Description
Operational Transformation Engineer: For Those Who Build Systems, Not Teams
At Trilogy, we don't just acquire software companies—we transform them with ruthless efficiency. While others scale with headcount, we scale with systems. We need elite operators who can rebuild entire operational frameworks using code, automation, and AI—not management layers.
This role puts you at the helm of high-stakes transformations across our 100+ product portfolio. You'll replace legacy systems with AI-powered workflows, eliminate thousands of manual hours through automation, and execute complex transitions that others would staff entire departments to handle.
We operate with fewer layers, faster cycles, and higher expectations than traditional enterprises. This is your opportunity to drive massive impact without bureaucratic friction. If you're the rare technical leader who uses automation as leverage and speed as strategy—Trilogy is where you belong.
What you will be doing
- Executing complex M&A integrations, enterprise system migrations, and organizational transitions with minimal oversight
- Engineering automation solutions in Python that replace entire CRM and task management systems
- Deploying sophisticated AI workflows via Cursor, Windsurf, and MCP that eliminate manual processes
- Driving initiatives from initial diagnosis to full deployment using proven playbooks and executive judgment
- Demonstrating technical prowess through hands-on challenges that validate your ability to architect AI-first solutions
What you will NOT be doing
- Building and managing large teams to accomplish what code and automation can do
- Navigating consensus-driven decision processes or sitting through alignment meetings
- Outsourcing technical implementation to IT teams or external vendors
- Maintaining steady-state operations or incremental improvements to existing systems
Key responsibilities
Design and implement AI-powered operational systems that eliminate manual effort, compress complexity, and enable scalable execution across Trilogy's global software portfolio.
Candidate requirements
- Based in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years of operational leadership in enterprise software environments
- 3+ years in customer-facing roles (Support, Sales, Collections, etc.)
- Demonstrated proficiency in Python automation development and LLM API integration
- Experience with Cursor, Windsurf, MCP, or equivalent tools for production-grade automation deployment
- Proven track record of independent execution and delivering high-stakes results without supervision
Nice to have
- Experience leading large-scale organizational transitions including M&A integrations or mass offboarding
- History of designing and implementing AI-driven operational systems at scale
- Portfolio of self-developed automations successfully deployed in enterprise environments
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.
Pass Cognitive Aptitude Test.
Pass English Proficiency Test.
Prove Real-World Job & AI Skills.
Ace An Interview Or Two.
Accept Job Offer.
Frequently asked questions
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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.
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