Description
This role is designed for operators who own outcomes — not advisors, not coordinators, but executives who deliver multi-million-dollar results. You will command the most critical operational challenges within a global software portfolio and convert complexity into quantifiable financial performance. You will design the programs, lead the execution, and witness your contributions reflected directly in margin expansion, customer retention, and post-acquisition integration success.
Trilogy operates a broad, multifaceted portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant financial opportunity ready to be captured. You will spearhead the transformations that realize that opportunity. Whether you are scaling a $2M per quarter renewal uplift program, reducing cloud expenditure without compromising system performance, or integrating a newly acquired company into the Trilogy operating model within 30 days, your impact will be evident at the executive level. You will shape profitability outcomes across dozens of business units.
This position is structured for candidates who perform best in high-visibility, high-autonomy settings. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, organize insights, and generate impact more rapidly than conventional operating teams. You will not be constrained by hierarchy or process overhead; you will possess both the latitude and the mandate to establish clarity, secure alignment, and act with conviction. If you are motivated by transforming intricate operational challenges into reliable, scalable wins, you will thrive in this environment. Apply if you are prepared to drive transformative initiatives that redefine how an entire software portfolio operates.
What you will be doing
- Directing cross-functional customer renewal initiatives that avert ≥$2M ARR churn each quarter by diagnosing root causes and synchronizing product, support, and finance teams on unified remediation strategies.
- Managing cloud cost optimization programs that achieve $500K or greater quarterly reductions in AWS expenditure while preserving performance benchmarks and system reliability.
- Overseeing acquisition due diligence and integration frameworks that identify critical risks and synergy opportunities — and produce measurable margin enhancements within the first quarter post-close.
- Deploying Claude Code or comparable platforms (Codex, Gemini CLI) to construct repeatable analyses, automate operational processes, and enhance both execution velocity and precision.
- Coordinating cross-functional stakeholders and ensuring initiatives are completed on schedule, meet targets, and deliver validated financial results.
- Producing weekly executive reporting that clearly conveys progress, obstacles, and confirmed financial outcomes.
What you will NOT be doing
- Reporting on results you do not own — you are responsible for driving and achieving outcomes, not merely tracking them.
- Working in isolation — your initiatives span products, functions, and business units to generate enterprise-level impact.
- Spending time on manual analysis or low-impact administrative tasks — you default to AI-enabled execution.
- Awaiting consensus, instruction, or approval — this role demands operators who build alignment and execute swiftly.
- Depending exclusively on manual methods — you are required to apply AI tools to accelerate and scale your contributions.
- Being consumed by planning cycles, governance rituals, or presentation development — weekly updates are concise, structured, and metric-driven.
Key responsibilities
Architect and execute portfolio-wide transformation programs that demonstrably enhance retention, cloud efficiency, and acquisition integration — with executive-level visibility and direct & impact.
Candidate requirements
- 5+ years leading cross-functional operational or transformation programs with ≥$3M annual financial impact.
- Demonstrated capability to analyze large, complex datasets and convert insights into validated outcomes of ≥ $500K.
- Track record optimizing cloud infrastructure spend (AWS or equivalent) with documented examples of cost savings and maintained performance.
- Solid financial acumen: P&L analysis, budgeting, ROI modeling, and decision-making grounded in financial rationale.
- Working knowledge of AI platforms such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution.
- Capability to work remotely with a minimum of 6 hours overlap with the CST time zone.
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