Personal Financial Forecasting & Cash Flow Analyst

Overview I am looking for an experienced financial professional or small firm to help me build and maintain a practical, forward-looking view of my personal finances. I am not looking for investment management, retirement planning, tax preparation, insurance advice, or wealth management services. Instead, I need someone who can organize monthly financial data, anticipate upcoming expenses, build realistic cash flow forecasts, model financial decisions, and identify potential issues before they become surprises. This is a highly collaborative, conversation-driven role. I have ADHD and work best through live discussion, not forms or worksheets. You will be responsible for driving the agenda, asking probing questions, pulling information out of me, and following up proactively. If your process depends on clients arriving prepared with organized data, this role is not a fit. Financial Setup This is not a simple household budget. You will be working with a multi-account structure across six institutions: • Primary checking account — paychecks land here; all fixed bills paid from here • Day-to-day lifestyle account — funded by bi-weekly transfers; pays lifestyle credit card • Irregular expense buffer account — maintained as a standing cash reserve • Lifestyle credit card — day-to-day spending; paid from lifestyle account • Business and reimbursement card — work travel, board expenses, and business costs pending employer reimbursement; reimbursements roll back into payroll rather than as direct credits • Irregular expense card — trips, medical, home projects, trainer, vet • Subscription card — all recurring subscriptions and household bills on autopay Statement data will be provided as exported CSVs and PDFs from each institution each month. You must be comfortable parsing and categorizing raw bank exports, not just pre-formatted spreadsheets. Direct account access may be offered over time as trust is established. What You’ll Do • Organize monthly exported bank and credit card statements into a clean, usable format • Categorize and reconcile transactions across seven accounts and six institutions • Track reimbursable business expenses separately and reconcile against payroll deposits • Build and maintain rolling 3-, 6-, and 12-month cash flow forecasts • Project upcoming Citi card payments 45–60 days in advance, itemizing every known and anticipated charge • Identify upcoming known and anticipated expenses across all spending categories • Help estimate costs when exact amounts are not yet known • Create financial scenarios and decision models for major purchases or life decisions • Track recurring, annual, and irregular expenses including travel, medical, home projects, and childcare • Analyze spending trends and identify patterns that may impact future cash flow • Develop practical, filterable planning tools and dashboards. • Conduct live planning sessions to gather information, update forecasts, and flag gaps • Drive the agenda for each session proactively — come prepared with open questions, missing information, and items that need decisions • Prepare concise summaries, recommendations, and action items after each session • Identify financial blind spots and planning gaps before they become problems Examples of Topics We May Work Through • Childcare and education expenses across multiple providers and billing cycles • Family travel planning including flights, hotels, pet boarding, and trip-specific costs • Home improvement projects financed through a HELOC • Medical and veterinary expenses including upcoming procedures • Major one-time purchases and their impact on monthly cash flow • Business acquisition opportunities and their financial feasibility • Long-term savings goals and alignment with current cash flow • Employer reimbursement tracking and reconciliation • Irregular expenses that require multi-month planning What Success Looks Like At any point, I should be able to answer: • What significant expenses are likely over the next 90 days? • What large expenses should I be preparing for over the next year? • How much discretionary cash do I realistically have available right now? • How would a particular financial decision affect my cash flow over the next 3–6 months? • Which upcoming expenses need additional planning or decisions now? • What is building on my Citi card right now and what will the next payment look like? • What reimbursable expenses are outstanding and when will they be recovered? The goal is not a complicated financial model. The goal is clear visibility, reliable projections, and confidence that important expenses have been identified and planned for. What We’re Looking For • Experience in financial analysis, FP&A, budgeting, forecasting, accounting, or a closely related field • Strong cash flow modeling and multi-account forecasting skills • Ability to parse and categorize raw bank statement exports (CSV and PDF formats) • Experience tracking reimbursable expenses and reconciling against payroll or invoice payments • Advanced Google Sheets skills; ability to build interactive, filterable dashboards • HTML output skills are a plus — we use interactive HTML tables for financial visibility • Ability to make reasonable, documented assumptions when information is incomplete • Strong analytical and problem-solving abilities • Excellent communication skills in English • Comfortable facilitating live sessions and asking probing questions to surface missing information • Proactive, not reactive — you bring the agenda, flag the gaps, and follow up without being asked • Comfortable working with confidential financial information • Reliable, detail-oriented, and consistent across months Important • Statement data is provided as exports from six institutions each month. You will organize and process this data yourself rather than having direct account access. Direct access may be offered over time as trust is established. • This role requires genuine financial and analytical expertise. It is not a bookkeeping or data-entry role. Forecasting, assumption-making, and proactive planning are core expectations. • I have ADHD and work best through conversation and collaboration. You are responsible for driving the process. Do not apply if your process depends on clients arriving prepared, completing forms independently, or organizing data before sessions. • Live collaborative sessions are a core and non-negotiable part of this role. Individual freelancers and small firms are both welcome, provided live working sessions are part of your model. • This role is well-suited for finance professionals based in the Philippines, Colombia, Argentina, or similar markets seeking a flexible part-time remote engagement. Hours & Rate • Hours: 8–15 hours per month to start, with potential to grow • Rate: $8–20/hr depending on experience, analytical depth, and location • Engagement type: Ongoing monthly retainer once initial fit is established • International applicants are welcome. This role may be particularly well-suited for finance professionals located outside the United States seeking a flexible part-time engagement.