Description
This role is for the operator who drives multi-million-dollar results—not the advisor who observes them. You will own the most critical operational challenges across a global software portfolio, converting complexity into measurable financial outcomes. You will design the programs, lead the execution, and watch your contributions surface in margin performance, customer retention, and acquisition integration success.
Trilogy operates a large and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and substantial financial opportunity. You will lead the initiatives that unlock that opportunity. Whether driving a $2M/quarter renewal uplift program, reducing cloud infrastructure costs while preserving performance, or integrating a newly acquired company into the Trilogy operating model in 30 days, your impact will be visible to senior leadership. You will directly shape profitability across dozens of business units.
This position is built for someone who excels in high-autonomy, high-visibility settings. You will leverage advanced AI technologies such as Claude Code to accelerate insight generation, structure analysis, and deliver outcomes faster than conventional operating teams. You will not be constrained by hierarchy or process overhead; you will have the latitude—and the mandate—to establish clarity, secure alignment, and execute with speed. If you are motivated by turning intricate operational challenges into repeatable, scalable wins, this role will suit you well. Apply if you are prepared to lead transformative initiatives that redefine how an entire software portfolio operates.
What you will be doing
- Directing cross-functional customer renewal programs that prevent ≥$2M ARR churn per quarter by diagnosing root causes and coordinating product, support, and finance teams on targeted solutions.
- Managing cloud optimization projects that cut AWS spend by $500K or more quarterly while sustaining performance and reliability standards.
- Overseeing acquisition diligence and integration processes that identify critical risks and synergies—and produce measurable margin gains within the first quarter post-acquisition.
- Leveraging Claude Code or comparable tools (Codex, Gemini CLI) to create reproducible analyses, automate operational processes, and enhance execution speed and precision.
- Securing alignment across cross-functional stakeholders and ensuring initiatives are completed on schedule, on target, and with verified financial results.
- Producing weekly executive reports that transparently present progress, obstacles, and validated financial impact.
What you will NOT be doing
- Reporting on results you do not control—you are responsible for driving and delivering outcomes, not merely tracking them.
- Working in isolation—your initiatives span products, functions, and business units to generate enterprise-wide value.
- Spending time on manual analysis or low-impact tasks—you default to AI-accelerated execution methods.
- Waiting for consensus, guidance, or approval—this role demands operators who establish alignment and act decisively.
- Depending exclusively on manual analysis—you are expected to employ AI tools to scale and accelerate your efforts.
- Getting caught up in planning cycles, governance structures, or presentation decks—weekly reporting is concise, structured, and metric-driven.
Key responsibilities
Design and execute portfolio-wide transformation programs that deliver measurable improvements in retention, cloud efficiency, and acquisition integration—with executive 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 optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and maintained performance.
- Strong financial literacy: P&L interpretation, budgeting, ROI modeling, and prioritization based on financial logic.
- Familiarity 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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