# Vasko Ckorovski -- Fractional CTO & independent AI delivery advisor

> The independent advisor who makes sure your AI delivery is right -- before you get burnt. For the operators commissioning, inheriting, or running AI-built work -- from an operator who ships.

## About

Vasko Ckorovski is a Fractional CTO and independent AI delivery advisor based in Australia, with eighteen years across eCommerce, retail, media, and marketplace platforms. He holds the seat independent technical advisors have held for decades -- the person in the room deciding whether something is the right thing to build, whether it's being built right, and whether it will survive once it's live -- now pointed at a new kind of vendor. Anyone can vibe-code a demo; whether it survives a real business is the question he's there for. He works buyer-side and early, for the founders, GMs, and heads of digital who commission, inherit, or run AI-built work and are accountable when it fails. And unlike most people advising on AI, he builds it: the products on his AI Projects page are designed, shipped, and governed end to end, with the same discipline he'd bring to assuring yours. The moat is eighteen years of scar tissue -- what actually breaks when the demo meets a real business. That's the part that can't be generated.

## Services

### AI Second Opinion (start here)
An independent, buyer-side read on what you already have -- a build, a vendor's proposal, a plan, or a running system. Bring it, and get back a straight answer: is this right, will it survive contact with a real business, and what would I do next. Best used early, before you commit, but useful at any point across a delivery (before, during, or after). Outputs vary by scale and topic -- a verdict, a risk map, or a recommendation on whether to proceed, who to hire, or what to fix first -- examples, not a fixed deliverable. No fixed price; it starts with a conversation. -- /ai-second-opinion

### AI & Platform Opportunity Audit (flagship engagement)
A structured, time-boxed assessment of where AI and platform decisions create genuine leverage -- and where they don't. The AI market in particular runs on hype; this cuts through it to a clear view of where AI or platform change creates real business value, a shortlist of credible options with the trade-offs spelled out, and a decision-ready brief your board or leadership team can act on. Typically 2 to 4 weeks, fixed fee.

### AI-Era Transformation Blueprint
A programme plan that survives contact with reality -- not a deck in a drawer. A sequenced roadmap for a major platform migration, operating-model change, or multi-workstream transformation in which AI now changes the shape of the work, with AI factored in where it earns its place. Includes a vendor shortlist and procurement framework, a resourcing model, risk register, and business case. Typically 4 to 8 weeks, or an ongoing advisory retainer.

### Fractional CTO Advisory
Senior technology leadership embedded in your business -- including the AI calls. A consistent senior perspective across the decisions that matter, vendor relationships managed with commercial discipline, and team capability built over time rather than dependent on a single person. Ongoing monthly retainer, typically two days per week.

### Interim CTO
Hands-on technology leadership when you need it most, without the lag of a permanent hire. Full accountability for architecture, hiring, delivery, and vendor relationships -- and a pragmatic line on where AI actually fits. Typically three to four days per week, 3 to 12 months.

### Build with me (AI Product Build)
For founders and operators who need a working AI product in weeks, not quarters. Strategic framing, architecture and tooling decisions, hands-on build using Claude Code and the multi-model AI toolchain Vasko developed building ProductMatch -- v1 fast, then iterated to land. Full Linear-based planning artefacts and live launch. Typically 6 to 10 weeks ending with a working commercial product.

## Expertise

Vasko has deep experience in: shipping live AI products end to end (multi-tenant SaaS, autonomous agents, AI-assisted delivery pipelines), AI adoption and governance in retail, eCommerce platform strategy and replatforming, customer data architecture and CDP evaluation, technology due diligence for PE and VC, post-acquisition technology integration, digital transformation programme delivery, vendor evaluation and selection, and building technology capability in growing businesses.

## Topic Areas

### AI Strategy, Adoption & Delivery
Where AI delivers real operational value versus where it stays oversold, the data foundations enterprise AI actually needs, AI readiness and governance for retailers, whether AI-built work -- your own or a vendor's -- is right and will survive in production, and what it takes to design and ship production AI products hands-on.

### Replatforming & Migration
When to replatform, platform selection frameworks, what typically goes wrong in retail technology transformation, and how to manage large-scale platform transitions.

### AI in Retail & Commerce
Where AI delivers real operational value in retail (demand forecasting, customer service, content generation) versus where it remains oversold (hyper-personalisation, autonomous pricing).

### Data, CRM & CDP
Customer data strategy, CRM implementation, CDP evaluation and selection, and building unified customer identity across channels.

### Architecture & Integration
Headless vs monolith decisions, integration architecture patterns, middleware strategy, and managing technical complexity at scale.

### Technology Leadership
Fractional and interim CTO models, retail technology operating models, building internal capability, and translating technology strategy for boards and investors.

### Due Diligence & Investment
Technology due diligence for acquisitions, post-acquisition playbooks, portfolio technology standardisation, and aligning technology roadmaps to value creation plans.

## Published Articles

- The adult in the room: what eighteen years taught me that AI can't -- /insights/adult-in-the-room
- Meet ProductMatch: how I shipped an AI SaaS in two weeks -- /insights/meet-productmatch
- Data: the foundation of enterprise AI success -- /insights/data-foundation-enterprise-ai
- Where AI actually helps retail operations today -- /insights/ai-in-retail-operations
- AI in retail: separating what works from what's theatre -- /insights/ai-in-retail-what-actually-works
- Sally doesn't sleep: building an AI agent that runs my practice -- /insights/meet-sally
- When is it actually time to replatform? -- /insights/when-to-replatform
- Do you actually need a CDP? -- /insights/do-you-need-a-cdp
- What usually goes wrong in retail technology transformation -- /insights/what-goes-wrong-in-retail-transformation
- Technology due diligence: what investors actually need to know -- /insights/tech-due-diligence-for-investors
- Post-acquisition technology playbook: the first 100 days -- /insights/post-acquisition-technology-playbook
- What a fractional CTO actually does (and when you need one) -- /insights/fractional-cto-what-it-actually-means
- How to choose an eCommerce platform without getting it wrong -- /insights/how-to-choose-an-ecommerce-platform
- Headless vs monolith: a practical decision framework for retailers -- /insights/headless-vs-monolith
- Building an integration strategy that does not collapse under its own weight -- /insights/integration-strategy
- The retail operating model nobody talks about: technology as a product function -- /insights/retail-operating-model
- Vendor selection without the theatre: a structured evaluation approach -- /insights/vendor-selection-without-theatre
- Standardising technology across a PE portfolio: where to start -- /insights/pe-portfolio-technology-standardisation
- Why your CRM implementation failed and what to do about it -- /insights/crm-implementation-failure

## Guides

- Digital transformation readiness checklist -- /guides/digital-transformation-checklist
- Platform selection framework for eCommerce and digital businesses -- /guides/platform-selection-framework

## Lab Notes

Experiments in progress -- what Vasko has tried, what worked, what broke, and what surprised him, shared while the work is still rough.

- The system I built to deliver on my potential -- why the bottleneck in autonomous AI execution has moved upstream to the question itself; a personal AI ops stack in three parts (Vasko OS, FortyTwo, Hermes) built with scale-up rigour, and what each part is reaching for -- /lab-notes/three-streams
- Patches welcome -- why open source is having a moment again, and how AI coding tools let a solo consultant contribute fixes upstream rather than just consume -- /lab-notes/patches-welcome
- Bubble wrap to merged PR: eight hours with gstack -- installing an open-source Claude Code skill pack on a fresh mini PC and watching an autonomous AI engineering team plan, build, review, test, and ship a feature to production -- /lab-notes/bubble-wrap-to-merged-pr
- Operation Last Drinks -- shipping a video game about a local pub without writing a line of code; notes from four autonomous milestones, a humbling soft launch, and a manifest doctrine that earned its keep -- /lab-notes/operation-last-drinks
- I built my friend an offline trip companion. The code was the easy part. -- building a custom, offline-first travel app for one friend's month in Cyprus and the Greek islands; what the AI got confidently wrong, and why the valuable part was never the code -- /lab-notes/trip-companion
- The dashboard I tore down this week -- a gstack sprint shipped a cross-project status dashboard in April; eighty-two days later it was deleted, and the teardown taught more than the build -- why a surface that reports about your work loses to a chat window that answers follow-up questions -- /lab-notes/dashboard-teardown
- The internet keeps naming my stack -- four teams (Vercel's eve, Google's Open Knowledge Format, LangChain's openwiki, "graph engineering") shipped names in five weeks for patterns already running in the practice; the honest scoreboard, why convergence proves the constraint was real rather than proving anyone was clever, and the cost-per-successful-completion bill the wave still ignores -- /lab-notes/convergence-receipts
- Nothing Is Ever As It Seems -- a fortnight where the agent tooling built to make one operator fast instead ate the sprint it was meant to protect; a parade of verification failures (a self-defeating sync marker, a doctrine line measured false, a script that lost its executable bit and killed an alarm silently, a test that grepped for a token and passed over the regression it guarded), the round-economics table showing executable contracts converge a review loop where prose compounds it, and why the tooling that slows you down is the tooling that can't tell you it's broken -- /lab-notes/nothing-is-ever-as-it-seems

## AI Projects

Vasko builds AI products and tools, not just advises on them. These are products he has designed and shipped himself -- live SaaS in market, a productised website business, governance tooling for enterprise retailers, and the autonomous agent that runs his own practice.

### ProductMatch — AI Competitive Pricing Intelligence (live)
A live self-serve SaaS for Australian retailers. Upload a product image, get a defensible pricing recommendation in 90 seconds -- visual matching against AU competitors (Temple & Webster, Freedom, Amart, West Elm, plus 40+ more), with floor/sweet-spot/ceiling pricing and the reasoning behind each number. v1 shipped in two weeks with the full commercial loop (AI pipeline + multi-tenant auth + Stripe billing), then iterated through polish and v2 using Claude Code, Claude Design, and a Linear-based planning discipline. -- https://www.productmatch.com.au -- /ai-projects -- /insights/meet-productmatch

### Digital Starter Kit — AI-Assisted Small-Business Websites (live, pilot)
Properly built small-business websites, live in days and fully managed for one flat monthly fee. An AI-assisted design-and-build pipeline Vasko built in-house removes the slow, expensive part of an agency build, taking a business from brief to a live site in days rather than the month-plus an agency quotes. Fully managed after launch -- hosting, security, backups, and the content and design updates -- so the client never logs into a CMS or chases a developer. Tiered plans from a single-page presence site to a managed Shopify store. Currently in pilot, taking on founding customers. -- https://www.digitalstarterkit.com.au -- /ai-projects

### MyWealthTracker — AI Digital Financial Advisor (live)
A live AI-powered financial advisor built on current Australian tax law, superannuation rules, and financial planning frameworks. Features white-label functionality for mortgage brokers and financial planners, with lead generation capabilities. -- https://www.mywealthtracker.com.au -- /ai-projects

### Sally — Autonomous AI Practice Agent (live)
An AI agent that operates as the operational backbone of Vasko's consulting practice. Sally lives in Telegram, manages project pipelines, scaffolds new engagements from a voice note, maintains persistent memory across every client interaction, and surfaces priorities autonomously. She turns a solo practice into something that operates like a product company. -- /ai-projects -- /insights/meet-sally

### AI Capability Matrix & Governance Framework
A structured capability matrix for retailers evaluating AI adoption. Maps AI use cases against business readiness, data maturity, and governance requirements. Includes model risk assessment, bias monitoring, and board-ready reporting. -- /ai-projects

### AI Project Manager for Startups
An autonomous AI project manager that integrates with ClickUp and Slack to provide real-time project governance across departments. Flags scope drift, missed dependencies, and resource conflicts. Built for startup and scale-up environments. -- /ai-projects

## Case Studies

- Re-platforming a $200M+ multi-brand e-commerce operation -- /experience/ecommerce-replatform
- Unifying customer data across a fragmented retail ecosystem (CDP & CRM selection) -- /experience/cdp-crm-selection
- Building the technology function for a high-growth marketplace (Fractional CTO) -- /experience/fractional-cto-scaleup
- Standing up the technology function for a greenfield startup with aggressive growth targets (Interim CTO) -- /experience/interim-cto-greenfield-startup
- Stabilising peak trading for a $300M+ pure-play online retailer -- /experience/pure-play-retailer-peak-trading
- Unifying digital and store technology for a national multi-brand retailer -- /experience/omnichannel-retail-transformation
- Launching an Asian commerce platform into the ANZ market from a standing start -- /experience/commerce-platform-anz-launch
- Rebuilding the core platform of a Series B vertical SaaS without a feature freeze -- /experience/series-b-vertical-saas-rebuild
- Operational enablement for a scaleup after the founder-CEO transition -- /experience/scaleup-operational-enablement

## Contact

Website: https://vasko.com.au
Email: hello@vasko.com.au
LinkedIn: https://www.linkedin.com/in/vaskockorovski/
Booking: https://calendly.com/vasko-vasko