Description
This position is built for operators capable of engineering and reengineering systems at scale.
Operational excellence at Trilogy isn't optional—it's the foundation of our competitive edge. We acquire software businesses rapidly and scale them with even greater velocity. Sustaining that momentum requires executives who can architect lean, automated infrastructure—not add layers of management to absorb complexity.
You'll take ownership of complete operational transformations spanning our global portfolio. This might include redesigning the offboarding process for over 1,200 employees following an acquisition, substituting Jira and Salesforce with AI-driven agents, or deploying automation that removes thousands of hours of manual effort. Execution happens quickly through Python, LLM APIs, and tools such as Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks that keep you focused on measurable results.
Trilogy manages a portfolio of more than 100 products with operational discipline. We function with reduced hierarchy, compressed timelines, and elevated performance standards compared to conventional enterprise settings. This represents an opportunity to create large-scale impact without navigating bureaucracy or overseeing inflated teams.
Steady-state operations aren't part of our model. We don't delegate transformation externally. And we don't bring on people who require approval chains or extensive teams to produce results. We're seeking a select group of highly technical, execution-focused leaders who treat automation as a force multiplier and speed as a core strategy. If that describes you—this environment will suit you well.
What you will be doing
- Driving high-stakes operational initiatives including M&A integration, enterprise platform migration, and organization-wide transitions
- Building and launching automation solutions that supplant CRM and task tracking systems through Python and LLM APIs
- Implementing AI-enabled workflows using Cursor, Windsurf, and MCP to remove manual processes and shorten response times
- Owning projects end-to-end—from problem identification through final deployment—guided by established playbooks and executive-level decision-making
What you will NOT be doing
- Building or managing large teams, or depending on organizational depth to accomplish goals
- Participating in protracted coordination meetings or waiting for consensus before taking action
- Handing off technical challenges to IT departments or third-party vendors—you will design and implement solutions directly
- Running steady-state operations—this role centers entirely on transformation and rapid execution
Key responsibilities
Architect and implement AI-centric operational frameworks that remove manual intervention, simplify complex processes, and enable scalable execution across Trilogy's worldwide software portfolio.
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.