Description
This role is designed for operators who own multi-million-dollar financial results — not those who observe or advise. You will assume direct responsibility for the most consequential operational challenges inside a global software portfolio and convert uncertainty into concrete financial performance. You will design the programs, lead the execution, and witness your contributions reflected directly in margin improvement, customer retention, and acquisition integration success.
Trilogy manages a broad, global portfolio of enterprise software businesses, each presenting complex operational dynamics and significant untapped financial opportunity. You will spearhead the transformations required to capture that opportunity. From driving a $2M per quarter renewal uplift program to reducing cloud infrastructure costs without sacrificing reliability, or integrating a newly acquired company into the Trilogy operating model in under 30 days — your contributions will be visible to senior leadership. Your decisions will directly shape profitability across multiple business units.
This position is suited for candidates who perform best in high-visibility, high-autonomy settings. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, structure actionable insights, and deliver impact at speeds that surpass traditional operating models. You will not be constrained by hierarchy or organizational friction; instead, you will have the latitude — and the mandate — to establish clarity, drive alignment, and execute with conviction. If you are motivated by solving intricate operational challenges and translating them into reliable, scalable outcomes, this is your opportunity. Apply if you are prepared to lead work that reshapes how an entire software portfolio operates.
What you will be doing
- Directing cross-functional customer renewal programs that avert ≥$2M ARR churn each quarter by diagnosing root causes and orchestrating coordinated responses across product, support, and finance.
- Managing cloud cost reduction initiatives that deliver $500K or more in quarterly AWS savings while preserving system performance and uptime.
- Overseeing acquisition due diligence and integration processes that uncover critical risks and synergies — and generate measurable margin gains in the first quarter post-close.
- Deploying Claude Code or equivalent platforms (Codex, Gemini CLI) to create repeatable analytical frameworks, automate operational tasks, and enhance execution velocity and precision.
- Coordinating cross-functional stakeholders to ensure initiatives are delivered on schedule, meet targets, and produce verified financial results.
- Producing weekly executive reports that transparently document progress, obstacles, and quantified financial outcomes.
What you will NOT be doing
- Reporting on results you do not control — you are responsible for driving and achieving outcomes, not merely tracking them.
- Working in isolation — your initiatives span products, functions, and business units to unlock enterprise-level value.
- Spending time on manual data work or low-impact tasks — you will default to AI-powered execution methods.
- Waiting for approval, alignment, or guidance — this role demands operators who build consensus and act decisively.
- Depending exclusively on manual processes — you are expected to integrate AI tooling to amplify and scale your impact.
- Being consumed by planning cycles, governance rituals, or presentation decks — weekly updates are concise, metric-driven, and outcome-focused.
Key responsibilities
Architect and execute portfolio-wide transformation programs that demonstrably enhance retention, cloud cost efficiency, and acquisition integration — with executive oversight and direct financial impact.
Candidate requirements
- 5+ years leading cross-functional operational or transformation programs with ≥$3M in annual financial impact.
- Demonstrated capability to interpret large, complex datasets and convert insights into validated outcomes worth ≥$500K.
- Hands-on experience reducing cloud infrastructure expenses (AWS or equivalent) with documented examples of cost savings and sustained performance.
- Solid financial acumen: P&L analysis, budgeting, ROI modeling, and decision-making grounded in financial reasoning.
- Working knowledge of AI tools including Claude Code, Codex, or Gemini CLI to streamline analysis and enhance execution quality.
- Ability to work remotely with a minimum of 6 hours of daily overlap with the CST time zone.
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