Description
This position is designed for an operator who delivers multi-million-dollar financial outcomes — not through advisory work or status reporting, but through direct execution. You will assume ownership of the most critical operational challenges within a global software portfolio and convert complexity into concrete financial performance. Your focus will be on designing the programs, directing the execution, and ensuring your efforts translate directly into improvements in margin, retention, and acquisition integration metrics.
Trilogy operates a broad and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant untapped financial opportunity. Your mandate will be to lead the transformations that unlock this potential. From driving a $2M/quarter renewal uplift program to reducing cloud expenditures without compromising system performance, or integrating a newly acquired company into the Trilogy framework within 30 days — your contributions will be tracked at the executive level. Your decisions will shape profitability outcomes across multiple business units.
The role suits candidates who excel in settings that combine high visibility with high autonomy. You will leverage sophisticated AI capabilities such as Claude Code to expedite analysis, structure strategic insights, and produce results faster than conventional operating teams. Hierarchy and process overhead will not constrain you; instead, you will be empowered — and expected — to establish clarity, foster alignment, and act with conviction. If you are motivated by converting intricate operational challenges into scalable, repeatable success, this is where you belong. Apply if you are prepared to spearhead transformative initiatives that redefine performance across an entire software portfolio.
What you will be doing
- Directing cross-functional customer renewal programs that avert ≥$2M ARR churn each quarter by diagnosing underlying issues and coordinating product, support, and finance teams around unified solutions.
- Overseeing cloud optimization projects that deliver $500K or more in quarterly AWS savings while preserving performance benchmarks and system reliability.
- Implementing acquisition diligence and integration frameworks that uncover critical risks and synergy opportunities — and produce verifiable margin gains within the first quarter post-acquisition.
- Applying Claude Code or equivalent platforms (Codex, Gemini CLI) to create repeatable analytical models, automate operational processes, and enhance both execution speed and precision.
- Coordinating cross-functional stakeholders to ensure programs are delivered on schedule, meet targets, and achieve validated financial results.
- Producing weekly executive reports that transparently document progress, identify obstacles, and confirm financial impact with evidence.
What you will NOT be doing
- Reporting on results you do not own — you are responsible for driving and achieving outcomes, not simply tracking them.
- Working in isolation — your initiatives span products, functions, and business units to generate enterprise-level value.
- Expending effort on manual analysis or low-impact tasks — your standard approach is AI-enhanced execution.
- Awaiting consensus, guidance, or approval — this role demands operators who build alignment and act decisively.
- Depending exclusively on manual methods — you are expected to employ AI tooling to amplify and scale your output.
- Becoming mired in planning cycles, governance routines, or presentation decks — weekly reporting is streamlined, precise, and anchored to tangible metrics.
Key responsibilities
Design and execute portfolio-wide transformation programs that produce measurable improvements in retention, cloud efficiency, and acquisition integration — with executive-level visibility and direct financial 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.
- Experience optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and sustained performance.
- Strong financial acumen: P&L interpretation, budgeting, ROI modeling, and prioritization driven by financial reasoning.
- Proficiency with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution.
- Remote work capability with at least 6 hours of overlap with the CST time zone.
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