Description
This is not a conventional VP position. You will not manage a team. You will not attend recurring status meetings or fill your week with strategy sessions. You will not oversee steady operations that run themselves.
Instead, you will lead M&A diligence and integration efforts for enterprise software companies, take ownership of P&L targets for business units, develop AI-driven automations using cutting-edge tools, negotiate contracts with vendors, and deliver presentations to portfolio CEOs, CFOs, and functional leaders. You will handle all of this independently, in parallel, spanning multiple companies.
Trilogy purchases distressed enterprise software businesses and executes turnarounds, aiming to complete one acquisition each week. The 10-person VP of Operations team manages operations for more than 50 portfolio companies. The work is divided into three areas: acquisitions (from due diligence through integration), serving as the de facto COO for business units (managing budgets, P&L, and vendor relationships), and providing consulting services to central functions (Support, SaaS, Engineering) to align their activities with business outcomes.
This is a high-impact, high-exposure role with constant variation. You will shape decisions involving key stakeholders throughout the organization—from portfolio CEOs and functional leaders to deal-side partners. The person who excels in this role does not seek consensus first; they form conviction, present the case, and drive action.
What you will be doing
- Leading M&A due diligence alongside leading investment banks and financial institutions, overseeing VDR organization, executing vendor consolidation, managing international payroll transitions, and maintaining closing checklists
- Holding accountability for quarterly P&L budgets within a multi-product business unit, surfacing margin improvement opportunities, and delivering cost reduction proposals to portfolio CEOs, CFOs, and senior Finance leadership
- Using AI tools (Claude Code, Cursor, and the best available technology for each task) every day to assess vendor expenditures, automate decision workflows, develop cost models, and generate executive-ready reports without assistance
- Overseeing the complete vendor lifecycle for more than 70 contracts, covering negotiation, legal review, procurement, invoice handling, and termination
- Serving as the single integration point for portfolio operations by coordinating across more than 6 central functions (Finance, Legal, Engineering, SaaS, HR, IT) and deal-side partners (banks, legal counsel, target C-Suite)
What you will NOT be doing
- Leading a team or assigning tasks to direct reports. You execute the work yourself.
- Creating strategy presentations or abstract frameworks. Every deliverable is tied to a specific dollar figure.
- Attending status meetings or reporting on KPIs. You are accountable for the KPIs.
- Waiting for direction on your next task. You identify problems, design solutions, and deliver them.
- Focusing on one project at a time. You will manage 3-5 parallel work streams across different companies.
Candidate 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
You will be working for
Quick links
Applying for a role? Here’s what to expect.
Crossover's skill assessment process combines innovative AI power with decades of human research, to take the guesswork, human bias, and pointless filters out of recruiting high-performing teams.
Chat-style
screening interview.
Cognitive 
aptitude test.
Prove real-world 
job skills.
Interview with the hiring manager.
Pass
proctored test.
Accept job offer.
Frequently asked questions
About the role
Recruitment sucks. So we’re fixing it.
The Olympics of work
It’s super hard to qualify—extreme quality standards ensure every single team member is at the top of their game.
Premium pay for premium talent
Over 50% of new hires double or triple their previous pay. Why? Because that’s what the best person in the world is worth.
Shortlist by skills, not bias
We don’t care where you went to school, what color your hair is, or whether we can pronounce your name. Just prove you’ve got the skills.
Join the world's largest community of 
AI-first remote workers.