Architecture decisions are business decisions.
Every re-platforming or cloud migration I've led was justified by a business outcome — uptime, capacity, cost, or speed — not by novelty.
About Tony
From hands-on engineer to CTO for 600-person organizations.
I started as a software engineer and never really stopped thinking like one — even after the title became CTO and the team grew past 500 people. That's the perspective I bring into every engagement: technology decisions judged by business outcomes, team clarity, and durable delivery.
Background
One throughline: ship software that people depend on.
I began as a software engineer at Apple, then spent years writing and architecting software commercially — including as Chief Software Architect at Intuition Publishing — before moving into technology leadership. Since then I've run engineering, product technology, IT, QA, and architecture functions — including AI/ML initiatives — for education and enterprise SaaS companies ranging from 10-person teams to a 600-person, 51-product organization with a $70M budget.
Alongside those full-time operating roles, I've worked independently as a fractional and interim technology executive — CTO and SVP Engineering engagements focused on strategic technology leadership, team building, risk and compliance, and transition support.
I hold a Bachelor of Science in Computer Science (Honours) from University College Cork, Ireland.
How I Operate
A few things I believe about running engineering.
Governance keeps teams honest, not slow.
Architecture and governance boards, standardized reporting, and clear metrics are how large distributed teams stay aligned without a meeting for everything.
Compliance is a growth lever.
SOC2 and FERPA programs I've run weren't just risk management — they opened up RFPs and enterprise deals the business couldn't win before.
A transition should be boring.
Whether I'm handing off to a permanent CTO or a client's team is taking a system back in-house, a clean handoff is part of the job, not an afterthought.
Selected Career Chapters
The operating experience behind the advice.
The full chronology is available on LinkedIn. These are the chapters most relevant to the work I do with companies today.
Independent Fractional & Interim Technology Executive
CTO / SVP Engineering
- Strategic technology leadership, roadmap alignment, and interim executive coverage
- Team mentoring, delivery governance, cybersecurity, and risk & compliance
- Transition support that leaves a permanent leader with a clear operating system
Chief Technology Officer
BookNook, Inc.
- Reorganized the team for clearer accountability and a unified product/engineering roadmap
- Raised platform uptime from 99.7% to 99.95% in six months through QA and test automation
- Delivered a patent-pending tutor-matching algorithm reaching a 99% match rate
- Launched a generative AI initiative to help scale tutoring support
- Achieved SOC2 Type 1, then led the transition to Type 2; rolled out company-wide SSO
Enterprise SaaS Engineering Leadership
ConnectWise · CentralSquare Technologies
- Led a global engineering organization of 500+ people with full budget ownership
- Integrated four acquired entities into a unified engineering operating model
- Led a 600-person team across 51 products and 6 locations with a ~$70M annual budget
- Led engineering through a three-way merger (TriTech Software, Aptean Public Sector)
- Founded a machine learning team to build predictive models from public-safety data
EdTech Platform Scale & Modernization
Imagine Learning · McGraw-Hill Education
- Grew the technology team from 25 to 100+ people in six months
- Increased concurrent user capacity by 200%+ and raised uptime from 96% to 99.9%
- Took automated test coverage from near-zero to 75%+
- Hired a 20-person cross-functional team and led a platform move toward microservices
Architecture Leadership & Engineering Foundation
Houghton Mifflin Harcourt · Intuition Publishing · Vivendi Universal Games · Apple
- Consolidated disparate development teams into a single center of excellence
- Grew the permanent technology team from 10 to 60, plus a 400-person outsource network
- Progressed from software engineer to architect and engineering executive
Technical Foundation
Still fluent in the stack, not just the org chart.
Languages & Platforms
C, C++, C#, Java/J2EE, Go, Node.js, JavaScript, HTML5, XML/JSON, SQL, SOA/microservices, AI/ML, AWS, Azure.
Practice & Governance
Agile & test-driven development, CI/CD, architecture governance, IT infrastructure and managed services, AI/ML initiatives.
Want to talk through your specific situation?
A short call is the fastest way to find out if this is a fit.