AI Systems Specialist

Hillpointe is hiring an AI Systems Specialist to design, build, and implement AI workflows that reduce manual effort, improve accuracy, and lower operating costs. Working directly with the Managing Partner and department leaders, this person will take projects from process discovery through deployment, training, and ongoing support.

Claude will be a primary platform. Initial priorities span Finance, Construction, Investments, Asset Management, HR, Legal, and shared internal tools. Marketing and other departments will be supported as opportunities are prioritized with leadership.This is a hands-on individual contributor role. Success requires practical judgment about when to use AI, conventional code, or human review, and the ability to deliver simple, reliable systems that teams use and can maintain.

Key Responsibilities:

• Partnering with Departments
  • Understand workflows, repetitive tasks, decision rules, exceptions, and data sources; simplify processes before automating them.
  • Prioritize projects with the Managing Partner based on business value, effort, risk, and capacity; establish baseline measures of manual work.
  • Partner with Legal on document intake, contract review support, and obligation tracking, using counsel-approved playbooks and appropriate confidentiality, access controls, and legal review.
• Building AI Systems and Integrations
  • Build internal tools, automations, and integrations using Claude and AI development tools such as Claude Code or OpenAI Codex.
  • Connect business systems through APIs and supported imports, including ERP platforms such as Sage Intacct and Entrata.
  • Validate calculations and outputs, detect duplicates, preserve source references and audit trails, and route missing or uncertain information for review. Ensure reruns do not create duplicate records.
  • Test with unfamiliar documents and realistic exceptions. Partner with IT on security, credentials, and access controls; retain appropriate financial approvals and HR review.
• Shared Knowledge and Departmental Claude Skills
  • Work with departments to design, test, deploy, and maintain Claude skills for specific tasks. Capture approved methods, inputs, outputs, and escalation rules, with a departmental owner for each skill.
  • Build shared context and knowledge infrastructure using AI Skills and MCP integrations, including approved brand facts, voice guidelines, product information, business rules, and templates. Maintain reusable components and access controls so teams build on prior work.
• Deployment, Adoption & Ownership
  • Deploy shared applications with appropriate authentication, permissions, and storage. Use version control and maintain clear documentation and handoff procedures.
  • Train users, monitor failures and recurring costs, and troubleshoot workflows after launch.
  • Measure time saved after review and correction effort, accuracy, turnaround time, and sustained adoption; improve systems based on results.
  • Keep current with AI models, tools, and capabilities. Test proposed changes against representative Hillpointe workflows for accuracy, reliability, and cost before adoption.

Initial Project Priorities:

• Construction draw packages: Combine the monthly G703 from Hillpointe Construction with categorized invoices, update draw forms, and check packages against lender requirements before review and submission.
• Corporate accounts payable: Automate invoice intake, extraction, coding, validation, and duplicate detection; produce ERP-ready files or integrations and route exceptions for review.
• Construction Accounting Workflows: Assign subcontractor invoices to the correct project and general ledger or cost code using approved rules, automating routine construction invoice coding.
• Investment and debt memos: Automate investment memo and debt memo creation using approved underwriting, diligence materials, templates, and traceable sources.
• HR administration: Automate administrative intake, recordkeeping, follow-ups, and ER reporting with restricted access and appropriate HR review.
• Shared internal AI tools: Deploy team-created Claude artifacts and prototypes as shared applications. Maintain and extend useful tools already built by Brand & Creative and other teams, including the brand guidelines hub, property knowledge bases, and job description builder.
• Monthly asset management reports: Combine property financial and operating data, validate calculations and variances, and generate reports and draft commentary for review.
• Automate Critical List Creation: Collect and consolidate weekly updates, flag missing inputs, and prepare the critical list in the agreed format.
• Loan database audits and obligation tracking: AI-audit the entire current loan database against executed loan documents and amendments. Audit all future loans, amendments, and database changes; flag missing, inconsistent, or unsupported entries with source references for review. Track validated terms, reporting obligations, covenant testing dates, maturities, and extension deadlines.
• Monthly lease audits: Use Claude to audit active leases and amendments against rent rolls, resident charges, and approved policies each month. Flag rent and fee discrepancies, incorrect concessions, missing signatures or addenda, and date mismatches; assign exceptions, track resolution, and report potential financial impact for review.
• Month-end close and reconciliations: Automate bank, payables, property-system, and intercompany reconciliations. Investigate unmatched items, assemble supporting schedules, prepare proposed entries under approved rules, and track close tasks for accounting review. Begin with a focused bank reconciliation pilot before expanding.
• Departmental Claude skills: Build and deploy a shared library of skills with department leaders. For example, develop a Legal NDA skill that checks agreements against counsel-approved requirements, flags deviations, and prepares suggested edits for Legal review.

Qualifications:

• Required:
  • A portfolio of AI tools, automations, or applications you personally built and deployed for real users. Substantive personal projects count.
  • Hands-on experience with Claude or comparable platforms, document processing, structured outputs, and AI coding tools.
  • Ability to translate departmental expertise into reusable instructions, knowledge resources, and task-specific Claude skills, and evaluate their outputs against real examples.
  • Ability to write and troubleshoot Python, JavaScript, or TypeScript; work with APIs, SQL, spreadsheets, and PDFs; and deploy internal applications using version control.
  • Sound judgment about accuracy, exception handling, data access, and when a simpler solution is appropriate.
  • Ability to explain technical decisions clearly, manage competing priorities, and independently own implementation and ongoing support.
• Preferred:
  • Experience with accounting, construction, real estate, asset management, HR, Legal, or other operational workflows.
  • Experience with ERP integrations, invoice automation, secure internal applications, custom AI agents, or MCP integrations.
  • Software engineering experience or relevant coursework. A specific degree or certification is not required if you can demonstrate what you build.