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

This role is designed for operators who own outcomes — not advisory roles, not reporting functions, but full accountability for delivering multi-million-dollar results. You will lead high-stakes operational initiatives across a global software portfolio, converting complexity into measurable financial performance. You will design the programs, execute the strategy, and witness your contributions reflected directly in margin expansion, retention rates, and acquisition integration success.

Trilogy manages a broad, diversified portfolio of enterprise software businesses, each characterized by intricate operational dynamics and significant unrealized financial potential. Your responsibility will be to lead the transformations that unlock that potential. From driving a $2M/quarter renewal uplift program to reducing cloud infrastructure costs without sacrificing performance, or integrating a newly acquired company into the Trilogy operating model in 30 days — your contributions will be tracked at the executive level. You will shape profitability across multiple business units.

This position suits candidates who perform best in high-visibility, high-autonomy settings. You will leverage advanced AI capabilities such as Claude Code to expedite analysis, structure decision-making, and execute faster than conventional operating teams. Hierarchy and bureaucracy will not constrain you; instead, you will have the latitude — and the responsibility — to generate clarity, secure alignment, and act with conviction. If you find energy in converting intricate operational challenges into reliable, scalable wins, you belong here. Apply if you are prepared to lead transformational initiatives that redefine how an entire software portfolio operates.

What You Will Be Doing

• Directing cross-functional renewal programs that prevent ≥$2M ARR churn per quarter by diagnosing underlying issues and coordinating product, support, and finance teams around targeted interventions.
• Managing cloud cost reduction initiatives that deliver $500K or more in quarterly AWS savings while preserving system performance and uptime.
• Overseeing acquisition diligence and integration playbooks that uncover critical risks and opportunities — producing measurable margin gains within the first post-close quarter.
• Applying Claude Code or comparable platforms (Codex, Gemini CLI) to construct repeatable analytical frameworks, automate operational processes, and enhance execution velocity and precision.
• Coordinating cross-functional stakeholders to ensure initiatives are delivered on schedule, on target, and with confirmed financial results.
• Producing weekly executive reporting that transparently tracks progress, obstacles, and validated financial outcomes.

What You Won’t Be Doing

• Reporting on results you do not control — you own the execution and delivery of outcomes, not just the documentation of them.
• Working in isolation — your initiatives span products, functions, and business units to unlock enterprise-level value.
• Spending time on manual analysis or low-impact administrative tasks — AI‑accelerated execution is your standard approach.
• Waiting for alignment, instruction, or approval — this role requires operators who build consensus and execute with urgency.
• Depending exclusively on manual methods — you are expected to use AI‑powered tools to scale and expedite your work.
• Losing momentum in planning cycles, governance frameworks, or presentation development — weekly reporting is concise, structured, and metric‑driven.

Vice President Strategy And Operations Key Responsibilities

Architect and execute portfolio‑wide transformation initiatives that produce measurable improvements in retention, cloud cost efficiency, and acquisition integration — with direct executive exposure and tangible impact.

Basic Requirements

• 5+ years leading multi‑functional operational or transformation programs with ≥$3M annual financial impact.
• Demonstrated capability to analyze large, complex datasets and convert insights into validated outcomes of ≥$500K.
• Experience reducing 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 prioritization grounded in financial reasoning.
• Proficiency with AI tools such as Claude Code, Codex, or Gemini CLI to automate analysis and enhance execution quality.
• Ability to work remotely 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.