Description
This role is designed for operators who take ownership of multi-million-dollar outcomes — not those who observe, advise, or report on them. You will assume direct responsibility for the most critical operational challenges spanning a global software portfolio, converting complexity and uncertainty into concrete financial performance. You will design the programs, execute the strategy, and watch your work translate immediately into improved margins, retention rates, and acquisition integration results.
Trilogy operates a broad and diversified portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant untapped financial potential. You will spearhead the transformations required to capture that potential. Whether it's executing a $2M per quarter renewal uplift program, reducing cloud infrastructure costs while preserving system performance, or integrating a newly acquired company into Trilogy's operating model in 30 days, your contributions will be highly visible to senior leadership. Your decisions will directly shape profitability across multiple business units.
This position suits 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 a pace that exceeds traditional operating models. You will not be constrained by organizational hierarchy or procedural overhead; instead, you will be empowered — and expected — to establish clarity, secure alignment, and act with conviction. If you find energy in solving intricate operational problems and building scalable, repeatable systems for success, this role will suit you well. Apply if you are prepared to lead transformative initiatives that redefine 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 underlying issues and coordinating product, support, and finance teams around unified solutions.
- Managing cloud cost optimization projects that cut AWS expenditures by $500K or more quarterly without compromising performance or system reliability.
- Overseeing acquisition due diligence and integration frameworks that identify critical risks and opportunities — delivering quantifiable margin gains within the first quarter post-acquisition.
- Applying Claude Code or comparable platforms (Codex, Gemini CLI) to produce reusable analyses, automate operational processes, and enhance both execution speed and precision.
- Coordinating cross-functional stakeholders to ensure initiatives are completed on schedule, meet targets, and produce verified financial results.
- Providing weekly executive-level updates that clearly outline progress, obstacles, and validated financial impact.
What you will NOT be doing
- Reporting on outcomes without ownership — you are responsible for driving and delivering measurable results, not merely tracking them.
- Working in functional isolation — your initiatives span products, departments, and business units to generate enterprise-level value.
- Spending time on manual data work or low-impact administrative tasks — your standard approach is AI-enhanced execution.
- Waiting for approval, consensus, or explicit instruction — this role demands operators who build alignment proactively and act decisively.
- Depending exclusively on manual analytical methods — you are expected to integrate AI tools to scale and accelerate your contributions.
- Becoming mired in governance processes, planning cycles, or presentation decks — weekly reporting is concise, outcome-focused, and metric-driven.
Key responsibilities
Architect and execute portfolio-wide transformation programs that generate measurable improvements in retention, cloud efficiency, and acquisition integration — with direct executive visibility and tangible impact.
Candidate requirements
- 5+ years leading cross-functional operational or transformation programs with ≥$3M annual financial impact.
- Demonstrated capability to analyze complex, large-scale datasets and convert insights into validated outcomes of ≥$500K.
- Track record optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of cost savings and maintained performance.
- Strong command of financial concepts: P&L analysis, budgeting, ROI modeling, and decision-making grounded in financial rationale.
- Working knowledge of 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 overlap with the CST time zone.
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