Charlie Dorsey · Fort Collins, Colorado

Senior product leader.
Platform, integrations
& applied AI.

I’ve spent 8+ years building software products, including strategy and roadmap ownership for a $10M+ ARR enterprise SaaS portfolio spanning 12+ products at PowerSchool. My strongest work lives where customer workflow, platform constraints, reliability, integrations, and product judgment collide. Since leaving PowerSchool, I’ve deliberately gone deeper into direct building—AI-enabled workflows, evaluation systems, developer tooling, and verification-first technical work.

Enterprise SaaS Platform & integrations Technical product AI / evals
See the work ↓ Résumé
Charlie Dorsey outdoors in a snowy forest
Product Leadership

The commercial floor underneath the technical work.

At PowerSchool, I owned product strategy, roadmap, investment decisions, and sequencing across a $10M+ ARR portfolio. The core Document Management business grew about 20% annually during my ownership. The work was rarely “just roadmap”: reliability, identity, integrations, migration, platform boundaries, and customer trust were part of the product.

$10M+ARR portfolio spanning 12+ products
~20%annual Document Management growth during ownership
8–10legacy SIS integrations owned with Engineering
7+years at PowerSchool across institutional software
Judgment

Reliability before redesign

I championed a major redesign, then stopped my own initiative when performance and reliability became the real constraint. Capacity moved to stabilization first; screens that could take 30+ seconds fell to roughly 2 seconds max, long-running jobs moved from 24+ hours or never to mostly about 30 minutes, and a 1,000+ backlog fell to roughly 50 in 3–4 months. Engineering implemented the fixes; I owned the product tradeoff and sequencing. Two quarters later, after the product was healthy enough to support it, we came back and built the new UI.

Platform

Shared capability, not another silo

I drove Document Management toward PowerHub as a shared capability across authentication, micro-frontend UI, and SIS data access, and owned roughly 8–10 bespoke SIS integrations against legacy REST APIs. The useful product work was often at the seams: identity, contracts, system-of-record dependencies, permissions, and customer-visible failure modes.

Prioritization

Kill the feature when the premise dies

A bulk-upload roadmap item only made sense if customers could move hundreds or thousands of documents. When the engineering constraint reduced that to a few dozen, I stopped the sunk work and reframed the problem toward migration and ETL. Later discovery surfaced needs far beyond the original uploader scale.

Read Product Leadership →

Current Work

Build close enough to the problem to change your mind.

Since leaving PowerSchool, I’ve deliberately gone deeper into direct building. The work ranges from product prototypes to AI systems, engineering experiments, and independent research; the through-line is staying close enough to the customer, system, and evidence that reality can change the plan.

Product build · discovery → rebuild

Matter — legal-document workbench

A practicing attorney falsified the initial intake premise, so I rebuilt around the actual discovery/document job: source-linked evidence, OCR fallback, conflicts, provenance, and evidence-gated consequential fields.

Read the case study →
AI handoff · public RC

OXBOW — carry the work, not the model

A self-orienting handoff for starting a fresh AI instance with an existing corpus, working context, provenance, and supporting tools—without pretending the new model is the one that came before.

Read the product story →GitHub ↗
Engineering proof

The check ships with the claim.

Engineering Verification records what I measured, how to reproduce it, where the mechanisms lose, and which claim boundaries remain. It is the inspectable evidence behind the technical work.

Read Engineering Verification →

Explore all current work →

Elsewhere

A real person, not a résumé rendered as HTML.

Advanced conversational Spanish. Ultramarathoner. 1,300+ consecutive days running. Photography when the light cooperates.

Charlie standing beside a red road bike in a mountain downpour
Three street musicians performing together
A hillside city under low clouds at night

Photography on Instagram →

Get in touch

If you’re building products where customers, systems, and evidence all have to agree, I’d like to talk.

I’m especially interested in senior product, technical product, forward-deployed product, and selective AI/evals work where the technical constraints actually matter.

Email me → LinkedIn → GitHub →