force behind our advisory clients’ breakthroughs. You’ll ensure every member has the roadmap, tools, and confidence to grow profits, build teams, and scale sustainably. In this seat, you’re not just consulting - you’re diagnosing and rebuilding. You’ll sit across from founders, dig into what’s actually breaking their business, and help them fix it in real time. You’ll walk in with a thesis, battle-test it live, and walk out with a battle plan that drives real growth. Then you’ll turn those hard-won insights into systems, frameworks, and playbooks we can run across every business in our ecosystem.

What You’ll Own

Strategic Coaching & Curriculum

• Design and lead a growth-focused curriculum (e.g., weekly office hours, monthly strategy calls, scaling workshops).
  
• Partner with leadership to evolve programming based on member results and feedback.
  
• Deliver actionable playbooks on hiring, systems, growth strategy, and leadership.

High-Touch Member Engagement

• Collaborate with your team to facilitate weekly, structured, and energizing group coaching calls.
  
• Provide real-time insights on scaling challenges in person and online.

Community Activation & Events

• Orchestrate quarterly flagship events for business builders (three in-person, one virtual each year).
  
• Drive community initiatives that highlight 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 key metrics (revenue growth, retention, NPS, operational efficiency) and propose initiatives to improve outcomes.
  
• Serve as a thought leader—publishing insights, case studies, and “lessons from the field” to elevate our brand.

Who You Are

Experienced Operator & Scaling Expert

• You’ve bought, built, or sold businesses yourself—or you’re operating one now.

Executive-Level Coach & Facilitator

• Proven track record coaching entrepreneurs 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 frameworks that drive measurable business growth.
  
• 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 live by our Creed (e.g., “Less words, more meaning,” “We do the dirty work,” “We want your weird”).

Soft Skills We Love

• Smart, 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

What Success Looks Like

• Members achieve measurable revenue growth, improved systems, and stronger leadership.
  
• Outstanding feedback (NPS) on group sessions, office hours, and events.
  
• Growth in program enrollment, retention, and referrals fueled by member success stories.

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 (5 Days a Week in Office)

During intensive workshop weeks, we expect the team to be available for extended hours.

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 401(k) plan via Accrue
• Learn expert deal-making and how to buy businesses with 100% free access to all of our courses and our flagship Contrarian Community