Head of Operations
$200,000 USD/year ($100 USD/hour)

Head of Operations $200,000 USD/year ($100 USD/hour)

Fully-remote

Description

This is not a normal VP role. There is no team reporting to you. No standing meetings to fill your calendar. No quarterly strategy decks. No steady-state operations to coast on.

In this role, you will run M&A diligence and integrations for enterprise software companies, own P&L targets for business units, build AI automations using the latest tools at your disposal, negotiate vendor contracts, and present directly to portfolio CEOs, CFOs, and functional leads. You will do all of this yourself, concurrently, across multiple companies.

Trilogy acquires distressed enterprise software companies and turns them around, with a target pace of one acquisition per week. The VP of Operations team is 10 people running operations across 50+ portfolio companies. The work falls into three buckets: acquisitions (end-to-end, from diligence to integration), acting as de facto COO for business units (budgets, P&L, vendors), and consulting for central functions (Support, SaaS, Engineering) to connect their work to business outcomes.

This is a high-stakes, high-visibility role where no two days look the same. You will influence decisions from key stakeholders across the organization, from portfolio CEOs to functional leads to deal-side partners. The person who thrives here does not wait for consensus; they build conviction, present the evidence, and move people to act.

What you will be doing

Coordinating M&A due diligence with leading investment banks and financial institutions, managing VDR structures, driving vendor consolidation, handling international payroll transitions, and owning closing checklists
Owning quarterly P&L budgets for a multi-product business unit, identifying margin improvement levers, and presenting cost reduction plans to portfolio CEOs, CFOs, and senior Finance leadership
Leveraging AI tools (Claude Code, Cursor, and whatever else is best for the job) daily to analyze vendor spend, automate decision-making workflows, build cost models, and produce executive-ready reports independently
Managing the full vendor lifecycle across 70+ contracts, including negotiation, legal review, procurement, invoice processing, termination
Coordinating across 6+ central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side partners (banks, legal counsel, target C-Suite) as the single point of integration for portfolio operations

What you will NOT be doing

Managing a team or delegating work to direct reports. You do the work.
Building strategy decks or theoretical frameworks. Every output has a dollar amount attached.
Sitting in status meetings or reporting on KPIs. You own the KPIs.
Waiting for someone to tell you what to do next. You identify the problem, build the solution, and ship it.
Working on one thing at a time. You will have 3-5 concurrent 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

How it works

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