Allan Leonard, Jr.
Founder & Principal Engineer, Plan Things Better | Former Interim Head of Product & Engineering
Based in United States · 16+ years experience
Summary
Fractional CTO and hands-on engineer with 16+ years building cloud-native, full-stack, and AI platforms. Founder of Plan Things Better; former Interim Head of Product & Engineering.
About
I'm a technology leader and hands-on engineer with 16+ years building and running cloud-native software, from early-stage products to regulated enterprise platforms. I work best as a player-coach: setting technical strategy with founders and executives, then getting into the architecture, code, pipelines, and vendor contracts to deliver it.
Most recently I was Interim Head of Product & Engineering at SkillUp Coalition, a national nonprofit helping workers without four-year degrees reach good-wage careers. I served on the Executive Leadership Team, reported to the CEO, and owned the full Product & Engineering budget. I directed a 14+ person distributed team across Costa Rica, the UK, and Denver, set technical strategy for an AI-native career-navigation platform (LLMs, agentic workflows, RAG, vector search, AI observability), consolidated tools and formalized sprints, and led the beta launch past its 1,000-user target.
Before that, I spent nearly seven years at M2GEN (now Aster Insights) as Engineering Manager reporting to the CTO, leading U.S. and international teams building secure platforms for oncology research. I architected a company-wide AWS-to-Azure migration with no major disruption, standardized CI/CD, contributed hands-on in TypeScript, React, Next.js, and NestJS, and managed vendor SOWs and budgets. Earlier roles include DoD enterprise applications and infrastructure automation at JPMorgan Chase.
Today I'm the founder of Plan Things Better, a multi-tenant project-management SaaS I built and launched myself. It includes a REST API and an MCP server with 70+ tools so AI assistants can work inside the app, runs on AWS with infrastructure as code and automated CI/CD, and ships with Stripe billing and 300+ automated tests. Its open-source Obsidian plugin, Vertex Flow, has 1,600+ downloads.
Where I help:
- Technical strategy, architecture, and roadmap
- Bringing AI into your product safely and measurably
- Building and scaling distributed and vendor teams
- Cloud, CI/CD, and platform reliability
- Budgets, vendor governance, and board-level reporting
Skills
Software Architecture, Cloud & Infrastructure, Platform Modernisation, Cybersecurity, Engineering Leadership, Vendor Management, DevOps, Governance & Risk, Data & AI
Regions covered
Singapore, Israel, France, New Zealand, United Kingdom, Brazil, Asia-Pacific, United Arab Emirates, South Africa, Australia, Netherlands, United States, Europe, North America, Africa, South America, Japan, Middle East, Ireland, India, Germany, Canada
Industry experience
Not-for-profit, Government, Professional Services, SaaS, Healthcare
At a glance
Allan brings hands-on experience across Software Architecture, Cloud & Infrastructure, Platform Modernisation, Cybersecurity, Engineering Leadership, Vendor Management and 3 other areas. Available for engagements across Singapore, Israel, France, New Zealand, United Kingdom, Brazil, Asia-Pacific, United Arab Emirates, South Africa, Australia, Netherlands, United States, Europe, North America, Africa, South America, Japan, Middle East, Ireland, India, Germany, Canada. Industry experience includes Not-for-profit, Government, Professional Services, SaaS, Healthcare.
How fractional CTO engagements with Allan work
Allan works on a fractional basis — typically one to three days a week for an agreed engagement length — so you get senior technical leadership without the cost or commitment of a full-time hire. Engagements commonly include technical due diligence, board reporting, engineering team leadership, technology strategy, architecture reviews, hiring support, and stepping in as interim CTO during a transition.