AI Operations Specialist
$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 role does not follow the traditional VP structure. You will not manage a team, attend recurring status meetings, or create quarterly strategy presentations. There is no established operation to maintain.

Your scope includes running M&A diligence and integrations for enterprise software companies, managing P&L objectives for business units, developing AI automations with cutting-edge tools, negotiating vendor agreements, and delivering presentations to portfolio CEOs, CFOs, and department heads. You will execute all of this independently, simultaneously, across multiple organizations.

Trilogy purchases distressed enterprise software businesses and executes turnarounds, targeting one acquisition weekly. A 10-person VP of Operations team operates across 50+ portfolio companies. The responsibilities span three areas: acquisitions (complete process from diligence through integration), serving as de facto COO for business units (budgets, P&L, vendor management), and advising central functions (Support, SaaS, Engineering) to align their efforts with business results.

This high-stakes, high-visibility position offers no two identical days. You will shape decisions involving key stakeholders throughout the organization—portfolio CEOs, functional leaders, and deal-side partners. Success here requires building conviction independently, presenting evidence clearly, and driving stakeholders to action without waiting for consensus.

What you will be doing

Leading M&A due diligence alongside premier investment banks and financial institutions, structuring VDRs, executing vendor consolidation initiatives, 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 reduction strategies to portfolio CEOs, CFOs, and senior Finance executives
Applying AI tools (Claude Code, Cursor, and the most effective alternatives) every day to evaluate vendor expenditures, automate decision workflows, construct cost models, and generate executive-level reports without assistance
Overseeing the complete vendor lifecycle spanning 70+ contracts, encompassing negotiation, legal assessment, procurement, invoice management, and termination
Serving as the single integration point for portfolio operations by coordinating across 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 direct reports. You execute the work personally.
Developing strategy presentations or theoretical models. All deliverables tie directly to financial impact.
Attending status meetings or providing KPI updates. You are accountable for the KPIs.
Awaiting direction on next steps. You diagnose the issue, create the solution, and deliver it.
Focusing on a single initiative. You will manage 3-5 parallel work streams 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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