Operations AI Lead, Trilogy (Remote) - $200,000/year USD
CrossoverPosted 19 hours ago
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This role breaks the traditional VP mold. You will not inherit a reporting team, attend recurring status syncs, or prepare quarterly strategy presentations. There is no existing operation to manage at steady state. Instead, you will lead M&A diligence and integration efforts for enterprise software acquisitions, take ownership of P&L goals for distinct business units, deploy AI-powered automations using cutting-edge tooling, negotiate agreements with vendors, and deliver findings directly to portfolio CEOs, CFOs, and functional leadership. All of this work is yours to execute—simultaneously, across multiple portfolio entities. Trilogy specializes in acquiring and revitalizing distressed enterprise software businesses, targeting a cadence of one deal every week. Our 10-person VP of Operations group oversees operational execution for more than 50 portfolio companies. The scope divides into three core areas: full-cycle acquisitions (from due diligence through integration), serving as effective COO for business units (managing budgets, P&L, vendor ecosystems), and advising central functions (Support, SaaS, Engineering) to align their initiatives with measurable business impact. This is a high-exposure, high-consequence position where daily priorities shift constantly. You will shape decisions made by key stakeholders throughout the organization—portfolio CEOs, functional heads, and deal execution partners. Success here demands initiative: you develop your own conviction, marshal the data, and drive stakeholders to action without waiting for alignment. What You Will Be Doing Orchestrating M&A due diligence alongside top-tier investment banks and financial institutions, structuring virtual data rooms, executing vendor consolidation initiatives, managing cross-border payroll transitions, and maintaining comprehensive closing checklists Taking full accountability for quarterly P&L planning across a multi-product business unit, surfacing margin enhancement opportunities, and delivering cost optimization proposals to portfolio CEOs, CFOs, and senior Finance teams Using AI platforms (Claude Code, Cursor, or any superior alternative) on a daily basis to evaluate vendor expenditures, automate decisioning processes, construct cost forecasting models, and generate executive-grade deliverables autonomously Overseeing the complete vendor management cycle for 70+ agreements, encompassing negotiation, legal compliance review, procurement execution, invoice reconciliation, and contract termination Acting as the unified integration point for portfolio operations by coordinating across 6+ central functions (Finance, Legal, Engineering, SaaS, HR, IT) and external deal partners (banking advisors, legal firms, target company executives) What You Won’t Be Doing Leading a team or distributing tasks to subordinates. You execute the work yourself. Producing strategic slide decks or conceptual models. Every deliverable ties directly to financial impact. Attending routine status check-ins or presenting KPI summaries. You are accountable for the KPIs themselves. Awaiting instructions on your next priority. You surface the issue, design the fix, and deploy it. Focusing on a single initiative. You will juggle 3-5 parallel workstreams spanning different portfolio entities. Basic Requirements Operations AI Lead 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-NG-Lagos-OperationsAILe.004