Description
This position is built for operators capable of designing and redesigning systems at scale.
Operational excellence at Trilogy is not optional—it is the competitive edge we rely on. We move quickly to acquire software companies, then scale them with even greater speed. Sustaining this pace requires executives who deliver lean, automated systems rather than adding layers of management to address complexity.
You will take ownership of end-to-end transformation initiatives across our global portfolio. This might involve redesigning post-acquisition offboarding for over 1,200 employees, replacing legacy platforms like Jira and Salesforce with AI agents, or deploying automations that save thousands of manual hours. Your execution will be powered by Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by a library of battle-tested playbooks designed to prioritize results.
Trilogy manages a portfolio of more than 100 products with disciplined efficiency. We maintain fewer organizational layers, tighter execution cycles, and higher performance standards than most enterprise settings. This is an opportunity to create measurable impact at scale without navigating bureaucracy or leading oversized teams.
We do not operate in steady-state mode. We do not delegate transformation to outside firms. And we do not hire individuals who require approval chains or large teams to produce results. We are seeking a select group of technically fluent, execution-oriented leaders who treat automation as leverage and velocity as a competitive advantage. If that describes you, this environment will suit you well.
What you will be doing
- Leading high-complexity operational initiatives including M&A integrations, enterprise-scale system migrations, and large organizational transitions
- Building and delivering automations to replace CRM and task management platforms using Python and LLM APIs
- Implementing AI-driven workflows through Cursor, Windsurf, and MCP to remove manual tasks and reduce process latency
- Driving projects from initial assessment through full deployment, leveraging established playbooks and executive-level decision-making
- Completing a technical challenge designed to validate your capability to architect and deploy AI-first operational solutions
What you will NOT be doing
- Building or managing large teams, or depending on multiple layers of personnel to deliver outcomes
- Spending time in prolonged alignment sessions or waiting for consensus before taking action
- Outsourcing critical execution to IT departments or third-party vendors—you will design and implement solutions directly
- Running steady-state operations—this role centers on transformation and speed of execution
Key responsibilities
Architect and implement AI-first operational systems that reduce manual workload, simplify complexity, and enable scalable execution across Trilogy's global software portfolio.
Candidate requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2)
- 5+ years of operational leadership within enterprise software environments
- 3+ years in customer-facing functions (Support, Sales, Collections, etc.)
- Proven capability to develop automation using Python and integrate with LLM APIs
- Hands-on experience deploying production-grade automations using Cursor, Windsurf, MCP, or comparable tools
- Track record of rapid execution, independent thinking, and delivering critical results without requiring close oversight
Nice to have
- Background leading large-scale organizational changes such as M&A integrations or workforce offboarding at scale
- Track record designing and launching AI-powered operational systems
- Documented portfolio of automations you have personally developed and deployed in production
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.