AI-Savvy Technical Project Manager / Chief of Staff — Multi-Project Founder (Long-Term)

ABOUT THE ROLE I run several things at once: an AI-powered accounting and finance tool I'm building, an early-stage sports performance app, finance and audit engagements, a systems implementation for a manufacturing client, and two podcasts. All of them move — just slower than they should, because they move when I have time. I'm looking for one person to change that. Not an assistant who waits for a task list. Someone who takes projects off my desk, drives them week to week, does the actual work where they can, and comes back to me only when they genuinely need a decision. The scope is broad. It spans my businesses and, where I need it, my personal admin. This is a chief of staff role, not a narrow project function. Critically: I want someone who uses AI as a force multiplier — on their own work and on mine. If your instinct when facing a repetitive task is to build a prompt, a workflow, or an automation rather than grind through it manually, we'll get along. WHAT YOU'LL OWN - An AI accounting/finance product — sprint tracking, testing releases, logging bugs, writing test cases, keeping the build moving between developer sessions. - An early-stage mobile app — research, vendor comparison, spec documentation, coordinating build partners. - A client systems implementation — an inventory/MRP rollout for a manufacturing business. Data mapping, UAT, training materials, chasing the vendor. Prior ERP or inventory implementation experience is a big plus. - Finance and audit workstreams — document chasing, tracker maintenance, deadline management. You don't need to be an accountant, but you need to be comfortable around financial documents and be discreet. - Business and personal administration — preparing bill payments across company and personal accounts, tracking renewals and subscriptions, managing recurring commitments, keeping expenses coded and reconciled, chasing invoices and statements, and flagging anything about to lapse or overrun. You prepare and queue; I approve and release. You will never hold payment authority, and I'm not looking for someone who wants it. - Two podcasts — one on AI in the accounting profession, one on faith and men's personal development. Episode scheduling, guest coordination, brief writing, coordinating editors, publishing, and helping grow the audience. - AI process improvement — an ongoing mandate. Find the repetitive work in my business and yours, and remove it. Build the prompt libraries, automations, and templates that make the whole operation faster. - The overview — a single weekly view of everything: what's blocked, what's slipping, and what needs me. WHAT A TYPICAL WEEK LOOKS LIKE - Monday: you send me a short status across all projects — what moved, what's stuck, and a shortlist of decisions you need from me. - Through the week: you're executing. Testing, documenting, coordinating vendors, drafting, following up on my behalf. - You maintain a running list of what's due, what's coming, and what needs my approval — so nothing lapses because I was busy. - You chase me. If I haven't answered something in 48 hours, you ask again. This is a feature of the role, not a nuisance. - Ongoing: you flag at least one thing a month that we should be doing with AI and aren't. - Friday: what shipped, what's next. WHO I'M LOOKING FOR - 3+ years running projects where you were also doing hands-on work — not purely a coordinator. - Genuinely technical: you can test software, read documentation, understand an API at a conceptual level, configure SaaS tools, and troubleshoot before escalating. - Fluent with AI tools in practice, not just in theory. You use Claude, ChatGPT, or similar daily. You understand what makes a good prompt, where these tools fail, and when not to trust the output. Bonus if you've built automations with Zapier, Make, n8n, or similar — or written scripts to glue systems together. - High trust and high discretion. You'll see company and personal financial information. I need someone meticulous with detail, comfortable working within an approvals process, and completely reliable about confidentiality. Verified Upwork identity, solid on-platform work history, and contactable references are required. - Strong written English. Most of our communication will be written and asynchronous. - Self-directed. You take an ambiguous goal, break it down, and come back with a plan rather than questions. - Some overlap with Sydney (AEST) business hours — at least 3–4 hours a day. NICE TO HAVE - Prior work with a founder, agency, or small consulting business. - Experience in an ERP, CRM, or inventory implementation. - Podcast or content production background. - Familiarity with accounting or finance operations. LOGISTICS - Start at [20-30] hours per week, with a view to increasing for the right person. - Long-term engagement — I'm hiring for years, not weeks. - Paid weekly through Upwork. - Two-week paid trial on a defined scope before we commit. - NDA in place from day one. HOW TO APPLY Skip the generic cover letter — I won't read it. Instead, answer these six: 1. Start your reply with the word "Overview" so I know you read this. 2. Describe one project you drove end to end. What was your role, what did you personally do, and what was the outcome? 3. Give me one specific example of a process you improved using AI. What was the before, what did you build, and what did it save? 4. What's your approach when the person you report to goes quiet for a week and you're blocked? 5. This role involves preparing payments and handling sensitive financial information under an approval process. Tell me briefly about a time you were trusted with something confidential or financial, and how you handled it. 6. Which of the areas above is your strongest, and which is your weakest? Be honest — I'd rather know upfront. Include your hourly rate and your available hours in AEST.