Head of Cloud
$200,000 USD/year Pay is set based on global value, not the local market. Most roles = hourly rate x 40 hrs x 50 weeks 

Not accepting applications on crossover.com at this time.

Description

There's a fundamental inefficiency in the SaaS world: operations traditionally don't scale. A typical VP of SaaS Operations oversees 1-3 products with headcount that grows linearly—add more products, add more people. Trilogy is demonstrating a different model. We're acquiring one SaaS company monthly and running 47+ products (expanding toward 100+) with team growth that's sublinear, proving that operations scale through 80-90% automation rather than proportional hiring.

This isn't routine operational maintenance. You'll drive the operational execution that supports 12 acquisitions annually. This is neither a corporate IT position nor an infrastructure management function. This is a hands-on leadership opportunity for someone who has built and owned SaaS Operations at a SaaS organization, not merely contributed as a team member. The right candidate combines technical depth with leadership capability, someone energized by designing operational frameworks that scale, embedding automation, and navigating high-impact operational decisions. You'll own the evolution of SaaS Ops across a varied portfolio of SaaS businesses, guaranteeing smooth product integrations and leveraging AI to build an automated, exceptionally efficient operations engine.

You'll collaborate with world-class colleagues spanning Engineering, Product, and C-Suite leadership to develop and deliver this vision. If you hold firm convictions about how SaaS Operations should function, relish the complexity of optimizing multi-product ecosystems, and want to pioneer AI-driven operations, this role is for you.

What you will be doing

  • Integrate newly acquired SaaS products into our standardized Ops framework: provision infrastructure-as-code, connect observability tools, establish SLOs, apply cost tagging, and generate runbooks.
  • Examine AWS cost shifts at the product level, identify root causes (change requests, workload fluctuations, pricing adjustments, inefficiency), and record findings in the Cost Change Registry.
  • Transform deterministic L2 operational runbooks into automated processes (Python/Go/IaC/AI-assisted).
  • Track uptime, MTTR, MTTD relative to product-specific SLOs; flag violations with incident analysis and corrective action documentation.

What you will NOT be doing

  • Supervising the repetitive manual work of conventional SaaS Ops; your emphasis will be automation and AI-driven innovation
  • Running operations for just one product; you'll be navigating complexity across hundreds of products within our SaaS portfolio
  • Accepting current practices; you'll be expected to challenge and transform operations using AI technologies

Key responsibilities

  • Lead a highly efficient, AI-powered SaaS Ops function delivering outstanding reliability, cost optimization, and frictionless operations for an expanding portfolio of acquired SaaS businesses

Candidate requirements

  • A minimum of 5 years managing and owning SaaS Ops in support of enterprise customers
  • Track record of personal accountability for MTTR/MTTD and incident response
  • Experience owning AWS budget targets for at least one SaaS product or portfolio
  • Demonstrated application of AI and automation technologies to SaaS operations (i.e., you've deployed at least one AI-assisted operational workflow - AIOps, predictive alerting, automated remediation, cost optimization ML - that reduced manual operational effort)
  • Infrastructure-as-Code proficiency using Terraform/CloudFormation including state management and CI/CD integration
  • AWS platform expertise spanning 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

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Fabiano Lucchese
Fabiano  |  SVP of Software Engineering
Brazil

Does your company encourage your natural creativity? This Brazilian engineering leader rediscovered his purpose after unleashing both his an...

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