Director of Revenue Systems and AI Automation

Job Overview

com 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.

Job Description

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.

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.

Key Responsibilities

• 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.
• 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 own the infrastructure - attribution architecture, lead pipeline connections, systems tracking what works from first ad impression through closed transaction.
• 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.
• 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.

Required Skills and Qualifications

• 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.
• CORE REQUIREMENTS 7+ yrs of hands-on experience in a lethal combination of revenue systems, CRM architecture, AI automation, RevOps, or technical operations.
• Direct experience deploying AI agents and AI-driven automations that are live in production, solving real business problems, with measurable outcomes.
• Mastery of Claude Projects, Claude Skills, and Claude Cowork is mandatory.
• residential real estate experience is strongly preferred.
• residential real estate experience on the technology side, not as an agent.
• 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.
• Expert-level mastery of Claude, Claude Projects, Claude Skills, and Claude Cowork is required, not preferred.

Work Location and Schedule

This role is listed as Remote USA with location information shown as Remote USA. The employment type is Full Time.

About the Company

Caul Group is the organization connected with this listing. USA Jobs Today displays this opportunity for job discovery only, so applicants should verify company details, application instructions, and eligibility on the official employer website.