Open to new opportunities

Darren
Akai

AI-Driven Technology Leader with 20+ years transforming financial services through DevOps innovation, agentic AI automation, and enterprise-scale platform engineering.

AI & Automation DevOps Leadership Platform Engineering Change Governance
20+Years in Tech
$500K+Annual Savings
45Apps Governed
0Change Collisions
Darren Akai Milton, Ontario
๐Ÿค–
$520K
Annual savings from AI-driven build/release automation โ€” with a 100% elimination of deployment failures across 45 applications.
โ˜๏ธ
$95K
Annual savings from migrating to GitHub Enterprise Cloud, at $1,600/month per application in infrastructure efficiencies.
๐Ÿ”
$72K
Annual savings from HashiCorp Vault secrets automation โ€” eliminating all manual credential administration.
๐Ÿ“‰
18%
Reduction in unplanned outages via structured change governance โ€” plus zero cross-team collisions across 45,000+ annual production changes.
Career

Professional Experience

Two decades building and leading technology teams in one of Canada's largest financial institutions โ€” delivering measurable outcomes at every level.

Director, Change Planning & SCM CIBC Apr 2024 โ€“ Nov 2025

The most AI-forward role of my career. Led enterprise-wide SCM and Change Planning for CIBC's Client Servicing Technology portfolio โ€” 45 applications, 9 direct reports across 2 teams, and a $1.3M software budget. Embedded AI automation directly into how software was governed and delivered.

  • Championed AI-augmented SDLC practices using CIBC's internal AI platform to accelerate GitHub Actions script authoring, saving 15โ€“20 hours/month per application โ€” a documented $432K annual saving.
  • Built a custom Jira-based change governance solution that delivered zero change collisions across the entire CST portfolio since implementation.
  • Introduced HashiCorp Vault to automate secrets and credential lifecycle management, generating $72K in annual savings.
  • Led migration to GitHub Enterprise Cloud (GHEC), achieving $95K in annual savings while modernizing SCM posture across 45 applications.
  • Aligned change initiatives with corporate objectives in partnership with senior executives across Enterprise Change Management and Technology Infrastructure.
GitHub ActionsHashiCorp VaultJiraGHECAI AutomationSDLC Governance
Director, DevOps & Change Planning CIBC Jan 2018 โ€“ Mar 2024

Six years managing two high-performing teams โ€” 8 DevOps engineers and a dedicated Change Planning function โ€” responsible for CI/CD pipeline operations and production change governance across 45 applications. This is where I introduced AI-driven automation into CIBC's delivery fabric.

  • Introduced AI-driven build/release automation, achieving $520K in annual savings and a 100% reduction in deployment failures.
  • Governed 45,000+ annual production changes in a 2,000+ application bank environment โ€” with zero cross-team collision impact.
  • Implemented a structured change governance framework that decreased unplanned outages by 18% and materially improved release predictability.
  • Built and mentored a team of CI/CD specialists who became trusted partners across multiple lines of business.
CI/CDJenkinsGitHubChange ManagementTeam Leadership
Technology Consultant โ€“ Performance Testing CIBC Jul 2015 โ€“ Jan 2018

Owned Performance Testing Services demand management and roadmap โ€” introducing cloud-based testing strategies and continuous improvement that dramatically accelerated throughput.

  • Reduced testing backlog by 40% and improved resource allocation efficiency by 10%.
  • Spearheaded a cloud-based testing roadmap, achieving 10% cost savings through on-demand environment provisioning.
  • Cut testing turnaround times from 10 to 6 days โ€” a 40% cycle time reduction.
Performance TestingCloud EnvironmentsDemand Management
Senior Application Consultant, App Operations CIBC Jul 2012 โ€“ Jun 2015

Supported the Compass/AIM program across 5 business portfolios, managing environment lifecycles across 3 concurrent releases with improved delivery accuracy.

  • Managed full environment lifecycle (DIT โ†’ SIT โ†’ UAT โ†’ PTE โ†’ Production) across 3 concurrent release streams.
  • Implemented demand management and pre-intake processes, reducing scheduling conflicts and improving accuracy.
Environment ManagementRelease PlanningUAT / SIT
Senior Manager, Development Technical Services CIBC Aug 2005 โ€“ Jul 2012

Managed a team of 9 supporting development and QA for Retail Branch applications โ€” $800K budget, 4 major releases annually. Received the CIBC Achiever Award for leadership and innovation.

  • Delivered $89K in annual savings through an alternative hardware maintenance strategy.
  • Partnered with Development, QA, and PMO to deliver 4 major releases annually with improved on-time delivery.
Team ManagementBudget ManagementQA Delivery
Senior Manager, Retail Branch Technology CIBC Jan 2005 โ€“ Aug 2008

Led Retail Branch Technology with $1M capital budgets. Honoured as Mentor of the Year in 2006 โ€” two direct reports subsequently received the CIBC President's Annual Achiever Award.

Capital PlanningMentorshipBranch Technology
Senior Network Engineer / Technical Lead Nortel Networks Prior to 2005

Built my technical foundation at one of Canada's most storied technology companies. Recipient of the Nortel President's Award of Excellence โ€” the company's highest recognition for technical achievement.

Network EngineeringTechnical LeadershipTelecom
Toolkit

Technologies & Skills

The platforms, tools, and disciplines I use to deliver โ€” from enterprise DevOps governance to full-stack products designed, built, and self-hosted end-to-end.

AI & Automation
๐Ÿค– Agentic AI Workflows ๐Ÿง  Claude / Anthropic API ๐Ÿพ OpenClaw AI โšก AI-Assisted Scripting ๐Ÿ  Home Assistant ๐Ÿ–ผ๏ธ AI Background Removal ๐Ÿ‘๏ธ Computer Vision
Full-Stack Web Development
๐ŸŸข Node.js ๐Ÿš‚ Express ๐Ÿ“œ JavaScript (ES6+) ๐ŸŽจ HTML5 & CSS3 ๐Ÿ—„๏ธ SQLite ๐Ÿ”Œ REST APIs ๐ŸŒ WebSockets / Real-Time
DevOps & CI/CD
๐Ÿ™ GitHub Enterprise ๐Ÿ”„ GitHub Actions ๐Ÿ”ง Jenkins ๐Ÿ“ฆ CI/CD Pipeline Design ๐Ÿš€ Release Automation
Self-Hosting & Web Infrastructure
๐Ÿง Debian Linux ๐ŸŒ nginx ๐Ÿ” Certbot / Let's Encrypt TLS โš™๏ธ systemd Services ๐Ÿงญ DNS & Subdomains ๐Ÿ“ค Custom Deploy Pipeline ๐Ÿ›ก๏ธ RAID1 / UPS Reliability
Cloud & Infrastructure
โ˜๏ธ GitHub Enterprise Cloud ๐Ÿ” HashiCorp Vault ๐Ÿง Linux / Debian ๐ŸŒ WebSocket / Real-Time ๐Ÿ—๏ธ Cloud Migration
Creative & Native Development
๐ŸŽฎ Three.js / WebGL ๐Ÿงฉ C++ / JUCE ๐ŸŽน VST Instruments (VSTi) ๐ŸŽ Swift / iOS ๐ŸชŸ Windows Desktop ๐Ÿ•น๏ธ Game Development
Change & Governance
๐Ÿ“‹ Jira ๐Ÿ›๏ธ Enterprise Change Mgmt ๐Ÿ”’ Risk & Compliance ๐Ÿ“Š ITIL / ITSM ๐Ÿ“… Release Governance
Leadership & Strategy
๐Ÿ‘ฅ Team Building (up to 9) ๐Ÿ’ฐ Budget Management ($1.3M) ๐ŸŽฏ Executive Stakeholders ๐ŸŒฑ Mentorship ๐Ÿ“ˆ Vendor Management
Testing & Quality
โš™๏ธ Performance Testing ๐Ÿงช DIT / SIT / UAT ๐Ÿ” Environment Lifecycle ๐Ÿ“ Test Demand Mgmt ๐Ÿ”Ž Web Quality & SEO Audits
Portfolio ยท ThinkTrail Solutions

Projects & Ventures

A working portfolio of products, platforms, and client sites I design, build, and self-host end-to-end through ThinkTrail Solutions โ€” from patent-pending live-event tech to AI tools, e-commerce, games, and audio software, all running on infrastructure I built and administer.

Products & Platforms
๐Ÿ“Š Platform

Hyland Sentinel

hyland.darrenakai.com โ†—

A portfolio-level project status & risk tracker โ€” "RiskLens" โ€” that gives visibility across an entire program and its partner network. Role-based dashboards serve administrators, executives, and external partner firms, each seeing exactly the projects and risk signals relevant to them across a multi-organization consulting ecosystem.

Type
Portfolio Tracker
Access
Role-Based
View the platform โ†’
๐Ÿค– AI-Powered

CareerAgent

careeragent.darrenakai.com โ†—

A personal AI job-search assistant. An account-based, mobile-first web app that helps job-seekers organize, track, and accelerate their search โ€” bringing agentic AI to one of the most stressful workflows there is.

Type
AI Web App
Design
Mobile-First
Explore it โ†’
๐Ÿงญ Platform

TrailHead

trailhead.darrenakai.com โ†—

A daily learning & growth platform โ€” "Where your path begins each day." A personal-development hub with secure accounts and a habit-forming daily structure, doubling as the home for my own development diary written straight from Claude Desktop via a custom MCP integration.

Type
L&D Platform
Integration
Custom MCP
Visit TrailHead โ†’
๐Ÿฆ AI + Home Automation

Birdfy Video Archive

birdfy.darrenakai.com โ†—

An AI wildlife-camera archive that auto-catalogues footage from a smart bird feeder โ€” 3,500+ clips with species detection (cardinals, sparrows, squirrels), date-based navigation, and search. Wired into my Home Assistant setup, it turns everyday backyard nature into a searchable, sustainably-run digital record.

Clips
3,500+
Feature
Species Detection
Browse the archive โ†’
๐Ÿ•น๏ธ 3D Game

Real Defender

realdefender.darrenakai.com โ†—

A browser-based, first-person 3D multiplayer shooter that reimagines Williams' 1981 arcade classic Defender for the modern web. Arcade, co-op, and competitive modes, keyboard or gamepad control, shareable host codes, and a Hall of Fame leaderboard โ€” all rendered in real time in the browser.

Engine
Three.js / WebGL
Modes
Arcade / Co-op / PvP
Play now โ†’
๐Ÿ•น๏ธ Multiplayer Game

WordGrid

wordgame.darrenakai.com โ†—

A real-time multiplayer word game where 2โ€“4 friends share a room and go head-to-head, drafting letters onto their own 5ร—5 grids in a race to build the highest-scoring words before the clock runs out โ€” all in the browser, no download, seamless across phone and desktop. Live opponent boards, a colour-coded countdown, emoji avatars, and a slick dark/light interface turn the humble word game into a fast, social, edge-of-your-seat showdown. Deliberately kept simple: a zero-build vanilla-JS frontend on an in-memory server with no database.

Stack
Node ยท Express ยท Socket.io
Players
2โ€“4, Real-Time
Play now โ†’
๐ŸŽต AI-Powered

Music Trivia

musictrivia.darrenakai.com โ†—

An AI-powered music trivia game built on the OpenClaw platform. Players face dynamically generated questions spanning genres, eras, and artists โ€” all orchestrated through Claude-based agentic workflows. A live demonstration of how AI can power engaging, replayable consumer experiences with zero static content.

Engine
OpenClaw / Claude
Type
Interactive AI game
Play now โ†’
๐Ÿ”Ž Web Tool

Sitegrade

thinktrailsolutions.com/audit โ†—

A website quality-audit portal, operated under ThinkTrail Solutions, that grades sites on performance, accessibility, SEO, and best-practice compliance โ€” the same standards I hold every one of my own builds to before it goes live.

Type
Audit Portal
Checks
Perf ยท A11y ยท SEO
Open the tool โ†’
๐Ÿพ Self-Hosted

OpenClaw AI Server

Debian Linux ยท Personal & Community Use

A self-hosted OpenClaw agentic AI server I run and administer on Debian Linux, extended to a community of AI-enthusiast friends and family. A hands-on environment for agentic orchestration, token optimization, and model-selection strategy โ€” actively integrated with Home Assistant to give real intelligence to the physical environment.

Platform
Debian Linux
AI Engine
Anthropic API
Integration
Home Assistant
Status
Live & Active
Discuss the build โ†’
E-Commerce
๐Ÿ‘• AI + Commerce

GOAT'eez

goateez.ca โ†—

Custom athletic apparel featuring an athlete's photo on the front โ€” for the supporters who show up to every game. AI background removal, a live customizer, emailed proofs within a business day, flexible sizing, and bulk discounts. Co-developed with Daniel Medina Lopez.

AI Feature
BG Removal
Concept
Athlete Photo Tees
Shop the store โ†’
๐Ÿ‘• AI + Commerce

TeamFace

teamface.darrenakai.com โ†—

The sister storefront to GOAT'eez, with a deliberately different look and feel โ€” AI-powered custom team tees for schools, leagues, and fundraisers across Canada and the USA. Six sports supported, tiered pricing down to $18/shirt, and a built-in fundraiser storefront.

Sports
6 supported
Use Case
School Fundraisers
See the platform โ†’
Client Work
๐Ÿš— Client Site

David's Detailing Garage

davidsgarage.darrenakai.com โ†—

A professional site for a Cambridge, ON auto-detailing business โ€” interior/exterior detailing, ceramic coating, and mobile service, with a before-and-after gallery, testimonials, and online booking.

Visit site โ†’
๐ŸŒฟ Client Site

GO Property Maintenance

gopropertymaintenance.ca โ†—

A landscaping & home-beautification site for a Cambridge-area business operating since 2013 โ€” service breakdowns, a before-and-after project portfolio, and a prominent free-estimate call-to-action.

Visit site โ†’
๐ŸŽฏ Client Site

Kaleidoscope Consulting

kaleidoscope.darrenakai.com โ†—

A polished brochure site for a Toronto executive-coaching practice led by an ICF-credentialed coach โ€” communicating the firm's philosophy, services, and engagement approach with a calm, confident voice.

Visit site โ†’
๐Ÿ Client Site

Main Street Italian Eatery

italianeatery.darrenakai.com โ†—

A warm, mouth-watering one-page site capturing the soul of a Milton family kitchen โ€” an immersive hero, a "made-from-scratch since 2011" story, a gallery of homemade favourites, glowing 4.7โ˜… Google reviews, and an embedded map, all wrapped in a rich terracotta-and-gold Italian palette. Thoughtfully accessible, it turns every scroll into a friendly "come sit at our table" invitation, with call-to-order and get-directions buttons never more than a tap away.

Visit site โ†’
Audio & Music
๐ŸŽน VST Plugin

Juno-106 VSTi

VST3 / AU ยท Six-Voice Polysynth

A faithful software resurrection of the Roland Juno-106 โ€” a six-voice VST3/AU plugin that recreates the legendary 1984 analogue polysynth's full signal path (PolyBLEP oscillators, sub, noise, a 24 dB ladder filter, delayed LFO, ADSR, and stereo chorus), right down to the complete original 128 factory patches decoded from Roland's own SysEx data. It even goes one better than the hardware, adding a Juno-6/60-style tempo-syncable arpeggiator and buttery hover-to-scroll mouse-wheel control on every fader and switch โ€” so the classic '80s sound is finally at your fingertips inside Studio One.

Ask about it โ†’
๐ŸŽน VST Plugin

Jupiter-8 VSTi

Standalone ยท VST3 / AU

A faithful software recreation of the legendary Roland Jupiter-8 โ€” a JUCE-powered virtual instrument that brings the warmth and grit of that iconic 1980s analog synth to your DAW, complete with the full front panel, arpeggiator, 16 factory presets, and an 88-key playable interface. Engineered to run natively as a Standalone app, VST3, and AU plugin โ€” and lovingly cross-built to keep a vintage Intel Mac and Studio One 4 rig singing โ€” it delivers classic Jupiter tone without the six-figure vintage price tag.

Ask about it โ†’
๐ŸŽผ Music Ed

NoteTrainer

notes.darrenakai.com โ†—

A sight-reading trainer that challenges players to identify 20 notes as fast as possible โ€” treble, bass, or both, with easy and hard modes and per-session accuracy tracking. A lean, focused tool for sharpening sheet-reading reflexes.

Start training โ†’
Native Apps
๐Ÿ“ฑ iOS App

Scrabble Buddy

iOS ยท Native App

Scrabble Buddy borrows the relentless discipline of the chess clock and brings it to the tile table for the very first time โ€” a sleek, up-to-four-player timer that tracks every player's thinking time independently and keeps even the most leisurely word-hunters honest. It adds a thrilling new dimension of pace and pressure to an 80-year-old classic, turning slow, sprawling Scrabble sessions into tight, competitive contests where managing your clock becomes as strategic as managing your tiles.

Ask about it โ†’
๐ŸชŸ Windows App

IMPACT

Windows ยท Offline-First Desktop App

IMPACT is a sleek, offline-first Windows desktop app that turns messy strategic guesswork into clear, defensible decisions โ€” score every initiative across six dimensions (Impact, Measure, People, Align, Complexity, Time), tune what matters most with interactive weight dials, and instantly see your priorities ranked. Built for leaders who want boardroom-ready results in one click, it exports polished PDF and Word reports, keeps all your data private on your own machine, and even lets you pick your vibe with theme options from Corporate Dark to LCARS and Cyberpunk.

Ask about it โ†’
Credentials

Education & Certifications

Continuous learning โ€” especially as AI reshapes the discipline.

๐ŸŽ“
March 2026
AI for Productivity
Duke University
๐Ÿค–
February 2026
Google AI Essentials
Coursera
โš–๏ธ
February 2026
Using AI Responsibly
Coursera
๐Ÿ”„
May 2017
DevOps Foundation Certificate
ProTech Training
โ˜๏ธ
April 2017
Moving to the Cloud
University of Melbourne
Contact

Let's Connect

Actively seeking my next senior leadership role in AI, DevOps, or platform engineering. If you're building something ambitious โ€” let's talk.

โœ‰๏ธ darren.akai@gmail.com ๐Ÿ“ž 416-300-7056 ๐Ÿ’ผ linkedin.com/in/darrenakai ๐ŸŽต livecanvas.darrenakai.com