Investment Ops Analyst

Location: Remote, US (Eastern or Central Preferred)

Compensation: $80,000 - $120,000

Employment Type: Full-Time

Who We Are: We're a lean single-family office supporting a New York–based serial entrepreneur whose investments and operating businesses span finance, technology, and real estate: public markets, derivatives, private funds, real estate, and digital assets. The team is small and high-trust. You'll work directly with the CFO and have regular access to the principal. We're rebuilding the back office from the ground up. Bookkeeping is coming in-house from an outside accountant, and we don't intend to rebuild it the old way. Quick Books Online will be the ledger; AI and automation will do the work that used to be manual entry. You'd be the person who designs that function and runs it. You Might Be Our Person IfYou're an accountant by training and a builder by habit. You close the books, then write the script that makes next month's close shorter. You've shipped something real with AI: a Python script, an Apps Script, a Zapier flow, a small agent. Claude, ChatGPT, or Cursor helped you write it, it runs, and it saves real hours. You can walk us through it. You're more interested in AI that does actual accounting work (categorizing transactions, parsing statements, flagging breaks) than in talking about what AI might do someday. You'd rather pull data from the source (a bank feed, a custodian file, an exchange API) than wait for someone to send you an export. Owning the books for 12+ entities, including LLCs, trusts, and investment vehicles, sounds like a design problem to you, not a burden. You're already picturing the chart of accounts and the intercompany map. Trusts, partnership allocations, K-1s, and basis tracking interest you, and you want a seat where that knowledge compounds. When something doesn't tie, you find out why, to the penny, and then fix the process so it can't break the same way twice. You know what the finished product looks like (a clean close package, a CPA-ready workpaper, a personal balance sheet) before you start building toward it. You pick up new tools for fun, automate things at home that nobody asked you to, and care about details without getting stuck on perfect.

Your Mission: Accounting and tax are the foundation of this seat and where most of your time goes. Investment reporting, FP&A, and analysis sit on top. Automation runs through all of it. Own the books and the close~45%Take over bookkeeping from our outside accountant and rebuild it around automation instead of manual entry. Own the general ledger and chart of accounts across 12+ entities (LLCs, investment vehicles, and trusts) in Quick Books Online. Run the monthly close: bank and credit card reconciliations, intercompany, AP/AR, and consolidated reporting packages. Reconciliations tie, entries have clean support, and deadlines hold. Prepare personal financial statements and net worth reporting with the CFO.Coordinate wires, transfers, and account maintenance with our private banking teams. Document what you build so the function is repeatable and auditable, and keeps running when you're on vacation. Run tax, trust, and entity administration~25%Be the internal point of contact for our outside CPAs: own the document request list, K-1 tracking, and workpapers. Support quarterly estimates, extensions, and year-end filings across entities and individuals. Maintain the tax and compliance calendar, including entity filings, registrations, and trust administration items. Build models that support estate planning, gifting, and charitable giving decisions. Report on investments and plan the cash~20%Reconcile investment performance across custodians and asset classes: public markets, derivatives, private funds, real estate, and digital assets. Track capital calls, distributions, commitments, unfunded balances, and side letter terms. Maintain digital asset reporting across exchanges and wallets, including cost basis, staking and yield activity, and reconciliation to on-chain records. Build the cash flow forecast and liquidity dashboard so the principal always knows what's available and what's committed. Own budgets, rolling forecasts, and monthly budget-to-actual reporting across the office and portfolio operating businesses. Research and model new opportunities for the principal and CFO: return modeling, fee and structure analysis, and comparison against alternatives. Automate everything that repeats~10% on paper; in practice, it's how you do the other 90%Find the manual, fragile steps in our workflows and replace them: auto-categorization, document parsing, anomaly detection, report drafting, and alerting. Build and maintain reconciliation pipelines, dashboards, and reporting templates using LLMs, Python, Apps Script, and workflow tools. Extend the tooling already in place, including Google Apps Script pipelines and webhook-based alerting, and recommend new tools to the CFO.Keep the tooling pointed at the accounting. Clean, accurate books are the goal; automation is how we get there faster.

What Success Looks Like: First 90 days: the books are in-house. The chart of accounts is standardized across entities, bank feeds and reconciliations are running, and there's a written close checklist. By month 6: the close runs on a calendar in a fraction of today's time, intercompany and consolidated reporting are automated where they can be, and every workflow is documented. By month 12: you own the tax calendar and the CPA relationship, the cash flow forecast and liquidity dashboard are live, and you're taking on estate and entity projects. The Stack You'll Work InQuick Books Online: the ledger for every entity. Google Sheets and Excel: still where a lot of the work lands. AI tools: Claude and agentic workflows are part of how the work gets done every day, and we budget for them. Python and Google Apps Script: you don't need to be a software engineer, but with an AI assistant next to you, you should be able to get a working script out the door. APIs and data sources: bank feeds, custodian and brokerage files, exchange APIs, and on-chain data. SQL: useful for querying and joining data at the source. Git Hub: we want our scripts and reconciliation logic versioned and reviewable, not living on one person's laptop. Must-Haves Bachelor's degree in Accounting, Finance, or a related field.2–5 years in accounting or financial operations, including hands-on ownership of a month-end close. Public accounting, fund administration, family office, and corporate backgrounds all count. Hands-on general ledger work in Quick Books Online or a comparable system (journal entries, reconciliations, chart of accounts structure), plus strong Excel and Google Sheets skills. Evidence that you build: a script, an automation, an AI workflow, or a seriously engineered spreadsheet that saved real time. You don't need to be a developer, but you do need to have made something that works. We will ask to see it. Fluency using AI to get work done: you prompt your way to a working script, formula, or workflow, not just a draft email. Discretion, attention to detail, and deadline discipline. The close calendar and the tax calendar run this seat. Nice-to-HavesCPA, CPA candidate, or planning to sit. Partnership, trust, or individual tax exposure: quarterly estimates, K-1s, basis tracking, or CPA coordination. Experience with multi-entity structures, trusts, funds, or UHNW / family office clients. Scripting beyond AI-assisted work (Python, Java Script, or Apps Script), plus SQL or API experience. Private investment administration: capital calls, distributions, and custodian reporting. Digital assets: exchange and wallet reporting, cost basis tracking, or crypto tax treatment. FP&A: budgeting, rolling forecasts, and budget-to-actual variance reporting. Coursework or experience in investment analysis, portfolio analytics, or quantitative finance. Coding coursework, a bootcamp, or a self-taught portfolio. We care about the evidence, not the credential. How We Think About Compensation The base salary range for this role is $80,000–$120,000. The range is broad because the role fits a range of experience, from a strong accountant with two years of close ownership to a CPA with five years and a portfolio of automations. Where an offer lands depends on experience, credentials (a CPA counts), depth in tax and multi-entity work, and what you've built.

Benefits: Medical, dental, and vision coverage. Unlimited PTO plus standard holidays. Remote, flexible work. An AI tools and technology budget. We'd rather pay for the tool than for the hours. Direct access to the principal and CFO, and a function you get to design from scratch. The Bottom Line We're looking for the person who can take a back office of 12+ entities that runs on an outside accountant and spreadsheets and turn it into one that mostly closes itself. You'll be the first in-house accountant, with a real tools budget, direct access to decision-makers, and a blank page. If you're an accountant first and a builder by habit, we want to hear from you.