Senior Bookkeeper

Reports to: CEO, Finance Lead and Financial Controller Who You’ll Work With This role reports directly to the CEO and works closely with external accounting partners, the internal operations team, and the Financial Controller FP&A. You will be the internal execution lead for financial systems, AP/AR processing, vendor coordination, and finance-related documentation across multiple entities and projects. We are a high‑performance, fast‑moving startup that values communication, clarity, and precision. This role is perfect for someone who thrives in a highly collaborative environment, is skilled in bookkeeping and financial coordination, and knows how to proactively manage systems and questions before they become bottlenecks. Key Responsibilities This role oversees financial management across all aspects of the CEO’s business and personal accounts, ensuring seamless operations across multiple entities, investments, and ventures. Manage weekly payment approvals and invoice processing via QuickBooks Coordinate with external controller for payment runs and coding Track accounts receivable and vendor contract obligations Maintain and monitor the finance@ inbox and related comms Pull and organize weekly AP, AR, and balance sheet reports across entities Reconcile accounts, credit cards, and recurring transactions for reporting accuracy Assist in flagging uncategorized or missing entries (e.g. rent, SaaS charges) Documentation & Internal Controls Maintain and organize key financial records in Google Drive (e.g. contracts, insurance, SPV documentation) Work with ops and compliance to support tax deadlines, quarterly filings, and audit prep Coordinate with vendors to ensure access to clean, categorized data SaaS & Subscription Oversight Track active subscriptions and flag duplications or overspending Support quarterly reviews of SaaS stack with operations Collaborate on savings opportunities and contract renegotiation where needed Execution Support for External Vendors Serve as the point‑of‑contact for all finance‑related documentation and follow‑up Organize information requests and deadlines from tax firms, CPAs, and legal partners Ensure internal systems (QuickBooks, Drive, ClickUp) reflect vendor inputs correctly What Were Looking For Experience 5+ years in bookkeeping, finance operations, or multi‑entity accounting Experience supporting external controllers, tax advisors, and vendors Background in startup or fast‑paced operational settings preferred Technical Skills Advanced proficiency in QuickBooks Online, QuickBooks Pro, and Excel. Experience with Xero, Google Sheets, and automation tools is a plus. Familiarity with ClickUp, Slack, and financial dashboard tools. Communication & Workflow Highly organized and proactive Clear communicator, both in written updates and async tools (Slack, email) Able to turn financial documents into actionable to‑dos and flags Comfortable working with ambiguity and incomplete data — and resolving it Bonus Points Experience working with CPAs and handling audit prep Prior exposure to venture capital, media, or creative industries Familiarity with SaaS contract negotiation or cost optimization Location: Remote Hours: 40hrs/week Benefits at Trolley Work from anywhere Flexible schedule and time off — no micromanaging Direct collaboration with the Founder Access to top‑tier AI tools (Perplexity, ChatGPT, ClickUp Brain and more) Clear path for long‑term career growth A supportive company culture grounded in ownership and prioritizing progress over perfection #J-18808-Ljbffr Trolley