Enterprise AI transformation
Shawn Lenker
I benchmark and govern LLMs against the systems enterprises actually run on.
Eleven years inside ERP taught me why enterprises reject working systems. Two years building agentic infrastructure taught me what these models can and cannot be trusted to do. The gap between those two is where enterprise AI keeps failing.
For hosts, founders, and teams
Conversations Shawn is built for
I help people make hidden systems legible: business systems, AI workflows, ERP complexity, and the human fears wrapped around them.
Invite Shawn to speak
Human-centered AI adoption, ERP translation, responsible automation, and systems thinking across technology, ecology, and language.
Where enterprise AI breaks
Why pilots stall at integration rather than intelligence, and why evaluation is the discipline most programs skip until it costs them.
Learn from Shawn
Make complex systems clear enough for executives, operators, engineers, and curious audiences to act on.
Second brain
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Examples
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Resume core
Career and credentials
The through-line is systems that have to work in production: fifteen years of ERP, integration, and delivery leadership, and two years building agentic infrastructure with evaluation harnesses and regression gates.
Independent AI Systems Work
Sabbatical
2025 - Present
Took a sabbatical after relocating from Washington to Texas to be closer to family, and spent it building and operating agentic AI infrastructure. Runs a multi-model system covering orchestration across local and frontier models, routing by cost and capability, retrieval-backed memory, and durable workflow execution. Built an evaluation harness with committed baselines and a regression gate, including benchmarks of local models against X++ code generation and grounding checks for hallucination.
Senior D365 Developer
Patagonia Inc.
2022 - 2025
Operated as technical lead for distributed development across the United States, Japan, and the Netherlands, coordinating agile delivery and training developers while the organization worked through developer hiring gaps. Led and owned D365 projects across global finance and operations: integrations, custom solutions, Azure Service Bus and Topics, Application Insights Node.js tracing, SKS treasury and Adyen payment work, and D365CE to D365FO connectivity.
Technical Consultant
Sikich (MS Gold Partner)
2021 - 2022
Served as a technical consultant for D365FO upgrades and Microsoft Dynamics 365 Finance and Operations implementations across client environments.
Application Developer
Biamp Systems
2019 - 2021
Specialized in D365 FO development with part-time D365 CE work. Designed test bed systems and developed third-party integrations and customizations for manufacturing operations.
IT Development Manager
National Technical Systems
2015 - 2019
Headed the Dynamics AX development team, managed developers integrating Dynamics 365 CRM with the in-house AX ERP system, and led upgrade and implementation projects for D365 FO.
Microsoft certifications, previously held. These credentials have since lapsed.
People Shawn studies and admires
Reference points for the work beneath the resume
Leonardo, Newton, and Lincoln are shorthand for three qualities Shawn keeps returning to: technical imagination, systems clarity, and grounded leadership under pressure.
LD Florentine workshop Leonardo da Vinci Technical
Invention, observation, and craft brought down to the workbench.
IN Principia table Isaac Newton Systems design
A whole system made legible: forces, rules, constraints, and the math beneath the motion.
AL Cabinet room Abraham Lincoln Leadership
Plain speech, steady judgment, and the courage to keep people oriented under pressure.
Research, writing, and public ideas
Ideas worth building conversations around
The same pattern runs through the writing: people-aware AI, ecological systems, language, cognition, and ethical infrastructure that can hold up under real pressure.
People-First AI Building Practices
A practical exploration of designing AI systems around human needs, responsible adoption, and durable operator value rather than novelty for its own sake.
Stanford HAI
Ecology and Agroforestry Study
Research into maintaining healthy Northwest forests, regenerative fertilization, soil health, and closed-loop systems that reduce dependence on unsustainable phosphorus mining.
USDA Agroforestry
Narrative-Driven Language Evolution
A cognitive systems study of how story arcs, sensory memory, engrams, and language processing may have shaped the evolution of human communication.
Evolutionary linguisticsWhat I bring
What I would own
Useful when the work needs technical depth, business context, and a person who can translate from vague intent to working systems.
Enterprise AI adoption
Deciding what to buy, what to build, and what to kill, with a business case a finance team can actually attack.
Evaluation and governance
Eval harnesses, regression gates, grounding checks, and the operating discipline that keeps agents trustworthy in production.
Legacy modernization
Reading systems nobody fully understands anymore, then sequencing their replacement by blast radius instead of by politics.
Distributed team leadership
Cross-region delivery, mentoring, and translating between executives, operators, and the engineers doing the work.
The working agreement
Why hire me?
Because hard systems work needs a steady human presence: plain truth, clean structure, and enough warmth to keep everyone thinking.
- I will tell you the truth plainly, even when the answer is inconvenient.
- I will treat your team with kindness and respect while we fix the hard thing.
- I know D365, Azure, integrations, and business systems well enough to keep the room calm.
- I can make complex systems understandable enough for executives, operators, engineers, and curious audiences to act on.
- I need the problem, the constraints, and a fair shot at doing useful work.
Resume and contact
Let's connect.
Download a resume format, send a short project note, or ask the second brain before you write.