Job Description
This role is designed for an operator ready to own multi-million-dollar outcomes — not to advise on them, not to track them, but to deliver them. You will lead the most critical operational challenges across a global software portfolio and convert uncertainty into quantifiable financial results. You will design the programs, oversee the execution, and witness your contributions reflected directly in margin performance, customer retention, and acquisition integration success.
Trilogy operates a broad and varied portfolio of enterprise software businesses, each presenting intricate operational dynamics and significant financial opportunity ready to be captured. You will spearhead the transformations that unlock that opportunity. Whether you are driving a $2M per quarter renewal uplift program, reducing cloud expenditure without compromising performance, or integrating a newly acquired company into the Trilogy operating model in 30 days, your efforts will be highly visible to senior leadership. You will directly shape profitability across multiple business units.
This position is intended for a candidate who performs best in high-visibility, high-autonomy settings. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, organize insights, and generate impact more rapidly than conventional operating teams. You will not be constrained by organizational hierarchy or procedural friction; you will have the latitude — and the accountability — to establish clarity, secure alignment, and act decisively. If you are motivated by converting intricate operational challenges into reliable, scalable results, you will thrive in this environment. Apply if you are prepared to lead transformative initiatives that redefine how an entire software portfolio operates.
What You Will Be Doing
Directing cross-functional customer renewal initiatives that prevent ≥$2M ARR churn per quarter by diagnosing underlying causes and coordinating product, support, and finance teams on unified solutions.
Overseeing cloud optimization efforts that decrease AWS expenditure by $500K or more each quarter while preserving system performance and reliability.
Implementing acquisition due diligence and integration frameworks that uncover critical risks and synergies — and produce measurable margin gains within the first quarter following acquisition.
Leveraging Claude Code or comparable platforms (Codex, Gemini CLI) to create reproducible analytical models, automate operational processes, and enhance execution speed and precision.
Coordinating cross-functional stakeholders and ensuring programs are delivered on schedule, on target, and with confirmed financial results.
Producing weekly, executive-level reports that clearly communicate progress, obstacles, and validated financial impact.
What You Won’t Be Doing
Reporting on results you do not own — you are responsible for driving and achieving outcomes, not merely tracking them.
Working in isolation — your initiatives span products, functions, and business units to generate enterprise-wide value.
Spending time on manual analysis or low-impact administrative tasks — your standard approach is AI-enhanced execution.
Waiting for consensus, instruction, or approval — this role requires operators who build alignment and execute rapidly.
Depending exclusively on manual analysis — you are expected to employ AI tooling to accelerate and expand your impact.
Becoming mired in planning cycles, governance structures, or presentation preparation — weekly reporting is streamlined, purposeful, and linked to concrete metrics.
SVP Of Operational Transformation Key Responsibilities
Design and execute portfolio-wide transformation programs that demonstrably enhance retention, cloud efficiency, and acquisition integration — with executive visibility and direct impact.
Basic 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 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.
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 www.crossover.com/help-and-faqs for more details on this topic.
Crossover Job Code: LJ-5710-CA-Toronto-SVPofOperation.004
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