Description
This position is designed for an operator prepared to own outcomes measured in millions of dollars — not to consult, not to observe, but to execute. You will assume ownership of the most critical operational challenges spanning a global portfolio of software businesses and convert complexity into quantifiable financial results. You will design the programs, lead the execution, and watch your contributions materialize in improved margins, retention metrics, and acquisition integration success.
Trilogy operates a broad and varied portfolio of enterprise software companies, each presenting intricate operational dynamics and substantial financial opportunity ready to be captured. Your responsibility will be to lead the initiatives that unlock that opportunity. Whether you are implementing a $2M per quarter renewal uplift program, reducing cloud infrastructure expenditure without compromising system performance, or integrating a newly acquired company into the Trilogy operating model in 30 days, your results will be visible to executive leadership. Your efforts will directly shape profitability across numerous business units.
This position suits a candidate who excels in settings characterized by high visibility and high independence. You will leverage cutting-edge AI capabilities such as Claude Code to expedite analysis, organize insights, and deliver impact at a pace beyond the reach of conventional operating teams. Hierarchy and bureaucracy will not constrain you; instead, you will be granted the latitude — and the mandate — to establish clarity, secure alignment, and act with conviction. If converting intricate operational challenges into reliable, scalable successes energizes you, this role will be a strong fit. Apply if you are prepared to drive transformational initiatives that redefine performance across an entire software portfolio.
What you will be doing
- Directing cross-functional customer renewal initiatives that prevent ≥$2M ARR churn each quarter by diagnosing underlying causes and coordinating product, support, and finance teams to implement unified solutions.
- Managing cloud optimization efforts that cut AWS expenditure by $500K or more quarterly while preserving performance standards and system reliability.
- Overseeing acquisition due diligence and integration frameworks that uncover critical risks and synergies — delivering quantifiable margin gains within the first quarter following acquisition.
- Leveraging Claude Code or comparable platforms (Codex, Gemini CLI) to create reusable analyses, automate operational processes, and enhance both the velocity and precision of execution.
- Coordinating cross-functional stakeholders and ensuring initiatives complete on schedule, meet targets, and produce confirmed financial results.
- Producing weekly executive reporting that clearly conveys progress, obstacles, and verified financial impact.
What you will NOT be doing
- Presenting 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 improvements.
- Spending time on manual analysis or low-impact administrative tasks — you operate with AI-accelerated execution as the standard.
- Waiting for alignment, guidance, or approval — this position requires operators who establish consensus and execute rapidly.
- Depending exclusively on manual methods — you are expected to deploy AI tools to amplify and extend your work.
- Becoming mired in planning, governance, or presentations — weekly updates are concise, purposeful, and anchored to actual metrics.
Key responsibilities
Architect and execute portfolio-wide transformation programs that produce measurable improvements in 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.
- Experience reducing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and sustained 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.
- Ability to work remotely with at least 6 hours of overlap with the CST time zone.
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