Description
This position is designed for an operator prepared to own—and deliver—multi-million-dollar outcomes rather than simply advise or observe. You will assume full accountability for the most critical operational challenges across a global portfolio of software businesses, transforming uncertainty into quantifiable financial results. You will design the programs, lead the execution, and witness your contributions reflected directly in margin performance, customer retention, and acquisition integration metrics.
Trilogy oversees a substantial and varied portfolio of enterprise software companies, each presenting intricate operational dynamics and significant untapped financial potential. You will spearhead the transformations that convert this potential into realized value. Whether you are executing a $2M per quarter renewal uplift program, reducing cloud expenditure while preserving system performance, or integrating a newly acquired entity into Trilogy's operating model within 30 days, your efforts will command attention at the executive level. Your influence will extend across profitability outcomes for dozens of business units.
This position suits a leader who flourishes in settings characterized by high visibility and significant autonomy. You will employ advanced AI capabilities such as Claude Code to expedite analysis, structure strategic insights, and generate impact at a pace traditional operating teams cannot match. Free from rigid hierarchy or procedural constraints, you will have both the latitude—and the mandate—to establish clarity, forge alignment, and act with conviction. If converting intricate operational challenges into scalable, repeatable successes energizes you, this role will be a strong fit. Candidates ready to drive transformative initiatives that redefine portfolio-wide performance are encouraged to apply.
What you will be doing
- Directing cross-functional customer renewal initiatives that avert ≥$2M ARR churn each quarter by diagnosing underlying issues and coordinating corrective action across product, support, and finance.
- Overseeing cloud optimization programs that deliver $500K or greater quarterly reductions in AWS spending without compromising performance or reliability standards.
- Implementing acquisition diligence and integration frameworks that identify critical risks and synergy opportunities — and generate measurable margin gains within the first quarter post-acquisition.
- Leveraging Claude Code or comparable platforms (Codex, Gemini CLI) to construct repeatable analytical models, automate operational processes, and enhance both execution speed and precision.
- Securing cross-functional stakeholder alignment and ensuring initiatives conclude on schedule, meet targets, and deliver validated financial results.
- Producing weekly executive reporting that transparently documents progress, identifies obstacles, and confirms realized financial impact.
What you will NOT be doing
- Reporting on results you do not control — you will be held accountable for driving and achieving outcomes, not merely tracking them.
- Functioning in isolation — your initiatives will span products, functions, and business units to unlock enterprise-level value.
- Expending effort on manual data tasks or low-impact administrative work — your standard approach leverages AI-enhanced execution.
- Waiting for consensus, instruction, or approval — this role demands operators who build alignment and act decisively.
- Depending exclusively on traditional analysis methods — you are expected to utilize AI tooling to accelerate and extend your capabilities.
- Becoming mired in planning cycles, governance procedures, or presentation development — weekly reporting is streamlined, targeted, and anchored to concrete metrics.
Key responsibilities
Architect and execute portfolio-wide transformation programs that produce measurable improvements in customer retention, cloud efficiency, and acquisition integration — with executive oversight and direct impact.
Candidate requirements
- 5+ years directing multi-functional operational or transformation programs with ≥$3M annual financial impact.
- Demonstrated capability to interpret 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, budgeting, ROI modeling, and decision prioritization 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 overlap with the CST time zone.
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