Senior Associate - Client Success & Program Management

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 Senior Associate - Client Success & Program Management, 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.

(Think: The Operator Behind the Curtain Who Turns Clients into Case Studies)

This isn’t a “service” role. It’s a growth role.

You’ll work side by side with founders, operators, and deal-makers inside Contrarian Thinking’s Boardroom to make sure every client doesn’t just get results—they get obsessed with them. Your mission is to turn the client journey into a repeatable growth engine that drives retention, and referrals.

You’ll design the systems, build the playbooks, and architect the kind of white-glove experience that turns our clients into walking proof that our frameworks work. You’ll be part strategist, part operator, part therapist - translating chaos into clarity and execution.

You’ll be the connective tissue between Sales, Advisory, Media, Events, and Marketing. You’re the one making sure what we promise is what we deliver.

• Own the client experience. From the first handshake to the renewal. Every interaction, every touchpoint, every handoff is your purview.
• Turn relationships into revenue. Design engagement cadences, event follow-ups, and communication rhythms that don’t just retain clients, they expand accounts and amplify lifetime value.
• Be the system architect. Build the CRM dashboards, SOPs, and reporting infrastructure that make our client health and renewal pipeline obvious at a glance.
• Get your hands dirty. Early on, you’ll personally drive bookings, lead calls, and set the gold standard while we scale the team.
• Design playbooks that scale. Codify what works, scripts, workflows, pre- and post-event comms, so the entire team can replicate it.
• Partner across functions. Sync with Sales, Events, Advisory, and Media so clients feel one cohesive experience (not five disjointed ones).
• Measure what matters. You’ll own KPIs for renewals, expansions, churn, NPS, and most important increasing our clients revenue - and obsessively improve them quarter over quarter.

• 5+ years leading client success, account management, or revenue-retention teams, preferably inside a high-growth or entrepreneurial environment.
• 3+ years managing leaders or building client-facing teams from scratch.
• Proven track record of driving renewals, expansions, and raving-fan retention.
• Built and scaled systems inside CRMs like HubSpot.
• Created playbooks that made “client success” measurable and repeatable.
• Operated with a founder’s mindset: commercial acumen, ownership, and grit.
• You’ve got high EQ, executive presence, and can hold your own in any room—from founder dinners to C-suite reviews.

• 80%+ renewal rate across all Consultancy Practice Customers
• Double digit Increase in revenue in your cohorts
• Scalable systems that create faster, smoother client outcomes
• A high-performing team that hits and exceeds KPIs—consistently

You’re the kind of person who can walk into chaos and build a system, spot a client risk before it becomes a churn, and turn a dinner conversation into a deal renewal. You think in frameworks, lead with empathy, and operate like an owner.

You don’t just manage relationships—you multiply them.

Austin, TX — Full time (5 Days a Week in Office)
During intensive workshop weeks we expect the team to be available for extended hours.

Full-Time

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:

1. 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.
2. 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.
3. 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.

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.

• Salary: Based upon experience plus performance bonus
• Benefits: 100% company-paid health, dental & vision; unlimited PTO; 401(k) via Vestwell with competitive match
• Perks: VIP access to all Contrarian events.
• Community Access: 100% free access to our full suite of courses and Contrarian Community resources