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Hi, I'm Michael Schofield, a founding engineer and VP of Engineering with deep experience building and scaling omnichannel communication and personalization platforms, including integrations with HubSpot. I have designed and led complex systems for content delivery across various channels like email, SMS, in-app notifications, and social media, with a strong focus on audience targeting, pacing logic, and extensibility. I'm a hands-on technical leader who grows autonomous teams, builds scalable systems with measurable impact, and partners across product, data, and design to ship high-impact features. Experienced in AI-assisted developer tooling, experimentation frameworks, and compliance-heavy enterprise SaaS, I thrive in growth-stage environments and enjoy solving challenging technical and organizational problems.…Hi, I'm Michael Schofield, a founding engineer and VP of Engineering with deep experience building and scaling omnichannel communication and personalization platforms, including integrations with HubSpot. I have designed and led complex systems for content delivery across various channels like email, SMS, in-app notifications, and social media, with a strong focus on audience targeting, pacing logic, and extensibility. I'm a hands-on technical leader who grows autonomous teams, builds scalable systems with measurable impact, and partners across product, data, and design to ship high-impact features. Experienced in AI-assisted developer tooling, experimentation frameworks, and compliance-heavy enterprise SaaS, I thrive in growth-stage environments and enjoy solving challenging technical and organizational problems.

Michael Schofield

Developer, Full Stack Developer, AI Developer, +2

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Hi, I'm Michael Schofield, a founding engineer and VP of Engineering with deep experience building and scaling omnichannel communication and personalization platforms, including integrations with HubSpot. I have designed and led complex systems for content delivery across various channels like email, SMS, in-app notifications, and social media, with a strong focus on audience targeting, pacing logic, and extensibility. I'm a hands-on technical leader who grows autonomous teams, builds scalable systems with measurable impact, and partners across product, data, and design to ship high-impact features. Experienced in AI-assisted developer tooling, experimentation frameworks, and compliance-heavy enterprise SaaS, I thrive in growth-stage environments and enjoy solving challenging technical and organizational problems.…Hi, I'm Michael Schofield, a founding engineer and VP of Engineering with deep experience building and scaling omnichannel communication and personalization platforms, including integrations with HubSpot. I have designed and led complex systems for content delivery across various channels like email, SMS, in-app notifications, and social media, with a strong focus on audience targeting, pacing logic, and extensibility. I'm a hands-on technical leader who grows autonomous teams, builds scalable systems with measurable impact, and partners across product, data, and design to ship high-impact features. Experienced in AI-assisted developer tooling, experimentation frameworks, and compliance-heavy enterprise SaaS, I thrive in growth-stage environments and enjoy solving challenging technical and organizational problems.

Available to hire

Hi, I’m Michael Schofield, a founding engineer and VP of Engineering with deep experience building and scaling omnichannel communication and personalization platforms, including integrations with HubSpot. I have designed and led complex systems for content delivery across various channels like email, SMS, in-app notifications, and social media, with a strong focus on audience targeting, pacing logic, and extensibility.

I’m a hands-on technical leader who grows autonomous teams, builds scalable systems with measurable impact, and partners across product, data, and design to ship high-impact features. Experienced in AI-assisted developer tooling, experimentation frameworks, and compliance-heavy enterprise SaaS, I thrive in growth-stage environments and enjoy solving challenging technical and organizational problems.

Skills

Experience Level

Expert

Expert

Expert

Expert

Expert

Expert

Expert

Intermediate

Intermediate

Language

Work Experience

VP of Engineering at Letterhead

July 1, 2021 - Present

As founding engineer and VP of Engineering at Letterhead, I designed and built the content curation, personalization, conditional promotion, and delivery platforms that became the company's core suite. I iterated the platform through growth stages, migrations, and scaled it to handle hundreds of millions of enterprise business emails. I grew the engineering organization to 25 engineers distributed across autonomous squads on- and offshore, maintaining low churn, strong ownership, and measurable ROI with few regressions and frequent releases. I briefly served as interim Head of Product, hiring the first PMs and UXR team members. I also drove compliance and due diligence readiness for SOC2, GDPR, CAN-SPAM, unlocking enterprise deals, strategic integrations, and Seed and Series A funding rounds.

Director of Engineering at Where By Us

July 1, 2021 - September 4, 2025

Led engineering at Where By Us, a local media network that spun out Letterhead. Unified legacy city-based publishing infrastructure and stabilized DevOps across distributed markets. Built internal tooling that monetized email-first journalism and adapted it for external use in Letterhead. Built and mentored the engineering team through the spin-out, drafting early playbooks for software development lifecycle, hiring, and platform growth.