Gary MacDougall

Chief Technology Officer

Pypestream · Boston, Massachusetts, United States

Present

Passionate technology leader heading up Pypestream's dynamic landscape of conversational AI and innovative technology. I am dedicated to driving technological excellence, fostering innovation, and leading high-performing teams to achieve strategic business objectives. My commitment to staying at the forefront of industry trends and leveraging emerging technologies positions me as a valuable asset in shaping the future of Pypestream Corporation. - Spearheading the development and execution of Pypestream's technology vision and strategy. - Driving product innovation by integrating AI, machine learning, and natural language processing into our conversational AI platform. - Leading a top-performing technology team to deliver scalable, reliable, and secure software solutions. - Collaborating closely with cross-functional teams to define and execute the product roadmap, ensuring alignment with business goals. - Establishing technology/strategic partnerships to enhance technological capabilit…

Vp of Engineering

DigsUp · Greater Boston Area

Heading up product development and engineering at a stealth PropTech startup in the Boston area.

Vp of Technology

Token Report · Boston

ACQUIRED by New Alchemy in 2018: Token Report is a financial data network covering novel cryptocurrency assets, including token generation events, sometimes called "initial coin offerings" (ICOs). These projects are built on blockchains, the same distributed data technology that made Bitcoin possible. A fast-growing population of sophisticated buyers and technologists looks at tokenized blockchain startups and open-source projects as the potential vessels of a third wave of the digital economy--or at least a reimagining of the global financial system. Token Report serves this user with reliable information, bringing transparency into an emerging asset class.

Vp of Product Development

Freestyle Solutions · Greater New York City Area and Boston

ACQUIRED by Constellation Software in 2018: Led Product management, Engineering, DevOps, Tech Doc and QA in both Parsippany New Jersey and Boston. Managed on-site and multiple offshore teams. Recruited and obtained talent in multiple locations. Developed and launched Freestyle O.M.S, a leading-end multi-tenant SaaS Order Management System. Introduced and implemented a hybrid agile Scrum into the development process which improved overall delivery. Architected and redesigned various back-end processes to improve integration to various e-commerce platforms. Implemented a CD/CI into the delivery process to allow for immediate updates and improved delivery of features. Defined and developed Roadmap, features, functionality and architectural strategy, and other key technology decisions.

Co-Founder / Cto

ChannelBrain / BizSyncXL · Boston

ACQUIRED By Freestyle Solutions (2014): Bootstrapped from the ground up—delivered SaaS integration products and services allowing small- and mid-sized businesses to synchronize data between shopping cart platforms and back-office order management and inventory management systems. BizSyncXL was acquired by Dydacomp Development Corporation in February 2014.

Founder

FreeportWeb, Inc. · Boston

Boutique consulting company focused on developing SaaS based software solutions for companies including IdeaLab, Celerix, eMT, and other significant Boston-based companies. ★ Led development services to a portfolio of over # startups and Fortune 1000 ★ Collaborate directly with clients to define development strategy and design roadmaps Languages: Python, Node.js, GoLang, Elixir, JavaScript, PHP, C#, C++, C, Java, Easel, ESL, VB, Xojo Interchange Formats: JSON, XML, XSLT, GraphQL, Smarty, Jinja2, EEx, Jade Frameworks: Express, Flask, DJango, SQLAlchemy, Peewee, Revel, Phoenix, Laravel, Zend, Cake, Symphony, COM/ATL, Swing, WTL, .NET MVC, ODBC, ADO, Entity Framework Frontend: React.js, Vue.js, Bootstrap, Material Design Processes: Agile, Scrum (PSM I), LEAN, RAD, Hybrid Tools: Git, Bash, Puppet, Chef, Docker, Kubernetes, Vagrant, AWS, Jenkins OS: Linux (Debian, Ubuntu, Fedora, Unix etc.), Windows, Mac OSX Databases: Oracle, MS SQL Server, MySQL, MariaDB, Postgresql, SQLLite, MongoDb Plat…

Manager of Software Development

Webhire (IPO 1998) · Lexington, MA

Team Lead, Software Engineering | Webhire - Directed a team of software engineers in the development of HIRE 4.0, overseeing project schedules, setting strategic goals, and ensuring product stability through comprehensive middleware component upgrades from MFC to ATL/COM. - Led the redesign of the SkillLoader module, effectively addressing and resolving challenges related to bulk data loading and OCR functionality. - Collaborated closely with key clients, including Marriott, to facilitate smooth transitions from version 3.0 to 4.1, ensuring seamless integration and enhanced customer satisfaction.

Software Engineer

Willow Pond Corporation · Newton, MA.

A small Windows device driver, sound card OEM and driver company located in Newton, MA. Created a telephony suite and WillowPhone a telephony PC telephone application. Worked on mainly OEM delivered products to the home PC marketplace. Software was shipped on very HP desktop that was pre-installed with Windows.

Software Engineer

Virtual Entertainment / SmarterKids.com

Worked on children's "click and chirp" games such as Vote America and the IQ Test series. Learned an abundance about multimedia, good UI design, met some wonderful people. Worked mainly on Macromedia Director using event-driven programming in Lingo.

R&D Senior Software Architect

HomeView

Angel funded "restart" of an early Real Estate platform that was originally build on MSDOS. Was brought into a be the technical leader to restart the business with some private equity funding. Ported to a modern technology and created a Web based technology.