Description
This position is designed for an operator prepared to own multi-million-dollar results — not to advise or observe, but to execute and deliver. You will assume responsibility for the most critical operational challenges spanning a global portfolio of software businesses, converting complexity into quantifiable financial performance. You will design the programs, lead execution, and watch your contributions directly influence margin, retention, and acquisition integration metrics.
Trilogy operates a large and varied collection of enterprise software companies, each with intricate operational dynamics and significant financial opportunity waiting to be captured. You will spearhead the transformation efforts that unlock that potential. From driving a $2M per quarter renewal uplift program to reducing cloud infrastructure spend without compromising system performance, or integrating a newly acquired company into the Trilogy operating model in 30 days, your initiatives will have visibility at the executive level. Your work will directly shape profitability across numerous business units.
This position suits a candidate who excels in settings defined by high visibility and high autonomy. You will leverage advanced AI technologies such as Claude Code to expedite analysis, organize insight, and generate impact at a pace traditional operating teams cannot match. Hierarchy and red tape will not constrain you; instead, you will have both the latitude and the mandate to establish clarity, foster alignment, and act decisively. If you are motivated by transforming intricate operational challenges into scalable, repeatable success, this role will be a strong fit. Apply if you are prepared to lead transformation work that redefines performance across an entire software portfolio.
What you will be doing
- Spearheading cross-functional customer renewal initiatives that prevent ≥$2M ARR churn each quarter through root cause identification and coordinated action across product, support, and finance teams.
- Directing cloud optimization projects that deliver $500K or more in quarterly AWS cost reductions while preserving performance standards and system reliability.
- Overseeing acquisition diligence and integration playbooks to identify critical risks and synergy opportunities — and achieve measurable margin gains in the first quarter post-close.
- Applying Claude Code or comparable platforms (Codex, Gemini CLI) to produce reproducible analytical outputs, automate operational processes, and enhance both speed and precision of delivery.
- Building alignment among cross-functional stakeholders and ensuring programs are delivered on schedule, on target, and with validated financial results.
- Producing weekly executive reporting that clearly communicates progress, obstacles, and confirmed financial impact.
What you will NOT be doing
- Reporting on results you are not responsible for delivering — you are accountable for driving outcomes, not merely tracking them.
- Working in isolation — your initiatives span multiple products, functions, and business units to generate enterprise-level value.
- Spending time on manual data work or low-impact administrative tasks — your approach centers on AI-enabled execution.
- Waiting for approval, consensus, or instruction — this position demands operators who build alignment and execute with urgency.
- Depending exclusively on manual analytical methods — you are expected to employ AI tooling to amplify and scale your output.
- Getting mired in planning sessions, governance rituals, or slide production — weekly updates are streamlined, metric-driven, and outcome-focused.
Key responsibilities
Architect and execute portfolio-wide transformation initiatives that produce measurable improvements in retention, cloud efficiency, and acquisition integration — with executive exposure 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 data sets and convert insights into validated outcomes of ≥$500K.
- Track record optimizing cloud infrastructure expenses (AWS or equivalent) with documented examples of cost savings and sustained performance.
- Strong financial acumen: 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 analytical tasks and enhance execution quality.
- Ability to work remotely with a minimum of 6 hours overlap with the CST time zone.
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