My Profile Photo

James Armstrong | Engineering Leadership & AI Strategy


Engineering leadership insights, AI strategy, and practical guides for modern software development. Learn about product-aware engineering, team scaling, and building in the age of AI.


James Armstrong | Seasoned SaaS Engineering Leader

Vancouver, British Columbia, Canada

Seasoned SaaS Engineering Leader with a reputation for building high performing teams to efficiently deliver reliable and scalable solutions. Creating cloud-first engineering approaches that balance velocity with reliability and scale. Provides proactively conscious leadership for large teams and delivers exceptional outcomes, including managing 60,000,000 accounts with over $70,000,000 in sales. Excels in fast-paced and challenging environments.

Experience

HubSpot | Engineering Group Lead

November 2024 - Present Vancouver, Canada & Boston, USA

Leading engineering teams within the CommerceHub focused on CPQ and quote-to-cash solutions.

Cacheflow (acquired by HubSpot) | Head of Engineering

November 2023 - November 2024 Vancouver, Canada & San Francisco, USA

Supported Co-founding CTO with engineering leadership for Cacheflow, a fintech startup building a Quote-to-Cash platform for B2B SaaS companies, driving the technical foundation through to successful acquisition by HubSpot.

Armstrong Engineering

August 2023 - November 2023 Vancouver, Canada

Provided fractional engineering leadership and data development consulting for various clients including:

MediaValet | Vice President of Engineering

April 2022 - July 2023 Vancouver, Canada

Led Engineering for MediaValet, supporting 40% year-on-year revenue growth through delivery of global Digital Asset Management platform serving 650+ organizations for digital asset storage, interaction, and distribution.

Uplight | Vice President and Director of Engineering

January 2020 – February 2022 Vancouver, Canada

Led distributed Platform Engineering (~120 people) managing core data platform for 60M+ energy accounts and $70M+ annual eCommerce sales. Drove 50% YoY revenue growth, integrated 6 company tech stacks across 20 teams, and established Technical Program Management practices. Key focus areas: API strategy, SOX-compliant financial services, data lake architecture, IoT Virtual Power Plant, and technical coaching.

Contino | Principal Consultant

January 2018 - December 2019 London UK

Led high-value cloud transformation engagements for enterprise clients including Nationwide Building Society (Open Banking/PCI compliance), IRESS (global AWS migration), and Allianz UK (greenfield platform with Auth0, Java microservices, Angular). Focused on AWS architecture, DevOps implementation, and technical leadership across global teams.

Vision Critical | Director & Sr Director, Core Engineering & TechOps

May 2013 - Jan 2018 Vancouver, Canada

Built and led Core Engineering, Systems Engineering and Infrastructure teams (~30 people, $5M budget) at Market Research SaaS. Delivered 50% cost reduction, complete AWS migration, and full-stack automation using Chef, Terraform, ELK, and CI/CD practices. Established SRE team and infrastructure cost modeling.