Member Success Manager - Real Estate Mastermind

Member Services Manager The Boardroom Mastermind | Remote | W-2 | $150,000–$200,000+ OTE About The Boardroom Mastermind The Boardroom Mastermind is a 14-year-old, invite-only private mastermind for elite real estate operators and business owners. We are not a coaching program, not a course, and not a seminar. We are a highly curated room of experienced, high-net-worth operators, developers, lenders, syndicators, portfolio investors, and business owners who have outgrown their local circle and need a peer group that matches their level. Membership starts at $26,000 to $66,000 per year. Getting in is not easy. That is the point. And once someone is in, what happens next determines whether they stay for one year or fifteen. The Opportunity The Boardroom already has a member experience infrastructure in place — you're being hired to elevate it and run it with real intention. You'll design and own the full member experience — from the moment someone enrolls through their first 90 days, their ongoing engagement, their renewal, and their upgrade into higher tiers of membership. You are not a customer service manager. Customer service people want the sales and revenue conversations to belong to someone else. This role owns renewal revenue, retention, and ascension revenue — and the way you generate all three is by elevating the member experience. World-class here isn't a vibe — it's measurable: members who feel seen before they ask to be, upgrade opportunities surfaced at the right moment instead of missed, and disengagement caught and reversed weeks before a renewal conversation ever happens. You'll have administrative support from day one. Existing team members currently handle pieces of this work and will continue supporting the role as their responsibilities transition to you over time. As you build out a stronger playbook, you will hire and lead a small team of Member Success Advisors who execute what you've designed, while you retain the highest-profile accounts and personally handle every escalation — including exit conversations when a member is considering leaving. What You Will Do Own the full member lifecycle: welcome call, 90-day onboarding milestones, quarterly touchpoints, health checks, renewal, and ascension Design and run onboarding calls for every new member, scheduled within days of enrollment Elevate the systems and SOPs supporting the member experience Proactively re-engage members who miss events or go quiet — before they disengage further Facilitate warm introductions between members based on their business and goals Identify and place upgrade/ascension opportunities (higher membership tiers, 1:1 coaching) in front of members at the right moment, rather than waiting to be asked Own the renewal conversation and, when needed, the exit interview — finding alternative solutions (downgrades, custom arrangements) before a member leaves Eventually hire, train, and manage a team of Member Success Advisors who follow the SOPs you build What You Bring 2+ years in high-touch client success, account management, or membership experience — ideally within a paid membership, high-ticket coaching, or mastermind environment Exposure to real estate entrepreneurs (wholesalers, flippers, brokers, developers, commercial investors) or experience working closely with founders/business owners scaling a company — you understand how busy, revenue-focused people think and operate A revenue mindset, not a pure service mindset — you see retention and renewal as things you own, not things you hand off The instinct to solve problems before being asked — you notice when someone's falling out of engagement and go get them The ability to elevate a process that already exists into something considerably better — you're not waiting for someone to hand you a script A polished, professional presence suited to working with high-net-worth clientele Comfort being measured on outcomes (renewal rate, ascension revenue) rather than activity What Makes This Different You're stepping into an existing, resourced function and elevating it into something considerably more intentional — with administrative support already in place and a clear path to leading a team as you build. You report directly to Noah Cosby, CRO, who has built and led sales and service functions producing over $100M annually. This Role Is NOT For You If... You want revenue and sales conversations to be someone else's job You need everything fully built and scripted before you can perform You've only worked in low-ticket, transactional customer support You wait for members to come to you rather than proactively checking in Real estate or business ownership are worlds you've never been curious about Compensation and Benefits Base salary $75,000–$85,000 + monthly performance bonus + commission on membership ascension/upgrades | OTE $150,000–$200,000+ 401k Company healthcare plan Access to Boardroom Mastermind quarterly in-person events and virtual sessions as part of the team Direct mentorship from Noah Cosby, CRO Fully remote; anywhere in the United States (quarterly in-person travel required) How to Apply Submit your application and complete all screening questions. Incomplete applications will not be reviewed. Qualified applicants will be contacted by the recruiting team regarding next steps.