AI Automation Engineer (Family Office)

Green Circle Projects is hiring an AI Automation Engineer to design, build, and maintain the AI-assisted workflows, automations, integrations, and internal tools our Family Office will soon run on. This is a new role and a deliberate change in how we staff it: rather than hiring an investment professional and hoping they pick up AI, we are hiring someone who builds… and teaching them our investments. Green Circle manages several family office functions including investment planning, private and public investment portfolios, real estate, and a range of nonprofit activities. As we scale, the constraint is not analytical horsepower. It is that too much of our team's time goes into moving information by hand: pulling numbers out of property manager reports, turning meeting notes into follow-ups, rebuilding the same summary every quarter, and hunting for a document someone remembers seeing. Every one of those is a system waiting to be built. You will design, build, implement, and maintain AI-assisted workflows and automations that connect our documents, meetings, communications, and data into organized records, reporting, executive summaries, and actionable follow-ups. You will then keep them running and improve them as we grow. You are not a consultant delivering a pilot; you own these systems. This is a hands-on building role embedded inside an investment team. You will sit with the people whose work you are automating, learn how they actually do it, and build accordingly. You will also do real investment work (roughly 40% of your time) because you cannot automate a process you do not understand. This is a full-time, salaried role at $95,000 – $125,000, depending on experience, plus annual bonus. On-site in Bentonville, Arkansas, with a target start date of October 2026. What we are and are not asking for We need you to be financially literate: able to read statements, understand capital structure, interpret return metrics like cap rates and IRR, and build solid Excel models. We don’t require years of institutional experience in asset management, commercial real estate, or private equity. We prioritize builders with business or finance training and strong analytical instincts. Job Conditions The position requires adaptability to frequent shifts in priorities, new investment and opportunity analysis, coordination with third-party managers, responsiveness to material asset issues, and adherence to deadlines. Requires periodic asset visits and use of a personal vehicle. Requires attendance at occasional company, investment, property, and community events or meetings outside regular business hours. While the company encourages a flexible work environment that accommodates work-life balance and individual productivity, this role depends on consistent proximity to the office, the executive team, and portfolio assets because the workflows that you build will be developed alongside the people and processes they support. Intellectual Property All models, files, drafts, workflows, prompts, agents, scripts, integrations, and work assets produced while employed by Green Circle Projects are the property of Green Circle Projects and will be kept in the appropriate file location at ALL TIMES. A strict non-disclosure and privacy agreement will be signed upon hiring. Primary Role — AI Workflow Development & Automation (60%) • Build internal workflows. Design, build, and maintain AI-assisted workflows and automations that convert investment documents, meetings, and correspondence into structured records, models, dashboards, executive summaries, and tracked follow-ups. • Own it. Maintain, monitor, correct, and improve what you build. A workflow that silently breaks is worse than no workflow, so instrumentation, error handling, and version control are part of the job. • Work with the team. Sit with the people whose work you are automating. Identify where time is actually being lost, rather than where it appears to be lost, and prioritize by hours saved and error reduction. • Build the investment data layer. Develop and maintain the real estate and investment database and the internal dashboards that read from it. • Automate recurring reporting. Standardize and automate the executive summaries, portfolio dashboards, and ownership reporting that are currently rebuilt by hand each period. • Institutional knowledge management. Build workflows and tools that make our own history -- records, meetings, decisions, and reasoning -- searchable and usable. • Design for human review. Decide what AI should handle, what a person must review, and where a system should refuse to act. Design the review checkpoints and make them explicit. • Evaluate and choose the stack. Assess tools, models, and platforms on their merits. Build what should be built, buy what should be bought, and be able to explain the difference. • Document and train. Write the documentation and train the team so that what you build survives your vacation. Secondary Role — Investment Analysis & Reporting (40%) • Financial modeling. Build, review, and maintain models for underwriting, valuation, asset performance, capital structures, and return analysis. • Underwriting and diligence support. Support research, diligence, and underwriting for prospective investments, including review of third-party models and presentations. • Portfolio monitoring. Track investment performance, risks, capital needs, and financing obligations across the portfolio, and flag material developments. • Owner-side asset oversight. Green Circle uses third-party property managers for day-to-day real estate operations. Help monitor performance from the ownership level, with attention to financial results, leasing, capital planning, and execution of approved business plans. • Reporting and coordination. Coordinate information gathering across investments — diligence requests, periodic reporting, compliance, audits, and dispositions — and help consolidate private equity, real estate, and other reporting into executive and ownership updates. • Meetings and follow-through. Participate in investor, lender, property manager, and other investment-related meetings, and convert what happens in them into updated records and decisions. • Family Office planning support. Support planning related to asset allocation, acquisitions, dispositions, liquidity, estate matters, gifting, and grants. • Perform all other duties as assigned. Qualifications Required • Demonstrated building. You have designed and implemented working AI-assisted workflows, automations, or internal tools that other people used regularly. You will be asked to walk us through one in detail, including what broke and how you fixed it. • Financial literacy. You can read financial statements, follow capital structure, interpret return metrics, and build a sound model. Advanced Excel proficiency is required. • Business or finance education. Bachelor's or master's degree in business, finance, accounting, economics, real estate, information systems, computer science, or a related field. A technical degree paired with financial fluency works; so does a business degree paired with building ability. • Practical technical skill. Comfort with scripting (Python or similar), APIs and integrations, structured data, and version control. You do not need to be a career software engineer, but you must be able to build things that are beyond ordinary use of consumer AI. • AI judgment, not AI enthusiasm. Fluency with tools such as Claude, Gemini Notebook, Granola, and comparable platforms, and, more importantly, the judgment to know what to delegate, how to direct it clearly, how to check outputs critically, and when a human must stay in the loop. We care far more about how well you work with AI than how many tools you have touched. • Communication. Strong written and verbal skills. You will explain technical tradeoffs to nontechnical colleagues, and translate messy financial context into working systems. • Ownership. Nobody will assign you a backlog. You need to find the problems, decide what matters, and finish things. Helpful, not required • Experience in investment analysis, underwriting, asset management, private equity, real estate, or a comparable analytical role. • Exposure to family office, fund administration, or investor reporting environments. • Experience with APIs, automation platforms, agent frameworks, MCP connectors, retrieval tools, or document-processing workflows. • Background in a lean or entrepreneurial organization where you had to do the whole job rather than a slice of it. Experience level We are flexible on years. A candidate with three years of experience who has built real systems is more interesting to us than one with ten who has managed them. What matters is evidence that you have built something, that people used it, and that it kept working. How We Will Evaluate You We are being explicit about this because a resume cannot tell us what we need to know. AI capability is nearly impossible to read off a page. 1. Application. Resume plus a short note describing one AI-assisted system you built: what problem it solved, how you built it, **what went wrong**, and whether it is still running. Links, screenshots, or other examples are welcome. This note matters more to us than the resume. 2. Conversation. A discussion of your work, our portfolio, and how you think about what should and should not be automated. Depending on your certs, we may ask you to complete an AI fluency test. 3. Working session. A practical exercise using real materials of the kind you would handle here: a property manager report, an operating statement, and a thread of correspondence. You will design and build a repeatable workflow that turns them into an executive summary, and then walk us through your reasoning, including where you would require human review. We are evaluating judgment and process, not polish. 4. Final conversation and references. Show more Show less