Senior Bookkeeper

Trolley • Florida, PR

10h • Remote

About The Position

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.

This role oversees financial management across all aspects of the CEOs business and personal accounts, ensuring seamless operations across multiple entities, investments, and ventures.

Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions. We collaborate with high-profile clients to strategize, produce, and optimize compelling content that drives engagement, brand visibility, and business growth. Our creative team functions as a fully integrated powerhouse—combining strategy, design, production, and performance analysis to deliver world-class results.

We operate with an AI-first mindset and look for people who use technology to work faster, smarter, and more creatively. At Trolley, AI is part of everyday work, and we expect new hires to support a culture of curiosity, experimentation, and continuous improvement.

Trolley operates on a Founder Mode mindset—focused on ownership, strategic thinking, and fast execution. We seek proactive, entrepreneurial thinkers who use AI to optimize work. Founder Mode emphasizes high-trust, collaborative teams where contribution outweighs control. We value creativity, resourcefulness, and clear communication. If you're impact-driven, thrive in dynamic environments, and believe in scaling through systems, this is the place for you.

At Trolley, we believe in building a company that works for you — not the other way around. That means freedom, tools, and culture that support both your creativity and your execution.

Requirements

• 5+ years in bookkeeping, finance operations, or multi-entity accounting
• Experience supporting external controllers, tax advisors, and vendors
• Advanced proficiency in QuickBooks Online, QuickBooks Pro, and Excel.
• 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

Nice To Haves

• Background in startup or fast-paced operational settings preferred
• Experience with Xero, Google Sheets, and automation tools is a plus.
• Familiarity with ClickUp, Slack, and financial dashboard tools.
• 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

Responsibilities

• Accounts Payable, Receivable & Vendor Coordination
• 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
• Financial Reporting & Reconciliation
• 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

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed