Description
This role is designed for operators who take ownership of multi-million-dollar results — not those who advise from the sidelines or prepare status updates. You will assume direct accountability for the most critical operational challenges across a global software portfolio and convert complexity into quantifiable financial performance. You will design the programs, lead execution end-to-end, and watch your contributions surface in margin expansion, customer retention, and acquisition integration metrics.
Trilogy manages a broad, diversified portfolio of enterprise software businesses, each presenting intricate operational dynamics and substantial financial opportunity. You will drive the transformations that unlock that opportunity. From executing a $2M per quarter renewal uplift program to reducing cloud infrastructure expenses without performance degradation, or integrating a newly acquired company into the Trilogy operating model in 30 days, your initiatives will command executive attention. Your decisions will shape profitability across multiple business units.
This position is structured for candidates who perform best in high-visibility, high-autonomy settings. You will leverage advanced AI technologies such as Claude Code to expedite analysis, organize insights, and deliver results faster than conventional operating teams. Hierarchy and bureaucracy will not constrain you; instead, you will have both the latitude and the mandate to establish clarity, secure alignment, and act with speed. If you are motivated by transforming intricate operational challenges into scalable, repeatable success, this role will suit you. Apply if you are prepared to lead high-impact work that redefines performance across an entire software portfolio.
What you will be doing
- Driving cross-functional customer renewal initiatives that prevent ≥$2M in annual recurring revenue churn per quarter by diagnosing underlying issues and coordinating product, support, and finance teams on unified solutions.
- Overseeing cloud cost reduction programs that lower AWS expenditure by $500K or more each quarter without compromising system performance or reliability.
- Managing acquisition due diligence and integration frameworks that identify critical risks and synergy opportunities — delivering confirmed margin gains within the first quarter post-acquisition.
- Applying Claude Code or comparable platforms (Codex, Gemini CLI) to create repeatable analytical models, automate operational processes, and enhance execution speed and precision.
- Building alignment across cross-functional stakeholders and ensuring initiatives are completed on schedule, meet targets, and produce verified financial outcomes.
- Producing weekly executive reports that clearly convey progress, obstacles, and validated financial impact.
What you will NOT be doing
- Documenting results you do not control — you are responsible for both driving and delivering outcomes, not simply tracking them.
- Working in isolation — your initiatives span products, functions, and business units to generate enterprise-level value.
- Spending time on manual data tasks or low-impact activities — your standard approach relies on AI-enabled execution.
- Waiting for approval, direction, or agreement — this role demands operators who forge alignment and act decisively.
- Depending exclusively on manual methods — you are required to use AI tooling to amplify and scale your contributions.
- Getting mired in strategy sessions, governance processes, or slide decks — weekly updates are streamlined, purposeful, and anchored in concrete metrics.
Key responsibilities
Architect and execute portfolio-wide transformation programs that deliver measurable improvements in retention, cloud efficiency, and acquisition integration — with direct executive visibility and clear financial impact.
Candidate requirements
- 5+ years leading cross-functional operational or transformation programs with ≥$3M in annual financial impact.
- Demonstrated capability to analyze large, complex datasets and convert insights into validated outcomes of ≥$500K.
- Track record optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of cost savings and sustained performance.
- Strong financial acumen: P&L analysis, budget management, ROI modeling, and decision-making grounded in financial reasoning.
- Working knowledge of AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution quality.
- Ability to work remotely with a minimum of 6 hours of daily overlap with the CST time zone.
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