Senior Bookkeeper / Finance Operations Lead | 60188065074

• 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.

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.

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.

• 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.

• 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.

• 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.

• 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.

• 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.

• 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.