Description
This role is designed for operators who take full ownership of multi-million-dollar business outcomes—delivering results, not simply advising or tracking them. You will assume responsibility for the most critical operational priorities across a global software portfolio and convert complexity into concrete financial performance. You'll design the programs, lead the execution, and watch your contributions reflect directly in margin improvement, customer retention, and acquisition integration success.
Trilogy operates a large and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant untapped financial opportunity. You will be accountable for the transformations that unlock that value. Whether it's driving a $2M quarterly renewal uplift program, reducing cloud infrastructure costs while preserving system performance, or integrating a newly acquired company into the Trilogy operating model in 30 days, your efforts will have direct visibility at the executive level. Your work will shape profitability across a wide array of business units.
This position is suited for candidates who perform best in environments characterized by high visibility and substantial autonomy. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, organize insights, and produce impact at a velocity that exceeds traditional operating functions. Hierarchical constraints and bureaucratic friction will not limit you; instead, you'll have both the latitude and the mandate to establish clarity, secure alignment, and act with conviction. If you are motivated by the challenge of transforming intricate operational problems into scalable, repeatable successes, this role offers that opportunity. Consider applying if you are prepared to lead work that redefines how an entire software portfolio operates.
What you will be doing
- Directing enterprise-wide customer renewal initiatives that avert ≥$2M in annual recurring revenue churn each quarter by diagnosing underlying issues and orchestrating coordinated remediation across product, support, and finance teams.
- Overseeing cloud cost optimization programs that cut AWS expenditure by $500K or more quarterly without compromising performance or system reliability.
- Managing acquisition due diligence and integration protocols that identify critical risks and value-creation opportunities—then deliver quantifiable margin gains within the first quarter post-close.
- Deploying Claude Code or comparable platforms (Codex, Gemini CLI) to construct reusable analytical frameworks, automate operational processes, and enhance both speed and precision of delivery.
- Coordinating cross-functional stakeholders to ensure initiatives are completed on schedule, meet targets, and produce validated financial outcomes.
- Producing executive-level weekly reports that clearly present progress, obstacles, and verified financial impact.
What you will NOT be doing
- Providing status updates on initiatives you do not control—you are responsible for both driving execution and achieving results, not merely tracking them.
- Working in isolation—your mandate spans multiple products, functions, and business units to unlock enterprise-level value.
- Spending time on repetitive manual analysis or low-impact administrative tasks—you are expected to default to AI-enabled execution.
- Seeking approval, direction, or consensus before acting—this role requires operators who build alignment autonomously and move with urgency.
- Depending exclusively on traditional analysis methods—AI tooling is a core expectation for accelerating and scaling your output.
- Losing momentum in planning cycles, governance processes, or presentation development—weekly reporting is concise, metric-driven, and outcome-focused.
Key responsibilities
Architect and execute transformation programs across the portfolio that demonstrably enhance customer retention, cloud cost efficiency, and acquisition integration performance—with direct executive oversight and measurable impact.
Candidate requirements
- 5+ years directing cross-functional operational or transformation programs with ≥$3M in annual financial impact.
- Demonstrated capability to interpret large, complex datasets and convert findings into validated outcomes of ≥$500K.
- Track record optimizing cloud infrastructure expenses (AWS or similar platforms) with documented examples of cost reductions and sustained performance.
- Solid financial acumen: interpreting P&L statements, budgeting, ROI modeling, and applying financial reasoning to prioritization decisions.
- Working knowledge of AI-driven tools such as Claude Code, Codex, or Gemini CLI for automating analysis and improving execution quality.
- Ability to work remotely with a minimum of 6 hours of overlap with the CST time zone.
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