Description
This role does not resemble a traditional VP position. You will not oversee a team, attend recurring standing meetings, produce quarterly strategy presentations, or manage steady-state operations.
Your responsibilities will include leading M&A due diligence and integration efforts for enterprise software firms, managing P&L objectives for business units, developing AI-driven automations with cutting-edge technology, negotiating contracts with vendors, and delivering presentations to portfolio CEOs, CFOs, and functional leadership. You will execute these tasks independently and simultaneously across a portfolio of companies.
Trilogy specializes in acquiring and revitalizing distressed enterprise software businesses, targeting approximately one acquisition each week. The VP of Operations team consists of 10 professionals overseeing more than 50 portfolio companies. The scope of work encompasses three core areas: complete acquisition lifecycle management (from due diligence through integration), serving as acting COO for business units (handling budgets, P&L oversight, and vendor relationships), and providing consulting support to central functions (Support, SaaS, Engineering) to align their activities with measurable business results.
This position offers high stakes and high visibility, with each day bringing distinct challenges. You will shape decisions among key stakeholders throughout the organization—portfolio CEOs, functional leaders, and deal-side collaborators. Success in this role demands someone who does not seek consensus passively; instead, they develop strong conviction, marshal supporting evidence, and mobilize others toward action.
What you will be doing
- Leading M&A due diligence coordination with top-tier investment banks and financial institutions, overseeing VDR organization, executing vendor consolidation initiatives, managing international payroll transitions, and maintaining accountability for closing task lists
- Managing quarterly P&L budgets for multi-product business units, pinpointing opportunities for margin enhancement, and delivering cost optimization proposals to portfolio CEOs, CFOs, and senior Finance executives
- Utilizing AI platforms (Claude Code, Cursor, and other optimal tools) on a daily basis to evaluate vendor expenditures, automate decision workflows, construct cost projection models, and generate executive-level reports without assistance
- Overseeing complete vendor management across 70+ contracts, encompassing negotiation, legal assessment, procurement processes, invoice management, and termination procedures
- Serving as the sole integration point for portfolio operations by coordinating among 6+ central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side stakeholders (banks, legal advisors, target company C-Suite)
What you will NOT be doing
- Leading a team or assigning tasks to direct reports. You execute the work personally.
- Creating strategy presentations or abstract frameworks. All deliverables tie directly to financial impact.
- Participating in status update meetings or providing KPI reports. You have ownership of the KPIs.
- Awaiting direction on next steps. You pinpoint issues, design solutions, and deliver results.
- Focusing on a single initiative. You will juggle 3-5 simultaneous workstreams 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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