Description
This role operates outside the conventional VP structure. You will not oversee a reporting team, attend recurring status calls, develop quarterly strategy presentations, or manage established processes.
Your responsibilities span M&A due diligence and integration for enterprise software businesses, ownership of business unit P&L objectives, deployment of AI-driven automations with cutting-edge platforms, vendor contract negotiation, and direct engagement with portfolio CEOs, CFOs, and department heads. You execute these tasks independently and in parallel across several companies.
Trilogy purchases underperforming enterprise software firms and executes operational turnarounds, targeting approximately one transaction weekly. The VP of Operations function consists of 10 professionals managing operations for more than 50 portfolio entities. Activities are organized into three categories: transaction execution (from diligence through integration), operational leadership for business divisions (budget oversight, P&L management, vendor relations), and advisory support to centralized departments (Support, SaaS, Engineering) connecting their initiatives to financial performance.
This position demands agility and carries significant organizational visibility. Daily work varies substantially. You will shape decisions among critical stakeholders including portfolio CEOs, department leaders, and transaction advisors. Success requires independent conviction-building, evidence-based recommendations, and the ability to drive stakeholder action.
What you will be doing
- Orchestrating M&A diligence processes alongside premier investment banks and financial partners, structuring virtual data rooms, executing vendor consolidation initiatives, transitioning international payroll operations, and maintaining accountability for transaction close requirements
- Managing quarterly P&L budgeting for multi-product business divisions, pinpointing margin enhancement opportunities, and delivering cost optimization proposals to portfolio CEOs, CFOs, and Finance leadership
- Applying AI platforms (Claude Code, Cursor, and emerging tools as appropriate) on a daily basis to evaluate vendor expenditures, automate operational workflows, construct financial models, and generate executive reporting autonomously
- Overseeing complete vendor relationship cycles spanning 70+ agreements, encompassing negotiation, legal validation, procurement execution, invoice reconciliation, and contract termination
- Serving as the central integration liaison across 6+ core functions (Finance, Legal, Engineering, SaaS, HR, IT) and transaction counterparties (banking institutions, external counsel, target leadership) for portfolio operational activities
What you will NOT be doing
- Leading a team or assigning responsibilities to subordinates. You execute the work directly.
- Developing strategic presentations or conceptual models. All deliverables connect to financial impact.
- Attending routine meetings or providing KPI updates. You have direct ownership of the KPIs.
- Awaiting direction on priorities. You surface issues, design solutions, and implement them.
- Focusing on sequential tasks. You will manage 3-5 simultaneous initiatives across multiple portfolio entities.
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.