Senior Accountant - Counterpart

Counterpart is the first Agentic Insurance™ platform, combining trusted insurance expertise with cutting-edge AI to deliver tailored management and professional liability solutions. By integrating Agentic Underwriting™, Agentic Broker Services™, Agentic Risk Mitigation™, Agentic Claims Management™, Agentic Coverage™, and Agentic Capacity™ into one platform, Counterpart empowers brokers and businesses to do more with less risk. Backed by A-rated carriers, Counterpart has been recognized by CB Insights as a 2025 “Top 50 Insurtech,” by Great Place to Work, and by Business Insurance as one of its 2025 “Best Places to Work.”

As Senior Accountant, you will execute day-to-day financial operations within Agentic Finance—premium accounts receivable, cash application, accounts payable, bank and balance sheet reconciliations, bordereau and premium reconciliation, carrier and claims payments, expense management, and audit and tax support. You will build and use AI agents to automate routine execution as the company scales. This role reports to the Controller and works closely with the Accounting Manager.

Responsibilities

Support Accounts Receivable, Accounts Payable, Reconciliations, and Vendor Administration

• Assist with premium accounts receivable from brokers, including invoicing, installment billing, daily cash application, unapplied cash research, and aging/collections follow-up.
• Reconcile broker premium remittances into the premium trust account, clearing unapplied cash and escalating past-due balances and write-offs.
• Prepare monthly reconciliations of policy-level premium receivable and payable detail from Counterpart's reporting platform to the general ledger, supporting recurring AR aging attestations.
• Assist with day-to-day accounts payable within the spend-management platform (invoice intake, coding, approval routing, payment runs, and card-spend policy enforcement).
• Assist with monthly bank reconciliations across operating, premium trust, and loss fund accounts, and prepare balance sheet account reconciliations for month-end close.
• Administer employee expense reimbursements against company policy.
• Manage vendor records, W-9 collection, and year-end 1099 filings.
• Support recurring program-level reimbursement invoicing from calculation to submission.

Support Bordereau, Carrier Payment Operations, and Claims Payments

• Prepare bordereau assembly and premium reconciliations across carrier and reinsurance relationships, researching and resolving discrepancies.
• Maintain the carrier payment calendar and prepare weekly/monthly carrier premium remittance and sweep calculations for Controller approval.
• Prepare monthly loss fund reporting to carrier partners (bank-to-book reconciliation, top-up requests, and check registers).
• Execute claims payments from loss fund accounts in partnership with the Claims team.
• Support monthly net commission, claims-handling fee, and revenue estimate calculations by program.

Support Audit Administration

• Prepare and compile supporting documentation for the annual audit, carrier financial requests, and R&D tax credit.
• Support Counterpart Insurance Company's statutory (STAT) reporting cadence and regulatory filings.
• Maintain and continuously improve the accounting due dates calendar.

Support Monthly Close and Financial Reporting

• Execute assigned monthly close tasks (journal entries, accruals, balance sheet reconciliations) against close checklists.
• Help prepare recurring carrier partner reporting packages (unaudited financials, cash position summaries, standard deliverables).
• Document and maintain step-by-step accounting procedures and audit-ready workpapers.

Drive Agentic Automation Across Accounting Operations

• Build and use AI agents to automate cash application, bank reconciliations, bordereau assembly, premium reconciliation, and claims processing.
• Feed clean, structured financial data and workflows into Counterpart's Intelligence System.
• Identify automation opportunities and collaborate with technical platform teams to continuously improve workflows.

Requirements

• Experience: 3–5 years of progressive accounting experience, ideally at a high-growth company. Experience in insurance, insurtech, or fintech is a plus.
• Education: Bachelor's degree in Accounting, Finance, or a related field, or equivalent practical experience.
• Accounting Knowledge: Working knowledge of GAAP; exposure to STAT (Statutory Accounting Principles) and regulated multi-entity insurance business operations is a plus.
• Core Operations: Proven experience owning core processes like cash application, accounts payable, and reconciliations.
• Technical Tools: Hands-on experience with ERPs (QuickBooks, NetSuite, Sage Intacct) and spend management platforms (Ramp, Bill.com).
• AI & Automation: Demonstrated experience using AI tools or agents to streamline reconciliations and bookkeeping workflows.
• Data Skills: Strong Excel / Google Sheets skills; experience reconciling data from BI tools (Looker) to general ledger systems.
• Communication: Excellent written and verbal communication skills to manage external relationships with brokers, carriers, banks, tax agencies, and auditors.

Team Structure

• Rob Hamilton, Controller
• Dave Fanger, VP of Finance

Company Values

• Conjoin Expectations: Clearly articulate what you expect of others and clarify what is expected of you.
• Speak Boldly & Honestly: Give direct feedback and learn from mistakes.
• Be Entrepreneurial: Embrace action over perfection, leverage AI tools ruthlessly, and focus on outcomes.
• Practice Omotenashi: Build trust through selfless hospitality and going above and beyond.
• Hold Nothing As Sacred: Regularly reflect and adapt routines as the business evolves.
• Prioritize Wellness: Maintain a fulfilling work environment without sacrificing personal well-being.

Benefits & Compensation

• Compensation: Estimated base pay range of $110,000 – $130,000/year.
• Equity: Stock options package.
• Workplace: Fully remote / work from anywhere with optional in-person team retreats.
• Time Off: Unlimited PTO policy plus no working birthdays.
• Health Coverage: Medical, Dental, and Vision insurance.
• Retirement: 401(k) plan.
• Perks & Stipends: Home office setup allowance, wellness stipend, book stipend, professional development reimbursement, and charitable contribution matching.