Software engineer and technology leader with over 40 years of experience building scalable systems, leading
technical teams, and entrepreneurship. Currently focused on personal ventures and select client advisory work,
with long-standing passions for software reliability, language design, and computational linguistics.
Background spans diverse domains including home security systems, healthcare technology, FinTech, AdTech, and
early internet infrastructure. Known for architecting mission-critical systems where reliability directly impacts
user safety and business success.
Professional Background
Independent Projects / Retired
Jun 2024 – Present
Working on personal ventures and advising select clients.
Director / Co-owner — Datamuse Corporation
Jan 2000 – Present
Datamuse is an umbrella for experiments in language and computational
linguistics, most notably
RhymeZone (sold) and
OneLook.
Recent Positions
Chief Architect, Monitoring Integration — SimpliSafe
Feb 2020 – Jun 2024 · 4 yrs 5 mos — Boston, MA
Led monitoring integration strategy between SimpliSafe's platform and security
monitoring centers. Designed and implemented real-time data pipelines that enabled seamless communication
between home security devices and professional monitoring services. Architected scalable systems handling
millions of security events daily, ensuring 99.9% uptime for critical alarm processing.
Senior Software Development Engineer — PillPack (Amazon Pharmacy)
Oct 2018 – Dec 2019 · 1 yr 3 mos — Boston, MA
Senior Software Development Engineer on the fulfillment and logistics team at
PillPack, Amazon's prescription medication delivery service. Designed and implemented critical backend systems
for medication delivery optimization. Built scalable microservices handling thousands of prescription orders
daily, ensuring HIPAA compliance and pharmaceutical regulatory requirements.
Tech Lead / Cloud Architect — Airfox
Apr 2018 – Jul 2018 · 4 mos — Greater Boston
Tech Lead and Cloud Architect for Airfox, a blockchain-based fintech startup
focused on financial inclusion in emerging markets. Helped build backend services for a mobile-first platform
designed to provide banking services to "unbanked" populations in Brazil and other Latin American markets.
Tech Lead / Architect — Ambi.work
Jun 2017 – Oct 2017 · 5 mos — Cambridge, MA
Tech Lead and Architect for Ambi.work, a Cambridge-based EdTech startup focused
on creating a comprehensive student portal application that provided community building and support tools for
university students.
Senior Staff Software Engineer — Yieldbot
Oct 2014 – May 2017 · 2 yrs 8 mos — Maynard, MA
Senior Staff Software Engineer at Yieldbot, a programmatic advertising
technology company focused on intent-driven ad targeting. Helped develop real-time bidding systems and machine
learning algorithms that analyzed user behavior to deliver highly targeted advertising experiences.
Notable Early Career
CTO — Compliance Week
Jun 2005 – Dec 2010 · 5 yrs 7 mos
Built and led technology strategy for Compliance Week, a leading publication and
events company serving corporate compliance professionals. Developed web platforms, content management systems,
and digital marketing infrastructure.
Founder / Chief Scientist — The Internet Company
Jan 1991 – Sep 1997 · 6 yrs 9 mos — Cambridge, MA
The first business services company on the Global Internet. Helped hundreds of
companies understand how to use the Internet as a business resource.
Developer — O'Reilly Media
1991 – 1992
Introduced the Internet to O'Reilly. Marked up the first magazine article using
fledgling HTML. Helped launch the Global Network Navigator (GNN) - the first commercial publication online.