Web teams, useful software, and dependable delivery.

Stefano
Tomasello.

I lead technical teams and build useful software. My work connects people, priorities and technical decisions, from deciding what matters to checking what ships.

A little contextDenver area, Colorado

Still hands-on.
Always curious.

Twenty-plus years at the intersection of engineering, design and the work people actually need to do.

I set priorities, coach engineers and build technical ownership. That means working through scope and dependencies with other teams, then staying close enough to delivery to make useful decisions.

My independent work keeps me close to implementation. Each project starts with something a person needs to do.

Read my resume

Leadership,
close to the work.

Strategy and delivery belong in the same conversation.

JumpCloud

Website Manager · Sep 2020–present

Lead web engineering and CRO. Coach engineers, develop technical owners, and shape quarterly priorities with Marketing, Product and RevOps. Led Pardot-to-Marketo integration and Vue modernization, and introduced practical AI workflows.

TrainingPeaks / Peaksware

Senior Software Engineer / Full Stack Developer
Feb 2019–Sep 2020

Refactored a content API with AWS Lambda, Node.js and GraphQL. Extended headless WordPress with React and Gatsby, and contributed to reusable web components and automated testing.

A career of making

2002 onward

Websites, software, integrations and the operational details that make them dependable. More than two decades of building and learning.

Selected workFull experience ↗

The decisions
behind the work.

A team needs clear priorities.
A product needs a reason to exist.

These projects show the problems I work on, the choices behind the implementation and what is ready to use. Prototypes and internal builds are labeled separately.

Web engineering leadership

Balance platform modernization and growth work. I lead priorities, technical ownership and hands-on delivery at JumpCloud.

Website Manager · September 2020–present

Read the leadership case study ↗

AI workflows with human control

Connect team intake and delivery. I built TIbot with duplicate detection, approvals and guarded Slack and Jira updates.

Built and in use · Public overview

Read the automation case study ↗

Shipped product engineering

Connect booking, staff workflows and operations. I built PolyshOS across web, API, worker and native clients.

Web/API/worker production · Native internal testing

Read the PolyshOS case study ↗
Web engineering & growth

Web
platforms.

Design, engineering
and growth at one table.

From signal to insight: aggregate exposure, engagement and friction flow into findings.Built to connect: layered content, experience and growth systems, joined by shared delivery paths.
Illustrated feature studies: platform architecture / PageInsights collection and findings.

A company website has to work for its visitors and the teams responsible for it.

At JumpCloud, I lead web engineering and conversion work as Website Manager: shaping priorities, coaching engineers, building technical ownership and staying close to implementation. The work spans Vue modernization, Pardot-to-Marketo integration, reusable components and the systems behind content and measurement.

Earlier at TrainingPeaks, I helped refactor a content API around AWS, Node.js and GraphQL, extend headless WordPress with React and Gatsby, and bring reusable components and automated tests into delivery.

My work
Engineering direction, hands-on delivery, team development and cross-functional planning.
Where it stands
Current web leadership at JumpCloud. Delivered platform work at TrainingPeaks.
Read the web engineering case study ↗
AI, automation & agents

Teams
of agents.

Connect the workflow.
Keep decisions accountable.

Workflow improvements move through observation, proposal and comparison with a baseline, with adoption and rollback paths.TIbot routes intake through specialists and a human approval gateway before action.
Illustrated feature studies: TIbot coordination and approvals / workflow learning and baseline evaluation.

Useful agents need more than a good prompt. They need a place in the work.

I build specialist workflows for intake, audits, planning, engineering, security and delivery. TIbot brings that approach into Slack and Jira, with webhooks, scheduled work, deduplication, human approval and guarded updates. Reusable specialist skills connect intake and planning to implementation, review and handoff.

I’m developing Agent Workflow Learning to turn execution reviews into tested changes to instructions. PageInsights addresses a separate problem: understanding where visitors encounter friction on a page.

TIbot & orchestration
Built and in use. Public overview of team workflows.
Workflow learning
In development. Evaluation and instruction refinement, rather than model training.
PageInsights
Built and tested in isolated WordPress. Staging and live use remain unverified.
Experimentation
Architecture and technical spike for variants, goals, consent and reporting.
Read the AI workflow case study ↗
Search, integrations & scheduling

Connect
the details.

Find the right thing.
Make the next step work.

Calendar inputs pass through buffer rules and a final recheck before confirmation.Semantic and keyword retrieval converge on ranking, with inspectable sources behind the answer.
Illustrated feature studies: hybrid retrieval and source grounding / calendar availability and booking reliability.

The useful part happens between the question, the source and the next action.

Client search work for House of Destiny combines WordPress, OpenAI embeddings, Supabase vector retrieval and keyword matching. Grounded summaries, filters, caching and analytics connect a visitor’s question to material they can inspect.

A calendar scheduling system connects Google Calendar and iCloud CalDAV with timezone-aware availability and meeting creation. Locks, request identifiers, conflict checks and recovery turn an attractive booking interface into something dependable.

AI search
Delivered beta. Migration to the main target site remains unverified.
Scheduling
Live integration across Google Calendar and iCloud.
My work
Retrieval design, application engineering, integration architecture and delivery reliability.
Read the hybrid search case study ↗
Selected product engineeringArchitecture, implementation & delivery
Vehicle identity & events

Bilt:Spec

A build is more than a parts list.

Visit Bilt:Spec ↗
Vehicle entrants move through classes and judging, with a separate path for offline support.An exploded vehicle illustration connects a build to its identity, modifications, history and media.
Illustrated feature studies: build identity, modifications and QR sharing / event operations, judging and offline work.

One place for a vehicle’s history, modifications, media and the story behind the build.

Build profiles connect modifications, dyno results, photography and QR sharing. The event side brings organizer workflows, judging and offline support into the same system.

My work
Product direction and full-stack engineering across the web, native apps and shared contracts.
Built with
React and TypeScript, Expo / React Native, PHP and MySQL.
Where it stands
Delivered web releases and internal TestFlight builds.
Social publishing workflows

CrossPost

One workflow.
Every platform’s reality.

Media passes through connection, upload and a platform inbox, with publication shown as a separate state.Ordered media panels form a continuous sequence through preparation and delivery.
Illustrated feature studies: ordered media and preparation / delivery states and publication boundaries.

A publishing tool that treats the awkward platform details as part of the product.

OAuth connections, ordered carousels, JPEG normalization, optional FFmpeg processing and chunked TikTok uploads. R2 media storage, diagnostic history and delivery states help make failures explainable.

My work
Workflow design, PHP / JavaScript engineering and platform integrations.
The important distinction
Delivery to a platform inbox is tracked separately from actual publication.
Where it stands
Web deployed. Live end-to-end posting and public adoption have not been independently verified.
Salon operations

PolyshOS

The business behind
the appointment.

A shared data model connects staff, public booking, workers and native clients.Parallel staff schedules organize availability and appointments into a shared booking flow.
Illustrated feature studies: staff scheduling and appointments / shared data model and operational clients.

An operating system for bookings, calendars, waitlists and the people keeping a salon moving.

A multi-tenant platform with role-based permissions and operational workflows. The web, API and background worker share a data model, with a native SwiftUI companion in development.

My work
Product and system architecture, web / API / worker implementation and native application work.
Built with
Next.js, Fastify, PostgreSQL, Drizzle and SwiftUI.
Where it stands
Web and API in production. Native app in internal testing.
Local-first dictation

Mumbl

Hold. Talk.
Get back to it.

Dictated text passes through dictionary correction and cleanup, with a separate fallback path that preserves meaning.A spoken waveform becomes text through hold, speak and insert, using local recognition.
Illustrated feature studies: local recognition and focused-app insertion / guarded cleanup, dictionary and fallbacks.

Dictation designed to fit around the work, with local recognition and careful text cleanup.

A SwiftUI macOS and iOS app with a compact HUD, keyboard workflows and a personal dictionary. Apple Speech, optional Parakeet Core ML and WhisperKit provide recognition options.

My work
Native product design and engineering, speech integration, dictionary and guarded cleanup workflows.
Design choice
Local-first recognition. Cleanup gets explicit boundaries rather than silently rewriting intent.
Where it stands
Delivered notarized macOS releases and internal iOS TestFlight builds.
How I workDecisions, tests and ownership

Make the work
work better.

Faster implementation makes choosing the right work more important.

Start with the problemPriorities

I balance growth work with modernization, reliability and technical debt. The roadmap has to account for team capacity and the people responsible for delivery.

In product work, the same question becomes more concrete. Can someone find the right source, book an appointment or dictate without losing their place?

Give AI a defined jobContext & scope

My delivery workflows connect discovery and planning to implementation, testing and release. Specialist roles get the context and scope they need, with explicit ownership when work runs in parallel.

Approvals and guarded updates keep consequential decisions with people.

Check the result separatelyReview & release

I require completion evidence and independent review before work advances. A working prototype is useful evidence about an idea. Production readiness still needs testing, clear ownership and a way to recover.

I label prototypes and isolated tests according to what they establish. Each answers a narrower question than a production rollout.

Revisit the methodLearning

I’m developing a way to record execution reviews and feedback, then compare proposed instruction changes with a baseline before adoption or rollback.

The aim is to improve the workflow with evidence. It does not train model weights.

A good place to startResume ↗

Let’s build
what’s next.

Tell me about your team, what you need to build, and where the work is getting stuck.

Book a conversation

LinkedIn ↗

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Start with a message.

Tell me about your team, the problem, or what you’d like to discuss.