Description
This position is designed for operators prepared to own multi-million-dollar financial results—not merely provide input or generate reports, but deliver verified outcomes. You will assume responsibility for the most critical operational challenges within a global software portfolio and convert uncertainty into quantifiable financial value. You will design the strategic programs, lead the implementation, and observe your contributions materialize directly in margin expansion, customer retention, and acquisition integration metrics.
Trilogy operates an expansive, varied portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant untapped financial opportunity. You will spearhead the transformation efforts that convert that opportunity into realized gains. Whether you are managing a $2M per quarter renewal uplift program, reducing cloud expenditures while preserving system performance, or integrating a newly acquired company into the Trilogy operating framework within 30 days, your contributions will be visible to senior leadership. Your work will directly shape profitability across multiple business units.
This role suits a professional who excels in high-visibility, high-independence settings. You will leverage sophisticated AI technologies such as Claude Code to expedite analysis, organize insights, and deliver results more rapidly than conventional operational teams. You will not be constrained by organizational layers or procedural friction; you will possess both the latitude and the mandate to establish clarity, secure alignment, and act with conviction. If you find energy in transforming intricate operational problems into dependable, scalable successes, you will thrive in this environment. Proceed with your application if you are prepared to drive transformational initiatives that redefine how an entire software portfolio operates.
What you will be doing
- Directing cross-functional customer renewal efforts that avert ≥$2M ARR churn each quarter by diagnosing underlying issues and coordinating product, support, and finance teams on unified corrective actions.
- Overseeing cloud optimization projects that decrease AWS expenditure by $500K or more quarterly while sustaining performance and system reliability.
- Implementing acquisition due diligence and integration frameworks that reveal critical risks and synergy opportunities—and produce measurable margin enhancement within the first quarter following acquisition.
- Leveraging Claude Code or comparable platforms (Codex, Gemini CLI) to construct repeatable analyses, automate operational processes, and enhance execution velocity and precision.
- Coordinating cross-functional stakeholders and ensuring programs are delivered on schedule, on target, and with confirmed financial results.
- Producing weekly executive-level reports that transparently convey progress, obstacles, and verified financial impact.
What you will NOT be doing
- Documenting outcomes without ownership — you are responsible for driving and achieving results, not simply tracking them.
- Working in isolation — your initiatives span products, functions, and business entities to generate enterprise-level value.
- Spending time on manual analysis or low-impact administrative tasks — your standard approach is AI-enhanced execution.
- Waiting for stakeholder consensus, executive guidance, or formal approval — this role demands operators who generate alignment and act decisively.
- Depending exclusively on manual analytical methods — you are expected to employ AI tooling to accelerate and expand your impact.
- Becoming mired in extended planning, governance frameworks, or presentation development — weekly updates are concise, targeted, and anchored to actual metrics.
Key responsibilities
Architect and execute portfolio-level transformation initiatives that demonstrably enhance retention, cloud cost efficiency, and acquisition integration outcomes—with executive oversight and direct impact.
Candidate requirements
- 5+ years directing multi-functional operational or transformation programs with ≥$3M annual financial impact.
- Demonstrated capability to examine large, complex datasets and convert insights into validated results of ≥$500K.
- Background in optimizing cloud infrastructure expenditures (AWS or equivalent) with documented examples of cost reduction and sustained performance.
- Solid financial acumen: P&L analysis, budgeting, ROI modeling, and decision prioritization based on financial rationale.
- Working knowledge of AI tools including Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution efficiency.
- Ability to work remotely with at least 6 hours of daily overlap with the CST time zone.
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