Head of Operations, Trilogy (Remote) - $200,000/year USD

This position differs fundamentally from a conventional VP role. You will have no direct reports. Your calendar will not be filled with recurring meetings. You will not be preparing quarterly strategy presentations or managing steady-state business operations. Your work will span M&A due diligence and integrations for enterprise software businesses, ownership of P&L objectives for operating units, development of AI-driven automations with cutting-edge tools, vendor contract negotiations, and direct presentations to portfolio CEOs, CFOs, and department leaders. You will execute all of these responsibilities independently and simultaneously across multiple organizations. Trilogy purchases distressed enterprise software businesses and executes turnarounds, targeting one acquisition weekly. The VP of Operations group consists of 10 professionals managing operations for more than 50 portfolio companies. The responsibilities are divided into three categories: acquisitions (comprehensive execution from diligence through integration), serving as effective COO for business units (budget management, P&L oversight, vendor relationships), and providing consulting support to central functions (Support, SaaS, Engineering) to align their activities with business results. This is a high-impact, high-exposure position with substantial daily variation. You will shape decisions involving critical stakeholders throughout the organization, including portfolio CEOs, functional leaders, and transaction partners. The ideal candidate does not seek consensus before acting; they develop conviction, marshal evidence, and drive stakeholders to decision. What You Will Be Doing

• Leading M&A due diligence efforts with prominent investment banks and financial institutions, structuring VDR environments, executing vendor consolidation initiatives, managing cross-border payroll transitions, and maintaining responsibility for closing checklists
• Taking ownership of quarterly P&L budgets for multi-product business units, uncovering margin enhancement opportunities, and delivering cost optimization proposals to portfolio CEOs, CFOs, and Finance leadership
• Applying AI technologies (Claude Code, Cursor, and other optimal tools) on a daily basis to evaluate vendor expenditures, automate decision processes, construct cost models, and generate executive-level reports without assistance
• Overseeing complete vendor lifecycle management across more than 70 contracts, encompassing negotiation, legal assessment, procurement execution, invoice management, and termination
• Serving as the sole integration point for portfolio operations by coordinating across more than 6 central functions (Finance, Legal, Engineering, SaaS, HR, IT) and transaction partners (banks, legal advisors, target executive teams)

What You Won’t Be Doing

• Leading a team or assigning responsibilities to subordinates. You execute the work directly.
• Creating strategy presentations or abstract frameworks. All deliverables have financial impact.
• Attending status update meetings or delivering KPI reports. You are accountable for the KPIs.
• Waiting for direction on your next task. You diagnose the issue, design the solution, and deliver results.
• Focusing on a single project. You will manage 3-5 parallel workstreams across separate companies.

Basic Requirements Head of Operations 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-US-Atlanta-HeadofOperatio.020