Thimble
Staff Accountant
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Own the daily accounting cycle for a SaaS company, including order-to-cash processing, billing, invoicing, cash application, collections, accounts receivable, journal entries, accruals, prepaids, reconciliations, and monthly close support. Manage billing inquiries, coordinate with Sales Operations and Customer Success, support compliance reporting, maintain audit documentation, and improve accounting processes and documentation.
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Information Technology
Performs accounts receivable, invoicing, journal entries, accounts payable and credit card transaction entry, month-end closing, bank reconciliations, account reconciliations, and accounting adjustments. Maintains accurate financial records and supports accounting operations, controls, budgets, and financial reporting. Requires collaboration across business units, strong communication, organization, attention to detail, and independent work in a fast-paced environment.
Information Technology
Performs accounting operations including accounts receivable, invoicing, journal entries, accounts payable transactions, bank and account reconciliations, month-end closing, and financial record adjustments. Maintains accurate accounting information and supports departmental activities while following established controls and accounting principles.
About Us
Thimble is a leading insurtech platform for small business customers and agents. Thimble allows customers to quickly get insurance coverage by the job, month or year using its award-winning app, website, or over the phone.
Founded by serial entrepreneurs, Thimble works with a variety of carriers to bring the best insurance solutions to small businesses, brokers and agents. Since it was founded, Thimble has delivered more than 170,000 policies to small businesses across the United States.
Thimble was acquired by Arch Insurance, a unit of Arch Capital Group Ltd. (Nasdaq: ACGL), a publicly listed Bermuda exempted company with approximately $24.3 billion in capital at March 31, 2025. Arch, which is part of the S&P 500 Index, provides insurance, reinsurance and mortgage insurance on a worldwide basis through its wholly owned subsidiaries.
Thimble's innovative culture and technical expertise are an incredible addition to Arch Capital’s portfolio of offerings. The acquisition expands Arch’s suite of digital solutions for small business customers and brokers. Thimble will remain a separate subsidiary, working closely with the Arch Group team.
For more information, visit thimble.com.
Our Values
Our unique culture is built around our six core values:
Think Wild, Act Tame
Be relentlessly creative. Question everything. Get to know the rules so well, you can use them in new ways. Be the industry’s compliant radicals.
Green Means GO
Act. Move forward. Learn. You can only make a decision based on the best information you have – so make it.
Own Every Detail
Be ruthlessly precise. Disciplined. Sweat the small stuff.
Simplify, Simplify, Simplify
Get to the point. Make it crystal clear. Cut everything else. It’s our job to make insurance easy – however hard that is for us.
Every Moment Counts
Show up early and ready. Deliver on time or before. Make the most of your time, so others can make the most of theirs.
Stay Human
Treat every person, and their ideas, with respect. Cherish diversity.
About the Role
We are seeking a detail-oriented, reliable, and execution-focused Staff Accountant to join our small but nimble Finance team. Reporting to the Manager of Finance and Accounting, this role will play a key part in maintaining accurate financial records, ensuring compliance with accounting standards, and supporting month-end and year-end closing activities.
What You’ll Do
- Prepare and post journal entries, accruals, and adjustments in the general ledger
- Reconcile bank statements, credit card transactions, and other balance sheet accounts
- Assist with accounts payable and accounts receivable processing
- Prepare monthly reporting for insurance carriers
- Support month-end and year-end closing processes, ensuring timely and accurate reporting
- Prepare and maintain supporting documentation for audits and tax filings
- Monitor compliance with internal controls and accounting policies
- Assist with budgeting and forecasting activities as needed
- Collaborate cross-functionally to gather financial data and resolve discrepancies
- Perform ad hoc analyses and projects as assigned by manager and/or our President
What We’re Looking For
- 3+ years of Accounting & Finance experience including general ledger experience
- Solid understanding of US GAAP and general accounting principles
- Self-starter with the ability to analyze and problem-solve
- Relentless attention to detail, accuracy, and organizational skill
- Ability to meet deadlines in a fast-paced environment
- Proficiency in Microsoft Excel; experience with Sage Intacct is a plus
- Ability to work and communicate effectively with employees and leaders from different teams
- Bachelor’s degree in accounting, finance, or related field
What You’ll Do in 30 Days
- Get to know the team and understand their skills and challenges
- Become comfortable with our platform
- Become familiar with our insurance accounting and reporting
What You’ll Do in 60 Days
- Understand our accounting processes and how it affects financial statements
- Prepare journal entries and balance sheet reconciliations
- Compile our monthly insurance carrier reporting
What You’ll Do in 90 Days
- Take ownership of accounting processes from month end close to reconciliation
- Understand the financial statements and prepare monthly variance analysis
- Assist in management of insurance carrier relationships
Thimbler Benefits & Perks!
-Fully remote company
-Thimble Fridays! (out of office at 12:00pm local time)
-Comprehensive health, vision, and dental coverage
-401(k) auto enrollment and matching (100% of the first 3% and 50% of the next 3%)
-PTO: 20 days vacation + 8 floating days + 10 company-wide holidays + 1 VTO (Volunteer Time Off) + unlimited sick time
-Parental Leave: 100% paid 12 weeks + 2 weeks gradual return
-Computer choice of Mac or PC
-Work from home setup reimbursement
-Monthly co-working space and/or child care reimbursement
-Monthly ClassPass credit
-Quarterly wellness reimbursement
-Other health & wellness perks including: One Medical, Teladoc, Talkspace, Kindbody, and Health Advocate
-Virtual events, happy hours, trivia, and fun!
What you need to know about the Chicago Tech Scene
With vibrant neighborhoods, great food and more affordable housing than either coast, Chicago might be the most liveable major tech hub. It is the birthplace of modern commodities and futures trading, a national hub for logistics and commerce, and home to the American Medical Association and the American Bar Association. This diverse blend of industry influences has helped Chicago emerge as a major player in verticals like fintech, biotechnology, legal tech, e-commerce and logistics technology. It’s also a major hiring center for tech companies on both coasts.
Key Facts About Chicago Tech
- Number of Tech Workers: 245,800; 5.2% of overall workforce (2024 CompTIA survey)
- Major Tech Employers: McDonald’s, John Deere, Boeing, Morningstar
- Key Industries: Artificial intelligence, biotechnology, fintech, software, logistics technology
- Funding Landscape: $2.5 billion in venture capital funding in 2024 (Pitchbook)
- Notable Investors: Pritzker Group Venture Capital, Arch Venture Partners, MATH Venture Partners, Jump Capital, Hyde Park Venture Partners
- Research Centers and Universities: Northwestern University, University of Chicago, University of Illinois Urbana-Champaign, Illinois Institute of Technology, Argonne National Laboratory, Fermi National Accelerator Laboratory
