Senior Bookkeeper/ Financial Analyst

About The Role

We're looking for a detail-oriented and analytically strong Senior Bookkeeper & Financial Analyst to own HighScale's financial operations end-to-end. This role goes beyond traditional bookkeeping, you'll manage day-to-day accounting, support financial planning and analysis, handle multi-country payroll and contractor payments, and serve as a financial thought partner to leadership.

What You'll Do

• Manage Accounting Operations
• Oversee day-to-day accounting functions including accounts payable, accounts receivable, general ledger, and bank reconciliations.
• Maintain accurate and up-to-date financial records in compliance with GAAP.
• Prepare month-end, quarter-end, and year-end closing reports.
• Manage full-cycle payroll across US, and abroad team members and contractors, ensuring timely and accurate payments.
• Handle multi-currency transactions and reconciliations across USD, COP, PHP, and more, ensuring accurate conversion and reporting.
• Manage contractor and vendor invoicing, PO tracking, freelancer payment schedules, and vendor contract documentation.
• Financial Planning & Analysis
• Create, monitor, and analyze budgets across multiple departments, clients, and projects.
• Provide actionable insights and financial forecasts to support strategic decision-making.
• Track KPIs, profitability, gross margin per client, utilization rates, and campaign-level financial performance.
• Analyze retainer vs. project-based revenue streams and surface trends to leadership.
• Support pricing decisions with cost-basis and margin analysis.
• Compliance & Audit Readiness
• Ensure compliance with local, state, and federal tax regulations across all operating jurisdictions.
• Prepare for audits and liaise with external accountants as needed.
• Implement internal controls and ensure proper documentation across all financial processes.
• Maintain compliance for international contractor agreements and cross-border payment regulations.
• Partner with Leadership
• Provide financial guidance to executives, department heads, and project managers.
• Translate complex financial data into clear insights to inform business strategy.
• Identify opportunities to optimize costs, improve processes, and maximize profitability.
• Scale Finance Systems
• Streamline accounting workflows, systems, and reporting processes to support rapid growth.
• Recommend and implement finance technology tools (e.g., QuickBooks, Rho, Gusto, Deel, or equivalent) to improve efficiency.
• Standardize reporting and dashboards for real-time financial visibility across clients, pods, and departments.

Who You Are

• Experienced Finance Professional
• 5–8 years of experience in bookkeeping, accounting, or finance operations.
• CPA or equivalent certification preferred.
• Strong understanding of GAAP, tax compliance, and financial reporting.
• Experience managing payroll and contractor payments across multiple countries and currencies.
• Familiarity with agency financial models (retainers, project fees, utilization, margin).
• Detail-Oriented & Analytical
• Obsess over accuracy and precision.
• Skilled at analyzing data, identifying trends, and providing actionable insights.
• Comfortable building financial models and translating numbers into clear narratives.
• Tech Proficient
• Hands-on experience with accounting software such as QuickBooks Online, Rho, or equivalent.
• Proficient in Excel or Google Sheets for financial modeling and reporting.
• Experience with contractor payment platforms (Deel, Gusto, Wise, or similar) is a plus.
• Comfortable implementing new finance systems and automation tools.
• Collaborative & Strategic
• Strong communication skills; able to explain financial concepts to non-financial stakeholders.
• Trusted advisor to leadership with both a big-picture and detail-oriented perspective.
• You can design workflows that scale efficiently as the company grows.
• Fast-Paced & Adaptable
• Thrives in high-growth, dynamic environments.
• Able to manage multiple priorities while maintaining accuracy and meeting deadlines.
• Comfortable working across time zones with a distributed international team.

Compensation

Full-time US-based: 3k-5k per month