Senior Bookkeeper / Finance Operations Lead * Location: Fully Remote * Hours: Full-time (40 hours/week). Daily live overlap 9:00 AM – 5:00 PM ET required. * Compensation: $2,000 – $3,000 USD/month base (depending on experience). * Engagement: Long-term contractor. * Start Date: ASAP. About Property Shield We are a fast-growing, founder-led B2B SaaS company operating at the intersection of real estate, property management, and listing platforms. We serve institutional single-family rental owners, property managers, and Multiple Listing Services (MLSs), counting some of the largest names in residential property management among our clients. With a tight-knit team of under 20 people, we are expanding our finance department. Backed by a fractional CFO and a US CPA, we are now hiring our first dedicated, in-house Finance Operations Lead to own our financial machinery end-to-end. The Role As the Senior Bookkeeper / Finance Operations Lead, you will sit at the center of our financial ecosystem. You will execute everything between the high-level strategy handled by our fractional CFO and the annual filings managed by our US CPA. This is a build-from-scratch role. You aren't just maintaining a system; you are the architect of our future finance operations. You will build the standard operating procedures (SOPs), establish the monthly cadence, and completely de-risk this function for our leadership team. Key Responsibilities 1. Accounts Receivable & Accounts Payable * Manage end-to-end AR for 40+ recurring B2B clients (invoice generation, delivery, tracking, and collections). * Establish and enforce an AR aging cadence (Day 30 / 45 / 60) utilizing professional, documented follow-up scripts. * Handle full-cycle AP, bill-pay execution, and credit card/merchant processor reconciliations. * Resolve routine billing disputes and accurately apply incoming payments. 2. Books & Monthly Close * Maintain absolute ownership of QuickBooks Online (expense categorization, chart of accounts management, and bank reconciliations). * Deliver a comprehensive monthly close package by Business Day 7, including AR aging, AP register, reconciliations, P&L, balance sheet, and variance commentary. * Maintain an audit-ready digital trail of receipts and documentation, specifically tracking R&D credit-qualifying expenses. 3. Compliance, Tax & Payroll * Own a 90-day forward-looking compliance calendar covering payroll tax, sales tax, BOI, state registrations, and 1099s. * Triage IRS and state tax mail, resolving administrative issues and escalating strategic inquiries to the CFO. * Run US payroll via Gusto and execute approved compensation or headcount updates. * Coordinate annual tax document collection and R&D credit substantiation with our US CPA. 4. Vendor Management & Reporting * Manage vendor onboarding (collecting W-9s, setting up ACH) and maintain the vendor master file. * Deliver a weekly cash flow snapshot to the Founder every Monday morning. * Author and continually optimize SOPs for all recurring financial processes. What We Are Looking For Must-Haves: * Experience: 7+ years of dedicated bookkeeping experience working directly with US-based clients. * Certification: Active QuickBooks Online ProAdvisor certification (fully completed, not in-progress). * Technical Compliance: Proven experience handling US multi-state payroll, sales tax, and 1099 reporting. * Portfolio: Direct experience managing a recurring B2B AR portfolio (SaaS, professional services, or PropTech preferred). * Communication: Exceptional written English with a polished, professional, client-facing email voice. * Availability: Strict ability to work full-time hours overlapping 9:00 AM – 5:00 PM ET. Nice-to-Haves: * Experience in Property Management, Real Estate, or the PropTech sector. * Familiarity with modern fintech tools: Stripe, Bill.com, Ramp, Brex, or Gusto. * Background tracking and documenting R&D tax credit expenses. Why Join Us? Build Your Legacy: As our first dedicated finance hire, you get to skip the corporate red tape. You will shape our tooling stack, design the processes, and build the function from the ground up. Direct Impact & Visibility: You will work directly with the Founder and Fractional CFO. Your voice matters, your work is visible, and your impact will be felt daily. Stability & Growth: This is not a short-term gig. We are looking for a long-term partner who wants to grow alongside the company, unlocking expanded scope and compensation milestones as we scale.