Description
Join the elite ranks of operators at Trilogy, where building and rebuilding scalable systems is your playground. If operational excellence is your game, we've got the ultimate arena for you.
What you will be doing
- Lead high-impact operational projects, including M&A integrations and enterprise system migrations, with precision and speed.
- Innovate by designing and implementing automations to replace traditional CRM and task management tools using Python and LLM APIs.
- Utilize AI-powered workflows via cutting-edge tools like Cursor, Windsurf, and MCP to streamline processes and eliminate manual tasks.
- Drive initiatives from concept to execution, leveraging proven playbooks and your executive acumen.
- Showcase your technical skills by completing hands-on challenges focused on AI-first solutions.
What you will NOT be doing
- Managing sizable teams or relying on hierarchical structures to achieve results.
- Enduring endless meetings for alignment or seeking consensus before acting.
- Outsourcing complex tasks to IT or external vendors—you're the architect and executor.
- Maintaining status quo operations—your focus is on transformation and rapid execution.
Key responsibilities
Candidate requirements
- Located in North America (excluding California), South/Central America, or Western Europe (UTC -8 to UTC +2).
- Minimum of 5 years in operational leadership within enterprise software.
- At least 3 years in customer-facing roles such as Support, Sales, or Collections.
- Proficiency in writing automation scripts in Python and integrating with LLM APIs.
- Experience with tools like Cursor, Windsurf, MCP, or similar for deploying production-grade automations.
- Track record of independent thinking, rapid execution, and delivering high-stakes results without supervision.
Nice to have
- Background in leading significant organizational transitions, including M&A integrations and mass offboarding.
- Experience in designing and deploying AI-driven operational systems.
- Showcase of automations you've personally developed and deployed at scale.
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
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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.
Join the world's largest community of 
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