Sarasota, Florida, United States
Information technology executive with significant experience leading large-scale software development efforts on advanced Internet-based platforms. Built teams of 100+ engineers at both rapidly growing start-ups and publicly traded companies. Typically operated as member of the senior leadership team. Launched numerous instances of engaging, consumer-facing Internet services. Extensive experience in social apps, advertising systems, content management, e-commerce, product catalogs and peer-to-peer marketplaces. Responsible for highly-scalable computing infrastructure across multiple cloud environments. Deep technical expertise in systems architecture, software services, APIs, security, UI/UX, payment systems, enterprise tool development, big data and analytics, search, automated testing, cloud hosting and DevOps practices. Most recently, transitioned into applying my broad understanding of modern software infrastructure towards the evaluation of publicly-traded companies and capital investment. Founded the popular investment research site, Software Stack Investing, where I regularly publish analysis of trends in the software services sector and coverage of leading providers. I frequently conduct expert calls with major hedge funds and my research has been cited in prominent sell-side analyst reports. Have presented for numerous investor conferences, media outlets and popular podcasts, including the Motley Fool and the Colossus Media Network. Member of the Executive Committee of Bridge Angel Investors and the Investment Committee of Nassau Street Ventures. Guest lecturer for the London Business School. Technical advisor for several start-ups, including Fliptop (acquired by LinkedIn), Clickability (acquired by Limelight) and Care Bridge International. Named inventor on three US patent applications.
BRIDGE Angel Investors is a group of seasoned accredited investors located in Sarasota, FL. We support entrepreneurship on a local and state level by providing capital, network access and mentoring to assist early-stage businesses achieve high growth. As Board Chair, set overall strategy and growth objectives for the organization. See our recent coverage in the Business Observer: https://www.businessobserverfl.com/news/2026/mar/20/sarasota-angel-investor-group-growing/
Investment research firm with focus on software infrastructure sector. Regularly publish deep analysis on trends in software development, cloud hosting, data storage and security operations. Conduct expert calls with analysts at capital funds, including several of the largest hedge funds. Regularly tapped for presentations to industry events, investment conferences and popular podcasts. Research citations have been included in sell-side research reports. Guest lecturer at the London Business School. softwarestackinvesting.com
Boatsetter is applying technology to disrupt the boating industry. We connect renters, owners and captains directly on our software platform, allowing renters to easily schedule a boating trip, while offering owners a way to monetize their boats when not in use. We have often been described as the “Airbnb of boating.” Boatsetter represents over 5,000 boats in several hundred locations in the U.S. and recently expanded overseas through our partnership with Luxury Retreats, a division of Airbnb. After acquiring a competitor in 2017 (Boatbound), the combined entity is now the largest boat-sharing marketplace in the U.S. https://techcrunch.com/2017/08/17/peer-to-peer-boat-rental/ https://www.economist.com/business/2018/06/23/yacht-sharing-startups-vie-to-rule-the-waves As CTO, led the technology team, including software development, testing and DevOps. Responsible for system architecture, tooling, development processes and organizational structure. Support the executive team in development of the technology roadmap and building out a world-class transactional platform.
Led application development for Catalina, a premier targeted marketing services company that creates one-to-one interactions with consumers through omni-channel digital media platforms. Over 500 CPG brands and 37,000 retailers utilize Catalina to create personalized ad offers through mobile, online and in-store networks targeted at 350 million shoppers in the U.S., Europe and Japan. As VP of Technology, directed multiple development teams in the creation of applications to schedule advertiser campaigns, collect transaction data and deliver targeted offers to individual consumers in real-time. Consumer-facing applications span web, mobile and in-store IoT devices. Systems supported are extremely high-scale, responsive and resilient, built on a modern technology stack using agile development principles. The platform processes over 800 million events per day and utilizes advanced machine learning models to generate personalized targeting recommendations. Back-end infrastructure centers around an event-based architecture, built on a Kafka message bus for high transaction processing. Other system components include HBase, HDFS, Hive, Tomcat, Zookeeper, node.js and zeromq. Application logic is written in Java. Infrastructure is fully configured in Puppet and hosted on multiple regions within Microsoft Azure.
Led engineering through rapid growth period for one of the world’s largest online dating platforms. With over 35 million active monthly users, Zoosk is translated into 26 languages and accepts payment in over 60 currencies. iOS app is consistently a top 10 grossing app in the App Store. Rapidly grew small start-up team to over 100 engineers, including structuring organization into dynamic teams and mentoring young leaders to run them. Oversaw development, testing and release of Zoosk applications to deliver cutting-edge user experiences across disparate platforms, including the primary web site, social networks, mobile devices (iOS, Android, mobile web) and a stand-alone desktop client. Designed and delivered many highly scalable, encapsulated back-end services to support all user-facing functionality, fronted by a performant, RESTful API layer. Service highlights included real-time chat (XMPP), data access, multiple search capabilities, photos, content management, payment processing, email communications, messaging and fraud/abuse. Also responsible for quality assurance, automated testing, build/release and site operations. Built a Hadoop-based data analytics platform that uses machine learning to process over 100 million daily events and form recommendations for user matches. Managed two redundant data centers, in addition to a significant presence on AWS, to deliver highly available production, testing and development environments. Oversaw compliance and governance issues, including IPO preparations. Extensive focus on security matters, covering PCI, DDOS mitigation, intrusion detection, data isolation and incident response. Established agile software development processes for the organization that supported rapid feature iterations through multiple, reliable releases per day. Started Appium project, the most popular open-source mobile test automation framework. Built strong engineering culture that attracted top talent and maintained high retention.