Description
This role does not follow the traditional VP structure. You will not inherit a team, fill your week with recurring meetings, deliver quarterly strategy presentations, or oversee steady-state operations.
Your responsibilities will include leading M&A diligence and integration for enterprise software companies, managing P&L objectives for business units, developing AI automations with cutting-edge tools, negotiating contracts with vendors, and delivering presentations to portfolio CEOs, CFOs, and department leaders. You will execute all of this independently, in parallel, across multiple companies.
Trilogy purchases underperforming enterprise software companies and executes turnarounds, targeting one acquisition each week. The VP of Operations team consists of 10 professionals managing operations for more than 50 portfolio companies. The scope of work divides into three areas: acquisitions (covering the full process from diligence through integration), serving as interim COO for business units (overseeing budgets, P&L, and vendor relationships), and advising central functions (Support, SaaS, Engineering) to align their initiatives with business outcomes.
This is a high-impact, highly visible position where daily work varies significantly. You will shape decisions among key stakeholders throughout the organization, including portfolio CEOs, functional leaders, and deal-side partners. The ideal candidate does not seek consensus; they develop conviction, present supporting evidence, and drive stakeholders to action.
What you will be doing
- Leading M&A due diligence in collaboration with top-tier investment banks and financial institutions, structuring VDR environments, executing vendor consolidation, overseeing international payroll transitions, and managing closing checklists
- Managing quarterly P&L budgets for multi-product business units, surfacing margin improvement opportunities, and delivering cost reduction proposals 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 expenditures, automate decision workflows, develop cost models, and generate executive-ready reports without assistance
- Overseeing the complete vendor lifecycle for 70+ contracts, encompassing negotiation, legal review, 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 work to direct reports. You execute the work.
- Creating strategy presentations or conceptual frameworks. Every deliverable is tied to a financial outcome.
- Attending status meetings or providing KPI updates. You are accountable for the KPIs.
- Waiting for direction on next steps. You surface the problem, design the solution, and deliver it.
- Focusing on one initiative at a time. 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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