Description
This role is designed for operators who deliver multi-million-dollar outcomes rather than observe or advise on them. You will assume ownership of the most critical operational challenges spanning a global software portfolio, converting uncertainty into quantifiable financial results. You will design the programs, lead execution, and witness your contributions reflected directly in margin performance, customer retention metrics, and acquisition integration success.
Trilogy operates a broad and varied portfolio of enterprise software businesses, each presenting complex operational dynamics and significant untapped financial opportunity. You will spearhead the transformations that realize that opportunity. From scaling a $2M/quarter renewal uplift program to reducing cloud infrastructure costs without degrading performance, or integrating a newly acquired entity into Trilogy's operating model in 30 days, your efforts will be scrutinized at the executive level. Your decisions will shape profitability across multiple business units.
This position suits candidates who perform best under high visibility and high autonomy. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, structure findings, and generate impact at a velocity traditional operations teams cannot match. Hierarchy and bureaucratic constraints will not limit you; instead, you will have the mandate—and the responsibility—to establish clarity, secure alignment, and act with conviction. If solving intricate operational challenges and converting them into reliable, scalable wins energizes you, this is where you belong. Apply if you are prepared to lead transformative initiatives that redefine how an entire software portfolio operates.
What you will be doing
- Directing cross-functional customer renewal efforts that avert ≥$2M ARR churn each quarter by diagnosing underlying causes and coordinating product, support, and finance teams around unified solutions.
- Overseeing cloud optimization programs that cut AWS expenditure by $500K or more quarterly while preserving system performance and reliability standards.
- Implementing acquisition diligence and integration frameworks that expose critical risks and synergies — delivering confirmed margin gains in the first quarter following acquisition.
- Applying Claude Code or comparable platforms (Codex, Gemini CLI) to construct reusable analyses, automate operational processes, and enhance both execution speed and precision.
- Coordinating cross-functional stakeholders to ensure initiatives are completed on schedule, meet targets, and produce verified financial results.
- Producing weekly executive reports that communicate progress, obstacles, and validated financial impact with full transparency.
What you will NOT be doing
- Reporting on results outside your accountability — you own the delivery and execution of outcomes, not merely their observation.
- Working in isolation — your initiatives span products, functions, and business units to unlock enterprise-level value.
- Spending time on manual analysis or low-impact activities — AI-accelerated execution is your standard approach.
- Awaiting consensus, guidance, or authorization — this role demands operators who forge alignment and act decisively.
- Depending exclusively on manual methods — you are required to employ AI tools to amplify and extend your capacity.
- Becoming mired in planning cycles, governance meetings, or presentation development — weekly reporting is streamlined, purposeful, and anchored in real metrics.
Key responsibilities
Design and execute portfolio-wide transformation initiatives that produce measurable improvements in retention, cloud efficiency, and acquisition integration — with executive oversight and direct impact.
Candidate requirements
- 5+ years leading multi-functional operational or transformation initiatives with ≥$3M annual financial impact.
- Demonstrated capability to analyze large, complex datasets and convert insights into validated outcomes of ≥$500K.
- Background in optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of cost savings and performance maintenance.
- Solid financial acumen: P&L interpretation, budgeting, ROI modeling, and prioritization grounded in financial reasoning.
- Working knowledge of AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and strengthen execution.
- Ability to work remotely with a minimum of 6 hours overlap with the CST time zone.
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