Founder Success Advisor (FSA)

Be the force behind legendary founder experiences.

At Founder OS, our mission is to help 100,000 entrepreneurs scale their businesses and unlock freedom. We help founders architect their personal brands so that they're predictable, scalable, and systemized, helping them with things like:

• Landing pages
• Social media (YouTube, LinkedIn, Instagram, X)
• Lead magnets
• Content strategy
• Newsletters
• Monetizing their attention through helping them craft and scale their offer

The Founder Success team makes that mission real, ensuring every founder is supported, challenged, and retained through world-class coaching, community, and accountability.

As a Founder Success Advisor, you'll be more than support or a typical "CSM." You'll be a strategist, guide, and operator ensuring every founder gets the most out of their journey. This role directly drives retention, upsells, testimonials, and overall program success.

The Role

The FSA role blends coaching, community leadership, sales, and client success management. You'll own a portfolio of founders and ensure they're hitting milestones, fully engaged in the program, and seeing clear ROI.

You will:

• Lead community calls and coaching sessions that equip founders with actionable strategies
• Drive community engagement by sparking conversations, sharing wins, and curating resources in Skool
• Follow up 1:1 with founders to ensure progress, hold them accountable, and close gaps before they escalate
• Review call recordings to maintain quality, identify red flags, and surface insights to leadership
• Collect Trustpilot reviews, testimonials, and case studies to showcase founder success
• Identify and drive upsell opportunities through roadmap calls and value expansion
• Own renewal conversations and retention metrics
• Create and post content, Looms, and FAQs to scale support across the community
• Close the feedback loop with sales, product, and leadership, surfacing what founders need and where they're blocked
• Help founders set up automations, workflows, and AI tools that accelerate their business (if you're technical, this is where you shine)
• You take the work the last mile, getting the details across the finish line with minimal oversight

What Success Looks Like

• 80%+ portfolio retention across assigned founders
• 90%+ of founders leaving reviews/testimonials on Trustpilot or case studies
• Weekly upsell opportunities identified and converted into extensions/upsells
• Consistent, high-quality community calls with strong attendance and engagement
• Call reviews and founder follow-ups documented and visible to leadership
• Clear feedback loops improving both the founder experience and internal systems
• Zero dropped balls: issues flagged early, solutions implemented fast

Who You Are

This role attracts a specific kind of person. The best FSAs we've seen share a few things in common: they've built something themselves, they're competitive by nature, and they don't need anyone to hold their hand.

You might be:

• An ex-agency owner who sold, closed, or stepped back from your agency. You already know client management, delivery, and accountability because you lived it. You understand the grind and you can coach founders through it because you've been on the other side.
• An ex-founder You have entrepreneurial DNA and you coach from real experience, not theory. You've made the mistakes, learned the lessons, and now you want to help other founders avoid them and you don't want to continue to build on your own.
• A vibe coder, AI automation specialist, or technical builder who can help founders actually set up their systems. You can walk a founder through building their content workflow, automating their lead gen, or getting their tech stack running.
• A social media manager who's been in the trenches growing accounts, building content calendars, and understanding what actually moves the needle on platforms. You know what works because you've done it, and you can coach a founder through their content strategy with real, tactical advice, not generic best practices.
• Someone from an ad agency background who's managed client relationships, run campaigns, and delivered results under pressure. You know how to manage expectations, hit deadlines, and communicate with business owners who are spending real money. We know ad agency work is brutal, come have fun working with real founders.
• A freelance coach or consultant who's been running 1:1 client work and wants to do it inside a world-class program with a built-in audience instead of chasing your own clients.
• A startup COO or ops leader who's burned out on chaos but still wants meaningful, high-impact work. You're a systems thinker who wants to help founders build without the overhead of running your own company.
• A creator economy operator who understands content, personal branding, and audience building from the inside. You've worked with creators or been one yourself.

Requirements

• 3+ years in one of the above roles / in high-growth environments
• Strong facilitation skills: confident leading group coaching and community calls
• Proven track record of retaining and expanding client accounts
• Excellent written and verbal communication
• Tech-fluent: comfortable with HubSpot, Skool, Slack, Zoom, Loom, CRM tools. Bonus if you're fluent in AI tools and automation platforms.
• High attention to detail: impeccable call notes, follow-ups, and execution discipline
• Sales-aware: able to spot upsell opportunities and handle renewal conversations naturally
• Thrives in a fast-paced, high-expectation, founder-facing environment with extreme ownership
• Competitive drive: you played sports, you keep score, you hate losing. The best people in this role have that edge.

Ideal Candidate

• Operates with rigor: systematic, reliable, and proactive
• Balances coaching skill with operational excellence, knows how to inspire and how to track
• Passionate about serving ambitious entrepreneurs and helping them win
• Sees around corners: anticipates founder needs before they become issues, manages up with clarity and clear action
• Obsessed with continuous improvement for themselves, the team, and the founders they support
• Has an affinity for AI and automation. This is an AI-native team. If you're excited about using AI to work smarter, you'll thrive here. If you're resistant to it, this isn't the right fit.

Compensation

• Base salary + performance-based bonuses
• Fully remote role on a global team
• Must have overlap with EST

Our Culture

Founder OS is built on freedom, community, creativity, and simplicity. We operate with extreme ownership and high standards, and we expect the same from everyone on our team. This is a place where:

• Founders are at the center of everything. We exist to serve and scale them.
• We deliver white-glove, proactive service to every founder.
• Team members bring solutions, not problems. We value operators who take full ownership. If you need constant oversight, this isn't the role for you.
• Growth is the standard, professionally and personally. Feedback is embraced, learning is constant, and improvement never stops.
• We build authentic community connections that keep founders engaged and inspired.
• We move fast, execute with clarity, and keep systems simple.
• Community matters, internally with our team and externally with the founders we serve.
• We celebrate wins loudly and tackle challenges directly.

If you want to be part of a team that's rewriting how founders scale and thrive, and you're ready to match our intensity and ownership, you'll fit right in.