Join to apply for the Senior Bookkeeper role at Trolley AIJoin to apply for the Senior Bookkeeper role at Trolley AIGet AI-powered advice on this job and more exclusive features.Who You'll Work WithThis 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 ResponsibilitiesThis role oversees financial management across all aspects of the CEOs business and personal accounts, ensuring seamless operations across multiple entities, investments, and ventures.1. Accounts Payable, Receivable & Vendor CoordinationManage weekly payment approvals and invoice processing via QuickBooksCoordinate with external controller for payment runs and codingTrack accounts receivable and vendor contract obligationsMaintain and monitor the finance@ inbox and related comms2. Financial Reporting & ReconciliationPull and organize weekly AP, AR, and balance sheet reports across entitiesReconcile accounts, credit cards, and recurring transactions for reporting accuracyAssist in flagging uncategorized or missing entries (e.g. rent, SaaS charges)3. Documentation & Internal ControlsMaintain 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 prepCoordinate with vendors to ensure access to clean, categorized data4. SaaS & Subscription OversightTrack active subscriptions and flag duplications or overspendingSupport quarterly reviews of SaaS stack with operationsCollaborate on savings opportunities and contract renegotiation where needed5. Execution Support for External VendorsServe as the point-of-contact for all finance-related documentation and follow-upOrganize information requests and deadlines from tax firms, CPAs, and legal partnersEnsure internal systems (QuickBooks, Drive, ClickUp) reflect vendor inputs correctlyWhat Were Looking ForExperience: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 preferredTechnical 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 itBonus 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 optimizationJob DetailsLocation: RemoteHours: 40hrs/weekCompensation: $15/hourNote: We are not considering applications from agencies or recruiters at this time. Only individual candidates will be reviewedSubmit your application ==> hereAbout UsWho We Are: Trolley is an online marketplace and platform that pairs best-in-class people with best-in-class companies. We are the future of work, create, and play, powered by our proprietary LiveWorkOS.What We Do: Trolley builds world-class teams using best-in-class SaaS tools, AI, and project management systems. Our mission is to empower professionals with world-class training and the latest tools to work smarter, faster, and more efficiently.Why Join Us?Work with the Best: We recruit globally to connect top talent with forward-thinking companies.Tech-Driven Efficiency: Leverage the latest AI and tools to amplify your impact.Human-Centric Approach: Our systems are designed to support and elevate people, not replace them.Training for Success: We provide world-class training to ensure you excel in every aspect of your role.Be Part of the Future of Work. Trolley is now accepting applications from ambitious professionals who want to work at the intersection of technology and creativity. Join us in shaping the next era of work.Seniority levelSeniority levelNot ApplicableEmployment typeEmployment typeFull-timeJob functionJob functionAccounting/Auditing and FinanceIndustriesTechnology, Information and MediaReferrals increase your chances of interviewing at Trolley AI by 2xGet notified about new Senior Bookkeeper jobs in Greater Buenos Aires.We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.
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