Senior Bookkeeper

• Location: Remote
• Hours: 40 hrs/week (must be aligned with and available during PST working hours)
• Reports to: CEO, Finance Lead and Financial Controller

• →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)

• 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

• 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

• 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

• 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

• 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.

• 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

• 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

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.

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.