Chief Financial Officer

Location: Boston, MA and Remote

Reports to: Chief Executive Officer

Employment type: Full-time

About Assail

Assail develops autonomous offensive security platforms powered by sovereign AI. Our platforms help organizations test their applications and systems, identify weaknesses, and validate how those weaknesses could be exploited. Assail, Inc. serves commercial organizations, while Assail Federal, Inc. supports government and defense customers.

The role

The Chief Financial Officer will provide financial leadership for both Assail, Inc. and Assail Federal, Inc., reporting directly to the CEO. This is a hands-on executive role responsible for financial strategy, day-to-day financial operations, and building the systems, team, and controls needed to support growth across both entities.

You will partner with the CEO, board, and leadership team to translate business priorities into clear financial plans, manage cash and capital, and give decision-makers an accurate view of performance. The role is based in Boston, MA and Remote, with travel for leadership, board, investor, and other business meetings as needed.

What you will do

• Lead financial strategy, annual planning, budgeting, forecasting, and scenario analysis for both companies.
• Own cash management, runway planning, working capital, banking relationships, and capital allocation.
• Oversee accounting, the monthly close, payroll coordination, accounts payable and receivable, revenue recognition, and timely financial reporting in partnership with internal staff and external advisers.
• Maintain entity-level and consolidated financial reporting, including appropriate intercompany accounting and cost allocation.
• Build clear reporting for the CEO, board, and investors, explaining results, forecast changes, risks, and recommended actions in plain English.
• Track recurring revenue, retention, gross margin, customer acquisition costs, unit economics, and other operating metrics with sales and customer success leadership.
• Support fundraising, investor diligence, financial modeling, capitalization planning, and relationships with investors and financing partners.
• Provide financial oversight for Assail Federal, including contract budgeting, pricing support, project profitability, cost allocation, and coordination with capture and contracts teams on applicable government requirements.
• Establish scalable financial systems, internal controls, purchasing discipline, and financial policies; coordinate tax, audit, insurance, and other financial matters with qualified advisers.
• Build and develop the finance function, selecting internal hires and outside support as the business grows.

What you bring

• Progressive finance leadership experience, including responsibility for financial planning, accounting oversight, cash management, and executive reporting.
• Experience supporting a growing technology or SaaS business and a practical understanding of recurring revenue models and business economics.
• Experience partnering with CEOs, boards, and investors, with the ability to explain complex financial matters clearly.
• A record of building reliable forecasts, improving financial processes, and implementing sound controls in a changing business.
• Strong financial modeling and analytical skills, with the willingness to work directly in the details.
• Sound judgment, integrity, discretion, and the ability to lead collaboratively across commercial and federal operations.

Experience that would be valuable

• Experience with venture-backed companies, fundraising, and investor due diligence.
• Experience with government contracting finance, contract pricing, project accounting, and applicable federal cost and reporting requirements.
• Experience managing multiple legal entities and consolidated reporting.
• A CPA, MBA, or comparable professional experience.

What success looks like

Leadership has timely, accurate financial information and dependable forecasts. Both entities operate with disciplined cash management and clear financial accountability. The finance function scales with the business, supports funding and diligence needs, and helps the CEO and board make informed growth decisions.