Technical Operations Leader · Cloud Infrastructure & Reliability

I keep complex systems running and move them forward.

20+ years leading technical operations for SaaS and hosted platforms. I've run a team through a company-wide move to cloud delivery, then went back to hands-on AWS, security and SRE work. When something breaks, I follow the logs and metrics to the root cause. I work comfortably between executives, customers and engineers.

20+ yrsIT and technical operations
115+customer organizations moved to hosted delivery
62%hosted revenue growth over five years
32%AWS spend reduction

About

An operations leader who went back to the console on purpose.

I spent 20 years at Rapattoni, a SaaS and hosted-software provider for real-estate associations and MLSs. I started as a technical contributor and became Manager of Technical Operations, leading about ten people across support, infrastructure, hosted operations, implementations, integrations and QA.

The biggest thing we did was move the business from customer-hosted software to a hosted, cloud-delivered model. I led the operational side of that shift: playbooks, cutovers, customer conversations and reporting to the VPs and CTO.

In 2024 I chose to go deep on modern cloud operations. At PropStream I worked hands-on in AWS on release management, security remediation, monitoring and on-call, and cost governance. Now I bring both sides together: I understand the work well enough to lead it, and I know how to lead people through it.

Selected work

Four projects, told plainly.

What the situation was, what I actually did, and what changed.

Rapattoni · Cloud migration

Moving 115+ customer organizations off their own servers

Manager of Technical Operations · multi-year program

90%+of customers migrated
  1. ReadinessEnvironment and data checks
  2. Data moveSecure transfer
  3. Test envCustomer validates
  4. CutoverScheduled, communicated
  5. RollbackReady at every step
  6. Sign-offCustomer approval

Situation

Customers ran the company's association-management software on their own infrastructure. Every install was different, support was expensive, and cloud-native competitors were starting to pull customers away.

What I did

  • Made the case for a hosted, private-cloud delivery model and ran its operational rollout
  • Turned one-off migrations into a repeatable playbook the team could run
  • Worked directly with hesitant customers on their objections and approvals
  • Reported progress and risk to the VPs and CTO

Result

  • 115+ organizations and 1,300+ users on hosted delivery
  • Customers kept software they knew without running servers, which helped keep them from leaving
  • Supported hosted revenue growth from about $1.6M to $2.6M over five years
Windows ServerActive DirectorySQL ServerHosted app deliveryPrivate cloudChange management

PropStream · Cloud cost

Cutting AWS spend by about a third without cutting corners

Cloud Operations & Site Reliability Engineer

~32%AWS spend reduction

Situation

A cloud-first SaaS platform running dev, QA, beta and production environments in AWS, where spend had grown along with them.

What I did

  • Reviewed utilization and rightsized over-provisioned resources
  • Planned reserved-instance and commitment purchases against real usage
  • Cleaned up unused resources
  • Put governance practices in place so the savings held

Result

  • Roughly 32% lower AWS spend
  • Savings kept through ongoing governance, not a one-time cleanup
AWS EC2RDSS3CloudWatchReserved InstancesFinOps practices

PropStream · Security & release operations

Safer releases and security findings driven to closure

Cloud Operations & Site Reliability Engineer

4 envsdev · QA · beta · prod

Situation

Production SaaS with frequent releases, a steady flow of cloud security findings, and an on-call rotation that needed better signal.

What I did

  • Ran blue/green production releases with validation and rollback readiness
  • Worked Wiz and Ionix findings with security and engineering: prioritize, track, resolve
  • Administered CrowdStrike Falcon; worked with AWS WAF and Shield
  • Tuned CloudWatch and PagerDuty alerting; automated remediation with SSM and CloudFormation

Result

  • Every release had a tested way back
  • Security findings tracked through to closure
  • Less manual intervention and faster recovery during incidents
Blue/greenWizIonixCrowdStrike FalconAWS WAF / ShieldPagerDutySSMCloudFormationPostgreSQL

Observability · Root cause analysis

Finding the memory leak instead of buying a bigger server

Log, metric and trace correlation across the stack

Root causefixed in code, not with more resources
  1. SymptomAlerts, slowdowns, restarts
  2. MetricsCloudWatch, New Relic, Datadog
  3. EventsCloudTrail: what changed
  4. LogsInstance and app logs
  5. Root causeEvidence devs can act on

Situation

Backend services degraded over time. The usual response is to scale up and move on: bigger instances, more of them, a higher bill, and the problem comes back anyway.

What I did

  • Correlated performance metrics with CloudTrail events and instance logs to line up the timeline
  • Traced memory growth patterns back to the backend code behind them
  • Handed developers a clear, evidence-backed root cause instead of a vague "it's slow"

Result

  • Memory leaks fixed at the source by development
  • Avoided throwing more infrastructure at a software problem
  • Better working trust between ops and engineering
CloudWatchNew RelicDatadogAWS CloudTrailLog analysisPerformance troubleshootingRCA

Experience

Two companies, 22 years.

One long run of building and leading, then a deliberate move to hands-on cloud work.

Apr 2024 – Aug 2026

Cloud Operations & Site Reliability Engineer

PropStream (Stewart) · Lake Forest, CA

  • AWS operations across dev, QA, beta and production
  • Release management, incident response and on-call
  • Security remediation, PostgreSQL administration and cost governance
Feb 2004 – Mar 2024

Manager of Technical Operations

Rapattoni Corporation · Westlake Village, CA

  • Grew from technical contributor to leading a team of about ten across support, infrastructure, hosted ops, implementations, integrations and QA
  • Hiring, performance management and mentoring; promoted internal talent into larger technical roles
  • Led the move from customer-hosted software to hosted delivery for 115+ organizations
  • Grew API adoption to about 70% of customers through REST integrations and third-party vendor coordination
  • Operational advisor to executive leadership on staffing, modernization and customer retention

Skills

What I've run in production, and what I'm still learning.

Grouped by how deep the experience is.

Production

Used in real environments with real stakes

Cloud
AWS: EC2, RDS, S3, IAM, CloudWatch, SSM, CloudFormation, Route 53, CLI
Infrastructure
Windows Server, Active Directory, Group Policy, Linux, networking, hosted/private cloud
Data
PostgreSQL, SQL Server: administration, backup and recovery
Reliability
PagerDuty, CloudWatch alerting, incident response, post-incident review
Observability & RCA
CloudWatch, New Relic, Datadog, AWS CloudTrail, instance and application logs, performance and root cause analysis
Security
CrowdStrike Falcon, Wiz, Ionix, AWS WAF / Shield, vulnerability management
Delivery
Blue/green releases, Git, GitHub Actions, Jira, Agile/Scrum

Working knowledge

Comfortable using, not my daily specialty

Automation
PowerShell, Bash, SQL; some Python; limited Terraform
Identity
Microsoft Entra ID / Azure
APIs
REST, Postman, Kong Gateway
Practice
SLIs/SLOs, ITIL-aligned incident, problem and change management

Learning now

Certs and courses, completed and in progress

Completed
Kong Gateway Foundations (KGAC-101), 2026
In progress
ITIL 5 Foundation (PeopleCert)
OpenTelemetry (LFS148), Linux Foundation
Coursework
Moorpark College, Cybersecurity & Cloud Infrastructure (CNSE)
Exploring
Model Context Protocol and AI tooling for operations

Notes

Coming soon

Making a portfolio readable by AI agents

How I exposed a personal site to AI assistants through a small read-only MCP endpoint, and what it taught me about where operations and AI tooling meet.

Contact

Hiring for operations, cloud or customer-facing technical leadership?

Email is the fastest way to reach me. I usually reply within a day.