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. 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 (FSA), 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.
• You take the work the mile - getting the details across the finish line with minimal oversight or needs from leadership.

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 Extension/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

Requirements

Transparently, candidate’s backgrounds can look very different in this role; however, we have found the best success with past closers or candidates with a strong sales background who are looking to support high-tier founders truly grow and transform. 

• 3+ years in sales, account management, or coaching 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 skills
• Tech-fluent (HubSpot, Skool, Slack, Zoom, Loom, CRM tools)
• High attention to detail: impeccable call notes, follow-ups, and execution discipline
• Sales-aware: able to spot upsell opportunities and handle renewal conversations
• Thrives in a fast-paced, high-expectation, founder-facing environment with extreme ownership

Ideal Candidate

• Passionate about serving ambitious entrepreneurs and helping them win
• Operates with rigor: systematic, reliable, and proactive
• Balances coaching skill with operational excellence - knows how to inspire and how to track
• 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

Compensation 

• Competitive salary + performance-based bonuses tied to retention, upsells, and case studies
• 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.
• Delivering 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.
• Building 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.
• Celebrating wins loudly, and tackling 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.

Founder OS is an equal opportunity employer committed to building a diverse team of exceptional humans who dazzle founders every single day.