Deputy Chief Financial Officer – Remote, $800k/year

About the role

Trilogy seeks a Deputy Chief Financial Officer to redesign its finance system and drive capital allocation across a portfolio of software businesses. You will work directly with the CEO, board, lenders and capital partners, using AI‑native tools to create a lean, high‑leverage finance organization.

Key responsibilities

• Allocate capital across the portfolio by ranking competing uses on risk‑adjusted return and making fund, hold, restructure, exit or acquisition recommendations.
• Architect an AI‑native finance function, redesigning planning, reporting, consolidation, controls and workflow automation.
• Lead investment and transaction analysis, building integrated models, downside scenarios, covenant calculations and execution plans.
• Communicate financial truth and recommendations to the CEO, board and capital partners with clear, quantified analysis.
• Build and mentor a small, high‑performing finance leadership team while scaling systems without adding layers of management.

Required profile

• Senior finance decision‑maker for a $100M+ revenue business or portfolio, with personal ownership of major capital‑allocation decisions.
• Direct responsibility for at least one $25M+ M&A, financing or refinancing transaction, including negotiation and board recommendation.
• Experience presenting to a board of directors and managing external audit relationships under US GAAP or IFRS.
• Hands‑on experience with an enterprise ERP (e.g., SAP, NetSuite, Oracle, Workday) and recent AI‑driven finance workflow redesign.
• Strong written and verbal English; able to operate in UTC‑8 to UTC+3 time zones.

Required skills

• SAP, NetSuite, Oracle, Workday (enterprise ERP platforms)
• AI‑enabled finance workflow design and automation
• Integrated three‑statement financial modeling
• US GAAP and IFRS accounting standards