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AI Systems Specialist

hillpointe · Winter Park, FL · 631 W Morse Boulevard, Winter Park, FL 32789
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<div class="content-intro"><p></p> <p><strong>WHY HILLPOINTE?</strong><em> Hillpointe is a fully integrated real estate development and investment management firm focused on developing market-rate workforce housing across the Sun Belt. Ranked at the top of NMHC's list of Builders and Developers, our team ensures best-in-class execution.</em></p> <p><em>Built on its long and proven track record of real estate development, the firm’s investment approach is centered around its in-house general contracting expertise, enabling direct control of cost and delivery timeframe. For each project, Hillpointe directly controls land acquisition, land development, construction, procurement of building materials, asset management, and capital markets. This is more than just a job - it's a career-defining opportunity! At Hillpointe, you'll be part of a dynamic, innovative team that has tangible impacts on day-to-day operations and contributes directly to overall success.</em></p> <p></p></div><p style="text-align: center;"><span style="text-decoration: underline;"><strong>AI Systems Specialist<br><br></strong></span></p> <p>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.</p> <p>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.</p> <p> </p> <p><strong>Key Responsibilities:</strong></p> <ul> <li>Partnering with Departments <ul> <li>Understand workflows, repetitive tasks, decision rules, exceptions, and data sources; simplify processes before automating them.</li> <li>Prioritize projects with the Managing Partner based on business value, effort, risk, and capacity; establish baseline measures of manual work.</li> <li>Partner with Legal on document intake, contract review support, and obligation tracking, using counsel-approved playbooks and appropriate confidentiality, access controls, and legal review.</li> </ul> </li> <li>Building AI Systems and Integrations <ul> <li>Build internal tools, automations, and integrations using Claude and AI development tools such as Claude Code or OpenAI Codex.</li> <li>Connect business systems through APIs and supported imports, including ERP platforms such as Sage Intacct and Entrata.</li> <li>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.</li> <li>Test with unfamiliar documents and realistic exceptions. Partner with IT on security, credentials, and access controls; retain appropriate financial approvals and HR review.</li> </ul> </li> <li>Shared Knowledge and Departmental Claude Skills <ul> <li>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.</li> <li>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.</li> </ul> </li> <li>Deployment, Adoption & Ownership <ul> <li>Deploy shared applications with appropriate authentication, permissions, and storage. Use version control and maintain clear documentation and handoff procedures.</li> <li>Train users, monitor failures and recurring costs, and troubleshoot workflows after launch.</li> <li>Measure time saved after review and correction effort, accuracy, turnaround time, and sustained adoption; improve systems based on results.</li> <li>Keep current with AI models, tools, and capabilities. Test proposed changes against representative Hillpointe workflows for accuracy, reliability, and cost before adoption.</li> </ul> </li> </ul> <p> </p> <p><strong>Initial Project Priorities:</strong></p> <ul> <li>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.</li> <li>Corporate accounts payable: Automate invoice intake, extraction, coding, validation, and duplicate detection; produce ERP-ready files or integrations and route exceptions for review.</li> <li>Construction Accounting Workflows: Assign subcontractor invoices to the correct project and general ledger or cost code using approved rules, automating routine construction invoice coding.</li> <li>Investment and debt memos: Automate investment memo and debt memo creation using approved underwriting, diligence materials, templates, and traceable sources.</li> <li>HR administration: Automate administrative intake, recordkeeping, follow-ups, and ER reporting wi

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