Description
This position is designed for operators who take full ownership of multi-million-dollar financial outcomes — not those who observe, advise, or simply track. You will assume direct control of the most critical operational initiatives across a global software portfolio, converting uncertainty into concrete, measurable financial performance. You will design the programs, lead the execution, and witness your contributions reflected in margin expansion, retention metrics, and acquisition integration results.
Trilogy operates a broad and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and substantial untapped financial opportunity. You will spearhead the transformations necessary to unlock that value. Whether you are executing a $2M quarterly renewal uplift program, reducing cloud expenditure without compromising system performance, or integrating a newly acquired company into the Trilogy operating model within 30 days, your contributions will be clearly visible to executive leadership. Your work will directly shape profitability across dozens of business units.
This position suits candidates who perform best in high-visibility, high-autonomy settings. You will leverage advanced AI capabilities such as Claude Code to accelerate analytical work, structure strategic insights, and drive outcomes more rapidly than conventional operating teams. You will not be constrained by rigid hierarchy or bureaucratic process; you will have both the latitude — and the mandate — to establish clarity, secure cross-functional alignment, and execute with conviction. If you are motivated by transforming complex operational challenges into scalable, repeatable 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 protect ≥$2M ARR per quarter by diagnosing underlying causes and aligning product, support, and finance teams on unified corrective actions.
- Managing cloud cost optimization programs that deliver $500K or greater quarterly reductions in AWS expenditure while preserving performance and system reliability.
- Overseeing acquisition diligence and integration frameworks that identify critical risks and synergy opportunities — and produce measurable margin gains within the first quarter following acquisition.
- Leveraging Claude Code or comparable AI platforms (Codex, Gemini CLI) to construct repeatable analytical frameworks, automate operational processes, and enhance execution speed and precision.
- Securing alignment across cross-functional stakeholders and ensuring initiatives are completed on schedule, meet targets, and produce validated financial results.
- Producing weekly executive reporting that clearly conveys progress, obstacles, and confirmed financial impact.
What you will NOT be doing
- Tracking results you do not control — you are responsible for driving and delivering outcomes, not merely monitoring them.
- Working in functional isolation — your initiatives span products, functions, and business units to generate enterprise-level impact.
- Spending time on manual analysis or low-impact administrative tasks — your standard approach is AI-enabled execution.
- Awaiting consensus, guidance, or authorization — this position is for operators who establish alignment and execute rapidly.
- Depending exclusively on manual analytical methods — you are expected to employ AI tooling to accelerate and scale your contributions.
- Becoming mired in planning cycles, governance routines, or presentation preparation — weekly reporting is structured, concise, and anchored to tangible metrics.
Key responsibilities
Design and execute portfolio-wide transformation programs that deliver measurable improvements in retention, cloud efficiency, and acquisition integration — with executive-level visibility and direct financial impact.
Candidate requirements
- 5+ years leading multi-functional operational or transformation initiatives with ≥$3M annual financial impact.
- Proven ability to analyze large, complex datasets and translate insights into validated outcomes of ≥ $500K.
- Experience optimizing cloud infrastructure costs (AWS or equivalent) with clear 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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