Jeremy Longshore

When you’re responsible for bringing a new senior team member onto a complex platform spanning multiple GCP projects, hundreds of database tables, and interconnected services, the quality of your onboarding process becomes a direct reflection of your technical leadership capabilities.

Today I want to share how I approached onboarding Opeyemi Ariyo as Senior Cybersecurity Engineer to the DiagnosticPro platform - not just the technical work, but the leadership thinking and systematic problem-solving that made it successful.

The Challenge: Multi-Project Architecture Complexity

The DiagnosticPro platform represents the kind of system complexity that separates senior engineers from junior ones:

When a new team member needs to understand, maintain, and enhance this system, standard documentation approaches fall short. This required a senior-level approach to knowledge transfer and access management.

The Systematic Approach: Building for Scale

Rather than creating project-specific documentation, I took a systematic approach that demonstrates scalable thinking:

1. Framework Development First

I started by creating a comprehensive analysis framework with specific requirements:

This wasn’t just documentation - it was building a repeatable process for future team growth.

2. Universal Template Creation

Here’s where senior-level thinking becomes apparent: I didn’t just solve this problem once. I built a universal template with placeholders that can be adapted for any project:

# [PROJECT_NAME]: Complete System Analysis for [ENGINEER_NAME]
## [Cloud Provider] Architecture Overview
## Directory Deep-Dive (project-specific structure)

This template approach demonstrates several leadership qualities:

3. Real-World Testing Through Infrastructure Access

Documentation without access is useless. This is where the rubber met the road - getting Opeyemi connected to development infrastructure in the diagnosticpro-relay-1758728286 project.

The Technical Leadership Moment

What started as “give him VM access” became a comprehensive lesson in systematic troubleshooting and stakeholder management.

Initial Attempt: Standard Permissions

gcloud projects add-iam-policy-binding diagnosticpro-relay-1758728286 \
  --member="user:opeyemi.ariyo@gmail.com" \
  --role="roles/compute.instanceAdmin.v1"

Result: Connection failed. This is where many people would start ad-hoc permission grants.

Senior-Level Approach: Systematic Diagnosis

Instead of randomly adding permissions, I took a diagnostic approach:

  1. Network analysis: Firewall rules and IAP configuration
  2. Policy investigation: Organization constraints affecting OS Login
  3. Infrastructure assessment: VM health and service status
  4. Cost-benefit analysis: When the existing VM had OS Login issues, should we fix or replace?

The Business Context Decision

When I initially created an e2-medium VM ($25/month), Jeremy’s immediate feedback was clear: “dont ever assume i have extra money delete that and give him small.”

This moment highlighted a crucial senior engineer capability: balancing technical solutions with business constraints. The e2-small instance ($7/month) was perfectly adequate for development needs. Senior engineers understand that every technical decision has business implications.

The Permission Architecture Solution

Rather than piecemeal grants, I implemented comprehensive access:

This demonstrates systems thinking - understanding how permissions interact rather than treating them as isolated grants.

Professional Growth Through Problem-Solving

This project highlighted several aspects of senior technical leadership:

1. Template-Based Thinking

Creating reusable frameworks instead of one-off solutions shows maturity in software development. The universal template is now being used for additional team onboarding across other projects.

2. Stakeholder Management

Managing Jeremy’s concerns about costs while ensuring Opeyemi had proper access required balancing technical needs with business constraints - a core senior engineer skill.

3. Documentation That Actually Works

The 20,000-word analysis isn’t impressive because it’s long - it’s valuable because it covers operational reality, including failure modes and troubleshooting steps that someone actually needs.

4. Security-First Architecture

Choosing IAP tunneling over traditional SSH demonstrated security-conscious thinking:

The Multiplier Effect

What makes this work valuable from a career perspective is the multiplier effect:

Senior engineers create leverage - their work makes the entire team more effective.

Technical Capabilities Demonstrated

This project showcased several technical competencies:

Cloud Architecture: Multi-project GCP management with proper IAM boundaries Infrastructure: Cloud Run, Firestore, BigQuery, Vertex AI integration Security: IAP implementation, OS Login compliance, permission management Documentation: Systematic knowledge transfer and institutional memory creation Cost Management: Infrastructure optimization with business context Problem-Solving: Systematic diagnosis and resolution of complex issues

Looking Forward

This experience reinforced my approach to technical leadership: build systems, not just solutions.

The template framework is now part of our standard onboarding process. The IAP access patterns are being replicated across other projects. The systematic documentation approach is being adapted for client handoffs.

More importantly, this demonstrates readiness for larger technical leadership challenges:

The Senior Engineer Mindset

What separates senior engineers from junior ones isn’t just technical knowledge - it’s the ability to:

This onboarding project exemplified all of these qualities, from the universal template creation to the cost-conscious infrastructure decisions to the systematic troubleshooting approach.

Ready for the next complex challenge.


This post reflects on real technical leadership work completed October 1, 2025, demonstrating systematic approaches to team onboarding, infrastructure management, and scalable process development.

#Technical-Leadership #Devops #Team-Building #Problem-Solving #Cloud-Infrastructure