Joe DeGregorio

Joe DeGregorio

Principal Applied AI Leader

I help teams turn ambiguous AI opportunities into practical systems with measurable business value.

My work sits at the intersection of product, analytics, and engineering, taking AI/ML systems from early prototypes through evaluation and instrumentation to real operational use and product adoption.

Joe DeGregorio portrait

Approach

How I work.

The same pattern shows up repeatedly: understand the system, scope something credible, and build evidence teams can trust.

01

Understand the system before changing it

The best opportunities usually sit behind a deeper constraint. I use product and systems thinking to find the real friction before reaching for AI, ML, or automation.

  • Map workflow bottlenecks, decision gaps, and broken feedback loops.
  • Use interviews, JTBD framing, and root-cause analysis to find leverage.
  • Target interventions where tooling can create durable value.

02

Scope for traction, not just speed

Early systems need to move quickly without feeling flimsy. I aim for the smallest system that delivers real value, meets critical requirements, and earns trust.

  • Define functional and non-functional requirements early.
  • Choose the right technical shape for the job.
  • Build versions strong enough to gain traction, not just demo well.

03

Build trust through evidence

AI/ML systems need credibility before they get adoption. I make quality visible early with benchmarks, evals, instrumentation, and comparisons against meaningful baselines.

  • Measure against the status quo and simpler alternatives.
  • Use scorecards and expert review to surface blind spots.
  • Give teams evidence they can use to decide what to invest in next.

Experience

How the stack took shape.

My career built upward in layers: engineering foundations, requirements discipline, analytics and machine learning, experimentation, and applied AI systems. That layered stack lets me frame problems clearly, build practical systems, and judge them with rigor.

Open resume

Layer 01

2012 - 2016

Engineering foundations

Caterpillar · Senior Design Engineer

Built the habits that still anchor my work: structured problem-solving, root-cause analysis, and systems thinking shaped by complex design work and FMEAs.

Layer 02

2016 - 2018

Requirements discipline

PACCAR · Senior Systems Engineer

Learned how to define functional, non-functional, and technical requirements clearly enough that complex systems can be built with fewer surprises.

Layer 03

2018 - 2023

Analytics and ML depth

PACCAR · Senior Analyst to Data Scientist

Added Python, R, statistics, text mining, and end-to-end machine learning to the stack, applying them directly to operational and decision problems with real business costs.

Layer 04

2023 - 2025

Experimentation and support systems

Atlassian · Senior Data Scientist

Applied that toolkit to experimentation and customer support, improving self-help, live chat, and the broader support experience while championing early AI-assisted workflows.

Layer 05

2025 - Present

Applied AI systems and automation

Atlassian · Principal Data Scientist

Now focused on applied AI systems, evaluation, and automation, turning messy opportunities into durable products that teams can adopt, trust, and build on.

Contact

Interested in applied AI, product systems, or principal-level technical leadership?

I’m always open to thoughtful conversations about applied AI/ML, modern evaluation practices, product systems, and high-ambiguity technical leadership.