Director of Strategy & Growth: SMB Boardroom

Contrarian Thinking • Austin, TX

121d

About The Position

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.

Requirements

• Experience in buying, building, or selling businesses.
• Proven track record coaching entrepreneurs to achieve stretch outcomes.
• Superior facilitation skills with the ability to command the room and create a culture of accountability.
• Experience designing programs, workshops, or frameworks that drive measurable business growth.
• Analytical mindset with the ability to measure impact and iterate based on data.
• Strong storytelling skills to inspire and educate members.

Nice To Haves

• Smart, direct communication skills.
• Tech-savvy with tools like Notion, Zoom, and community platforms.
• Empathetic, curious, and relentlessly solution-focused.
• Proactive, reliable, and driven by purpose.

Responsibilities

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

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.
• Free access to all courses and the flagship Contrarian Community.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 11-50 employees