This VP role does not follow convention. You will have no direct reports. No calendar cluttered with recurring meetings. No quarterly decks to assemble. No stable operations to maintain.
Your work will include running M&A diligence and integration for enterprise software companies, managing P&L goals for business units, creating AI automations with the most capable tools available, negotiating contracts with vendors, and delivering presentations to portfolio CEOs, CFOs, and functional leaders. You will execute all of this independently, in parallel, across multiple organizations.
Trilogy purchases distressed enterprise software businesses and executes turnarounds, aiming to close one acquisition each week. The 10-person VP of Operations team operates across more than 50 portfolio companies. The scope includes three primary areas: acquisitions (from diligence through integration), serving as acting COO for business units (handling budgets, P&L, and vendors), and consulting for central functions (Support, SaaS, Engineering) to align their efforts with business results.
This role demands high performance under scrutiny, with constant variety in daily responsibilities. You will shape decisions made by key stakeholders throughout the organization, including portfolio CEOs, functional leaders, and deal-side collaborators. Success requires building conviction without waiting for approval, presenting evidence clearly, and driving action.
What You Will Be Doing
Leading M&A due diligence in partnership with leading investment banks and financial institutions, overseeing VDR organization, executing vendor consolidation, managing international payroll transitions, and controlling closing checklists Managing quarterly P&L budgets for a multi-product business unit, pinpointing opportunities for margin expansion, and delivering cost reduction strategies to portfolio CEOs, CFOs, and senior Finance teams Applying AI tools (Claude Code, Cursor, and the most effective options available) on a daily basis to review vendor spend, automate decision workflows, develop cost models, and generate executive-ready reports without assistance Overseeing the complete vendor lifecycle across more than 70 contracts, covering negotiation, legal review, procurement, invoice management, and termination Serving as the single integration point for portfolio operations, coordinating across more than 6 central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side partners (banks, legal counsel, target C-Suite)
What You Won’t Be Doing
Leading a team or assigning tasks to direct reports. You execute the work. Creating strategy presentations or conceptual frameworks. Every deliverable is tied to a financial impact. Attending status meetings or updating KPI dashboards. You are accountable for the KPIs. Waiting for direction on your next task. You spot the issue, create the solution, and deliver it. Focusing on a single project at a time. You will manage 3-5 simultaneous work streams spanning different companies.
Basic Requirements
AI Operations Specialist key responsibilities
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
About Trilogy
Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today's modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.
There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!
Working with us
This 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-KE-COUNTRY-AIOperationsSp.001
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