Senior Bookkeeper

Trolley AI; San Juan (PR); Remote; USD 45,000 - 60,000; Full time

Job summary

Trolley AI is seeking a Senior Bookkeeper to oversee financial management and operations in a dynamic startup environment. This role requires precision in executing financial tasks and collaborating with various stakeholders to maintain accurate financial records and reports.

Benefits

AI-driven work environment

Remote-friendly culture

Collaborative learning opportunities

Qualifications

• 5-7 years of bookkeeping or accounting experience.
• Experience with multi-entity bookkeeping.
• Strong verbal and written communication skills.

Responsibilities

• Maintain accurate accounting records for multiple entities.
• Process invoices and manage accounts payables.
• Generate financial reports and ensure compliance.

Skills

Attention to detail

Communication

Organization

Education

Bachelor's degree in Finance, Accounting, or Business Administration

Chartered Accountant

Tools

QuickBooks Online

Excel

Xero

ClickUp

Slack

Job description

Join to apply for the Senior Bookkeeper role at Trolley AI

4 days ago Be among the first 25 applicants

Join to apply for the Senior Bookkeeper role at Trolley AI

Get AI-powered advice on this job and more exclusive features.

Who You'll Work With

This role reports directly to the CEO and Managing Partner and works under the direction of the Financial Controller FP&A to support the financial operations of a high-profile venture fund and its associated media projects and initiatives. The Senior Bookkeeper is responsible for executing financial processes, ensuring accuracy, and maintaining standard recurring reports. We are a fast-moving, dynamic startup that values collaboration, inclusion, and a strong team culture. Our team is diverse, young, and energetic, with most members in their 30s and 40s. We need someone who thrives in a startup environment, understands American business culture, and values respect, teamwork, and open communication. We are actively working to create an inclusive, non-toxic work environment and need a bookkeeper who is professional, respects all team members, and aligns with our culture of fairness, teamwork, and innovation. If you enjoy working with diverse teams, have a sense of humor, and value a collaborative, forward-thinking workplace, this is the role for you. This is a hands-on execution role that requires a high level of precision and efficiency. You must be able to execute financial tasks swiftly while maintaining absolute accuracy in reporting and reconciliation. Your performance will be reviewed regularly to ensure compliance with expected turnaround times and financial accuracy standards. We operate in a horizontal, collaborative organization where all financial decisions are made by the CEO, but teamwork and transparency are highly valued. You will work closely with the Financial Controller FP&A to ensure seamless execution of financial operations, reconciliations, and compliance reporting.

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. Financial Record Keeping Maintain accurate and up-to-date accounting records for multiple entities. Ensure transactions are recorded correctly in accordance with standard accounting principles. Reconcile bank accounts, credit cards, and financial statements on a monthly basis.

2. Accounts Payable & Receivable Process invoices, vendor payments, and expense tracking. Monitor accounts receivable and follow up on outstanding payments. Collaborate with finance operations on weekly payment approvals and billing processes.

3. Compliance & Tax Support Prepare and file Sales & Use tax, quarterly estimates, and Year-End 1099 Forms. Assist with business registrations, regulatory filings, and compliance tracking. Support tax preparation and audit processes.

4. SaaS & Subscription Management Track recurring SaaS expenses and software subscriptions, flagging inefficiencies for review. Ensure cost-effective management of business software and automation tools.

5. Vendor & Banking Management Handle vendor onboarding, W9 management, and contract tracking. Serve as the point of contact for banking, credit card companies, and financial vendors.

6. Financial Reporting & Reconciliations Generate standard financial reports including profit & loss statements, balance sheets, and cash flow reports. Work closely with the Financial Controller FP&A to flag discrepancies, inefficiencies, or irregularities.

7. Audit, Documentation, & Process Improvement Maintain organized financial records for audits and compliance checks. Identify and flag opportunities for process improvement and financial efficiency. Implement best practices in bookkeeping, expense tracking, and reporting.

8. Execution, Not Decision-Making This role is purely execution-focusedyou will implement financial operations as directed. All financial decisions are made by the CEO, with guidance from the Financial Controller FP&A.

What We're Looking For

Experience: 5-7 years of experience in bookkeeping, accounting, or financial management. Experience handling multi-entity bookkeeping. Background in financial compliance and audits.

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.

Soft Skills: Highly organized and detail-oriented. Ability to work efficiently under deadlines. Strong verbal and written communication skills. Must be comfortable working in a fast-paced startup environment.

Preferred Qualifications: Chartered Accountant (Preferred but not required). Bachelors degree in Finance, Accounting, or Business Administration. Experience in venture capital, media, or startup environments.

What We Offer

The opportunity to work alongside a high-caliber finance team supporting a diverse set of technology, media, and investment ventures. A fast-moving, AI-driven environment that prioritizes efficiency and innovation. A role where your work directly supports the Financial Controller FP&A in managing financial execution. An autonomous, remote-friendly work culture with a focus on collaboration and learning.

Job Details Location: Remote

Hours: 40hrs/week (First two months: 50hrs/week)

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

Submit your application here

About Us

Who 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 level

• Seniority level

  Not Applicable

Employment type

• Employment type

  Full-time

Job function

• Job function

  Accounting/Auditing and Finance

• Industries

  Technology, Information and Media

Referrals increase your chances of interviewing at Trolley AI by 2x

Get notified about new Senior Bookkeeper jobs in San Juan, Puerto Rico.

Accountant Controller (Hotel Industry Required)

Accountant Controller (Hotel Industry Required)

We’re unlocking community knowledge in a new way. Experts add insights directly into each article, started with the help of AI.