Senior Bookkeeper

Job Details

• Location: Remote
• Hours: 40hrs/week
• Compensation: $15/hour

Senior Bookkeeper

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 CEOs business and personal accounts, ensuring seamless operations across multiple entities, investments, and ventures.

1. 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

2. 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)

3. 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

4. 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

5. 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

Submit your application here ==> https://forms.clickup.com/9017085020/f/8cqbk2w-42837/3DOGJC91PTSWVPORZI

Note: We are not considering applications from agencies or recruiters at this time. Only individual candidates will be reviewed

About Us

Who We Are

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 power-house combining strategy, design, production, and performance analysis to deliver world-class results.

We Operate Under Founder Mode

Trolley is built on a Founder Mode mindset - an operating system rooted in ownership, strategic thinking, and execution at speed. Here, we look for people who take initiative, think like entrepreneurs, and use tools like AI to optimize how work gets done. But Founder Mode isn't about going it alone, it's about working within high-trust, collaborative teams where contribution matters more than control. We value creativity, resourcefulness, and clear communication. If you're driven by impact, thrive in dynamic environments, and believe in scaling through systems, not stress - this is the place for you.

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.