Description
This role does not follow the typical VP structure. You will not oversee a reporting team. Your calendar will not be filled with recurring meetings. You will not deliver quarterly strategy presentations. There is no baseline operational routine to maintain.
Your responsibilities will span M&A diligence and integration for enterprise software companies, ownership of P&L objectives for business units, creation of AI-driven automations using cutting-edge tools, negotiation of vendor agreements, and direct presentations to portfolio CEOs, CFOs, and functional leaders. You will execute all of this independently, in parallel, across multiple companies.
Trilogy purchases distressed enterprise software companies and executes turnarounds, targeting one acquisition weekly. The VP of Operations group consists of 10 individuals managing operations for 50+ portfolio companies. Work is organized into three categories: acquisitions (complete lifecycle from diligence through integration), serving as functional COO for business units (budget management, P&L oversight, vendor relations), and providing advisory support to central functions (Support, SaaS, Engineering) to align their activities with business results.
This position operates at high stakes and high visibility, with daily variation in scope. You will shape decisions among key stakeholders throughout the organization—portfolio CEOs, functional leaders, and deal partners. The ideal candidate does not seek consensus; they develop conviction, deliver evidence, and drive action.
What you will be doing
- Managing M&A due diligence alongside leading investment banks and financial institutions, structuring VDR environments, executing vendor consolidation, overseeing international payroll transitions, and controlling closing checklists
- Taking ownership of quarterly P&L budgets for multi-product business units, pinpointing margin optimization opportunities, and delivering cost reduction strategies to portfolio CEOs, CFOs, and senior Finance teams
- Applying AI tools (Claude Code, Cursor, and the most effective available options) on a daily basis to evaluate vendor expenditure, automate workflows for decision-making, construct cost models, and generate executive-ready reports without assistance
- Overseeing the complete vendor lifecycle for 70+ contracts, encompassing negotiation, legal assessment, procurement, invoice management, and termination
- Acting as the single integration point for portfolio operations, coordinating across 6+ central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side partners (banks, legal advisors, target C-Suite)
What you will NOT be doing
- Leading a team or assigning tasks to subordinates. You execute the work directly.
- Creating strategy presentations or conceptual models. All deliverables are tied to financial impact.
- Attending status update meetings or providing KPI reports. You are accountable for the KPIs themselves.
- Awaiting instructions on next steps. You diagnose the issue, design the solution, and deliver it.
- Focusing on a single initiative. You will manage 3-5 simultaneous work streams spanning different companies.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience making presentations to C-suite executives
- Experience writing automation in Python and integrate with LLM APIs
- Experience using Cursor, Windsurf, MCP, or similar tools to ship production-grade automations
- Remote work capability with at least 6 hours of overlap with the CST time zone
You will be working for
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