Director of Revenue Systems and AI Automation (Offshore)
Caul Group
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About This RoleAI processing…
This search is open exclusively to candidates based in Latin America. Preference for Uruguay, Costa Rica, or Colombia. BACKGROUND CONTEXT Every department at Caul Group is generating AI and automation ideas faster than they can be built. This role turns those ideas into operational reality — and finds the ones nobody thought to ask about yet. You are not advising. You are not consulting. You own the systems layer of this business and make it faster, cleaner, and more profitable — auditing what we have, identifying what is broken, redundant, or missing, and building the infrastructure that fixe
Key Responsibilities
- 1Scoped and deployed a Zapier integration between Follow Up Boss and ClickFunnels so new leads from Ylopo automatically get tagged, assigned, and entered into the correct pipeline, eliminating the daily manual lead routing the team was doing every morning and stopping revenue from falling through the cracks
- 2Built an automated coaching intelligence system that pulls agent call data from Follow Up Boss, breaks it down by agent, and delivers a weekly report to each coach using Claude to analyze call patterns, flag agents avoiding follow-ups, identify cold databases, and surface conversion gaps so coaches walk into one-on-ones with data-backed talking points instead of guessing
- 3Created a Replit dashboard pulling listing data from Open to Close and Baserow so the Founder has real-time visibility into active listings, pending transactions, and closed deals without digging through three platforms
- 4Architected the full new agent onboarding automation, functioning as an HR system in a box, where a signed agent triggers auto-generation of their 90-day drip campaign, onboarding checklist, and Follow Up Boss contact setup, with Agently automations monitoring task completion and sending accountability nudges when agents fall behind
- 57+ yrs of hands-on experience in a lethal combination of revenue systems, CRM architecture, AI automation, RevOps, or technical operations. Hard floor. We are paying top of LATAM independent contractor market and expect depth, not potential.
- 6Direct experience deploying AI agents and AI-driven automations that are live in production, solving real business problems, with measurable outcomes. Not demos. Not prototypes.
- 7Expert-level Claude fluency. We are a Claude-first organization. Mastery of Claude Projects, Claude Skills, and Claude Cowork is mandatory.
- 8Ability to teach at the highest level. You can explain complex systems architecture to non-technical leaders and teach department heads how to use and maintain what you build. This is not a role for someone who builds in isolation.
- 9Comfortable in fast-moving, imperfect environments where infrastructure is incomplete and priorities shift.
- 10Comfortable working with high-driver, direct personalities. This is not a soft culture.
- 11U.S. residential real estate experience is strongly preferred. Ability to ramp on it independently is the minimum acceptable alternative.
- 12CRM data schema design, normalization, and governance
- 13Tag taxonomy design and enforcement at scale
- 14Contact lifecycle mapping and pipeline logic
- 15Data deduplication and clean record management
- 16Follow Up Boss at a deep architectural level, or a directly comparable CRM
- 17Lead routing logic and source attribution methodology
- 18UTM parameter design and source integrity
- 19Multi-touch attribution models including first-touch, last-touch, linear, and time-decay
- 20Tracing broken source attribution back through an integration chain
- 21Funnel analytics and conversion tracking from first contact through close
- 22REST API design, consumption, authentication via OAuth 2.0, rate limiting, pagination, and error handling
- 23Webhook architecture and event-driven integration design
- 24Custom connector development when no off-the-shelf option exists
- 25Automation platform architecture across Zapier, Make, and n8n, and when to build custom instead
- 26Data pipeline design and cross-platform data routing with proper error handling
- 27Marketing technology integrations, including ad platform APIs and digital-to-CRM lead journey mapping
- 28AI agent design, orchestration, and production deployment
- 29Model Context Protocol (MCP) and context-aware AI system design
- 30LLM API integration with Anthropic Claude as the primary platform
- 31Prompt engineering at a systems level with structured input handling, fallback logic, and formatted outputs
- 32Retrieval-Augmented Generation for business context applications
- 33Scope brief execution, self-QA, and building systems that are maintainable by others
- 34Anyone whose AI experience is limited to building custom ChatGPT bots
- 35Zapier-only candidates presenting themselves as systems architects
- 36Agency consultants who have overseen builds without hands-on implementation
- 37Traditional operations managers or people-management-heavy ops leads
- 38Anyone whose case studies are outcomes with no architecture behind them
- 39Anyone who needs a task list to understand what to work on
- 40Apply via LinkedIn only. Do not email us. Do not contact our team through any other channel. Applications submitted outside this posting will not be reviewed.
- 41Answer all pre-screening questions in full. Skip them and you do not move forward.
- 42Stage 1: Interview with the Founder's Chief of Staff. She is a technical powerhouse and an AI witch, and she will be your closest collaborator inside this organization. She is the primary gatekeeper for this process. Come prepared with a minimum of four concrete examples of systems you have built, with full technical specifics, and be ready to share your screen.
- 43Stage 2: Interview with the Founder.
- 44Stage 3: Interview with the Broker in Charge.
- 45Stage 4: Group interview with the Founder, Broker in Charge, and Chief of Staff. You will present a project plan or case study demonstrating how you would approach this role based on what you have learned in the process. No work is performed unpaid. This is your opportunity to show how you think and how you lead.
- 46Offer extended. 90-day trial period begins. At the successful completion of 90 days, you are officially our person.
- 47Structure: Full-time independent contractor (1099). This is an offshore role for candidates based in LATAM.
- 48Pay schedule: Paid in USD on the 1st and 15th of every month, deposited directly into your bank account.
- 49Location: Fully remote. Preference for Uruguay, Costa Rica, or Colombia.
- 50Professional Development: $1.5 to $3K annual budget for courses, certifications, conferences, and tools.
- 51Workspace: Coworking membership allowance or home office setup budget. Up to you!
Requirements
- 7+ yrs of hands-on experience in a lethal combination of revenue systems, CRM architecture, AI automation, RevOps, or technical operations. Hard floor. We are paying top of LATAM independent contractor market and expect depth, not potential.
- Stage 1: Interview with the Founder's Chief of Staff. She is a technical powerhouse and an AI witch, and she will be your closest collaborator inside this organization. She is the primary gatekeeper for this process. Come prepared with a minimum of four concrete examples of systems you have built, with full technical specifics, and be ready to share your screen.
- Stage 4: Group interview with the Founder, Broker in Charge, and Chief of Staff. You will present a project plan or case study demonstrating how you would approach this role based on what you have learned in the process. No work is performed unpaid. This is your opportunity to show how you think and how you lead.
- Offer extended. 90-day trial period begins. At the successful completion of 90 days, you are officially our person.
- WHO YOU ARE You are not a generalist.
- You are not an AI enthusiast.
- You are a technical expert with a proven track record of building revenue infrastructure that works in production and the ability to teach what you build to the leaders around you.
- CORE REQUIREMENTS 7+ yrs of hands-on experience in a lethal combination of revenue systems, CRM architecture, AI automation, RevOps, or technical operations.
- You have lived inside Follow Up Boss, built or repaired lead routing, and understand the full sales funnel from capture through close.
- Expert-level mastery of Claude, Claude Projects, Claude Skills, and Claude Cowork is required, not preferred.
- Come prepared with a minimum of four concrete examples of systems you have built, with full technical specifics, and be ready to share your screen.
- You will present a project plan or case study demonstrating how you would approach this role based on what you have learned in the process.
- At the successful completion of 90 days, you are officially our person.
- Within your resume, make sure to include your LinkedIn profile and a minimum of 4 specific examples of systems, automations, or builds you have created, fixed, or significantly improved.
Perks & Benefits
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