Community Systems Designer — Build Real Human Connection Into a (Mostly) Automated Coaching Platform

Overview We've built a system that guides entrepreneurs toward their first $1M in revenue. Most of the guidance is automated. What we can't automate — and refuse to lose — is the feeling of being known, supported, and connected to other people on the same climb. We're hiring a consultant to design the connection layer: the structures, flows, and mechanics that make entrepreneurs feel part of a real community and build genuine relationships with each other — without us standing up an army of community managers to hold it together by hand. This is a design and systems challenge, not a staffing one. We want connection that scales through smart architecture and automation, not headcount. What you'll work on Community architecture — cohorts, pods, accountability pairs, peer groups: how members get grouped and how those groups stay alive Member-to-member connection — matching logic, intro flows, masterminds, peer accountability, so the right entrepreneurs actually find each other Engagement systems — onboarding journeys, rituals and cadences (check-ins, milestone celebrations), and trigger-based nudges that feel human, not robotic Integration with our automated system — defining where automation runs the experience and where lightweight human or AI-assisted touches create warmth Measurement — how we'll know connection and belonging are real (engagement, retention, connection density, belonging signals) You're a strong fit if you have Real experience designing online communities, cohort programs, or community-led growth — not just managing them day-to-day A track record of driving engagement through systems and automation rather than manual labor Comfort with tools like [Circle / Skool / Mighty Networks / Discord / Slack] and automation platforms like [Zapier / Make]; bonus for AI- or agent-driven facilitation A clear point of view on what actually makes people feel connected, grounded in behavioral or community design thinking Likely deliverables (adjust to your needs) A connection/community blueprint for the system Specific mechanics and flows we can build A recommended tool and automation stack Metrics and a way to track them