Ryan Kimber
Technology Transition Lead @Leap Tools
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WORK HISTORY
Technology Transition Lead @Leap Tools
Oakville, ON, CA
Leading the technology transition for Leap Tools’ acquisition of QFloors / Flooring Technologies Inc. • Enterprise Transformation: Integrated disparate systems post-acquisition, breaking down silos and creating a flexible, scalable architecture for future growth. • Legacy Modernization: Migrated a 20-year Visual Studio 6 codebase through successive upgrades to VS2022, enabling long-term maintainability and security. • Cloud & DevOps: Designed and implemented CI/CD pipelines with GitHub Actions, Terraform, and Packer; built Azure Virtual Desktop images for tenants. • Application Evolution: Introduced WebView2 into the legacy C++ stack, enabling screen-by-screen migration to modern web views without business disruption. • Team Enablement: Shifted culture from siloed waterfall practices to agile, energized the team around modern tools, and set the foundation for ongoing innovation.
EDUCATION
University of Toronto
Computer Science
Lester B. Pearson High School, Burlington, ON
Ontario Secondary School Diploma
The University of British Columbia
Engineering
SKILLS
ABOUT RYAN KIMBER
Technology executive with 25+ years of experience leading transformation across financial services, insurance, government, healthcare, and SaaS.I’ve operated at every level — from building technical solutions hands-on to negotiating enterprise contracts with Tier-1 banks, to scaling a startup to $10M ARR and 100+ staff before leading its successful acquisition. Along the way, I’ve driven seven-figure cost reductions, modernized legacy stacks, and delivered AI-driven transformation in complex, regulated environments.Career highlights:• Founder & CEO of Daylight Automation (FormHero) → scaled to $10M ARR, 100+ employees, enterprise clients (TD, RBC, BMO, Manulife, Loblaws).• M&A leadership: acquired ProofGov and successfully integrated its staff, clients, and offerings; later led Daylight’s sale to Quadient (2023) and managed the customer/payroll transition.• Chief Security & Technology Officer at Think Research → transitioned from paper to digital, delivered US Meaningful Use Certification, awarded patents, and built a 30-person tech team.• Early career: designed in-car mobile data and geo-location systems at Toronto Police Service (Chief’s Award, 2006); delivered core architecture at Fidelity Investments.• Recent: parachuted into LeapTools to modernize a legacy VS6 codebase, implement CI/CD with Terraform & Packer on Azure Virtual Desktop, and deliver seven-figure hosting savings through AI-driven optimization.What I deliver:• AI-driven cost reduction — millions saved through modernization, automation, and cloud transformation.• M&A experience on both sides of the table — acquiring and integrating companies, and successfully selling to a global enterprise.• Executive + hands-on credibility — I remove execution risk by bridging boardroom strategy with technical delivery.• Governance & compliance — led SOC2, PCI, and privacy programs with zero breaches.I’m passionate about making AI practical and profitable — driving enterprise resilience, lowering cost, and enabling organizations to move faster with less risk.
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