Technical Operations Leader · Cloud Operations & Reliability

Operations leadership with current cloud depth.

20+ years running technical operations for SaaS and hosted platforms, most recently in AWS. I manage operations around six pillars that hold each other up: cost, performance, security, releases, teams and customers. I connect executives, customers and engineers, so business and technical priorities stay aligned.

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

About

A leader who stays close to the work.

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 a distributed team of up to 12 (local, remote and overseas) across technical operations, development, QA, SSO and API/RESO integrations.

The defining project of my time there was moving 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 executive leadership.

In 2024, I joined PropStream to take that experience into AWS. I owned cost optimization, performance monitoring and security operations, and helped modernize how we released software. Now I bring both together: I understand the work well enough to lead it, and I know how to lead people through it.

How I work

Six pillars that hold each other up.

Cost, performance, security, releases, teams and customers all shape each other. Reinforce one and the whole structure gets stronger; let one weaken and the others have to carry its weight. That's why I lead them as one system.

Cost

Make spending visible to the people who drive it, so you can save where you can and invest where it matters.

How I know it's workingSpend trends, and savings reinvested

Performance

Watch the trends that come before degraded service, like saturation, database contention or scaling spikes, so fixes and capacity decisions happen before users notice.

How I know it's workingEarly warnings caught, capacity planned ahead

Security

Give every team early visibility and simple guardrails, so issues get fixed at the first warning sign and security never feels like a roadblock.

How I know it's workingTime to remediate findings

Releases

Ship whenever the business needs to, with a tested way back. Speed and stability aren't a trade-off.

How I know it's workingChange failure rate, rollback time

Teams

Stay close enough to the work to understand the decisions, and clear the path so engineers can focus on engineering. Never a bottleneck, never a micromanager.

How I know it's workingRetention and internal promotions

Customers

Every customer sees change through several lenses. Show each one what's in it for them.

How I know it's workingAdoption and retention

How they connect

A release gets pushed through late at night without clear visibility into logs and metrics. The next morning a backend server's memory starts climbing, and it peaks at 11 AM, in the middle of the company-wide meeting and the busiest hour of the day. Now the business is paying for emergency capacity, the platform is slow, and customers notice. One gap in the release process hit cost, performance and customers at once. Safer releases with a tested rollback, and monitoring that catches the memory trend early, fix the root of all three.

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 · led a distributed team of up to 12

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

↺ Rollback plan ready at every step, so any cutover could be reversed.

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. Hosting also meant a higher bill for the same application, so the move had to make sense to every audience.

What I did

  • Made the case for a hosted, private-cloud delivery model and led its rollout with a distributed team of up to 12
  • Turned one-off migrations into a repeatable playbook the team could run
  • Showed each audience its value: lower total cost for executives, remote access for staff, API access and dashboards for data, a refreshed portal for members
  • Led the API initiative, with read-only access to 1,500+ data fields, adopted by about 70% of customers
  • Reported progress and risk to executive leadership

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

CostPerformance
~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

SecurityReleases
0open critical findings

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

  • Proposed blue/green and canary strategies from 2024 AWS workshops and won approval for blue/green; the team moved releases to production validation with fast rollback, then automated the steps
  • 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
  • Zero open critical findings, with new ones resolved within SLA
  • Releases no longer tied to late-night windows
  • Less manual intervention and faster recovery during incidents
Blue/greenWizIonixCrowdStrike FalconAWS WAF / ShieldPagerDutySSMCloudFormationPostgreSQL

PropStream · Observability & root cause analysis

Finding the memory leak instead of buying a bigger server

Cloud Operations & Site Reliability Engineer

PerformanceCostCustomers
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

Projects

What I've been building.

Independent work since August 2026, built hands-on with AI tools, with the same guardrails I'd expect in production.

New · In daily use

AI Career Research Assistant

Not mass applying. A daily AI assistant that handles the busywork, so my time goes into strong-fit roles and reaching the right person.

  • Ranks roles by fit every morning, flagging fresh, low-competition ones
  • Roles from many sources, scored against my full resume, each with an honest tailored resume
  • Networking prompts: the right contact and a specific note, sent by me
  • Private dashboard behind Cloudflare Access; it never applies or messages anyone
Read the build story →
Live

An MCP server for my portfolio

Point Claude or any MCP client at jordanknox.com/mcp and your assistant can look up my experience, check my fit against a job description (gaps included), or send me a message.

  • Runs on a Cloudflare Worker alongside this site
  • Built to describe me accurately, not oversell me
Try it: jordanknox.com/mcp →

Experience

Two companies, 22 years.

Twenty years building and leading operations, then two owning cost, performance and security in AWS.

Apr 2024 – Aug 2026

Cloud Operations & Site Reliability Engineer

PropStream (Stewart) · Lake Forest, CA · Remote

  • Owned AWS cost optimization, performance and observability, and security operations across dev, QA, beta and production
  • Modernized release management with blue/green deployments and automation
  • Incident response, on-call and PostgreSQL administration
Feb 2004 – Mar 2024

Manager of Technical Operations

Rapattoni Corporation · Westlake Village, CA

  • Grew from technical contributor to leading a distributed team of up to 12 (local, remote and overseas, including contractors) across technical operations, development, QA, SSO and API/RESO integrations
  • 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
  • Led the API initiative (team, roadmap and development, with VP and CTO sponsorship), adopted by about 70% of customers
  • 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, canary deployments, 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 (built this site's MCP server) and AI tooling for operations

Notes

Coming soon

Making a portfolio readable by AI agents

How I built this site's MCP server on a Cloudflare Worker, how I kept an AI from overselling me, 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.

Prefer to have your AI assistant reach out? Point it at https://jordanknox.com/mcp