SVP Operations and Transformation, Trilogy (Remote) - $400,000/year USD

This position is designed for operators prepared to own multi-million-dollar financial outcomes — not simply advise on strategy or produce reports, but execute and deliver results. You will assume responsibility for the most critical operational challenges spanning a global software portfolio, transforming complexity and uncertainty into concrete, measurable financial gains. Your role will be to design the programs, lead their execution, and watch your contributions materialize in margin expansion, customer retention, and acquisition integration success.

Trilogy operates a substantial and varied portfolio of enterprise software businesses, each characterised by intricate operational dynamics and significant untapped financial potential. You will spearhead the transformation efforts that convert that potential into reality. From scaling a $2M-per-quarter renewal uplift program to reducing cloud infrastructure expenses without compromising system performance, or integrating a newly acquired company into the Trilogy operating model within a 30-day window — your work will command attention at the highest levels of the organization. You will shape profitability directly across dozens of business units.

This is a role built for candidates who flourish in high-visibility, high-autonomy settings. You will leverage cutting-edge AI tooling such as Claude Code to expedite analysis, structure actionable insights, and achieve impact at a pace that outstrips traditional operating teams. You will not be constrained by hierarchical structures or procedural friction; you will have both the latitude and the mandate to establish clarity, foster alignment, and act decisively. If converting intricate operational challenges into reliable, repeatable victories energises you, you will thrive in this environment. Apply if you are prepared to drive transformative initiatives that redefine how an entire software portfolio performs.

What You Will Be Doing

• Directing cross-functional customer renewal programs that avert ≥$2M ARR churn each quarter by diagnosing root causes and coordinating product, support, and finance teams on unified corrective measures.
• Managing cloud optimization projects that deliver $500K or greater quarterly reductions in AWS expenditure while preserving performance standards and system reliability.
• Implementing acquisition diligence and integration frameworks that identify critical risks and synergy opportunities — and produce quantifiable margin gains within the first quarter following acquisition.
• Employing Claude Code or equivalent tools (Codex, Gemini CLI) to construct reproducible analytical models, automate operational processes, and enhance both the velocity and precision of execution.
• Coordinating cross-functional stakeholders and ensuring programs are delivered on schedule, on target, and with validated financial results.
• Producing weekly executive-level reports that clearly convey progress, obstacles, and verified financial impact.

What You Won’t Be Doing

• Providing commentary on outcomes you do not own — you are responsible for driving and delivering results, not merely documenting them.
• Working in isolation — your initiatives span products, functions, and business units to generate enterprise-level impact.
• Expending effort on manual analysis or low-impact administrative tasks — your standard approach is AI-enhanced execution.
• Waiting for consensus, guidance, or approval — this is a position for operators who generate alignment and act with speed.
• Depending exclusively on manual methods — you are expected to deploy AI tooling to accelerate and scale your efforts.
• Becoming mired in planning cycles, governance processes, or presentation development — weekly reporting is streamlined, precise, and anchored to real metrics.

Key Responsibilities

• Architect and execute portfolio-wide transformation programs that deliver measurable improvements in retention, cloud efficiency, and acquisition integration — with executive-level visibility and direct impact.

Basic Requirements

• 5+ years directing multi-functional operational or transformation initiatives with ≥$3M annual financial impact.
• Demonstrated capability to analyze large, complex datasets and convert insights into validated outcomes of ≥$500K.
• Experience optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of cost savings and performance maintenance.
• Strong financial acumen: P&L interpretation, budgeting, ROI modeling, and prioritisation grounded in financial logic.
• Proficiency with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution quality.
• Remote work capability with a minimum of 6 hours of overlap with the CST time zone.

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for three things: Relentlessly seeking top talent, Innovating new technology, and incubating new businesses. Our technological innovation is spearheaded by a passion for simple customer-facing designs. Our incubation of new businesses ranges from entirely new moon-shot ideas to rearchitecting existing projects for today’s modern cloud-based stack. Trilogy is a place where you can be surrounded with great people, be proud of doing great work, and grow your career by leaps and bounds.

There is so much to cover for this exciting role, and space here is limited. Hit the Apply button if you found this interesting and want to learn more. We look forward to meeting you!

Working with us

This is a full-time (40 hours per week), long-term position. The position is immediately available and requires entering into an independent contractor agreement with Crossover as a Contractor of Record. The compensation level for this role is $200 USD/hour, which equates to $400,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.