Description
If you’re the kind of operator who wants to own multi-million-dollar outcomes — not advise, not report, but deliver — this role is built for you. You’ll take charge of the highest-stakes operational challenges across a global software portfolio and turn ambiguity into measurable financial impact. You’ll architect the programs, drive the execution, and see your work show up directly in margin, retention, and acquisition integration performance.
Trilogy runs a large, diverse portfolio of enterprise software companies, each with complex operational patterns and material financial upside waiting to be unlocked. You’ll lead the transformations that make that upside real. Whether you’re scaling a $2M/quarter renewal uplift initiative, cutting cloud costs without touching performance, or onboarding a newly acquired business into the Trilogy model within 30 days, your work will be visible at the top of the organization. You will directly influence profitability across dozens of business units.
This role is designed for a candidate who thrives in high-exposure, high-autonomy environments. You’ll use advanced AI tools like Claude Code to accelerate analysis, structure insights, and drive impact faster than traditional operating teams can move. You won’t be bound by hierarchy or bureaucracy; you’ll have the space — and the expectation — to create clarity, build alignment, and execute decisively. If you’re energized by turning complex operational puzzles into consistent, repeatable wins, you will excel here. Apply if you’re ready to lead transformative work that changes how an entire software portfolio performs.
What you will be doing
- Leading cross-functional customer renewal programs that prevent ≥$2M ARR churn per quarter by identifying root causes and aligning product, support, and finance on coordinated fixes.
- Running cloud optimization initiatives that reduce AWS spend by $500K or more per quarter while maintaining performance and reliability.
- Executing acquisition diligence and integration playbooks that surface key risks and synergies — and deliver measurable margin improvements within the first post-acquisition quarter.
- Using Claude Code or similar tools (Codex, Gemini CLI) to build reproducible analyses, automate operational workflows, and increase the speed and accuracy of execution.
- Aligning cross-functional partners and ensuring initiatives land on time, on target, and with validated financial outcomes.
- Delivering weekly, executive-facing reporting that transparently communicates progress, blockers, and validated financial impact.
What you will NOT be doing
- Reporting on outcomes you don’t own — you’re accountable for driving and delivering results, not just observing them.
- Operating in silos — your work cuts across products, functions, and businesses to drive enterprise-wide gains.
- Wasting cycles on manual analysis or low-leverage busywork — your default is AI-accelerated execution.
- Waiting for consensus, direction, or permission — this is a role for operators who create alignment and move fast.
- Relying solely on manual analysis — you’re expected to use AI tooling to accelerate and scale your work.
- Getting bogged down in planning, governance, or decks — weekly reporting is structured, focused, and tied to real metrics.
Key responsibilities
Design and deliver portfolio-wide transformation programs that measurably improve retention, cloud efficiency, and acquisition integration — with executive visibility and direct & impact.
Candidate requirements
- 5+ years leading multi-functional operational or transformation initiatives with ≥$3M annual financial impact.
- Proven ability to analyze large, complex datasets and translate insights into validated outcomes of ≥ $500K.
- Experience optimizing cloud infrastructure costs (AWS or equivalent) with clear examples of savings and performance preservation.
- Strong financial literacy: P&L interpretation, budgeting, ROI modeling, and prioritization using financial logic.
- Familiarity with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and improve execution.
- Remote work capability with at least 6 hours of CST overlap.
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