Description
This role does not resemble a traditional VP position. You will not inherit a team. Your calendar will not be filled with recurring meetings. There will be no quarterly strategy presentations. There is no established operation to maintain.
Instead, you will lead M&A diligence and integration efforts for enterprise software companies, take ownership of P&L objectives for business units, develop AI-driven automations using cutting-edge tools, handle vendor contract negotiations, and deliver presentations directly to portfolio CEOs, CFOs, and functional leaders. All of this work will be executed by you personally, simultaneously, spanning multiple companies.
Trilogy purchases and rehabilitates distressed enterprise software companies, targeting an acquisition cadence of one per week. The VP of Operations group consists of 10 individuals managing operations across more than 50 portfolio companies. The scope of work divides into three areas: acquisitions (complete process from diligence through integration), serving as effective COO for business units (budgets, P&L, vendor management), and advising central functions (Support, SaaS, Engineering) to align their efforts with business results.
This is a high-impact, highly visible position where each day presents different challenges. You will shape decisions made by key stakeholders throughout the organization, including portfolio CEOs, functional leaders, and deal-side partners. The individual who succeeds here does not seek consensus; they develop conviction, deliver the evidence, and drive stakeholders to action.
What you will be doing
- Leading M&A due diligence in partnership with leading investment banks and financial institutions, structuring VDR environments, executing vendor consolidation, managing international payroll transitions, and maintaining responsibility for closing checklists
- Taking 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 leadership
- Applying AI tools (Claude Code, Cursor, and the most effective solutions available) on a daily basis 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 review, procurement, invoice management, and termination
- Serving 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 counsel, target C-Suite)
What you will NOT be doing
- Leading a team or assigning tasks to direct reports. The work is executed by you.
- Creating strategy presentations or conceptual frameworks. All deliverables are tied to specific dollar values.
- Attending status update meetings or providing KPI reports. The KPIs are your responsibility.
- Waiting for direction on next steps. You surface the issue, develop the solution, and implement it.
- Focusing on a single project. You will manage 3-5 parallel work streams across 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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