Senior AI Systems Engineer – Executive Operations & Automation

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TYPE OF WORK

Full Time

SALARY

$2,000 - $3,000

HOURS PER WEEK

40

DATE UPDATED

Sep 26, 2026

JOB OVERVIEW

THE ONE OUTCOME
The owner of a group of U.S. companies (custom home building, concrete and excavation, automotive repair, retail, and land development) spends too many hours finding problems instead of working on strategy. Your job is to give him those hours back.

Success at 90 days: every morning, one brief tells the owner which issues across all companies actually need him today – built on clean, connected data, not manual reporting – and we can measure the hours it saves each week.

This is a long-term remote contractor role. Philippines-based candidates preferred.

WHAT THIS ROLE IS – AND ISN'T
- It IS an owner-level builder: understand the business problem, design the solution, build it, test it, document it, improve it.
- It IS someone willing to consolidate. We already run many apps and automations. We expect you to recommend what to keep, merge, or shut down – not just add more.
- It is NOT a virtual assistant, prompt-writing, or basic Zapier role.
- It is NOT a demo job. We want reliable systems people use daily.

YOUR FIRST 90 DAYS
- Days 1–30: Audit our tools and data, connect accounting and bank data first, ship version 1 of the daily brief.
- Days 31–60: Expand the brief across all companies, add exception alerts, route each issue to an owner until it's closed.
- Days 61–90: Measure hours saved, refine, and document everything.
After 90 days the role expands into financial monitoring, sales and marketing performance, internal apps, and our AI receptionist – prioritized by dollar impact.

WHAT YOU BRING
- Production experience with LLM APIs, AI agents, and agentic workflows
- API integrations, webhooks, and Make, n8n, or similar
- Python and/or JavaScript, databases, authentication and permissions
- QuickBooks (Online and Desktop) integration strongly preferred; Slack, Microsoft 365, and Replit a plus
- AI-assisted development tools (Claude Code, Codex, Cursor)
- Business judgment: you ask what problem is worth solving before you build
- Clear written communication and disciplined documentation

HOW WE WORK
- All work is built in company-owned accounts under a contractor agreement with IP assignment and confidentiality.
- Access is granted in stages, starting read-only.
- At least 2 hours of daily overlap with U.S. Mountain Time, plus a weekly review with the owner.
- The first 90 days are a proving period. The goal is a long-term relationship.

SELECTION PROCESS
1. Application
2. 45-minute interview with the owner
3. Paid test project ($400 USD, about one week): build a monthly website health agent for our company websites. Details shared at interview.

HOW TO APPLY
Begin your application with the phrase "BUSINESS FIRST, TECHNOLOGY SECOND."
1. Resume or LinkedIn profile
2. GitHub, portfolio, or examples of systems you personally built
3. A 5–10 minute Loom video walking through one complex AI or automation system you built: the business problem, the architecture, and what you built versus what others built
4. Short answers: (a) What would you need to know before designing a daily brief across multiple companies? (b) Tell us about a tool or system you consolidated or shut down, and why.

Applications without the video will not be considered.

SKILL REQUIREMENT
Python API Integration AI Automation
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