Senior-level consulting for technology strategy, operational efficiency, and the leadership needed to turn ambitious roadmaps into real results.
Overleap brings together two decades of hands-on technology leadership across engineering, program management, and executive strategy — from scaling AI startups to directing large engineering organizations at some of the world's most demanding companies.
We work with startups, growing companies, and enterprises navigating complex IT and technology decisions: modernizing aging systems, restructuring engineering teams, reducing costs without sacrificing capability, or building a roadmap that actually gets executed.
Whether you need experienced leadership to drive a transformation initiative or an independent perspective on your technology direction, we bring the seniority and candor to move things forward — serving clients across Canada and the United States.
We focus on the areas where senior IT leadership has the most impact — strategy, structure, and execution.
Translate business objectives into a clear, actionable technology roadmap. We help leadership teams align on priorities, sequence initiatives, and build a strategy that survives contact with reality.
Move beyond the buzzword. We guide organizations through meaningful modernization — from legacy system migration to cloud adoption — with a focus on adoption, not just deployment.
Identify and eliminate spend that isn't delivering value. We audit vendor contracts, licensing, infrastructure, and team structure to find sustainable savings — without cutting capability.
Build and develop high-performing IT teams. From org design and hiring strategy to leadership coaching and performance frameworks — we help organizations grow the talent they need.
Establish the policies, controls, and oversight frameworks that keep your IT function accountable, compliant, and resilient — without bureaucracy slowing you down.
Access senior technology leadership without a full-time executive hire. We embed with your organization to provide engineering direction, board-level reporting, and technology oversight on a flexible basis.
Our team has built, scaled, and led technology organizations at some of the world's most demanding companies — Amazon, Capital One, Autodesk, Wayfair, Morgan Stanley, IBM, and high-growth startups across AI, fintech, gaming, e-commerce, and travel.
Chief Technology Officer
Senior technology executive with a track record of building high-performing IT organizations, delivering complex transformations, and aligning technology investment with business outcomes. Industry experience spanning travel, e-commerce, financial services, and enterprise software.
Principal TPM · Former Director of Engineering · VP of Engineering
Engineering leader with deep roots in software development and a career path from senior engineer to VP — including directing 8 engineering teams at Capital One and launching quick-commerce programs at Amazon serving millions of customers worldwide. Published researcher with a background in AI and computer science.
We work in close partnership with your leadership team — practical, direct, and focused on outcomes you can measure.
We start by listening. A thorough assessment of your current state — technology, people, process, and strategy — before any recommendations are made.
We work with your leadership team to define success. Clear objectives, agreed priorities, and realistic timelines set the foundation for everything that follows.
Strategy only matters if it gets done. We stay engaged through implementation — removing blockers, adjusting as needed, and ensuring momentum.
We build capability inside your organization, not dependency on us. The goal is a team and a system that thrives long after we step back.