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

1. 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.

2. 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.

3. 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.

4. 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.

5. 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

1. 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).

2. Detail-Oriented & Analytical

You 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.

3. Technically 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.

4. 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.

5. 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