Head of Operations – Remote – $200,000/year

About the role

Trilogy is seeking a senior operations leader to drive M&A diligence, integration, and P&L ownership across its portfolio of underperforming enterprise software businesses. This remote position operates without a traditional reporting team, allowing you to work independently and influence senior stakeholders.

Key responsibilities

• Lead M&A due diligence and integration, coordinating with investment banks, legal advisors, and target executives.
• Own quarterly P&L budgeting for multi‑product business units, identify margin improvement opportunities, and present cost‑optimization proposals to CEOs and CFOs.
• Utilize AI platforms such as Claude Code and Cursor to automate vendor analysis, build financial models, and generate executive deliverables.
• Manage end‑to‑end vendor lifecycle for 70+ contracts, including negotiation, procurement, invoicing, and termination.
• Serve as the central integration contact, aligning Finance, Legal, Engineering, SaaS, HR, and IT functions with portfolio objectives.

Required profile

• Proven ability to work autonomously and influence senior leaders without formal authority.
• Strong analytical mindset with data‑driven decision making.
• Comfortable handling multiple high‑impact projects simultaneously.
• Experience in turnaround environments and fast‑paced acquisition cycles.

Required skills

• Claude Code (AI coding platform)
• Cursor (AI automation tool)

What we offer

• High‑visibility role with direct impact on portfolio performance.
• Competitive compensation of $200,000 USD per year.
• Fully remote work arrangement.