Head of Operations, Trilogy (Remote) - $200,000/year USD
Crossover · United States
- Hybrid
- Full-time
- $200,000 / year
- United States
Job highlights
- Lead M&A due diligence and integration for software firms.
- Own P&L goals and drive cost optimization strategies.
- Develop AI-driven automations for business processes.
- Manage vendor contracts and relationships for portfolio companies.
- Engage directly with C-suite executives across multiple businesses.
About the role
About The Role
This role does not resemble a traditional VP position. You will not oversee a reporting team, attend recurring status meetings, create quarterly strategy presentations, or maintain business-as-usual operations. Your responsibilities will span M&A due diligence and integration for enterprise software firms, ownership of P&L goals for business units, development of AI-driven automations leveraging cutting-edge tools, vendor contract negotiations, and direct engagement with portfolio CEOs, CFOs, and department heads. You will execute all of these responsibilities independently and simultaneously across several companies.Trilogy purchases distressed enterprise software businesses and executes turnarounds, targeting an acquisition rate of one per week. A team of 10 VPs of Operations manages operational activities across more than 50 portfolio companies. The scope of work encompasses three primary areas: acquisitions (comprehensive, from diligence through integration), serving as acting COO for business units (managing budgets, P&L, and vendor relationships), and providing consultative support to central functions (Support, SaaS, Engineering) to align their efforts with business results.
This position operates at high stakes and high visibility, with work that changes daily. You will shape decisions among key stakeholders throughout the organization, including portfolio CEOs, functional leaders, and deal-side collaborators. Success in this role requires the ability to form strong convictions independently, present supporting evidence clearly, and drive stakeholders to take action.
What You Will Be Doing
- Leading M&A due diligence coordination with top-tier investment banks and financial institutions, overseeing VDR organization, executing vendor consolidation initiatives, managing international payroll transitions, and maintaining responsibility for closing checklists
- Taking ownership of quarterly P&L budgets for multi-product business units, pinpointing opportunities for margin enhancement, and delivering cost optimization strategies to portfolio CEOs, CFOs, and senior Finance executives
- Applying AI tools (Claude Code, Cursor, and the most effective available solutions) on a daily basis to evaluate vendor expenditures, automate decision processes, construct cost models, and generate executive-level reports without assistance
- Overseeing the complete vendor management lifecycle spanning 70+ contracts, encompassing negotiation, legal assessment, procurement, invoice management, and termination
- Serving as the central integration point for portfolio operations by coordinating among 6+ central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side stakeholders (banks, legal advisors, target company C-Suite)
What You Won’t Be Doing
- Leading a team or assigning tasks to direct reports. You execute the work directly.
- Developing strategy presentations or conceptual frameworks. All deliverables are tied to financial impact.
- Participating in status update meetings or providing KPI reports. You have direct ownership of the KPIs.
- Waiting for direction on next steps. You pinpoint issues, develop solutions, and deliver them.
- Focusing on a single project. You will manage 3-5 parallel work streams across multiple companies.
Basic Requirements
- 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-COUNTRY-HeadofOperatio.020
Key skills/competency
- Operations Management
- M&A Due Diligence
- P&L Management
- AI Automation
- Vendor Contract Negotiation
- Business Unit Strategy
- Cost Optimization
- Executive Reporting
- Python Programming
- LLM API Integration
Skills & topics
- Head of Operations
- Operations Management
- M&A
- Due Diligence
- Integration
- P&L Management
- AI Automation
- LLM
- Python
- Vendor Management
- C-suite
- Remote
How to get hired
- Tailor your resume: Highlight 5+ years in operational leadership, C-suite presentation experience, and Python/LLM automation skills.
- Showcase automation expertise: Detail your experience with tools like Cursor, Windsurf, or MCP and LLM API integration.
- Emphasize remote work capability: Confirm your ability to work remotely with CST time zone overlap.
- Understand Trilogy's model: Research their M&A strategy and focus on distressed enterprise software turnarounds.
- Prepare for direct execution: Be ready to demonstrate how you execute tasks independently rather than manage teams.
Technical preparation
Practice Python scripting for automation tasks.,Integrate LLM APIs like Claude or GPT.,Simulate vendor expenditure evaluation processes.,Develop mock cost models and executive reports.
Behavioral questions
Demonstrate independent problem-solving.,Showcase clear evidence-based decision making.,Provide examples of driving stakeholder action.,Describe managing multiple parallel workstreams.
Frequently asked questions
- What is the primary focus of the Head of Operations role at Trilogy?
- The Head of Operations at Trilogy focuses on M&A due diligence and integration, P&L ownership for business units, developing AI-driven automations, and vendor contract negotiations. This role requires independent execution across multiple distressed enterprise software companies.
- What is Trilogy's business model?
- Trilogy acquires distressed enterprise software businesses with the goal of executing turnarounds, targeting an acquisition rate of one per week. They manage operational activities across over 50 portfolio companies through a team of VPs of Operations.
- What kind of team will I be managing in this Head of Operations role?
- This Head of Operations role does not involve managing a team. You will be directly executing responsibilities yourself, rather than overseeing direct reports or assigning tasks.
- What are the key technical skills required for the Head of Operations position?
- Key technical skills include 5+ years of operational leadership, experience presenting to C-suite executives, writing automation in Python and integrating with LLM APIs, and experience with tools like Cursor, Windsurf, or MCP for production-grade automations.
- Is this a remote position and what are the time zone requirements?
- Yes, this is a remote position. Candidates must have the capability to work remotely and maintain at least 6 hours of overlap with the CST time zone.
- What is the compensation for the Head of Operations role?
- The compensation for this role is $100 USD per hour, equating to $200,000 USD per year, assuming a 40-hour work week and 50 weeks per year. Payments are made weekly.
- What is the employment type for this Head of Operations position?
- This is a full-time, long-term position. It requires entering into an independent contractor agreement with Crossover as a Contractor of Record.
- How does Trilogy approach strategic decision-making in this role?
- Decision-making in this role is independent and evidence-based. You will need to form strong convictions, present supporting evidence clearly, and drive stakeholders to take action, rather than relying on traditional strategy presentations or status meetings.