About Michael D. Penn
I build AI-enabled business systems from zero to operating reality: methodology, product, platform, workflow, data, automation, content engine, revenue operations, integrations, and production support.
The through-line is simple: I see the business problem, design the operating model, build the system, wire the workflows, and support production. Senior solution architecture is part of the proof; it is not the whole story.
Real business problems do not sit inside one project. They surface at the integration points between systems, teams, revenue motion, data, technology, and the manual processes wrapped around them.
No solution lives on its own. Every solution I have built is interconnected with others, sometimes through APIs and webhooks, sometimes through email, paperwork, spreadsheets, approvals, and human handoffs. To optimize a business system, you have to design across the whole operating landscape.
The work is half business architecture and half technical execution. Planning, definition, build direction, validation, and production support have to stay connected.
Understand the business problem, economics, buyer journey, operating constraints, and workflow bottlenecks.
Design the operating model before designing the software: roles, data, automations, handoffs, content engine, and revenue operations.
Architect the platform, integrations, workflow layer, user experience, and production support model around that operating design.
Use AI-enabled execution to build, refactor, document, test, and deliver across the tools the system actually needs.
Review, validate, and own the output at the system level, including debugging the business process when the code is only part of the issue.
Plan for scalability, compatibility, supportability, and expansion from day one.
I lead with the business problem, then build the operating model and technical system that make the answer repeatable.
Co-founded and co-owned a streamlined HR training business that scaled past $125K/month, with LMS delivery, marketing automation, accounting integration, remote/hybrid operations, and lean-team execution by two founders plus one customer-support team member.
Built the operating umbrella and proof-bench layer connecting CriticalThink, CriticalThink HR, CriticalThink Advantage, SCMS / SCMS 2.0, SpectraCastr, HRTrainingClasses, and selected enterprise work.
Translated deep HR and decision-work into CriticalThink Advantage, an executive decision-governance methodology, and CriticalThink HR, the SHRM exam-preparation platform that applies it.
The original SCMS began in 2010 in a continuous sports contract management relationship. The new AI-powered SCMS 2.0 modernization supports contract data workflows connected to USA TODAY college coaches salary reporting without implying ownership of the public reporting product.
IT consultant to Director, Customer Self Service, to Director, Enterprise Integration Office. Led a team of 20+. Order Automation work helped charter.com sales more than double in 2005.
Built the Key Client Solutions 4Front Portal, the Financial Advisors Reporting Dashboard, and an iPad executive prototype consolidating multiple legacy systems.
Designed and built the Unified Member View Application for enterprise healthcare data integration.
Senior-level HR certification, founder/operator experience, business systems architecture, and production software delivery are rarely found in one person. That combination is why I partner well with leaders turning expertise and workflow into operating leverage.
I take on fractional and project engagements through Total Freedom Life - typically 3, 6, or 12 months - for founders, operators, PE-backed mid-market, Series B-C, established organizations, experts productizing methodology, and leaders launching AI-native initiatives. Remote, US-based.
Currently accepting one new engagement.