Lead Cloud Architect, Trilogy (Remote) - $200,000/year USD

The SaaS world harbors an uncomfortable truth: operations resist scale. A conventional VP SaaS Ops typically oversees 1-3 products while adding headcount linearly; expanding the product catalog demands proportional team expansion. Trilogy demonstrates a different model. We integrate one SaaS company monthly and run 47+ products (scaling toward 100+) with sublinear workforce growth, demonstrating that operations scale through 80-90% automation rather than personnel additions.

This role extends beyond maintenance operations. You'll perform the operational execution that supports 12 acquisitions annually. This is neither a corporate IT position nor an infrastructure management assignment. This is a hands-on leadership position for someone who has constructed and owned SaaS Ops at a SaaS organization, not merely participated on the team. The successful candidate combines technical mastery with leadership capability, thriving on architecting scalable operational systems, embedding automation, and rendering high-stakes operational judgments. You'll define the evolution of SaaS Ops across a varied portfolio of SaaS enterprises, guaranteeing frictionless product integrations and deploying AI to forge an automated, maximally efficient operations platform.

You'll collaborate with elite peers spanning Engineering, Product, and C-Suite leadership to design and implement this strategy. If you possess definitive perspectives on SaaS Ops management, welcome the complexity of optimizing multi-product ecosystems, and seek to pioneer AI-driven operations, this opportunity is designed for you.

What You Will Be Doing

* Integrate newly acquired SaaS products into the standardized Ops framework: provision infrastructure-as-code, embed observability stack, establish SLOs, apply cost tagging, and produce runbooks.

* Examine AWS cost fluctuations at the product level, trace to root cause (change request, workload shift, pricing adjustment, inefficiency), record in Cost Change Registry.

* Transform deterministic L2 operational runbooks into automated workflows (Python/Go/IaC/AI-assisted).

* Track uptime, MTTR, MTTD relative to SLOs for each product; escalate violations with incident assessment and corrective action plan.

What You Won’t Be Doing

* Managing the manual burden and monotony of conventional SaaS Ops; your emphasis will rest on automation and AI-driven advancement

* Operating a single product; you'll be navigating complexity across hundreds of products within our SaaS portfolio

* Accepting established practices; you'll be tasked with disrupting and reimagining operations through AI technologies

Lead Cloud Architect Key Responsibilities

* Lead a highly efficient, AI-enabled SaaS Ops function that delivers outstanding reliability, cost optimization, and fluid operations for an expanding portfolio of acquired SaaS businesses

Basic Requirements

* At least 5 years of experience managing and owning SaaS Ops supporting enterprise customers

* Experience maintaining personal accountability for MTTR/MTTD and incident response

* Experience owning AWS budget targets for at least one SaaS product or portfolio

* Experience deploying AI and automation technologies to SaaS operations (i.e., you've implemented at least one AI-assisted operational workflow - AIOps, predictive alerting, automated remediation, cost optimization ML - that reduced manual operational work)

* Infrastructure-as-Code proficiency with Terraform/CloudFormation including state management and CI/CD integration

* AWS platform expertise across EC2, RDS, S3, Lambda, CloudWatch, VPC, IAM, cost structure, and multi-AZ reliability patterns

* Scripting and automation proficiency in Python/Go/Bash with error handling, retry logic, comprehensive logging, and AWS SDK integration

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 $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. Consult www.crossover.com/help-and-faqs for more details on this topic.

Crossover Job Code: LJ-5326-DE-COUNTRY-LeadCloudArchi