Job Title

Automation & AI Systems ArchitectLocation: Remote (Global) Working Hours: U.S. Eastern Time, overlap required Engagement Type: Full-Time Company: Gather Circle About Gather CircleGather Circle is a U.S.-based, rapidly growing startup built at the intersection of real estate, systems, and education. The company was founded in wholesaling and creative finance, helping investors acquire properties through non-traditional structures. From there, it expanded into short-term rental ownership and operations, building and managing a growing STR portfolio.We are now launching several new business lines, including: A coaching and education program for real estate investors Interior design services for short-term rental properties Bookkeeping and financial reporting for real estate operators Cost segregation studies and tax strategy supportAlongside these services, we operate a growing member community focused on practical execution, not theory. Everything we build is systems-driven, with a strong emphasis on clarity, leverage, and repeatable execution. Role OverviewWe are hiring an Automation & AI Systems Architect to become a long-term, embedded systems leader inside the Gather Circle ecosystem.This role blends visual systems architecture, hands-on implementation, and community leadership. You will design how work flows, build the systems that run the business, and support our members and paid clients in implementing those same systems.This is not a short-term contractor role. We are looking for a long-term partner who will grow with the ecosystem and help shape its technical foundation. Role Phases & Focus First 3–6 Months: Internal Systems BuildYour initial focus will be on internal systems and tools, including: Designing and mapping core operational workflows Building automation-first systems using Zapier, Make, and n8n Implementing AI tooling to reduce manual work and improve decision-making Supporting the launch of coaching, design, bookkeeping, and cost segregation services Hardening data pipelines and internal reporting Establishing system standards and best practices After 3–6 Months: Systems Ownership & Community SupportOnce internal systems are stable, your focus will shift to: Ongoing ownership and optimization of all core systems Managing and evolving the automation and AI stack Supporting the Circle.so community with systems guidance Helping members and clients implement tools correctly Leading paid client implementations when needed Acting as the go-to systems authority across the ecosystem What You’ll Be Doing Visual Systems Architecture & Discovery Lead discovery sessions with internal teams, community members, and clients Translate messy real-world processes into clear, executable systems Design current-state and future-state workflows Map workflows visually using Miro, Figma, or similar tools Align stakeholders before implementation begins Automation & Implementation Design, build, and maintain automations using Zapier, Make, and n8n Replace manual and repetitive work with resilient system logic Own workflows end-to-end, from design through optimization Solve edge cases and ambiguous challenges with confidence Build systems that scale without unnecessary complexity AI & LLM Enablement Build custom GPT and Claude wrappers for operational use Apply AI to workflows involving data cleanup, enrichment, analysis, and decision support Turn AI into dependable tools teams rely on daily Continuously identify new opportunities for AI leverage Community Leadership & Client Implementation Be a visible, trusted presence inside our Circle.so community Support members with automation, AI, and systems implementation Teach systems thinking using real workflows and tools Support and lead paid client implementations Represent best practices across Gather Circle Future Projects & Platform Ownership You will be expected to spearhead new technical initiatives, including: Building and managing a GoHighLevel white-label instance Designing and implementing custom property management pages Creating new internal tools as the ecosystem grows Evaluating and integrating new SaaS platforms Owning technical execution for new services and programs Communication & Documentation Comfortable creating and sharing Loom videos for: Internal team walkthroughs Community education Client implementations and support Able to clearly explain systems, workflows, and decisions asynchronously Uses video and written communication to reduce meetings and increase clarity Tool Stack You’ll Work With Zapier Make n8n GoHighLevel Miro, Figma (or similar workflow tools) Slack SmartSuite Close CRM Circle.so Hostaway Breezeway PriceLabs Google Workspace LoomYour role is not to connect tools. Your role is to make them run the business. Who We’re Looking For A-player systems thinker with strong execution ability Comfortable designing visually and implementing technically Deep hands-on experience with Zapier, Make, and n8n Confident tackling complex SaaS, automation, and AI challenges Comfortable leading discovery and owning ambiguous projects Clear communicator who can present systems simply and confidently Comfortable being visible and trusted in a community setting Self-directed, accountable, and outcome-focused What Success Looks Like Internal systems launch cleanly and scale smoothly Manual work continues to disappear Automations run reliably with minimal oversight AI tools are embedded into daily operations Teams and members trust system guidance Community members implement systems successfully You become a core systems pillar inside Gather Circle Why This Role Matters This role is a technical cornerstone of the Gather Circle ecosystem.The systems you design and own will directly impact how fast we scale, how effectively our services launch, and how well our members succeed.We are building something long-term.We want someone who wants to build it with us.