Description
This position is for builders who design and scale operational systems from the ground up.
Trilogy's competitive edge is operational discipline. We purchase software businesses rapidly and expand them with even greater speed. Sustaining this requires leaders capable of architecting efficient, automated infrastructure—not adding layers of management to address complexity.
You will take ownership of complete transformation initiatives spanning our worldwide portfolio. This may involve redesigning offboarding workflows for 1,200+ employees following acquisition, substituting Jira and Salesforce with AI-powered agents, or creating automation that removes thousands of manual hours from operations. Execution will be swift, leveraging Python, LLM APIs, platforms such as Cursor, Windsurf, and MCP—plus a library of battle-tested frameworks that allow you to concentrate on delivering results.
Trilogy manages a portfolio of more than 100 products with uncompromising efficiency. We function with minimal hierarchy, accelerated decision cycles, and performance standards that exceed conventional enterprise norms. This opportunity enables you to generate meaningful impact at scale without navigating red tape or overseeing inflated teams.
We do not maintain status quo operations. We do not delegate transformation externally. And we do not bring on individuals who require consensus or large teams to produce results. We are seeking a select group of technically proficient, execution-oriented leaders who treat automation as leverage and velocity as competitive strategy. If this describes you—this environment will suit you well.
What you will be doing
- Leading complex operational projects including M&A integration work, enterprise platform migrations, and large-scale organizational transitions
- Building and deploying automation solutions that replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual processes and cut latency
- Driving projects from initial assessment through full deployment, applying established playbooks and senior-level decision-making
- Passing a practical technical assessment to validate your capability to architect and deliver AI-native solutions
What you will NOT be doing
- Building or managing large teams, or depending on multiple layers of staff to accomplish objectives
- Participating in prolonged consensus-building meetings or waiting for broad agreement before acting
- Handing off the technical work to IT departments or third-party vendors—you will design and implement the solution directly
- Running steady-state operations—this position centers on transformation and rapid execution
Key responsibilities
Architect and implement AI-native operational infrastructure that removes manual tasks, simplifies complexity, and enables scalable execution across Trilogy's international software portfolio.
Candidate requirements
- 5+ years of operational leadership in business operations
- Experience presenting to C-suite executives
- Experience building automation using Python and integrating with LLM APIs
- Experience deploying production-grade automations with Cursor, Windsurf, MCP, or equivalent tools
- Ability to work remotely with a minimum of 6 hours 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.
Accept job offer.
Pass
proctored test.
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.