Description
This role does not fit the traditional VP mold. You will not oversee a team, maintain recurring meetings, or prepare quarterly strategy presentations. There is no steady-state operation to manage.
Instead, you will execute M&A due diligence and integration work for enterprise software companies, take ownership of P&L goals for business units, develop AI-powered automations with cutting-edge platforms, negotiate agreements with vendors, and deliver presentations to portfolio CEOs, CFOs, and department heads. All of this work is performed by you, simultaneously, across several companies.
Trilogy specializes in acquiring and revitalizing distressed enterprise software businesses, maintaining a goal of one acquisition weekly. Our VP of Operations group consists of 10 professionals managing operations for more than 50 portfolio companies. The scope divides into three core areas: acquisitions (complete lifecycle from diligence through integration), serving as effective COO for business units (managing budgets, P&L, and vendor relationships), and advising central functions (Support, SaaS, Engineering) to align their efforts with financial results.
This high-stakes, high-visibility position ensures no two days are identical. You will shape decisions involving key stakeholders throughout the organization—from portfolio CEOs and functional leaders to deal-side collaborators. The ideal candidate does not seek consensus but instead develops conviction, presents supporting data, and drives stakeholders to action.
What you will be doing
- Coordinating M&A due diligence alongside leading investment banks and financial institutions, overseeing VDR structures, executing vendor consolidation initiatives, managing international payroll transitions, and controlling closing checklists
- Taking full ownership of quarterly P&L budgets for a multi-product business unit, pinpointing margin enhancement opportunities, and delivering cost reduction strategies to portfolio CEOs, CFOs, and senior Finance teams
- Using AI platforms (Claude Code, Cursor, and other best-in-class tools) on a daily basis to assess vendor expenditures, automate decision workflows, construct cost models, and independently generate executive-level reports
- Overseeing the complete vendor lifecycle for 70+ contracts, encompassing negotiation, legal assessment, procurement processes, invoice management, and termination
- Serving as the sole integration point for portfolio operations by coordinating with 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. Every deliverable includes a financial impact.
- Attending status update meetings or reporting KPI progress. You are accountable for the KPIs.
- Waiting for direction on your next task. You spot the issue, design the resolution, and implement it.
- Focusing on a single project at once. You will manage 3-5 parallel work streams spanning multiple 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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