About
An operator's perspective on technology leadership
I'm Vasko Ckorovski — a technology leader who has spent 18 years inside the businesses I now advise. My career has moved between engineering, architecture, and executive leadership, always in commercially-driven organisations where technology is the product or the engine behind it.
Today I work as an independent advisor and fractional CTO, helping leadership teams navigate the decisions that shape how their business runs: which platforms to invest in, how to adopt AI without theatre, when to rebuild versus extend, and how to build technology capability that lasts beyond any single project.
I'm not a management consultant who presents frameworks. I'm a practitioner who has built, rebuilt, and lived with the consequences of technology decisions — and I bring that perspective to every engagement.
How I think about technology
Principles that shape my work
Start with the business problem
Technology decisions should be anchored to commercial outcomes, not trends. I always start with what the business actually needs before reaching for solutions.
Prefer reversible decisions
The best architectures preserve optionality. I help teams make commitments where they need to and keep flexibility where they can.
Complexity is a cost
Every integration, every vendor, every abstraction layer carries ongoing cost. Simpler systems are faster to change, cheaper to run, and easier to reason about.
Execution reveals strategy
A strategy that can't be delivered is a document, not a plan. I stay close to execution because that's where real constraints and opportunities surface.
Build capability, not dependency
I structure engagements so that teams are stronger when I leave. The goal is always to build internal capability, not create an ongoing reliance on external advice.
Tell the truth early
Difficult truths about timelines, vendor capabilities, or team readiness are better surfaced early than discovered during delivery. I prioritise candour over comfort.
Where I've operated
Experience that shapes how I work
I've held technology leadership roles across some of Australia's most recognised consumer and enterprise brands. This isn't a CV — it's the context behind the advice.
E-commerce & Retail
Led platform strategy and engineering across multiple e-commerce re-platforms. CTO and Head of Engineering roles at businesses including Hanes Brands (Bonds, Bras N Things, Sheridan), Temple & Webster, and CarPlace. Deep experience with VTEX, Salesforce Commerce Cloud, Shopify Plus, and headless architectures.
Media & Marketplaces
Technology leadership at News Corp across digital publishing and marketplace platforms. Experience with high-traffic content systems, audience platforms, and the intersection of editorial and product technology.
Scale-ups & Growth Stage
Fractional CTO and advisory roles with growth-stage companies including Amplifyd, Carma, and Woolies X. Focused on building engineering capability, defining architecture, hiring technical leadership, and establishing delivery practices that scale.
Platform & Vendor Ecosystem
Direct experience evaluating, implementing, and managing relationships with major platform vendors — VTEX, Salesforce, Shopify, Adobe, Contentful, Segment, Braze, Snowflake. I understand how these platforms work from the inside, not from a sales deck.
I'm based in Australia and work with clients locally and internationally. Outside of work, I'm interested in how organisations make decisions under uncertainty, the intersection of design and engineering culture, and the long-term implications of AI on professional services.
I'm always happy to have a conversation — even if it's just to think through a problem with someone who's been in similar situations.
Want to work together?
I take on a small number of advisory and fractional engagements at any given time. If you're thinking through a technology decision, I'd welcome the conversation.