Vice President Strategy and Operations, Trilogy (Remote) - $400,000/year USD

This role is designed for operators who are ready to directly own outcomes worth millions of dollars — not to consult, analyze, or present, but to execute and deliver. You will assume responsibility for the most critical operational priorities spanning a global software portfolio and convert complexity into verified financial results. You will design the programs, lead the execution, and witness your contributions reflected in margin performance, customer retention metrics, and post-acquisition integration success.

Trilogy operates a broad, diversified collection of enterprise software businesses, each presenting intricate operational dynamics and significant financial opportunity ready to be realized. You will spearhead the transformations that unlock that potential. Whether you are driving a $2M per quarter renewal uplift program, reducing cloud infrastructure costs while preserving system performance, or integrating a newly acquired company into the Trilogy operating model in under 30 days, your contributions will be recognized at the executive level. Your work will directly shape profitability across multiple business units.

This position is built for individuals who perform best in settings that offer high visibility and significant autonomy. You will leverage cutting-edge AI capabilities such as Claude Code to expedite analysis, organise insights, and achieve impact at a pace that surpasses traditional operating structures. You will not be constrained by organisational layers or procedural friction; instead, you will have both the latitude and the mandate to establish clarity, secure alignment, and act with conviction. If you are motivated by converting multifaceted operational challenges into reliable, scalable successes, this role will suit you. Apply if you are prepared to drive transformational initiatives that redefine performance across an entire software portfolio.

What You Will Be Doing

• Driving cross-functional customer renewal initiatives that prevent churn of ≥$2M ARR each quarter by diagnosing underlying causes and coordinating product, support, and finance teams on unified solutions.
• Overseeing cloud cost optimisation projects that cut AWS expenditure by $500K or more per quarter without compromising performance or system reliability.
• Managing acquisition due diligence and integration frameworks that uncover critical risks and synergy opportunities — delivering measurable margin gains in the first quarter following acquisition.
• Applying Claude Code or comparable platforms (Codex, Gemini CLI) to create reusable analytical models, automate operational processes, and enhance both velocity and precision of delivery.
• Coordinating cross-functional stakeholders to ensure initiatives are completed on schedule, meet targets, and produce validated financial outcomes.
• Producing weekly executive reporting that clearly articulates progress, obstacles, and confirmed financial impact.

What You Won’t Be Doing

• Reporting on results outside your direct ownership — you are responsible for executing and delivering outcomes, not merely tracking them.
• Working in isolation — your initiatives span products, functions, and business units to generate enterprise-level value.
• Spending time on manual data work or low-impact tasks — AI-driven execution is your standard approach.
• Waiting for approval, guidance, or consensus — this role demands operators who establish alignment and act decisively.
• Depending exclusively on manual methods — you are required to integrate AI tools to accelerate and scale your efforts.
• Becoming mired in planning cycles, governance layers, or slide decks — your weekly reporting is concise, structured, and anchored in real metrics.

Key Responsibilities

• Design and execute portfolio-wide transformation programs that produce 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 programs with ≥$3M in annual financial impact.
• Demonstrated capability to analyse large, complex datasets and convert insights into validated outcomes of ≥$500K.
• Experience reducing cloud infrastructure costs (AWS or equivalent) with documented examples of savings and sustained performance.
• Strong financial acumen: P&L analysis, budgeting, ROI modelling, and prioritisation driven by 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.

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.