Description
This role departs sharply from the typical VP structure. You will have no direct reports, no calendar dominated by recurring meetings, no quarterly strategy presentations, and no routine operations to maintain.
Your scope will encompass M&A diligence and integration for enterprise software companies, ownership of P&L targets for business units, development of AI-driven automations using cutting-edge tools, vendor contract negotiations, and direct presentations to portfolio CEOs, CFOs, and functional leaders. You will execute all of this independently and simultaneously across multiple organizations.
Trilogy's business model centers on acquiring distressed enterprise software companies and executing turnarounds, targeting one acquisition per week. The VP of Operations group consists of 10 professionals managing operations for more than 50 portfolio companies. Responsibilities are organized into three categories: acquisitions (covering diligence through integration), serving as de facto COO for business units (including budgets, P&L, and vendor management), and advising central functions (Support, SaaS, Engineering) to align their initiatives with business outcomes.
This is a high-impact, high-profile position where daily work varies significantly. You will shape decisions involving key stakeholders throughout the organization—from portfolio CEOs and functional leaders to deal-side partners. Success in this role requires building conviction independently, presenting evidence clearly, and driving stakeholders to action without waiting for consensus.
What you will be doing
- Leading M&A due diligence in collaboration with prominent investment banks and financial institutions, overseeing VDR organization, executing vendor consolidation, managing international payroll transitions, and maintaining accountability for closing checklists
- Taking full ownership of quarterly P&L budgets for multi-product business units, pinpointing margin enhancement opportunities, and delivering cost reduction strategies to portfolio CEOs, CFOs, and senior Finance teams
- Using AI tools daily (Claude Code, Cursor, and other best-in-class solutions) to evaluate vendor expenditures, automate decision workflows, construct cost models, and generate executive-level reports without assistance
- Overseeing the complete vendor lifecycle for 70+ contracts, encompassing negotiation, legal assessment, procurement, invoice management, and termination
- Serving as the sole integration point for portfolio operations by 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 theoretical models. All deliverables tie directly to financial impact.
- Attending status update meetings or presenting KPI reports. You are accountable for the KPIs themselves.
- Waiting for direction on your next priority. You diagnose the issue, develop the resolution, and implement it.
- Focusing on a single initiative. You will manage 3-5 parallel 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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