Description
This position is for an operator prepared to take full ownership of multi-million-dollar business outcomes — not to advise from the sidelines or produce reports, but to deliver tangible results. You will assume responsibility for the most critical operational challenges within a global software portfolio and convert complexity into clear financial performance. You will design the programs, execute the strategy, and witness your contributions reflected directly in margin expansion, customer retention metrics, and post-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. Your mandate will be to lead the transformation efforts that unlock this value. From driving a $2M per quarter renewal enhancement program to reducing cloud infrastructure expenses while preserving system performance, or integrating a newly acquired entity into Trilogy's operational framework within 30 days — your impact will be clearly visible to senior leadership. Your decisions will directly shape profitability across numerous business units.
This role suits a candidate who excels in settings that offer high visibility and significant autonomy. You will leverage cutting-edge AI capabilities such as Claude Code to expedite analysis, organize insights, and generate impact more rapidly than conventional operating teams. You will not be constrained by organizational hierarchy or procedural bottlenecks; instead, you will have both the freedom and the responsibility to establish clarity, secure alignment, and act with conviction. If you find energy in transforming intricate operational challenges into scalable, repeatable successes, this role will be an excellent fit. Apply if you are prepared to spearhead transformative initiatives that redefine performance across an entire software portfolio.
What you will be doing
- Directing cross-functional customer renewal initiatives designed to prevent ≥$2M ARR churn per quarter by diagnosing underlying causes and coordinating product, support, and finance teams on targeted solutions.
- Managing cloud cost optimization programs that deliver $500K or greater quarterly AWS savings while safeguarding performance standards and system reliability.
- Overseeing acquisition due diligence and integration frameworks that uncover critical risks and synergy opportunities — producing measurable margin gains within the first quarter following acquisition.
- Applying Claude Code or equivalent platforms (Codex, Gemini CLI) to develop repeatable analytical models, automate operational processes, and enhance both speed and precision of delivery.
- Coordinating cross-functional stakeholders to ensure initiatives are completed on schedule, meet objectives, and achieve verified financial results.
- Producing weekly executive-level reports that clearly communicate progress, identify obstacles, and document validated financial impact.
What you will NOT be doing
- Reporting on results for which you lack ownership — you are responsible for driving and achieving 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-enhanced execution.
- Waiting for approval, guidance, or agreement — this role demands operators who forge alignment and act decisively.
- Depending exclusively on manual methods — you are expected to employ AI tooling to amplify and scale your efforts.
- Being slowed by excessive planning cycles, governance frameworks, or presentation preparation — weekly updates are concise, disciplined, and anchored in real metrics.
Key responsibilities
Architect and execute portfolio-wide transformation programs that demonstrably enhance customer retention, cloud cost efficiency, and acquisition integration outcomes — with direct executive oversight and measurable & impact.
Candidate requirements
- 5+ years leading cross-functional operational or transformation programs with ≥$3M annual financial impact.
- Demonstrated capability to assess large, complex datasets and convert insights into validated results of ≥ $500K.
- 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 prioritization based on financial reasoning.
- Hands-on experience with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution quality.
- Ability to work remotely with a minimum of 6 hours of overlap with the CST time zone.
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