Operations AI Lead
$200,000 USD/year ($100 USD/hour)

Not accepting applications on crossover.com at this time.

Description

This position does not function like a traditional VP role. You will not oversee a team, manage direct reports, or attend recurring status meetings. There are no quarterly decks to prepare and no stable operations to maintain.

Your responsibilities will include leading M&A diligence and integrations for enterprise software businesses, managing P&L objectives for business units, developing AI-driven automations with cutting-edge tools, negotiating with vendors, and delivering presentations to portfolio CEOs, CFOs, and department heads. All of this work is performed independently and in parallel across multiple organizations.

Trilogy's model centers on acquiring distressed enterprise software companies and executing turnarounds, targeting one acquisition each week. A 10-person VP of Operations team supports operations for over 50 portfolio companies. The work divides into three core areas: end-to-end acquisitions (from diligence through integration), serving as de facto COO for business units (handling budgets, P&L, and vendor relationships), and consulting for central functions (Support, SaaS, Engineering) to align their activities with business results.

This role demands high performance under visibility and constant change. You will shape decisions involving key stakeholders throughout the organization—portfolio CEOs, functional leaders, and deal-side counterparts. Success here requires building conviction independently, assembling evidence, and driving stakeholders to action without waiting for consensus.

What you will be doing

Leading M&A due diligence efforts alongside leading investment banks and financial institutions, structuring VDRs, executing vendor consolidation, managing international payroll transitions, and controlling closing checklists
Taking ownership of quarterly P&L budgets for a multi-product business unit, surfacing margin improvement opportunities, and delivering cost reduction proposals to portfolio CEOs, CFOs, and senior Finance teams
Using AI tools (Claude Code, Cursor, and other best-in-class platforms) on a daily basis to evaluate vendor spend, automate decision processes, develop cost models, and generate executive-ready reports without assistance
Overseeing the complete vendor lifecycle for 70+ contracts, covering negotiation, legal review, procurement, invoice handling, 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. You execute the work directly.
Creating strategy presentations or theoretical models. Every deliverable is tied to financial impact.
Attending status update meetings or tracking KPIs for others. You are accountable for the KPIs.
Waiting for direction on your next task. You surface the issue, design the solution, and deliver it.
Focusing on a single project at a time. You will manage 3-5 parallel 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

How it works

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