Director of Revenue Systems and AI Automation (Offshore) contract Full Time

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 fixes it permanently.

This is a deeply technical, execution-focused role for someone who thinks in system connections. When someone says “our Google LSA leads are not showing up correctly in Follow Up Boss,” you trace the integration chain, find where the handoff failed, and build the fix. You do not wait to be asked.

Your primary collaborators: the Founder, the Broker in Charge, the Director of Marketing, and the Founder’s Chief of Staff. The defining partnership is with the Director of Marketing. They own creative, campaigns, and the team. You own the infrastructure — attribution architecture, lead pipeline connections, systems tracking what works from first ad impression through closed transaction. They read the output. You build and tune the machine.

If you worked here last week, you might have:

• Scoped 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

• Built 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

• Created 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

• Architected 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

An immediate cross-functional initiative in your first 30 days:

We are running SISU as our performance reporting CRM with over 110 lead source categories that need to be consolidated into a clean, standardized taxonomy. This project runs in collaboration with our fractional CFO and directly enables accurate agent performance tracking, revenue attribution, and leadership visibility into who is producing and where. The right person for this role does not manually clean this data. They build the AI agent or automation system that executes it, then govern the schema so it never gets this bloated again.

CORE RESPONSIBILITIES

This is a leadership role of ownership, not task lists. Here is what you will lead:

AI Tool Building You build Claude projects, Claude skills, and prompt systems that replace manual work across every department. These are production tools team members rely on daily, with structured inputs, validation logic, and clean outputs. Not experiments. Infrastructure.

ClickFunnels Workflow Execution You build and maintain ClickFunnels funnels, pipelines, email automations, and workflow triggers. You handle integration between ClickFunnels, Follow Up Boss, and the broader stack and ensure nothing breaks during high-volume listing seasons.

Dashboard and Data Pipeline Development You build dashboards and connect data pipelines using Replit, Baserow, Zapier, and Claude. When leadership needs visibility into a metric, you architect the flow from data source to clean visual output and ship a working, reliable tool.

CRM and Transaction Integration You own and improve integrations across Follow Up Boss, Open to Close, Ylopo, ClickFunnels, and SISU, ensuring leads, contacts, and transactions flow cleanly between systems with zero manual handoffs.

Scope Brief Execution Every build starts with a structured scope brief. You review it, confirm deliverables, ask smart questions before you start, execute on spec, self-QA against success criteria, and log your hours. You do not wait to be walked through every step.

Documentation and Handoff Every build includes documentation: what it does, how it works, how to maintain it, and where it lives. You use AI to generate first drafts and edit for accuracy. A build without documentation is not a completed build.

WHAT SUCCESS LOOKS LIKE

You own these key metrics:

Build Velocity: Ship 6 to 10 completed builds per month, ranging from 2-hour quick builds to multi-day architecture projects.

Turnaround Time: Quick builds under 4 hours delivered within 24 to 48 hours of assignment. Larger builds delivered within scoped timeline with zero missed deadlines.

Quality and QA: 90% or more of builds pass first review without rework, meaning you self-checked against the scope brief before marking it complete.

Documentation Compliance: 100% of completed builds include clean documentation within 24 hours of delivery.

System Uptime: Automations, dashboards, and integrations maintain 95% or greater reliability, especially during high-volume listing seasons.

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. Hard floor. We are paying top of LATAM independent contractor market and expect depth, not potential.

• Direct experience deploying AI agents and AI-driven automations that are live in production, solving real business problems, with measurable outcomes. Not demos. Not prototypes.

• Expert-level Claude fluency. We are a Claude-first organization. Mastery of Claude Projects, Claude Skills, and Claude Cowork is mandatory.

• Ability 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.

• Comfortable in fast-moving, imperfect environments where infrastructure is incomplete and priorities shift.

• Comfortable working with high-driver, direct personalities. This is not a soft culture.

• U.S. residential real estate experience is strongly preferred. Ability to ramp on it independently is the minimum acceptable alternative.

Technical Fluency — CRM Architecture

• CRM data schema design, normalization, and governance

• Tag taxonomy design and enforcement at scale

• Contact lifecycle mapping and pipeline logic

• Data deduplication and clean record management

• Follow Up Boss at a deep architectural level, or a directly comparable CRM

Technical Fluency — Lead Routing and Attribution

• Lead routing logic and source attribution methodology

• UTM parameter design and source integrity

• Multi-touch attribution models including first-touch, last-touch, linear, and time-decay

• Tracing broken source attribution back through an integration chain

• Funnel analytics and conversion tracking from first contact through close

Technical Fluency — Integration and API Architecture

• REST API design, consumption, authentication via OAuth 2.0, rate limiting, pagination, and error handling

• Webhook architecture and event-driven integration design

• Custom connector development when no off-the-shelf option exists

• Automation platform architecture across Zapier, Make, and n8n, and when to build custom instead

• Data pipeline design and cross-platform data routing with proper error handling

• Marketing technology integrations, including ad platform APIs and digital-to-CRM lead journey mapping

Technical Fluency — AI Systems and Agent Development

• AI agent design, orchestration, and production deployment

• Model Context Protocol (MCP) and context-aware AI system design

• LLM API integration with Anthropic Claude as the primary platform

• Prompt engineering at a systems level with structured input handling, fallback logic, and formatted outputs

• Retrieval-Augmented Generation for business context applications

• Scope brief execution, self-QA, and building systems that are maintainable by others

CANDIDATE PATHS

Path A is a systems expert with direct U.S. residential real estate experience on the technology side, not as an agent. You have lived inside Follow Up Boss, built or repaired lead routing, and understand the full sales funnel from capture through close.

Path B is a technical expert whose background is in RevOps, growth engineering, or AI automation, with depth so strong you ramp on real estate context independently without needing fundamentals explained.

Path A is preferred. Path B is fully accepted if the technical depth is exceptional.

What We Will Not Accept

• Anyone whose AI experience is limited to building custom ChatGPT bots

• Zapier-only candidates presenting themselves as systems architects

• Agency consultants who have overseen builds without hands-on implementation 

• Traditional operations managers or people-management-heavy ops leads

• Anyone whose case studies are outcomes with no architecture behind them

• Anyone who needs a task list to understand what to work on

Every stage of our interview process requires you to demonstrate your work at a technical level, including sharing your screen.

TECH STACK

We are a Claude-first organization. Expert-level mastery of Claude, Claude Projects, Claude Skills, and Claude Cowork is required, not preferred.

Current Stack: Follow Up Boss, ClickFunnels, Open to Close, SISU, Ylopo, Agently, Zapier, Replit, Baserow, Notion, Google Workspace, Slack, ManyChat. This list is not exhaustive. Part of your mandate is to audit what we have, identify redundancies, and recommend what stays, what goes, and what we are missing.

INTERVIEW PROCESS

• Apply 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.

• Answer all pre-screening questions in full. Skip them and you do not move forward.

• 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 2: Interview with the Founder.

• Stage 3: Interview with the Broker in Charge.

• 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.

COMPENSATION STRUCTURE

$5 o $6K USD per month based on experience and test project evaluation.

• Structure: Full-time independent contractor (1099). This is an offshore role for candidates based in LATAM.

• Pay schedule: Paid in USD on the 1st and 15th of every month, deposited directly into your bank account.

• Location: Fully remote. Preference for Uruguay, Costa Rica, or Colombia.

• Professional Development: $1.5 to $3K annual budget for courses, certifications, conferences, and tools.

• Workspace: Coworking membership allowance or home office setup budget. Up to you!

HOW TO APPLY

Apply via Remotive or via LinkedIn only. 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. Apps without a minimum of 4 concrete technical examples will not advance. Each example must include the problem, what you built, the technical architecture, and the measurable outcome. Be prepared to share your screen during the interview process.