Stefano Tomasello

Professional summary

Connect business priorities, people and technical decisions to deliver useful software. More than 20 years across SaaS, agencies and independent products, with hands-on work in web platforms, native applications and connected systems.

Develop technical ownership through coaching and delegated responsibility. Build AI-assisted workflows with clear scope, independent review and controlled releases. Keep the customer’s problem, the team’s capacity and the work of maintaining the result in the same conversation.

JumpCloud

September 2020–present · Website Manager

Lead web engineering and conversion rate optimization for JumpCloud.com. Partner with Marketing, Product, Engineering, Security, Data and Revenue Operations on platform direction and delivery.

Team leadership and platform delivery

• Set roadmaps and quarterly priorities across growth experiments, modernization, security and reliability. Match scope to team capacity and keep technical debt visible.
• Coach engineers, support career planning and progressively delegate technical refinement and delivery ownership.
• Delivered Pardot-to-Marketo integration and Vue modernization through cross-functional coordination, consent requirements, testing and release readiness. Directed observability, maintenance and event-collection audits.

Automation, measurement and experimentation

• Built and introduced TIbot to connect intake, refinement and sprint-planning support in Slack and Jira. Duplicate detection, protected updates and approval gates preserve human decisions across automated workflows.
• Automated scheduled WordPress content reports with bounded queries, deduplication and repeatable reporting windows. Added health diagnostics to support troubleshooting.
• Built PageInsights to examine aggregate page behavior and form friction, with permissions, retention controls and collection disabled by default. Validated installation and health checks in isolated WordPress. Staging and production validation remain separate steps.
• Developed a business case and working prototype for AI-powered site search. Evaluated first-party experimentation through a build-versus-buy assessment and technical spike covering measurement, consent, caching and performance.
• Created a marketing AI toolkit and a framework for moving prototypes toward production, including privacy, accessibility, ownership and support. Co-organized and hosted a generative AI ideathon in 2023.

AI-assisted delivery

Developed reusable delivery workflows through independent product work and adapted the approach for team delivery. Connect discovery and planning to implementation, testing, security review and release.

• Coordinate specialist agents with scoped tasks, explicit file ownership and checkpoints. Require completion evidence and independent review before work advances.
• Match model capability and cost to the task. Build execution reviews and human feedback into reusable instructions.
• Developing Agent Workflow Learning to test instruction changes against baseline behavior, with decisions to adopt or roll back. The framework remains in development.

Selected engineering projects

Independent product and consulting work, from product direction and architecture through implementation and release.

PolyshOS

Built a salon operations platform connecting staff workflows, public booking and availability through shared appointment data. Delivered production web, API and worker releases using Next.js, Fastify and PostgreSQL. Native SwiftUI clients remain in internal testing.

Bilt:Spec

Built vehicle profiles, build histories, QR sharing and event workflows across web and native clients. Delivered production web releases and internal TestFlight builds using React, React Native and a PHP/MySQL API.

CrossPost

Delivered an invitation-access web application for reviewed Instagram-to-TikTok media transfers. Built OAuth connections, media preparation, uploads and diagnostics. Track inbox delivery separately from publication. Live end-to-end posting validation remains pending.

Mumbl

Built local-first dictation for macOS and iOS in Swift and SwiftUI. Combined speech recognition, dictionary correction and focused-app insertion with bounded text cleanup and fallbacks. Delivered notarized macOS releases and internal iOS TestFlight builds.

Search, scheduling and client systems

• House of Destiny: delivered a WordPress search beta combining embeddings, Supabase vector retrieval and keyword matching, with summaries grounded in source material. Main-site migration remains unverified.
• Relatable: developed a separate WordPress search plugin with local vectors, hybrid ranking and grounded responses.
• Calendar scheduling: delivered live Google Calendar and iCloud integration. Timezones, buffer rules, locking, conflict rechecks and reconciliation handle booking constraints and uncertain provider responses.
• MISMO: developed a Shopify storefront with reusable content blocks and booking paths. Prepared migration and redirects for preview and separate publication.
• Earlier projects: WordPress multisite and forum migration tools for BWW Media Group, Android endurance tracking for DueNorth Tracking, and ScatterBrain, an independent iOS note app.

Earlier professional experience

Peaksware / TrainingPeaks

Senior Software Engineer / Full Stack Developer · February 2019–September 2020

• Refactored the content API with AWS Lambda, Node.js and GraphQL. Extended headless WordPress with React and Gatsby.
• Contributed to reusable web components and added unit, end-to-end and API tests to delivery pipelines. Integrated Segment, Iterable and Workable.

Via Bicycle Cafe

Owner / Operator · November 2014–December 2017

Drumroll

Senior Developer · August 2008–September 2014

Led a small development team across client and internal projects, partnering with creative teams on interactive web experiences and native iOS apps.

Additional experience

• Senior Technical / Interactive Developer, T3 · March 2005–August 2008
• Senior Interactive Developer, The Well Advertising · November 2003–March 2005
• Webmaster / Developer, Data Junction Corporation · May 2002–July 2003

Technical capabilities

AI and delivery: scoped agent workflows, MCP, Cursor, Codex, independent review, evaluation, embeddings, hybrid search and grounded generation.

Web and native: TypeScript, JavaScript, PHP, Swift, SwiftUI, React, React Native, Vue, Next.js, Node.js, WordPress, Shopify, PostgreSQL and MySQL.

Platform and quality: AWS, Supabase, CI/CD, automated tests, observability, accessibility, performance and deployment verification.

Marketing technology: conversion rate optimization, first-party analytics, experimentation, Marketo, Segment and consent-aware collection.