Senior Customer Success Associate, Small Business Member Experience

Position Overview

Do you have a proven history of taking care of customers, driving measurable results, and increasing your scope of responsibility year over year? Are you currently building tools in AI to help you work more efficiently? Are you ready for bigger challenges, teammates who make you better, and a faster path to growth? If the answer is yes, then this is the role for you.

You'll work directly with senior leadership to own the entire member experience across the Contrarian Boardroom Small Business Advisory Practice. You will be responsible for driving engagement, managing curriculum delivery, collecting and organizing member data, segmenting members into targeted groups, facilitating peer collaboration, and delivering clean reporting to leadership that tells the real story of member health and business performance.

This role is not theoretical. It is hands-on, relationship-driven, and systems-heavy.

You will move fluidly between member outreach, engagement strategy, data analysis, cross-sell conversations, and curriculum management. One week you may be diagnosing why a cohort's engagement dropped and building a creative re-engagement campaign. Next week you may be guiding a member who just acquired a business through their transition from our acquisition consulting practice into our business consulting practice.

In this role you will learn exactly how a world-class advisory team operates at scale and what it takes to provide a top-tier advisory experience.

Though you are joining as a Sr. Associate, we expect you to outgrow this role. As we scale, this position can evolve into:

• Director of Member Experience
• VP of Client Success
• Head of Member Operations
• …or something we haven't even planned for and you are a perfect fit

We do not believe in stagnant roles. If you are not operating at a significantly higher level in 18–24 months, this likely is not the right fit.

Before you get excited, we have to tell you that this role is no joke.

You will be expected to personally get to know and build rapport with all of our members as we rapidly scale. You will be expected to diagnose disengaged members and have a creative plan to reach them before they churn. You will be expected to own renewal rates and cross-sell transitions. Your compensation depends on it.

This is not for someone who wants to “manage accounts.”

This is for someone who wants to build a world-class member experience that drives real results in real businesses.

If that's you, then keep reading.

What You'll Own

Here's what you'll be responsible for, day in and day out:

Client Relationship Management

• Build and maintain personal rapport with all ~1,600 members. Know their names, their stories, their goals, and where they are in their journey.
• Serve as the primary point of contact for member questions, concerns, and milestone celebrations.
• Proactively reach out to members to maintain high-touch engagement so that no one feels forgotten.
• Diagnose member health using engagement data, participation metrics, and direct communication to identify at-risk members early.
• Create and execute personalized re-engagement plans for disengaged or at-risk members with creative, high-impact outreach strategies.

Advisory Delivery

• Oversee the delivery and continuous improvement of the member curriculum across the business consulting practices.
• Plan, coordinate, and schedule educational programming that drive member engagement and progress.
• Gather member feedback on curriculum effectiveness and collaborate with subject matter experts to iterate and improve content.

Member Data, Segmentation & Peer Collaboration

• Collect and manage member financial and business information in a structured, secure, and accessible manner.
• Segment and organize members into targeted groups based on stage, goals, industry, engagement level, and other relevant criteria.
• Enable peer collaboration by facilitating group interactions and cohort-based learning among similarly situated members.

Systems, Processes & Reporting

• Design, build, and optimize scalable systems and processes that allow you to manage 1,600+ members efficiently without sacrificing quality.
• Quickly understand and track key engagement metrics, e.g. attendance, participation, NPS, content consumption, milestone completion, and more.
• Measure and report on improved business performance of members, connecting engagement activities to tangible business outcomes.
• Build and maintain clean, executive-ready dashboards that give senior leadership real-time visibility into member health, engagement trends, and revenue metrics.

Cross-Sell & Practice Transitions

• Own the transition process for members moving from the acquisition consulting practice to the business consulting practice once they purchase a business.
• Identify cross-sell opportunities early by tracking member progress and readiness signals.
• Manage the cross-sell conversation consultatively—positioning the business consulting practice as the natural next step in the member's journey.
• Drive cross-sell conversion rates through relationship trust, timing, and strategic nurture sequences.

Retention & Renewals

• Take full ownership of member renewal rates. Engaged members renew. Disengaged members churn. You own that outcome.
• Implement proactive retention strategies rooted in data, relationship quality, and demonstrated member ROI.
• Conduct renewal conversations with confidence and empathy, reinforcing value delivered and value ahead.

Skills and Qualifications

Here's what we believe is required to succeed in this role:

A minimum of 3 years of experience in one or more of the following:

• Client success, account management, or membership/community management at scale (500+ clients)
• Consultative sales with a focus on retention, renewals, or cross-sell/upsell
• Operations, systems design, or program management inside a high-growth company
• Consulting, coaching, or education-based business models

However, this role is NOT for people who hide behind dashboards and never pick up the phone. This is for someone who builds real relationships AND real systems. We need someone with exceptional interpersonal skills who is equally comfortable having a vulnerable conversation with a struggling member and presenting clean data to the CEO. Someone with strong analytical skills and experience building dashboards and reporting on engagement metrics. Someone with a bias for action who creates systems and processes from scratch that scale efficiently. Someone with high proficiency in CRM platforms, data/reporting tools, and webinar platforms. And above all, someone who thrives in an environment where results matter more than titles, and actions speak louder than words.

What is Contrarian Thinking and what do we do?

Contrarian Thinking is a new type of investment and advisory firm supported by highly leveraged media.

Led by Codie Sanchez, 15+ year veteran of private equity and operator of a portfolio of Main Street businesses, we help owners BUY, SCALE, SELL. We buy businesses, teach our partners how to do acquisitions, and then we help them scale to create enduring businesses they love to run.

We build tools like BizScout (one of the largest business acquisition marketplaces in the world), Growth Boardroom (an operating system and community for business owners over $1M+), and Contrarian Thinking Capital (a venture capital firm investing in innovation for the next generation of businesses).

In less than 5 years, we have:

• Rallied ~12 million followers
• Turned 9-to-5ers into owners, helping thousands ditch the corporate hamster wheel
• Bought into dozens of real-world businesses through our Main Street holding company
• Launched an investment fund that backs some of the world's fastest-growing companies

Compensation

Salary Competitive base + performance bonus tied directly to:

• Member renewal rates
• Cross-sell transitions from the acquisition consulting practice to the business consulting practice

High performers will be rewarded aggressively.

Location

Austin, TXIn the office with your team all of the time.

Type of Employment

Full-Time

Crew Benefits

All benefits begin Day 1.

• 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 Vestwell with competitive match options
• Learn expert deal-making and how to buy businesses with 100% free access to all of our courses and our flagship Contrarian Community