Description
This role is for operators who deliver multi-million-dollar outcomes — not those who advise from the sidelines or submit status reports. You will assume ownership of the most critical operational challenges spanning a global software portfolio and convert uncertainty into quantifiable financial results. You'll design the initiatives, lead the implementation, and watch your contributions materialize in margin expansion, customer retention rates, and acquisition integration metrics.
Trilogy operates a substantial and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant untapped financial potential. You'll spearhead the transformations that unlock that value. Your work may involve scaling a $2M per quarter renewal enhancement program, reducing cloud infrastructure expenses while preserving system performance, or integrating a newly acquired company into Trilogy's operational framework within a 30-day window. Every initiative you lead will command attention at the executive level and directly shape profitability across multiple business units.
This position suits candidates who perform best in high-visibility, high-independence settings. You'll leverage cutting-edge AI capabilities such as Claude Code to expedite analytical work, organize insight generation, and produce results more rapidly than conventional operating teams. You won't navigate traditional hierarchy or red tape; instead, you'll have both the latitude and the mandate to establish clarity, build cross-functional consensus, and act with conviction. If converting intricate operational challenges into scalable, repeatable successes energizes you, this role offers an exceptional fit. Apply if you're prepared to drive transformative initiatives that redefine performance across an entire software portfolio.
What you will be doing
- Directing cross-functional customer retention initiatives that avert ≥$2M in ARR churn each quarter by diagnosing underlying issues and coordinating product, support, and finance teams around unified solutions.
- Overseeing cloud cost reduction programs that lower AWS expenditures by $500K or more quarterly without compromising performance or system reliability.
- Managing acquisition due diligence and integration processes that uncover critical risks and synergy opportunities — delivering confirmed margin gains within the first quarter following acquisition.
- Applying Claude Code or comparable platforms (Codex, Gemini CLI) to create reproducible analytical frameworks, automate operational routines, and enhance execution velocity and precision.
- Coordinating cross-functional stakeholders to ensure programs are completed on schedule, meet objectives, and produce verified financial results.
- Producing weekly executive-level updates that clearly convey progress, obstacles, and substantiated financial outcomes.
What you will NOT be doing
- Documenting results you don't control — you're responsible for driving and achieving outcomes, not merely tracking them.
- Working in isolation — your initiatives span products, departments, and business units to generate enterprise-level value.
- Spending time on manual data work or low-impact administrative tasks — you'll default to AI-enabled execution methods.
- Seeking approval, waiting for guidance, or building consensus before acting — this role demands operators who forge alignment and execute rapidly.
- Depending exclusively on traditional analysis techniques — you're expected to deploy AI-powered tools to amplify and scale your impact.
- Drowning in planning cycles, governance meetings, or presentation preparation — weekly updates are concise, structured, and anchored to tangible metrics.
Key responsibilities
Design and execute portfolio-scale transformation programs that demonstrably enhance retention, cloud cost efficiency, and acquisition integration outcomes — with executive oversight and direct financial impact.
Candidate requirements
- 5+ years leading cross-functional operational or transformation programs with ≥$3M in annual financial impact.
- Demonstrated capability to examine large, complex data sets and convert findings into validated outcomes of ≥$500K.
- Background in optimizing cloud infrastructure expenses (AWS or equivalent) with documented evidence of cost savings and sustained performance.
- Strong command of financial principles: P&L analysis, budgeting processes, ROI modeling, and prioritization driven by financial reasoning.
- Working knowledge of AI platforms such as Claude Code, Codex, or Gemini CLI to automate analytical processes and strengthen execution.
- Ability to work remotely with a minimum of 6 hours of daily overlap with the CST time zone.
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
Reviews
Meet some people who've landed similar jobs
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.