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

This is not a conventional VP position. You will not inherit a team. Your calendar will not be dominated by recurring status calls. You will not be building quarterly strategy presentations or maintaining business-as-usual operations. Instead, you will execute M&A diligence and integration work for enterprise software acquisitions, take ownership of P&L accountability for business units, design AI-driven automations leveraging cutting-edge tools, lead vendor contract negotiations, and deliver presentations to portfolio-level CEOs, CFOs, and department heads. You will manage all of this independently, in parallel, spanning multiple companies. Trilogy focuses on acquiring and transforming distressed enterprise software businesses, targeting a cadence of one acquisition weekly. The 10-person VP of Operations group manages operations across a portfolio of over 50 companies. The scope includes three core areas: full-cycle acquisitions (diligence through integration), serving as operational COO for business units (managing budgets, P&L, and vendor relationships), and advising centralized functions (Support, SaaS, Engineering) to align their initiatives with measurable business results. This is a high-impact, high-exposure position where every day presents different challenges. You will shape decisions with senior stakeholders throughout the organization—from portfolio company CEOs to functional department leaders to deal execution partners. Success in this role requires building conviction independently, assembling supporting evidence, and driving stakeholders to action without waiting for alignment. What You Will Be Doing

• Leading M&A due diligence coordination with premier investment banks and financial institutions, structuring virtual data rooms, executing vendor consolidation initiatives, managing cross-border payroll transitions, and delivering closing task completion
• Taking full accountability for quarterly P&L budget planning for multi-product business units, surfacing margin expansion opportunities, and delivering cost optimization proposals to portfolio CEOs, CFOs, and Finance leadership
• Applying AI toolsets (Claude Code, Cursor, and the most effective available platforms) on a daily basis to evaluate vendor expenditure, build automated decision workflows, construct financial models, and generate board-level reports without assistance
• Overseeing end-to-end vendor management spanning 70+ contracts, covering negotiation, legal coordination, procurement execution, invoice administration, and contract termination
• Serving as the central integration point for portfolio operations, orchestrating collaboration among 6+ internal functions (Finance, Legal, Engineering, SaaS, HR, IT) and external deal partners (banks, legal advisors, target company executives)

What You Won’t Be Doing

• Leading a team or distributing tasks to subordinates. You execute the work directly.
• Developing strategy presentations or conceptual models. Every deliverable is tied to financial impact.
• Attending recurring status updates or reporting on performance indicators. You are accountable for the performance indicators.
• Waiting for direction on your next priority. You surface the issue, design the resolution, and implement it.
• Focusing on a single project at once. You will juggle 3-5 simultaneous initiatives 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.021