SVP of Operational Transformation, Trilogy (Remote) - $400,000/year USD

This position is designed for an operator prepared to own—and deliver—multi-million-dollar outcomes rather than simply advise or observe. You will assume full accountability for the most critical operational challenges across a global portfolio of software businesses, transforming uncertainty into quantifiable financial results. You will design the programs, lead the execution, and witness your contributions reflected directly in margin performance, customer retention, and acquisition integration metrics. Trilogy oversees a substantial and varied portfolio of enterprise software companies, each presenting intricate operational dynamics and significant untapped financial potential. You will spearhead the transformations that convert this potential into realized value.

Whether you are executing a $2M per quarter renewal uplift program, reducing cloud expenditure while preserving system performance, or integrating a newly acquired entity into Trilogy's operating model within 30 days, your efforts will command attention at the executive level. Your influence will extend across profitability outcomes for dozens of business units. This position suits a leader who flourishes in settings characterized by high visibility and significant autonomy. You will employ advanced AI capabilities such as Claude Code to expedite analysis, structure strategic insights, and generate impact at a pace traditional operating teams cannot match. Free from rigid hierarchy or procedural constraints, you will have both the latitude—and the mandate—to establish clarity, forge alignment, and act with conviction. If converting intricate operational challenges into scalable, repeatable successes energizes you, this role will be a strong fit. Candidates ready to drive transformative initiatives that redefine portfolio-wide performance are encouraged to apply.

What You Will Be Doing

• Directing cross-functional customer renewal initiatives that avert ≥$2M ARR churn each quarter by diagnosing underlying issues and coordinating corrective action across product, support, and finance.
• Overseeing cloud optimization programs that deliver $500K or greater quarterly reductions in AWS spending without compromising performance or reliability standards.
• Implementing acquisition diligence and integration frameworks that identify critical risks and synergy opportunities — and generate measurable margin gains within the first quarter post-acquisition.
• Leveraging Claude Code or comparable platforms (Codex, Gemini CLI) to construct repeatable analytical models, automate operational processes, and enhance both execution speed and precision.
• Securing cross-functional stakeholder alignment and ensuring initiatives conclude on schedule, meet targets, and deliver validated financial results.
• Producing weekly executive reporting that transparently documents progress, identifies obstacles, and confirms realized financial impact.

What You Won’t Be Doing

• Reporting on results you do not control — you will be held accountable for driving and achieving outcomes, not merely tracking them.
• Functioning in isolation — your initiatives will span products, functions, and business units to unlock enterprise-level value.
• Expending effort on manual data tasks or low-impact administrative work — your standard approach leverages AI-enhanced execution.
• Waiting for consensus, instruction, or approval — this role demands operators who build alignment and act decisively.
• Depending exclusively on traditional analysis methods — you are expected to utilize AI tooling to accelerate and extend your capabilities.
• Becoming mired in planning cycles, governance procedures, or presentation development — weekly reporting is streamlined, targeted, and anchored to concrete metrics.

Key Responsibilities

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

Basic Requirements

• 5+ years directing multi-functional operational or transformation programs with ≥$3M annual financial impact.
• Demonstrated capability to interpret large, complex 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 sustained performance.
• Strong financial acumen: P&L analysis, budgeting, ROI modeling, and decision prioritization grounded in financial reasoning.
• 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.

About Trilogy

Hundreds of software businesses run on the Trilogy Business Platform. For three decades, Trilogy has been known for 3 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.

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.