Description
This role is designed for operators who deliver multi-million-dollar outcomes — not advise on them, not track them, but own them. You will assume responsibility for the most critical operational challenges across a global software portfolio and convert complexity into quantifiable financial results. You'll design the programs, lead the execution, and watch your contributions materialize in margin performance, retention metrics, and acquisition integration success.
Trilogy operates a large and varied portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant financial opportunity awaiting activation. You will spearhead the transformations that unlock that opportunity. Whether you're driving a $2M per quarter renewal uplift program, reducing cloud expenditure without compromising performance, or integrating a newly acquired company into the Trilogy operating model in 30 days, your impact will be recognized at the executive level. Your work will directly shape profitability across dozens of business units.
This position is built 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 at speeds traditional operating teams cannot match. You will not be constrained by hierarchy or process overhead; you will have 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, repeatable victories, this role will suit you. Apply if you are prepared to lead work that fundamentally changes 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 coordinating product, support, and finance teams on unified solutions.
- Managing cloud optimization projects that cut AWS costs by $500K or more quarterly while preserving system performance and reliability standards.
- Overseeing acquisition diligence and integration frameworks that uncover critical risks and synergies — and produce measurable margin gains within the first quarter post-acquisition.
- Applying Claude Code or equivalent platforms (Codex, Gemini CLI) to construct repeatable analyses, automate operational processes, and enhance execution speed and precision.
- Securing alignment among cross-functional stakeholders and ensuring initiatives are completed on schedule, on target, and with confirmed financial results.
- Producing weekly executive reporting that clearly presents progress, obstacles, and validated financial outcomes.
What you will NOT be doing
- Tracking outcomes without ownership — you are responsible for driving and achieving results, not merely monitoring them.
- Working in isolation — your efforts span products, functions, and business units to produce enterprise-level improvements.
- Spending time on manual analysis or low-impact tasks — your standard approach is AI-enabled execution.
- Awaiting consensus, instruction, or approval — this role demands operators who build alignment and execute rapidly.
- Depending exclusively on manual methods — you are expected to employ AI tools to accelerate and scale your output.
- Becoming mired in planning cycles, governance routines, or slide decks — weekly updates are concise, purposeful, and anchored in real performance data.
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 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 reducing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and maintained performance.
- Strong financial acumen: P&L analysis, budgeting, ROI modeling, and decision-making grounded in financial reasoning.
- Proficiency with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution quality.
- Ability to work remotely with at least 6 hours of overlap with the CST time zone.
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