Accounting assistant/Bookkeeper
Backup Full-Charge Bookkeeper - Law Firm (QuickBooks, Trust/IOLTA, AI-Forward)
Full time in the office downtown Chicago
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THE ROLE IN ONE SENTENCE
When our full-charge bookkeeper is out - vacation, leave, or the unexpected - you ARE the bookkeeping department: payroll, closes, trust compliance, all of it, from the first morning, with no ramp-up and no hand-holding.
WHY THIS FIRM IS DIFFERENT
We are a Chicago Loop trial law firm that has genuinely built AI into how we work - in our law practice and in our operations. We are not looking for someone to tolerate new tools; we are looking for someone excited to help us keep modernizing the accounting function itself: smarter categorization, automated receipt and invoice capture, anomaly detection, faster closes, cleaner reporting. AI handles the repetitive entry here. Your time goes to judgment calls, compliance nuances, and communication - the things that actually need a human.
WHAT YOU WILL OWN DURING COVERAGE
- The complete books in QuickBooks (Online and Desktop): bank and credit-card reconciliations, AP/AR, payroll processing, month-end and year-end close
- Trust accounting: IOLTA and trust-account compliance - kept strictly separate from operating - including any filings or deadlines that land during your coverage
- Filevine-to-QuickBooks reconciliation: pulling matter-level cost, trust, and billing data from our case management system and tying it to the firm financials; flagging discrepancies before they become problems
- Personal and legacy accounts maintained in Quicken
- Financial statements and plain-English reporting for firm leadership, produced without oversight
- A documented, clean handoff with the primary bookkeeper at the start and end of every coverage period
WHAT YOU WILL HELP BUILD (THE TECH PART)
- Put AI-assisted tools to work in the daily flow: receipt/invoice parsing, transaction categorization, reconciliation assistants, anomaly detection - while keeping every number audit-ready
- Evaluate and recommend new automation for the accounting stack; if you have introduced a tool that made a finance function measurably faster or cleaner, we want to hear that story
- Help define where automation stops and professional judgment begins - especially around trust accounting, where accuracy is non-negotiable
WHAT YOU BRING
- 4+ years of full-charge bookkeeping or accounting: you have run an organization's entire books alone, not pieces of them
- Demonstrated QuickBooks proficiency (certification a plus) and working familiarity with Quicken
- Filevine experience, or proven speed learning legal practice-management software
- Working knowledge of trust/IOLTA accounting rules in a law-firm environment
- Real fluency with AI-powered accounting tools - paired with the judgment to know when not to trust them
- The attention to detail that catches the $12 discrepancy nobody else notices
- Independence, sound judgment without daily supervision, and the communication skills to explain financials to non-accountants
TO APPLY
Send your resume and a short note covering three things: (1) the books you have run solo; (2) your background in QuickBooks, Quicken, and Filevine or comparable legal software; and (3) one concrete example of a tool, automation, or AI workflow you introduced and what it changed. Candidates who can speak concretely about putting technology to work in a bookkeeping practice go to the top of the pile.
Susan E. Loggans & Associates, P.C. | Chicago Loop | logganslaw.com
Job Type: Full-time
Pay: $53,436.39 - $64,353.50 per year
Benefits:
- Dental insurance
- Disability insurance
- Health insurance
- Life insurance
- Paid sick time
- Paid time off
- Paid training
Work Location: In person
