This position does not resemble a traditional VP role. You will not manage a team. Your calendar will not be consumed by recurring meetings. You will not produce quarterly strategy presentations. There is no stable operational baseline to maintain.
Instead, you will lead M&A diligence and integration processes for enterprise software acquisitions, take ownership of P&L objectives for business units, develop AI-driven automations leveraging cutting-edge platforms, negotiate agreements with vendors, and deliver findings directly to portfolio CEOs, CFOs, and functional leaders. All of this work is performed independently and simultaneously across several companies.
Trilogy purchases underperforming enterprise software businesses and executes turnarounds, targeting one acquisition weekly. A 10-person VP of Operations team manages operations for more than 50 portfolio companies. The scope of work includes three core areas: acquisitions (from diligence through integration), serving as de facto COO for business units (managing budgets, P&L, and vendor relationships), and consulting with central functions (Support, SaaS, Engineering) to align their efforts with business results.
This is a high-impact, high-exposure role characterized by constant variability. You will shape decisions made by key stakeholders throughout the organization, including portfolio CEOs, functional leaders, and deal 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 alongside premier investment banks and financial institutions, structuring VDRs, executing vendor consolidation, overseeing international payroll transitions, and managing closing checklists end-to-end Taking full ownership of quarterly P&L budgets for multi-product business units, pinpointing margin enhancement opportunities, and delivering cost reduction strategies to portfolio CEOs, CFOs, and senior Finance teams Using AI platforms (Claude Code, Cursor, and whichever tools best suit the task) on a daily basis to evaluate vendor expenditures, automate decision workflows, construct cost models, and generate executive-ready analysis without assistance Overseeing the complete vendor lifecycle across more than 70 contracts, encompassing negotiation, legal coordination, procurement, invoice management, and termination Serving as the sole integration point for portfolio operations, coordinating across more than 6 central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side partners (banks, legal advisors, target company executives)
What You Won’t Be Doing
Leading a team or assigning tasks to direct reports. You execute the work personally. Developing strategy presentations or abstract frameworks. All deliverables are tied to financial outcomes. Attending status update meetings or tracking KPIs for others. You are accountable for the KPIs. Waiting for direction on your next priority. You define the problem, design the solution, and implement it. Focusing on a single initiative. You will manage 3-5 simultaneous workstreams spanning multiple companies.
Basic Requirements
Director of Operational Excellence 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-DirectorofOper.002
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