Director of Revenue Systems & AI Automation

Caul Group

Salary: $$$
Type: Tiempo completo

Tags: REST API Prompt Engineering Webhooks Data Pipeline

WHO WE ARE

Caul Group Residential is the number one resale real estate team in The Triangle, North Carolina, brokered by eXp Realty. Led by Tina Caul, ranked in the top 0.5% of Realtors nationwide, our team sells 800+ homes annually with 50 agents and a reputation for luxury service at every price point. We carry a 4.9 Google rating with over 700 public reviews.
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We are a partially on-site, partially remote, and globally distributed. We move fast, build things that work, and don't carry broken systems. Our culture runs on six values: Collaboration, Grit, Leaders Building Leaders, Intention, Fail Forward, and Evolve.

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

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Job functions

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.

Qualifications and 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

Desirable skills

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

Conditions

$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!

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Source: GetOnBoard | Main Category: Other