Senior Bookkeeper Billing And Finance Ops Lead

Entrepreneur with several small businesses (virtual mailboxes, construction, and international ventures) runs a unified playbook across Operations, Projects, and Marketing. This hire anchors the Operations lane and is the financial backbone across multiple entities. You’ll handle day-to-day accounting, build & enforce workflows, own billing/collections, and surface insights that drive cash flow and tax planning.

What You’ll Own

● Daily accounting across multiple entities

○ Reconcile all bank/credit card transactions every day in QuickBooks Online (multi-company).

○ Classify spend properly: company admin, job/Project costs, reimbursables, and COGS.

○ Maintain clean AR/AP, vendor records, and supporting documentation.

● Billing & collections (mission-critical)

○ Run invoicing cycles, apply payments, chase aging, and clear disputes.

○ Investigate open balances; identify root causes and fix upstream workflow

gaps to speed collections.

○ Partner with project/CS teams to confirm deliverables and release milestones.

● Financial workflows & controls

○ Design and document accounting workflows (intake → coding → approvals → reporting).

○ Establish checklists, SLAs, and audit trails; train teammates to follow them.

○ Create weekly exception reports that flag errors, inconsistencies, and risks—and close them out.

● Reporting, cash, and tax readiness

○ Prepare weekly dashboards (cash position, AR aging, WIP, gross margin by project/business).

○ Build/update monthly cash-flow forecasts; scenario plan around inflows/outflows.

○ Partner with the tax CPA on year-end planning (e.g., purchase timing, write-offs, accruals) and ensure books are tax-ready by Dec 1.

● Cross-functional coordination

○ Work closely with Customer Success, Project Management, and Design to align POs, change orders, receipts, and job costing.

○ Keep leadership informed with concise updates and “decision-ready” insights.

Must-Have Experience

• 4–7+ years progressive bookkeeping/accounting experience; multi-entity environment strongly preferred.
• Expert in QuickBooks Online (rules, classes/locations, products/services, job costing, recurring transactions, custom reports, multi-company).
• Proven track record owning AR and driving collections with measurable DSO improvements.
• Built/implemented accounting workflows and internal controls; comfort auditing others’ work.
• Strong Excel/Sheets skills (pivot tables, lookups) and comfort with bank feeds, receipt tools, and basic integrations.

Nice to Have

• Construction or project-based accounting (progress billing, retainage, change orders, WIP).
• Experience partnering with external CPAs for tax planning and year-end close.
• Familiarity with ticketing/CS tools or project systems and how they map to accounting.

Working Style — Who Thrives Here

• Strong, confident communicator: asks direct questions, challenges assumptions, and pushes for clarity. Not “yes-boss”—you drive accuracy and results.
• Ownership mindset: treats AR, cash, and books like your name is on them. You spot issues early and propose fixes.
• Process builder: you think in systems, write them down, and get others to follow them.
• Calm urgency: steady under pressure, but relentless about daily reconciliations and collections.
• High candor, low ego: comfortable giving/receiving feedback across cultures and time zones; team-first.

Success in 90 Days

• Daily reconciliations: 100% of transactions coded within 24 hours; <1% uncategorized.
• AR discipline: All invoices out on schedule; DSO trending down; clear plan for every invoice >15 days.
• Reporting rhythm: Weekly error/exception report delivered and closed; executive dashboard live.
• Workflow lift: At least 2 workflow improvements shipped that reduce leakage or cycle time (e.g., CO/PO guardrails, backup documentation).
• Tax readiness: Year-end checklist agreed with CPA; preliminary tax strategies drafted.

Tools You’ll Use

• QuickBooks Online (multi-company)
• Google Workspace/Sheet
• Banking portals/feeds,
• Receipt capture and basic integrations (rules/imports)
• Comfortable adopting other lightweight tools the team uses