Operations AI Lead, Trilogy (Remote) - $200,000/year USD

This role does not follow a traditional VP operating model. You will have no direct reports. No recurring calendar meetings. No quarterly strategy presentations. No legacy operations to maintain. Your scope includes running M&A diligence and integration for enterprise software acquisitions, managing P&L accountability for business units, deploying AI‑driven automations with cutting‑edge tooling, negotiating contracts with vendors, and delivering presentations to portfolio CEOs, CFOs, and department heads. You execute this work independently, managing multiple concurrent initiatives across a portfolio of companies.Trilogy specializes in acquiring and transforming distressed enterprise software businesses, aiming for roughly one acquisition per week. A team of 10 VPs of Operations oversees execution across 50+ portfolio companies. The role spans three core areas: acquisitions (from diligence through integration), functional COO responsibilities for business units (including budgeting, P&L management, and vendor oversight), and advisory support for central departments (Support, SaaS, Engineering) to align operational efforts with financial performance.This is a high‑impact, high‑exposure position with significant day‑to‑day variation. You will shape decisions made by senior stakeholders—portfolio CEOs, functional leadership, and transaction partners. Success in this role requires independent judgment, the ability to marshal evidence, and the confidence to drive action without waiting for group alignment.What You Will Be DoingLeading M&A due diligence efforts alongside major investment banks and financial partners, structuring virtual data rooms, executing vendor consolidation, overseeing cross‑border payroll transitions, and managing transaction close procedures.Holding full accountability for quarterly P&L budgets within a multi‑product business unit, surfacing opportunities for margin expansion, and delivering cost optimization proposals to portfolio CEOs, CFOs, and Finance leadership.Using AI tooling (including Claude Code, Cursor, and other appropriate platforms) on a daily basis to assess vendor expenditures, automate operational decision logic, construct financial models, and generate executive‑facing deliverables with minimal support.Overseeing the end‑to‑end vendor management process for a portfolio exceeding 70 contracts, encompassing negotiation, legal coordination, procurement workflows, invoice reconciliation, and contract termination.Serving as the central integration point for portfolio operations, coordinating with 6+ internal functions (Finance, Legal, Engineering, SaaS, HR, IT) and external transaction parties (investment banks, legal advisors, target executive teams).What You Won't Be DoingLeading a team or assigning tasks to subordinates. You execute directly.Creating strategic slide decks or conceptual models. All deliverables are financially grounded.Attending status update meetings or producing KPI summaries. You are accountable for the metrics.Waiting for direction on next steps. You surface the issue, design the fix, and deliver.Focusing on a single priority. You will manage 3-5 parallel initiatives spanning multiple portfolio companies.Basic Requirements5+ years of operational leadership in business operations.Experience making presentations to C‑suite executives.Experience writing automation in Python and integrating 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.Working with UsThis is a full‑time (40 hours per week), long‑term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly. Consult www.crossover.com/help-and-faqs for more details on this topic.Crossover Job Code: LJ-5145-GB-COUNTRY-OperationsAILe#J-18808-Ljbffr Remote Skills: Application Programming Interface (API), Artificial Intelligence (AI), Automation, Budgeting, Business Operations, Consulting, Contract Negotiation, Cost Control, Due Diligence, Enterprise Applications, Expense Analysis, Finance, Financial Modeling, Head of Finance, Investment Services, Leadership, Legal, MCP - Microsoft Certified Professional, Machine Tool, Mergers and Acquisitions, Metrics, Operational Expenditure (OPEX), Payroll Management, Performance Metrics, Presentation/Verbal Skills, Profit & Loss, Profit & Loss Management, Purchasing/Procurement, Python Programming/Scripting Language, Reconciliation, Software as a Service (SaaS), Strategic Planning, Transaction Processing/Management, Vendor/Supplier Evaluation, Vendor/Supplier Management, Work From Home About the Company: Crossover for Work Apply To This Job