Description
This position is designed for operators capable of constructing and reconstructing scalable systems.
Operational excellence at Trilogy is not optional—it serves as our competitive edge. Our acquisition model for software companies moves quickly, and our scaling strategy moves faster still. Success requires executives who architect lean, automated frameworks rather than adding layers of personnel to address complexity.
You will take ownership of comprehensive transformations spanning our global portfolio. Projects may include redesigning offboarding workflows for 1,200+ employees following acquisitions, substituting traditional platforms like Jira and Salesforce with AI-driven agents, or creating automations that remove thousands of manual hours from operations. Execution velocity will rely on Python, LLM APIs, and tools including Cursor, Windsurf, and MCP—supported by battle-tested playbooks that enable you to concentrate on measurable results.
Trilogy operates a portfolio exceeding 100 products with disciplined efficiency. Our structure features fewer hierarchical layers, shorter execution cycles, and elevated performance standards compared to conventional enterprise settings. This opportunity allows you to generate substantial impact without navigating organizational friction or overseeing inflated team rosters.
We do not maintain static operations. Transformation work is never outsourced. And we do not bring aboard individuals requiring extensive approval chains or large teams to produce results. Our search targets a select group of technically sophisticated, execution-oriented leaders who leverage automation and treat speed as core strategy. If this describes your approach—this environment will suit you.
What you will be doing
- Delivering operationally complex initiatives including M&A integrations, enterprise platform migrations, and organization-wide structural transitions
- Architecting and launching automations to replace CRM and task management systems through Python and LLM APIs
- Implementing AI-enabled workflows with Cursor, Windsurf, and MCP to remove manual processes and shorten response times
- Driving projects end-to-end from diagnosis through deployment, applying tested playbooks and executive decision-making
- Passing a practical technical assessment that validates your capability to design and execute AI-centric solutions
What you will NOT be doing
- Building or overseeing large teams or depending on multiple organizational layers for execution
- Attending protracted alignment sessions or waiting for collective agreement before advancing work
- Handing off complex technical challenges to IT departments or third-party vendors—you will design and implement solutions directly
- Operating in steady-state maintenance mode—this position centers on transformation and rapid delivery
Key responsibilities
Architect and implement AI-first operational frameworks that remove manual tasks, simplify complexity, and enable scalable execution throughout Trilogy's international 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.