online · UTC+8 · open to work

lester@buenaobra:~$ whoami

Lester Buenaobra

IT Support Engineer // MSP // Microsoft 365 & Entra ID

IT support engineer. Lifelong tinkerer. Builder of things that run themselves.

[email protected] · linkedin.com/in/mark-lester-buenaobra-53095b312 · buenaobra.net · Metro Manila, PH (UTC+8) · open to remote & relocation

📍 Metro Manila, PH
🌏 Remote · relocation (NZ first)
⏱ 15 yrs in tech support

[ hire me ] [ linkedin ↗ ]

15years supporting users

26,000+lessons taught (ESL)

20analysts led as team lead

100%CSAT at Genie Health

#1weekly ticket leaderboard, regularly

01 cat about.md

I've spent 15 years on the other end of the line when technology stops working. I started in telecom support for Telstra, AT&T and Verizon, taught English in more than 26,000 online lessons, ran parts of an enterprise service desk for a global investment firm, and now work in managed services for US businesses.

Teaching gave me the skill I use most: active listening. Users often don't know what they actually need. You listen, ask the right questions, and find the real root cause. The fix is usually the easy part.

Off the clock I'm still at it. I run a Proxmox homelab managed as code, build my own PCs, once ran a triple-boot Hackintosh, and break things on purpose to learn how they work. My old gamer tag was itinkerstuff, and it still fits.

02 git log --career

2025 → now
Helpdesk Engineer, End User Engineering

Chicago-based MSP/MSSP · via Kalutasan
- Weekend and after-hours coverage for an MSP/MSSP serving enterprise and private-equity clients. Often the only engineer on the queue.
- Regularly at the top of the weekly team leaderboard: 50–100 tickets closed a week, ~30 on a busy day.
- Onboarding and offboarding across many client tenants: M365 and line-of-business accounts, Partner Center licensing, encrypted credential delivery.
- Email security in Mimecast; servers via LogicMonitor; endpoints via Kaseya VSA; credentials in Secret Server; ITSM in ServiceNow.
2025
MSP Engineer

Effective Consulting LLC · Miami, FL
- Remote support across Windows, macOS, iOS and Android with Datto RMM.
- Microsoft 365 and Google Workspace administration in hybrid and cloud-only environments.
- Helped with on-prem Windows Server to Entra ID migrations; supported Ruckus and Ubiquiti networks; AppRiver email protection.
- Wrote and maintained client SOPs in IT Glue.
2024
Microsoft 365 Ambassador

Microsoft · via Upwork / GigPlus
- Guided Microsoft 365 Business trial customers to the right plan, through setup and domain integration, and introduced Copilot.
- Fed customer insights back to Microsoft's product team.
2023 → 2024
IT Tech Support

Genie Health (virtual physical therapy) · via Remoworks
- Supported patients and staff by voice, chat and email: 100% CSAT, ~20 tickets a day.
- Built Jira Service Management templates and workflows that cut resolution time.
- QA-tested app releases with DevOps; ran onboarding and offboarding; trained staff on new releases.
2021 → 2023
Senior Systems Engineer, Service Desk

Wellington Management · via Cognizant

T1 → T2 → Queue Czar → Knowledge Master → Incident Manager → Team Lead
- Hybrid AD and Entra ID identity and access: provisioning, groups, shared mailboxes, distribution lists.
- Rebuilt the knowledge base: removed outdated articles, recategorized everything, improved search.
- Led a left-shift program that moved Directory Services work to the service desk. Read the case study ↓
- Led a team of 20 analysts; supervised PowerShell automation; did root cause analysis as Incident Manager.
2011 → 2021
Technical Support Representative

Teleperformance · Teletech · VXI · AFNI: Telstra, AT&T, Verizon
- Repeatedly recognized as Employee of the Month and CSAT top performer; promoted to SME within ~3 months.
2014 → 2019
Online ESL Teacher

51Talk
- 26,000+ one-on-one lessons with top-tier ratings. Where I learned to explain anything to anyone.
2007 → 2009

Communication Arts

University of the East, Caloocan

03 ls ./case-studies

case_01_left-shift.log

Shifting Directory Services work to the service desk

problem

Access requests, such as for a network shared drive, were passed between teams. Slow, full of friction, and frustrating for users.

action

Designed and submitted ServiceNow stories for one end-to-end flow:

user requests access
manager validates path & approves
AD group task auto-created
follow-up task: remote in & map drive

with templated user messages at every step.

result

Almost no friction. The service desk took over the work of the entire Directory Services function, which made the desk more valuable to the client.

case_02_patience.log

The patient who couldn't start their therapy

situation: An elderly patient, in pain, not tech-savvy, and stuck on the app meant to guide their at-home physical therapy.
action: Stayed on the call as long as it took. Fixed every issue, then taught them step by step how to record and follow their own sessions.
result: They were emotional on the call and thanked me over and over. To them it was life-changing. That's the job.

04 ssh homelab

A small production environment I run at home, managed as code. I design the architecture, direct AI coding agents to build it, review every change, and operate it day to day.

              internet
                 │
     ┌───────────┴───────────┐
 cloudflare tunnel      tailscale (private)
     └───────────┬───────────┘
            [ caddy ]  reverse proxy · auto-HTTPS
                 │
 ┌──────┬────────┼────────┬──────────┐
 dns    hub      psa      vault     apps
 adguard forgejo itflow  vaultwarden chorecast
         beszel
         gatus ──► ntfy alerts

 ── proxmox VE · one service per VM ──
 ── ansible: baseline · packages · compose-sync ──

Proxmox VE
Ansible
Docker Compose
Caddy
Tailscale
Cloudflare Tunnel
AdGuard Home
Forgejo
Vaultwarden
ITFlow (PSA)
Gatus
ntfy
Beszel

// side projects

ChoreCast

Open-source, self-hosted family chore system. A FastAPI server, an Android TV app that sounds an alarm over the TV when a chore is overdue, and a phone app that locks until a parent approves. Kids can send photo proof.

FastAPI · Android · self-hosted

agentwatch

A read-only, animated terminal dashboard that shows in plain English what AI coding agents and their subagents are doing, so I can supervise automation as it runs.

terminal UI · AI agents · observability

The triple-boot Hackintosh

macOS, Windows and Linux on one hand-built PC, back when that meant hours of bootloaders and kexts. It's where I learned that the fastest way to understand something is to break it.

hardware · bootloaders · stubbornness

05 inventory --skills

STRONG used every day

Microsoft 365
Exchange Online
Entra ID
Active Directory
Group Policy
Email security: Mimecast, AppRiver, SPF/DKIM/DMARC
Windows
macOS
ServiceNow
Jira Service Management
Autotask
Kaseya VSA
Datto RMM
LogicMonitor
IT Glue & SOP writing
Onboarding / offboarding at scale

WORKING hands-on, homelab-proven

Intune & Autopilot
Linux
Docker / Compose
Proxmox
Caddy
DNS
Google Workspace
Ubiquiti / Ruckus
VMware · Citrix · Hyper-V · AVD

LEARNING leveling up now

PowerShell scripting
Networking
Ansible
Azure administration

PEOPLE the part that's hard to teach

Active listening
Teaching & training
Knowledge-base writing
Team leadership (20)
Calm with upset users
99 WPM

// achievements

AZ-900 Azure Fundamentals unlocked 2024
MS-900 Microsoft 365 Fundamentals unlocked 2023
AZ-104 Azure Administrator quest in progress
SC-300 Identity & Access Administrator quest in progress
Apple Device Support quest in progress

06 cat side-quests.txt

Motorcycle traveler. Long rides are how I recharge.
Ex-Twitch streamer. Streamed PC games and built a following for a while.
PC FPS player. Still the best way to stress-test a build.
PC builder. I'd always rather build it myself than buy prebuilt.

07 ping lester

Hiring for a remote or overseas sysadmin, cloud, or MSP role? I'd love to talk. New Zealand is the dream, but I'm open to anywhere.

[ [email protected] ] [ linkedin ↗ ]