Upside Capital Holdings

AI Systems Engineer (Claude-Centered Research Systems)

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: TYPE OF WORK

Any

: SALARY

Starts at $18 per hour

: HOURS PER WEEK

TBD

: DATE UPDATED

Mar 12, 2026

JOB OVERVIEW

AI Systems Engineer (Claude-Centered Research Systems)

Overview

Upside Auction is building a structured AI infrastructure to power real estate auction intelligence at scale as we expand into more states and properties.

We are seeking our first dedicated AI Systems Engineer / AI Engineer to architect and implement a Claude-centered research system that automates:

1. Foreclosure and lien research
2. Title and legal document analysis
3. Court notice and deed parsing
4. Property-level research and information gathering
5. CRM and workflow automation tied to AVP and HubSpot

We are looking for a builder who can design, deploy, and operationalize real-world LLM systems inside a production workflow, with hands-on implementation, setup, and virtual environment deployment experience.

Anthropic Claude will serve as the central orchestration layer (“bot manager”) for research and decision-support processes, coordinating AI agents to perform tasks.

What You’ll Build

You will design and deploy a scalable AI research infrastructure that:

1. Acts as an internal AI research assistant for property and auction data
2. Automates foreclosure, lien, and broader legal/title research workflows
3. Coordinates AI agents to:
3.1 Retrieve documents from multiple external sites and tools
3.2 Summarize and validate results
3.3 Flag mismatches (e.g., wrong document numbers, wrong property)
4. Parses and extracts structured data from:
4.1 Court filings and notices
4.2 Notices of sale
4.3 Deeds and title documents
4.4 Legal PDFs and scanned documents
5. Integrates directly with:
5.1 Internal data sources and research tools
5.2 AVP workflows
5.3 HubSpot CRM
6. Maintains structured logs, audit trails, and validation checks so humans can quickly review and correct edge cases
7. Optimizes cost and performance of LLM usage as we scale to hundreds of properties

You will help move Upside Auction from manual, research-heavy workflows (multiple people, many minutes per property) to structured, AI-assisted research systems.

Key Responsibilities

1. Architect Claude-centered LLM workflows for legal/property research and document handling
2. Design system prompts and multi-step reasoning chains for:
2.1 Document retrieval
2.2 Structured extraction
2.3 Validation and error detection
3. Build document parsing pipelines (PDF, OCR, text extraction, structured output)
4. Implement:
4.1 Error handling and retry logic
4.2 Validation layers to catch issues like mis-labeled or mis-indexed documents
4.3 Task feedback loops between AI agents and the Claude “manager” bot
5. Deploy and maintain services in virtual/cloud environments (virtual terminals/VMs)
6. Integrate LLM outputs into:
6.1 HubSpot CRM workflows
6.2 AVP and internal automation systems
6.3 Internal folders and knowledge repositories
7. Implement monitoring, logging, and cost tracking for AI usage
8. Document:
8.1 System architecture
8.2 Installation and configuration steps (virtual terminals/environments)
8.3 Operational playbooks for non-technical tea ---------- mbers
9. Work directly with leadership and research staff to translate current manual research processes into robust AI-powered workflows

You will own this function end-to-end and will be building this as a fresh project.

Required Skills & Experience

1. Production experience implementing Anthropic Claude (real workflows, not demos)
2. Experience with OpenAI GPT/Codex or comparable LLM APIs
3. Proven ability to design and ship production systems independently
4. Strong skills in Python (preferred) or JavaScript/TypeScript
5. Comfortable with Linux, virtual environments, and cloud/VM deployment
6. Experience building API integrations and document processing pipelines (PDF/OCR/structured extraction)
7. Working knowledge of databases and structured data modeling
8. Ability to translate manual business processes into automated, agent-driven workflows
9. Clear technical documentation and communication skills

Nice-to-Have

1. Experience designing agentic or multi-step LLM systems
2. Familiarity with RAG, vector databases, or retrieval systems
3. Experience integrating with HubSpot or similar CRMs
4. Exposure to LLMOps / monitoring / prompt versioning
5. Background in real estate, foreclosure, title, or legal-tech workflows
6. Startup experience with full ownership of systems

Send us your resume and portfolio to apply.

SKILL REQUIREMENT

Dev Tools - Cloud Control API ChatGPT AI Automation

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Upside Capital Holdings

AI Systems Engineer (Claude-Centered Research Systems)

Please login or register as jobseeker to apply for this job.

TYPE OF WORK

SALARY

HOURS PER WEEK

DATE UPDATED

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