Description
This role is designed for operators who own and deliver multi-million-dollar outcomes rather than observe or advise on them. You will assume responsibility for the most critical operational challenges within a global software portfolio, transforming complexity into quantifiable financial results. You will design the programs, oversee execution, and witness your contributions reflected in margin performance, retention rates, and acquisition integration outcomes.
Trilogy manages a broad and varied portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant untapped financial value. You will spearhead the transformations that convert this potential into realized gains. Your efforts—whether driving a $2M/quarter renewal uplift program, reducing cloud expenditure without compromising performance, or integrating a newly acquired company into the Trilogy framework within 30 days—will be directly visible to senior leadership. Your contributions will shape profitability across numerous business units.
This position is suited to candidates who perform best in high-visibility, high-autonomy settings. You will leverage advanced AI tools such as Claude Code to expedite analysis, structure findings, and generate impact at a pace that exceeds traditional operational teams. You will operate free from hierarchical constraints or procedural delays, with both the latitude and the responsibility to establish clarity, secure alignment, and act decisively. If you find energy in solving intricate operational challenges and converting them into consistent, scalable successes, you will thrive in this environment. 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 initiatives that prevent ≥$2M ARR churn per quarter through root-cause identification and coordinated alignment across product, support, and finance teams.
- Managing cloud optimization projects that deliver $500K or greater quarterly reductions in AWS expenditure while preserving performance and system reliability.
- Implementing acquisition diligence and integration frameworks that uncover critical risks and synergy opportunities—and yield measurable margin gains in the first quarter post-acquisition.
- Deploying Claude Code or comparable tools (Codex, Gemini CLI) to construct reproducible analytical models, automate operational processes, and enhance execution speed and precision.
- Coordinating cross-functional stakeholders to ensure initiatives are completed on schedule, meet targets, and produce validated financial results.
- Producing weekly executive-level reports that transparently track progress, surface obstacles, and confirm financial impact.
What you will NOT be doing
- Reporting on results you do not own — you are responsible for driving and delivering outcomes, not merely monitoring them.
- Working in isolation — your initiatives span products, functions, and business units to produce enterprise-wide improvements.
- Spending time on manual analysis or low-impact administrative tasks — your approach is centered on AI-accelerated execution.
- Waiting for consensus, instruction, or approval — this role requires operators who build alignment and act quickly.
- Depending exclusively on manual analytical methods — you are expected to employ AI tooling to scale and accelerate your output.
- Becoming mired in planning, governance, or presentation decks — weekly reporting is structured, concise, and metric-driven.
Key responsibilities
Design and execute portfolio-wide transformation programs that generate measurable improvements in 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 ability 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 performance preservation.
- Strong financial literacy: P&L interpretation, budgeting, ROI modeling, and prioritization using financial logic.
- Familiarity with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and improve execution.
- Remote work capability with at least 6 hours of overlap with the CST time zone.
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