Description
This role is for the operator who wants full ownership of multi-million-dollar outcomes — not advisory input, not status reports, but direct delivery. You will assume responsibility for the most critical operational challenges across a global software portfolio and convert complexity into quantifiable financial results. You will design the programs, lead the execution, and witness your contributions reflected in margin performance, customer retention, and post-acquisition integration success.
Trilogy operates a large and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant financial opportunity awaiting activation. You will spearhead the transformations that unlock that opportunity. From scaling a $2M-per-quarter renewal uplift program to reducing cloud expenditures without compromising system performance, or integrating a newly acquired company into the Trilogy framework in 30 days, your efforts will command attention at the executive level. Your work will directly shape profitability across dozens of business units.
This position is built for candidates who thrive under high visibility and high autonomy. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, organize insights, and deliver impact at a pace that outstrips traditional operating teams. Hierarchy and bureaucracy will not constrain you; instead, you will have the latitude — and the mandate — to establish clarity, secure alignment, and act decisively. If transforming intricate operational challenges into reliable, repeatable successes energizes you, you will perform exceptionally. 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 efforts that avert ≥$2M ARR churn each quarter by diagnosing underlying causes and coordinating product, support, and finance teams on unified remediation strategies.
- Managing cloud optimization projects that cut AWS expenditures by $500K or more quarterly while preserving performance standards and system reliability.
- Implementing acquisition diligence and integration frameworks that uncover critical risks and synergy opportunities — delivering measurable margin gains in the first quarter following acquisition.
- Leveraging Claude Code or comparable platforms (Codex, Gemini CLI) to construct repeatable analytical models, automate operational processes, and enhance both velocity and precision of execution.
- Coordinating cross-functional stakeholders and ensuring programs are delivered on schedule, on scope, and with confirmed financial results.
- Producing weekly executive-level updates that transparently document progress, obstacles, and validated financial impact.
What you will NOT be doing
- Reporting on results you do not own — you are accountable for both driving and delivering outcomes, not merely documenting them.
- Working in isolation — your initiatives span products, functions, and business units to achieve enterprise-scale improvements.
- Spending time on manual analysis or low-impact administrative tasks — AI-accelerated execution is your standard approach.
- Awaiting consensus, guidance, or authorization — this role demands operators who forge alignment and act with speed.
- Depending exclusively on manual methods — you are expected to employ AI tooling to amplify and scale your contributions.
- Becoming mired in planning cycles, governance processes, or presentation development — weekly reporting is streamlined, targeted, and anchored to actual metrics.
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 cross-functional operational or transformation programs with ≥$3M annual financial impact.
- Demonstrated capability to analyze large, complex datasets and convert insights into validated outcomes of ≥$500K.
- Experience reducing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and sustained performance.
- Strong financial acumen: P&L analysis, budgeting, ROI modeling, and decision-making driven by financial reasoning.
- Working knowledge of AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution.
- Ability to work remotely with at least 6 hours of daily overlap with the CST time zone.
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