Technology & product leader
Aaron Gregg
Founder · Fractional CTO · Australia & Europe
I've spent 20+ years helping software organisations improve their delivery, architecture, and team practices — and learning just as much in return.
About Aaron
I'm a technologist, product builder, and dad.
My Story
I started as a developer who loved clean code, patterns, and good design.
Over time, I realized the hardest problems in software aren't technical - they're human.
Why do good teams stall? Why do the same issues resurface? Why are we so busy yet delivering less?
That curiosity pulled me toward systemic change: aligning architecture, delivery, and product thinking.
I've led transformations in startups, scaleups, and established companies, helping them become product-led and engineering-empowered.
I approach technology with Don Norman's principles of discoverability and feedback:
If a system hides its structure, confuses its users, or punishes exploration, that's the system's fault - not the user's.
What I Enjoy
Turning messy legacy into clean systems and empowered teams.
Coaching product owners and tech leads toward continuous improvement.
Building secure, cost-effective platforms on Azure with managed identities and private networking.
Hands-on development with .NET, Vue, React - staying close to the code keeps me grounded.
How I Work
Transparency & discoverability
Make information findable and decisions explicit.
Small feedback loops
Learn faster, correct sooner.
Empowered teams
Give people the context to decide, not just tasks to perform.
Architecture as leverage
Design for change, not perfection.
Quality & security as defaults
Automate where possible, simplify everywhere else.
Recent Experience
Founder work, fractional CTO engagements, and leadership roles where the job was the same: turn strategy into delivery people can trust.
Founder
AI-assisted estimation, prioritisation, and Story Studio — so teams decide with evidence, not politics.
Built and launched a planning platform that brings past delivery data into today’s estimation and prioritisation sessions.
Connects to Jira, Azure DevOps, GitHub, and GitLab so cross-functional teams can plan asynchronously without losing the thread.
Focused on the decision problem behind “busy” roadmaps: what matters, what can wait, and what should never be built.
Founder
AI matching that connects Bavarian Bauausschreibungen with the right trades.
Launched a tender-matching product for Gewerke who need work that fits trade, region, and capacity.
Cuts through procurement noise so crafts businesses see relevant opportunities instead of drowning in listings.
Interim CTO & Consultant
Fractional CTO and technology strategy for software organisations that need clearer product direction and steadier delivery.
Partner with leadership to move from fragmented project delivery to accountable product teams.
Shape cloud architecture, agile operating models, and design-led collaboration that stick after the engagement.
Work spans short strategy sprints through multi-month interim CTO roles — always with an eye on outcomes, not theatre.
Fractional CTO
Kita management software — platform and organisation transformation through joining the Little Bird Group.
Led architecture and organisational change that improved delivery reliability and prepared Stay Informed to join the Little Bird Group.
Unified a multi-product vision around modern identity, multi-tenancy, and Azure-native infrastructure.
Established prioritisation governance, release stabilisation, and practical ISO 27001 / data-protection habits the team could own.
Co-Founder
Australian tender aggregation, search, and notification — cloud AI and data engineering at scale.
Designed scalable Azure architecture for aggregating and cleansing public tender data.
Built ingestion and classification pipelines so customers get fit-scored opportunities and deadline alerts — not raw feeds.
Defined platform boundaries and extensibility for multi-tenant growth and future productisation.
Development Partner
Hands-on .NET, Vue/React, and Azure delivery for Australian clients who need experienced execution.
Ship project-based software across .NET, Vue, React, and SQL Server with clear ownership and review habits.
Architect Azure-native solutions with security, operability, and maintainability as defaults — not afterthoughts.
VP Product Development
Product and technical strategy for a 300+ person network-monitoring business (PRTG).
Moved a flat, chaotic delivery environment toward accountable product teams with clear ownership.
Led multi-year product modernisation, portfolio acquisitions, and the creation of cloud and data-science strategy.
Re-organised a 100+ person engineering group around outcomes — product owners, discovery, and delivery transparency.
CTO
Led R&D across engineering, research, and psychology to ship AI products on Azure.
Connected company strategy with IT, research, and product delivery as CTO of the Symanto Group.
Packaged heterogeneous machine-learning work into a reusable cloud software platform on Microsoft Azure.
Grew from Enterprise Software Architect into CTO — owning feature selection through solution design and lighthouse integrations.
Earlier roles with Avanade Deutschland, Müller Verlag, Fujitsu Web Solutions Centre, and Fujitsu Darwin available on request.
Life Outside Work
I work to live. Family is my foundation.
We love traveling for food and culture - street markets in Asia, local bakeries in Europe. I'm fascinated by how people express care through cuisine.
At home, it's math and science projects, Minecraft worlds, and Disney movie marathons.
When I'm not behind a laptop:
In the garden, experimenting with irrigation or compost.
Renovating something, often learning new skills on YouTube.
Fixing our car, like the time I learned to replace the brakes from a video tutorial.
Life's better when you're always learning, and that applies just as much to technology as to everyday craft.
Guiding Principles
"Empathy is a design tool."
"Iteration beats intention."
"Good architecture is invisible."
"A healthy team is the best productivity framework there is."