SVP of Operational Transformation, Trilogy

SVP of Operational Transformation, Trilogy (Remote) - $400,000/year USD 1 day ago Be among the first 25 applicants This range is provided by Crossover. Your actual pay will be based on your skills and experience — talk with your recruiter to learn more. Base pay range $200.00/hr – $200.00/hr This role is built for operators who own multi‑million‑dollar outcomes—not those who advise on them or simply report findings. You will assume direct accountability for the most critical operational challenges within a global software portfolio, converting uncertainty into concrete financial results. Your remit includes designing the programs, leading their execution, and seeing your efforts reflected in margin expansion, retention gains, and acquisition integration success. Trilogy oversees a broad, diversified portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant financial opportunity awaiting activation. You will spearhead the transformations that unlock that value. Your initiatives may range from scaling a $2M per quarter renewal uplift program to reducing cloud expenses without sacrificing performance, or integrating a newly acquired company into the Trilogy operating model in 30 days. Your contributions will be visible at the executive level and will directly shape profitability across multiple business units. This position is tailored for candidates who excel in high‑visibility, high‑autonomy settings. You will leverage cutting‑edge AI tools such as Claude Code to expedite analysis, organize insights, and deliver impact at a pace that outstrips conventional operating teams. Freed from hierarchical constraints and bureaucratic friction, you will be expected to establish clarity, forge alignment, and act decisively. If you are motivated by transforming intricate operational challenges into dependable, scalable victories, this role will suit you. Apply if you are prepared to lead transformative initiatives that redefine performance across an entire software portfolio. What You Will Be Doing Driving cross‑functional customer renewal programs that avert ≥$2M ARR churn per quarter by diagnosing root causes and coordinating product, support, and finance teams around unified corrective action. Overseeing cloud optimization efforts that cut AWS expenditure by $500K or more quarterly while preserving system performance and reliability. Managing acquisition diligence and integration frameworks that uncover critical risks and synergies—delivering quantifiable margin enhancement within the first quarter post‑acquisition. Applying Claude Code or comparable tools (Codex, Gemini CLI) to construct replicable analyses, automate operational processes, and enhance both execution speed and precision. Coordinating cross‑functional stakeholders to ensure initiatives complete on schedule, meet targets, and achieve verified financial outcomes. Producing weekly executive‑level reports that clearly convey progress, obstacles, and confirmed financial impact. What You Won’t Be Doing Reporting on results you do not own—you are responsible for driving and delivering outcomes, not merely tracking them. Working in isolation—your initiatives span products, functions, and business units to generate portfolio‑wide value. Spending time on manual analysis or low‑impact tasks—your standard approach is AI‑enabled execution. Waiting for consensus, instruction, or approval—this role demands operators who establish alignment and act swiftly. Depending exclusively on manual methods—you are expected to deploy AI tooling to scale and accelerate your efforts. Becoming mired in planning cycles, governance frameworks, or slide decks—weekly updates are concise, structured, and anchored to tangible metrics. SVP Of Operational Transformation Key Responsibilities Architect and execute portfolio‑wide transformation programs that yield measurable improvements in retention, cloud efficiency, and acquisition integration—with executive‑level visibility and direct impact. Basic Requirements 5+ years leading cross‑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. Track record optimizing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and maintained performance. Strong financial acumen: P&L interpretation, budgeting, ROI modeling, and prioritization grounded in financial logic. Working knowledge of AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution. Ability to work remotely with at least 6 hours of CST overlap. 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. 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. Consult for more details on this topic. Crossover Job Code: LJ-5710‑CA‑Toronto‑SVPofOperation Seniority level: Executive Employment type: Full‑time Job function: Management, Engineering, and Strategy/Planning Industries: Software Development, Business Consulting and Services, Venture Capital and Private Equity Principals Referrals increase your chances of interviewing at Crossover by 2x. #J-18808-Ljbffr