Vice President Strategy and Operations, Trilogy (Remote)

This role is designed for operators who own multi-million-dollar results — not those who advise on them or track them. You'll assume direct accountability for the most critical operational challenges spanning a global software portfolio, converting uncertainty into quantifiable financial performance. You'll design the transformation programs, lead their execution, and witness your contributions reflected in retention metrics, margin expansion, and acquisition integration success.

Trilogy operates a broad portfolio of enterprise software businesses, each containing intricate operational dynamics and significant financial opportunity yet to be captured. You'll spearhead the initiatives that unlock that value. From driving a $2M per quarter renewal uplift program to reducing cloud infrastructure spend without degrading system performance, or integrating a newly acquired company into Trilogy's operating model in under 30 days — your efforts will be tracked at the executive level. Your decisions will directly shape profitability across multiple business units.

This position is structured for candidates who perform best in high-visibility, high-independence settings. You'll leverage advanced AI capabilities such as Claude Code to expedite analysis, organize insight, and generate impact at a velocity that outpaces conventional operating structures. Hierarchy and process overhead won't constrain you; instead, you'll have both the latitude and the mandate to establish clarity, secure stakeholder alignment, and act with conviction. If you find energy in solving layered operational challenges and building repeatable systems that scale wins, this environment will suit you. Apply if you're prepared to lead work that reshapes how an entire software portfolio functions.

What You Will Be Doing

• Directing cross-functional customer renewal initiatives that avert ≥$2M in ARR churn each quarter by diagnosing underlying issues and coordinating product, support, and finance teams around unified solutions.
• Managing cloud cost reduction programs that cut AWS expenditure by $500K or more quarterly without compromising system performance or uptime.
• Implementing acquisition due diligence and integration frameworks that uncover critical risks and value-creation opportunities — delivering confirmed margin gains in the first quarter post-close.
• Applying Claude Code or comparable platforms (Codex, Gemini CLI) to construct reusable analytical models, automate operational processes, and enhance both execution speed and precision.
• Building alignment across functional stakeholders and ensuring programs are completed on schedule, meet targets, and produce validated financial results.
• Producing executive-level weekly updates that clearly communicate progress, obstacles, and quantified financial impact.

What You Won’t Be Doing

• Tracking outcomes without ownership — you are responsible for generating and delivering results, not merely documenting them.
• Working in functional isolation — your initiatives span products, departments, and business units to unlock portfolio-wide value.
• Spending time on manual data work or low-impact administrative tasks — AI-powered execution is your standard approach.
• Waiting for approval, guidance, or group agreement — this role requires operators who establish alignment and act swiftly.
• Depending exclusively on traditional analysis — you're expected to integrate AI tooling to amplify and extend your effectiveness.
• Losing momentum in planning cycles, governance reviews, or slide preparation — your weekly reporting is concise, purposeful, and metric-driven.

Vice President Strategy And Operations Key Responsibilities Architect and execute portfolio-wide transformation programs that produce measurable gains in customer retention, cloud cost efficiency, and acquisition integration performance — with direct executive oversight and tangible impact.

Basic Requirements

• 5+ years leading cross-functional operational or transformation programs with ≥$3M in annual financial impact.
• Demonstrated capability to interpret large, complex datasets and convert findings into validated outcomes of ≥$500K.
• Hands-on experience reducing cloud infrastructure costs (AWS or equivalent) with documented examples of cost savings and maintained performance.
• Solid financial acumen: understanding P&L statements, budgeting processes, ROI modeling, and making prioritization decisions grounded in financial rationale.
• Working knowledge of AI platforms such as Claude Code, Codex, or Gemini CLI to streamline analysis and enhance execution quality.
• Ability to work remotely with a minimum of 6 hours daily 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-GB-London-VicePresidentS.002