Operations AI Innovator
$200,000 USD/year ^{Pay is set based on global value, not the local market.

Most roles = hourly rate x 40 hrs x 50 weeks}($100 USD/hour)

Not accepting applications on crossover.com at this time.

Description

This is not a conventional VP position. You will not oversee a team. Your calendar will not be filled with recurring meetings. There will be no quarterly strategy presentations. No established operations to maintain on autopilot.

You will execute M&A diligence and integration processes for enterprise software businesses, manage P&L objectives for business units, develop AI-driven automations with cutting-edge tools, negotiate agreements with vendors, and deliver presentations directly to portfolio CEOs, CFOs, and functional leaders. All of this will be executed by you personally, simultaneously, spanning multiple organizations.

Trilogy purchases distressed enterprise software businesses and executes turnarounds, targeting an acquisition rate of one per week. The VP of Operations group consists of 10 individuals managing operations across a portfolio exceeding 50 companies. The scope of work encompasses three areas: acquisitions (comprehensive, from diligence through integration), serving as de facto COO for business units (overseeing budgets, P&L, and vendors), and advising central functions (Support, SaaS, Engineering) to align their activities with business outcomes.

This is a high-stakes, high-visibility position where every day presents different challenges. You will shape decisions from key stakeholders throughout the organization, including portfolio CEOs, functional leaders, and deal-side partners. The individual who succeeds here does not seek consensus; they develop conviction, deliver evidence, and drive action.

What you will be doing

Orchestrating M&A due diligence alongside leading investment banks and financial institutions, structuring VDR environments, executing vendor consolidation, managing international payroll transitions, and controlling closing checklists
Managing quarterly P&L budgets for multi-product business units, pinpointing margin enhancement opportunities, and delivering cost optimization proposals to portfolio CEOs, CFOs, and senior Finance leadership
Utilizing AI tools (Claude Code, Cursor, and the most effective available solutions) on a daily basis to examine vendor expenditure, automate decision workflows, construct cost models, and generate executive-ready reports without assistance
Overseeing the complete vendor lifecycle spanning 70+ contracts, encompassing negotiation, legal assessment, procurement, invoice management, and termination
Aligning efforts across 6+ central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side partners (banks, legal advisors, target C-Suite) as the sole integration point for portfolio operations

What you will NOT be doing

Leading a team or assigning tasks to direct reports. You execute the work yourself.
Creating strategy presentations or abstract frameworks. Every deliverable is tied to a financial impact.
Attending status update meetings or providing KPI reports. You are accountable for the KPIs.
Waiting for direction on your next action. You diagnose the issue, create the solution, and deliver it.
Focusing on a single project sequentially. You will juggle 3-5 simultaneous work streams across separate 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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