Description
This position is designed for an operator who delivers multi-million-dollar outcomes — not by advising or reporting, but by executing. You will assume ownership of 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 directly shape margin performance, customer retention, and acquisition integration success.
Trilogy operates a broad, diversified portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant financial opportunity. You'll spearhead the transformations that unlock that value. 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 within 30 days, your efforts will be highly visible to senior leadership. Your decisions will directly affect profitability across multiple business units.
This role suits candidates who excel in high-visibility, high-autonomy settings. You'll leverage advanced AI capabilities such as Claude Code to expedite analysis, structure actionable insights, and deliver impact at a velocity traditional operating teams cannot match. Hierarchy and bureaucracy will not constrain you; instead, you'll have both the latitude and the mandate to establish clarity, build consensus, and act with conviction. If turning intricate operational challenges into reliable, repeatable wins energizes you, this role offers exceptional fit. Apply if you are prepared to drive transformative initiatives that redefine how an entire software portfolio operates.
What you will be doing
- Directing cross-functional customer renewal initiatives that prevent ≥$2M ARR churn each quarter by diagnosing root causes and coordinating product, support, and finance teams to implement targeted solutions.
- Overseeing cloud optimization projects that decrease AWS expenditure by $500K or more quarterly while preserving performance standards and system reliability.
- Managing acquisition due diligence and integration frameworks that uncover critical risks and synergy opportunities — delivering measurable margin enhancement 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 both execution speed and precision.
- Coordinating cross-functional stakeholders and ensuring programs are completed on schedule, meet targets, and produce validated financial results.
- Producing weekly executive reporting that clearly articulates progress, obstacles, and confirmed financial impact.
What you will NOT be doing
- Reporting on 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 unlock enterprise-scale value.
- Spending time on manual analysis or low-impact administrative tasks — you will default to AI-accelerated workflows.
- Awaiting consensus, guidance, or approval — this role demands operators who generate alignment and execute rapidly.
- Depending exclusively on manual methods — you are expected to harness AI tooling to amplify and scale your impact.
- Becoming mired in planning cycles, governance frameworks, or presentation decks — weekly updates are concise, structured, and metric-driven.
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 optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and sustained performance.
- Strong financial acumen: P&L interpretation, budgeting, ROI modeling, and prioritization grounded in financial logic.
- Proficiency with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution quality.
- Remote work capability with at least 6 hours of overlap with the CST time zone.
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