Description
This role is designed for operators who take full ownership of multi-million-dollar outcomes — not those who advise from the sidelines or produce status reports. You will assume direct responsibility for the most critical operational challenges spanning a global software portfolio, transforming uncertainty into quantifiable financial results. Your remit includes architecting programs, leading execution, and witnessing your contributions reflected in margin expansion, customer retention metrics, and acquisition integration success.
Trilogy manages an extensive and varied portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant untapped financial potential. You will spearhead the transformations that unlock this value. From scaling a $2M quarterly renewal uplift program to reducing cloud expenditure without compromising system performance, or integrating a newly acquired company into the Trilogy framework within 30 days — your contributions will be directly visible to senior leadership. Your decisions will shape profitability outcomes across dozens of operating units.
The position suits candidates who flourish in high-visibility, high-autonomy settings. You will leverage cutting-edge AI capabilities such as Claude Code to expedite analysis, structure insights, and generate impact at speeds unattainable by conventional operating teams. Hierarchy and bureaucracy will not constrain you; instead, you will have both the latitude and the mandate to establish clarity, forge alignment, and act with conviction. If solving complex operational challenges and converting them into reliable, repeatable successes energizes you, this role will be an exceptional fit. Apply if you are prepared to lead transformative initiatives that redefine performance across an entire software portfolio.
What you will be doing
- Directing cross-functional customer renewal initiatives that avert ≥$2M ARR churn each quarter by diagnosing underlying issues and coordinating product, support, and finance teams around unified solutions.
- Overseeing cloud optimization projects that deliver $500K or greater quarterly reductions in AWS expenditure while preserving performance standards and system reliability.
- Implementing acquisition diligence and integration frameworks that identify critical risks and synergy opportunities — and generate measurable margin enhancements within the first quarter post-acquisition.
- Deploying Claude Code or comparable platforms (Codex, Gemini CLI) to construct reproducible analytical models, automate operational processes, and enhance execution speed and precision.
- Building alignment among cross-functional stakeholders and ensuring initiatives are completed on schedule, meet defined targets, and produce verified financial results.
- Producing weekly executive reporting that clearly articulates progress, obstacles, and confirmed financial impact.
What you will NOT be doing
- Providing commentary on results you do not control — you are directly accountable for driving and achieving outcomes, not merely documenting them.
- Working in isolation — your initiatives span products, functions, and business units to unlock enterprise-wide value.
- Spending time on repetitive manual analysis or low-impact administrative tasks — you will default to AI-accelerated methods.
- Seeking approval, direction, or consensus before acting — this role demands operators who generate alignment and execute rapidly.
- Depending exclusively on manual techniques — AI tooling is an expectation to amplify and scale your contributions.
- Becoming mired in extended planning cycles, governance frameworks, or presentation preparation — weekly updates are streamlined, metric-driven, and outcome-focused.
Key responsibilities
Architect and execute portfolio-wide transformation programs that produce measurable improvements in customer retention, cloud cost efficiency, and acquisition integration — with direct executive oversight and tangible 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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