Description
This role is designed for operators who deliver multi-million-dollar outcomes — not those who advise on them or simply track progress. You will assume ownership of the most critical operational challenges spanning a global software portfolio, converting uncertainty into quantifiable financial results. Your responsibility will include designing the programs, leading execution, and ensuring your contributions are reflected directly in margin performance, customer retention metrics, and acquisition integration success.
Trilogy manages an extensive, multifaceted portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant untapped financial potential. You will spearhead the transformations required to realize that potential. Your initiatives may range from scaling a $2M-per-quarter renewal uplift program to reducing cloud infrastructure expenses without compromising system performance, or integrating a newly acquired entity into the Trilogy operating model in under 30 days. Your efforts will be highly visible to senior leadership and will directly shape profitability across numerous business units.
The ideal candidate thrives in settings defined by high visibility and substantial autonomy. You will leverage cutting-edge AI capabilities such as Claude Code to expedite analysis, structure actionable insights, and achieve impact at a pace that outstrips traditional operating teams. You will not be constrained by organizational hierarchy or procedural overhead; instead, 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 intricate operational challenges into dependable, scalable victories, this role will suit you well. Apply if you are prepared to drive transformative initiatives that redefine performance across an entire software portfolio.
What you will be doing
- Directing cross-functional customer renewal programs that avert ≥$2M in ARR churn each quarter by diagnosing underlying causes and coordinating product, support, and finance teams around unified solutions.
- Overseeing cloud optimization efforts that lower AWS expenditure by $500K or more quarterly while preserving system performance and uptime.
- Implementing acquisition diligence and integration frameworks that uncover critical risks and synergy opportunities — delivering measurable margin gains in the first quarter following acquisition.
- Applying Claude Code or comparable tools (Codex, Gemini CLI) to construct repeatable analyses, automate operational processes, and enhance both execution speed and precision.
- Coordinating cross-functional stakeholders and ensuring that initiatives are completed on schedule, meet objectives, and produce verified financial results.
- Producing weekly executive-level reports that transparently document progress, identify obstacles, and confirm validated 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 observing them.
- Working in isolation — your initiatives span products, functions, and business units to unlock enterprise-wide value.
- Spending time on manual analysis or low-impact tasks — your standard approach is AI-accelerated execution.
- Waiting for consensus, guidance, or approval — this role requires operators who forge alignment and act decisively.
- Depending exclusively on manual methods — you are expected to employ AI tooling to amplify and scale your contributions.
- Being slowed by excessive planning, governance cycles, or presentation decks — weekly reporting is concise, focused, and anchored in real metrics.
Key responsibilities
Architect and execute portfolio-wide transformation programs that deliver measurable improvements in customer retention, cloud efficiency, and acquisition integration — with direct executive visibility and tangible impact.
Candidate requirements
- 5+ years leading cross-functional operational or transformation initiatives with ≥$3M in 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: proficiency in P&L analysis, budgeting, ROI modeling, and prioritization grounded in 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 a minimum of 6 hours of overlap with the CST time zone.
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