Web, software & AI engineering

Stefano
Tomasello.

I build useful things.
And lead the people who build them.

Explore the work
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’m Stefano. I lead web engineering and conversion work at JumpCloud. I’m as comfortable shaping a roadmap and coaching a team as I am working through the implementation.

The through line: understand the problem, choose the right tools, make the useful change. Then check that it holds up.

Read my resume

Leadership,
with the sleeves up.

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 ↗

From idea.
To something useful.

Products. Platforms. Intelligent workflows.
Ideas made useful.

Engineering leadership, applied AI and hands-on product delivery across web, native apps and connected systems. Selected projects show how I turn complex requirements into working software.

Web engineering & growth

Web
platforms.

Design, engineering
and growth at one table.

Illustrated pageinsights collection and findingsIllustrated platform architecture
Illustrated feature studies: platform architecture / pageinsights collection and findings.

The website is a product, an operating system and a meeting point for a whole team.

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.
Explore the full experience ↗
AI, automation & agents

Teams
of agents.

Less handoff friction.
More considered action.

Illustrated workflow learning and baseline evaluationIllustrated tibot coordination and approvals
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.

Agent Workflow Learning closes the feedback loop: review an execution, propose a refinement, compare it with a baseline, then adopt or roll back. PageInsights approaches a different problem—turning aggregate page behavior into findings about section exposure, CTA friction and forms.

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.
Explore the systems and their boundaries ↗
Search, integrations & scheduling

Connect
the details.

Find the right thing.
Make the next step work.

Illustrated calendar availability and booking reliabilityIllustrated hybrid retrieval and source grounding
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 implementation overview ↗
Selected product engineeringArchitecture, implementation & delivery
Vehicle identity & events

Bilt:Spec

A build is more than a parts list.

Visit Bilt:Spec ↗
Illustrated event operations, judging and offline workIllustrated build identity, modifications and qr sharing
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
Web deployed. Native app in TestFlight, with App Store review pending.
Social publishing workflows

CrossPost

One workflow.
Every platform’s reality.

Illustrated delivery states and publication boundariesIllustrated ordered media and preparation
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.

Illustrated shared data model and operational clientsIllustrated staff scheduling and appointments
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.

Illustrated guarded cleanup, dictionary and fallbacksIllustrated local recognition and focused-app insertion
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
Used daily on Mac and tested on a physical iPhone. Public distribution is not fully verified.
AI & connected systemsBuilt with boundaries

Make the work
work better.

Automation earns its place by being useful, understandable and accountable.

Agents that help a teamBuilt & in use

TIbot connects specialized Slack and Jira agents with webhooks and scheduled workflows. Deduplication, guarded state changes and approval controls keep the action tied to the person who owns it. Colleagues use it in their work.

A reusable orchestrator brings specialist roles together across intake, audit, planning, frontend, backend, APIs, security and delivery. I built it and adapted the approach to JumpCloud.

Public overview only. Employer internals, configuration and metrics remain private.

Learning from executionIn development

Agent Workflow Learning turns execution reviews and user feedback into refinements to instructions and workflows. Candidate changes are evaluated against a baseline, with an explicit decision to adopt or roll back.

This is a workflow improvement framework. It does not train model weights.

PageInsightsBuilt & isolated testing

An installable WordPress behavior analytics plugin: aggregate heatmaps, section exposure, CTA and form friction, comparisons, findings and exports.

Role permissions, bounded storage, retention and suppression are part of the design. Collection is off by default. It excludes session replay, visitor identity and experiment assignment.

Tested in an isolated WordPress environment. Staging and live use remain unverified.

Experimentation & personalizationArchitecture & spike

Exploring sticky variants, goal instrumentation, statistical reporting, cache behavior and consent as an alternative platform architecture.

A proposal and technical spike, without claims of achieved savings or production outcomes.

Search that explains its sourcesDelivered beta

Client AI search for HOD combines WordPress, OpenAI embeddings, Supabase vector search and keyword matching. Grounded summaries and analytics connect retrieval with the visitor’s question.

Delivered in beta. Migration to the main target site remains unverified.

Scheduling across calendarsLive

A custom WordPress scheduler connects Google Calendar and iCloud CalDAV. Timezones, locks, idempotency and recovery handle the details that an appointment interface cannot ignore.

A good place to startResume ↗

Let’s build
what’s next.

Looking for an engineering leader who stays hands-on?
Let’s talk about your team and the role.

Book a conversation

LinkedIn ↗

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Stefano Tomasello / Resume

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