Job Description
Automation & AI Systems Architect
Location: Remote (Global)
Working Hours: U.S. Eastern Time, overlap required
Engagement Type: Full-Time
Company: Gather Circle
About Gather Circle
Gather 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 support
Alongside 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 Overview
We 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 Build
Your 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 Support
Once 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
Loom
Your 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.
Location: Remote (Global)
Working Hours: U.S. Eastern Time, overlap required
Engagement Type: Full-Time
Company: Gather Circle
About Gather Circle
Gather 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 support
Alongside 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 Overview
We 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 Build
Your 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 Support
Once 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
Loom
Your 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.
Apply for this Position
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