Senior Principal Architect, Trilogy (Remote) - $200,000/year USD

Traditional SaaSOps teams across the SaaS industry are falling behind, locked into manual workflows and reactive firefighting rather than building proactive, AI-first automation. The result: millions wasted on inefficient cloud infrastructure, recurring downtime, and stunted growth trajectories. Trilogy is charting a different course—acquiring a minimum of one SaaS company each month and executing aggressive AI transformation to engineer the industry's most sophisticated, fully automated SaaS Ops capability.

Our portfolio spans multiple SaaS businesses, each with unique architectural footprints, customer bases, and operational demands. Rather than viewing SaaS Ops as overhead, we position it as strategic infrastructure. We are constructing an AI-enabled, best-in-class SaaS Ops function engineered to deliver maximum uptime, operational efficiency, and cloud cost optimization across a portfolio of dozens of products. This role offers the chance to architect and implement SaaS Ops strategy at enterprise scale, combining automation, artificial intelligence, and operational design excellence to establish a new benchmark for the industry.

This is not infrastructure management or corporate IT oversight. This is a hands‑on leadership position requiring someone who has independently built and owned SaaS Ops within a SaaS organization—not merely contributed as a team member. We seek a technical authority first and a leader second: someone who excels at designing scalable architectures, embedding automation deeply, and executing high‑impact operational decisions. You will define the trajectory of SaaS Ops across a varied SaaS portfolio, driving seamless product integrations and deploying AI to construct a highly efficient, automated operations engine.

You will collaborate with exceptional talent spanning Engineering, Product, and executive leadership to bring this vision to life. If you hold strong convictions about how SaaS Ops should operate, relish the complexity of multi‑product optimization, and want to lead AI‑powered operational innovation, this role is for you. Apply now to claim a defining opportunity in your career.

What You Will Be Doing

• Establish and deploy world‑class SaaS Ops strategies rooted in deep operational expertise and well‑formed perspectives on excellence in operations
• Drive critical decisions around operational standards, AI infrastructure, and process architecture to safeguard reliability, security, and cost efficiency across the entire portfolio
• Design and refine a repeatable onboarding framework that integrates newly acquired SaaS products into a unified SaaS Ops function with minimal operational friction
• Leverage AI‑driven tools to their fullest extent, optimizing automation, cost management, and operational performance

What You Won’t Be Doing

• Managing the repetitive manual work typical of legacy SaaS Ops; your mandate is automation and AI‑led transformation
• Operating within a single‑product scope; you'll be architecting solutions across hundreds of products within our SaaS portfolio
• Accepting conventional approaches; you will be expected to challenge norms and reinvent operations using AI technology

Senior Principal Architect Key Responsibilities

• Build and sustain a high‑efficiency, AI‑driven SaaS Ops function delivering outstanding reliability, cost optimization, and frictionless operations across an expanding portfolio of acquired SaaS businesses

Basic Requirements

• At least 5 years of experience managing and owning SaaS Ops supporting enterprise customers
• Experience owning SaaS Ops and leading major cloud migrations at an SME with enterprise customers
• Experience applying AI and automation technologies to SaaS operations
• Advanced AWS and DevOps skills (including Docker and Kubernetes)

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.

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 $100 USD/hour, which equates to $200,000 USD/year assuming 40 hours per week and 50 weeks per year. The payment period is weekly.

We look forward to meeting you!

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