5+ years of experience running, scaling, leading, or advising entrepreneurial businesses. Strong communication and facilitation skills, especially in virtual, one-on-one settings. Familiarity with business operating systems like Scalable OS, EOS, Scaling Up, OKRs, or similar. Based in a U.S. or Canadian time zone with availability during standard business hours. Comfortable using CRM software (HubSpot preferred), Slack, and Zoom. Experience facilitating structured programs or planning sessions (Nice to Have). Prior experience in 'high-ticket' coaching, advisory, or mastermind programs (Nice to Have). Familiarity with multiple business types and models (Nice to Have).