About
Rich is currently a Director of Engineering at LinkSquares, where he works with data scientists, machine learning engineers, and full-stack developers to enable thousands of legal experts to analyze millions of contracts using the latest AI technology. He enjoys doing deep, technical, hands-on problem solving, delivering quality software, and coaching engineers and managers.
Previously, Rich was a Team Lead (Sr. Engineering Manager) at Elastic helping the Enterprise Search team make it easy for developers to build search experiences at petabyte scale.
Prior to Elastic, Rich was a Director of Engineering at Constant Contact, responsible for the development of their flagship web-based email editor used by hundreds of thousands of small businesses to create beautiful, effective marketing emails. Rich also managed their Contacts platform, a Ruby on Rails application that manages billions of customer email contacts and processes millions of API requests per day.
Career Objective
To use his talents as a passionate software engineer and technical leader to help people solve problems and build great products.
Skills and Achievements
- Scaled proprietary ML models to run inference on millions of legal contracts, combining traditional LSTM/NER models with the latest generative AI LLMs.
- Delivered superior search experiences for Fortune 500 Elasticsearch customers.
- Applied product analytics to develop an objectively better experience for Constant Contact’s flagship email marketing editor, which helped enable their $1B acquisition.
- Invented, designed, architected, managed, released, supported, and maintained a test automation product that earned millions of dollars in revenue for shareholders, helped hundreds of QA engineers test their software more efficiently, and played a key role in Oracle acquiring the Empirix web business unit.
- Consulted at customer sites, presented at technical conferences, and pitched products to C-level executives.
- Authored requirements, functional specs, design specs, prototypes, wireframes, and sequence diagrams.
- Over 10,000 hours of coding experience in languages such as Java, Ruby, and JavaScript.
- Closed thousands of customer support issues.
- Reverse-engineered and performance-tested hundreds of web apps.
- Designed, implemented, published and maintained concise, clear product APIs.
- Developed and released software using many languages and technologies, including: Java, Python, Ruby on Rails, JavaScript, React, JQuery, GraphQL, Docker, and AWS.
- Released features and products ranging in size and complexity from single engineers working a few hours, to tens of engineers working for 3 years.
- Initiated and delivered major rewrites of multiple highly complex, business-critical applications.
- Directed software teams from 1 to 50 engineers, across frontend, backend, documentation, and design.
Side Projects (just a few)
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Hacking the Brain conference talk (2015)
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Mutating HipChat with AWS, GraphQL, and React just for fun (2018)
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BrowserUp startup (2018)
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Schema-Tools Ruby Gem (2025)
Personality
- Rich’s peers and managers describe him as enthusiastic, optimistic, empathetic, and rational.
- Works effectively with any customer, employee, personality type, manager, and time zone, both remotely and on-site.
- Proven capacity to lead projects and teams through turbulent organizational change, including two corporate acquisitions.
- Perseverant; worked two jobs (paid support and volunteer development) to earn his first full-time developer role.
- Recognized valued contributor; consistently promoted to jobs with increased scope.
- Delivers tough, effective feedback when required.
- Has been seen typing at talking speed.
- “I can see the big picture, and I can focus on details. I can spot spelling mistakes and crooked pixels. I can fix legacy code. I can parse logs to find a needle in the haystack. I willingly take on the dirty, unglamorous jobs so the team can focus on the rest.”
Career History
- 1992 - Started writing BASIC code on a 386 at age 12.
- 1995 - Launched my first software business and sold my first shareware app.
- 1997 - Developed the first web-based defect tracking system at Amano Cincinnati, Inc.
- 2002 - Graduated from WPI with High Distinction and a BS/CS.
- 2002 - Joined Empirix as a Support Engineer.
- 2004 - Promoted to Developer.
- 2006 - Promoted to Lead Developer, acting as Architect.
- 2008 - Promoted to Development Manager.
- 2008 - Acquired by Oracle. Designated as Key Employee during acquisition phase.
- 2010 - Promoted to Senior Development Manager at Oracle.
- 2013 - Promoted to Director of Development.
- Managed 3 products and 20 developers across US, India, and China.
- Left my team after 11 years to start over in a new industry.
- 2013 - Joined Constant Contact as Engineering Manager
- 2018 - Promoted to Senior Engineering Manager
- 2019 - Promoted to Director of Engineering
- Managed 2 major application platforms, 4 managers, and 50+ engineers.
- Left Constant Contact to join Elastic to learn how to manage fully distributed software teams.
- 2020 - Joined Elastic as Team Lead / Senior Engineering Manager
- Managed a small, global team of engineers building Enterprise Search.
- Left to join LinkSquares to learn hands-on AI/ML development.
- 2023 - Joined LinkSquares as a Senior Engineering Manager of DS/ML Team
- 2024 - Expanded scope to include full-stack app development of 3 highest revenue products
- 2025 - Promoted to Director of Engineering
- Currently re-engineering LinkSquares products from the ground up with AI at the core.