SVP of Portfolio Operations, Trilogy

Overview SVP of Portfolio Operations, Trilogy (Remote) – $400,000/year USD. This role leads high-impact operational work across a global software portfolio, owning critical programs from design to execution and driving measurable financial results. What You Will Be Doing Directing enterprise-wide customer renewal initiatives that avert ≥$2M ARR churn each quarter by diagnosing issues and coordinating product, support, and finance around unified solutions. Managing cloud cost reduction programs that achieve $500K+ quarterly savings on AWS infrastructure while preserving performance and reliability. Overseeing acquisition due diligence and integration frameworks that identify risks and opportunities, delivering quantifiable margin gains in the first quarter after acquisition. Applying AI tools (e.g., Claude Code, Codex, Gemini CLI) to build repeatable analytical models, automate processes, and increase execution velocity and precision. Coordinating cross-functional stakeholders to ensure programs deliver on schedule, meet targets, and produce verified financial results. Producing weekly executive-level reports that clearly present progress, obstacles, and the confirmed financial impact. What You Won’t Be Doing Documenting results you do not directly control — you are responsible for driving and achieving outcomes, not merely tracking them. Working in isolation — initiatives span products, departments, and business units to unlock enterprise-wide value. Spending time on repetitive manual analysis or low-impact administrative tasks — AI-driven execution is the standard approach. Waiting for approvals, instructions, or agreement — this role demands operators who build alignment and execute with speed. Depending exclusively on manual methods — you are required to use AI-enabled tools to amplify and scale contributions. Getting mired in planning sessions, governance routines, or slide preparation — weekly reporting is concise, disciplined, and anchored to tangible metrics. SVP Of Portfolio Operations – Key Responsibilities Architect and execute portfolio-wide transformation initiatives that produce measurable improvements in customer retention, cloud cost efficiency, and acquisition integration, with direct executive oversight and clear financial impact. Basic Requirements 5+ years driving cross-functional operational or transformation projects with ≥$3M in annual financial impact. Ability to interpret large, complex data sets and convert findings into validated outcomes of ≥$500K. Track record optimizing cloud infrastructure expenses (AWS or equivalent) with documented cost savings and maintained performance. Solid financial acumen: P&L analysis, budget planning, ROI evaluation, and decision-making grounded in financial rationale. Working knowledge of AI platforms such as Claude Code, Codex, or Gemini CLI to automate analytical tasks and enhance execution quality. Ability to work remotely with a minimum of 6 hours overlap with CST. About Trilogy Hundreds of software businesses run on the Trilogy Business Platform. Trilogy is known for seeking top talent, innovating technology, and incubating new businesses. We focus on customer-facing designs and scalable cloud-based solutions. This is a full-time, long-term role with compensation aligned to market and performance. Working with us This is a full-time (40 hours per week) independent contractor position with Crossover as a Contractor of Record. Compensation is $200 USD/hour, totaling $400,000/year assuming 40 hours/week and 50 weeks/year. The payment period is weekly. For details, see Crossover Job Code: LJ-5710-CA-Toronto-SVPofPortfolio Note: EEO statements and job-related disclosures as required by law should be included here by the employer. #J-18808-Ljbffr