David Richards
Building AI products. ex Ketch, Twitter, Toast, and Zipcar
Greenville, South Carolina, United States of America
Building AI products. ex Ketch, Twitter, Toast, and Zipcar
Greenville, South Carolina, United States of America
Validated traits
Artifacts
As CTO and Co-Founder of Ketch AI, I set out with my co-founders to solve a core problem in retail marketing: brands were relying on generic, one-way advertising that consumers increasingly tuned out. We built an AI-driven platform that flipped this model, allowing consumers to opt in to the brands they shop from while our system did the work of identifying sales, scoring them against each user's past purchasing behavior, and surfacing only the most relevant deals. To power this recommendation engine, I designed a data pipeline that ingested historical sales data and used a scoring model to rank deals by predicted relevance to each user's shopping patterns. I architected this as an independent processing pipeline coupled with a shared backend driving business logic across a web app, browser extension, and iOS application — a deliberate choice to meet customers wherever they shopped while keeping engineering headcount and complexity minimal as we worked to prove product-market fit. The results validated the core hypothesis: our platform achieved 66% 30-day user retention, 59% email open rates, and 7% click-through rates (a 10x improvement over the 0.7% industry average for traditional retail email marketing), with users averaging 2 shopping sessions per month. These engagement metrics demonstrated that once users adopted the product, it became genuinely sticky. Despite this strong engagement, we faced a persistent top-of-funnel acquisition challenge. We experimented with referral incentives, paid social campaigns, and distribution partnerships with companies like Capital One Shopping, but customer acquisition costs remained too high relative to lifetime value. Unable to scale acquisition fast enough to match our retention strength, this became a key factor in the decision to wind down the company in late 2025 — a hard-earned lesson in balancing product engagement with sustainable growth economics.
Testimonials
Work history
Independent AI Ventures
Ketch AI
Toast, Inc.
Zipcar
IBM
Northeastern University
NOV 2025 - PRESENT · 10 months
Consultant & Technical Entrepreneur
NOV 2025 - PRESENT · 10 months
I build and ship products at the intersection of AI and real-world industries like private equity, real estate, and construction, taking them from zero to one end to end: user research, product strategy, and the hands-on technical execution to build them. I work two sides of AI, building AI-native products and using AI as leverage to ship faster than traditional approaches allow, while staying close to buyers through sales and demo calls. The throughline is finding where AI actually moves the needle and standing up working products that solve concrete problems.
JAN 2024 - SEP 2025 · 1.8 years
CTO and Co-Founder
JAN 2024 - SEP 2025 · 1.8 years
* Architected an agentic backend platform using Google Gemini, establishing the foundational AI standards and development practices for a multi-platform product suite. * Led cross-functional product strategy, working with a multidisciplinary team to align technical capabilities with long-term platform value and user retention (66% at 30 days). * Built and integrated reusable AI tools and browser-based interfaces to accelerate product adoption and feature velocity
JAN 2023 - FEB 2024 · 1.2 years
Director of Engineering
JAN 2023 - FEB 2024 · 1.2 years
* Led engineering for a group of 30+ engineers and cross functional roles focused on consumer interactions with Toast restaurants, including the Toast mobile app and Mobile Order & Pay products. * Responsible for cross functional collaboration in setting product strategy, driving alignment with peers and stakeholders, and ensuring execution of that strategy * Managed organizational shape to align people with objectives and create autonomous team * Coached and guided both managers and senior ICs on how best to lead and shape the technical strategy of the organization * Drove alignment behind measurable objectives at both the organization and team level, as well as execution on measurement and tracking of those objectives
APR 2013 - NOV 2022 · 9.7 years
Site Lead, Twitter Boston
AUG 2022 - NOV 2022 · 4 months
* Collaborated with cross functional partners such as real estate and corporate security for the ongoing running of a 150 person site * Helped build office culture and environment in a post-covid world through social events, shared interest groups, and working with the individuals in the office to understand how best to use our available resources
Senior Engineering Manager/Engineering Lead, Product Learning Platform Organization
JUN 2021 - NOV 2022 · 1.5 years
* Responsible for execution and technical strategy of 3 team organization, later growing scope to 6 teams * Collaborated with cross functional partners to set strategic direction on analytics, experimentation, and configuration domains that drove impactful changes to how the company shipped products and made decisions * Managed the largest data pipeline at the company, processing trillions of events and petabytes of data a day * Actively shaped culture and environment of the group * Hired managers as well as key senior engineers, designing organizational structure around areas of investment * Mentored other engineering managers to foster their career growth * Participated in CorpDev acquisitions, including organizational shaping to accommodate incoming engineers * Boston office lead for the Engineering Apprentice program. Helping to create and execute on a program to bring in engineering talent from non traditional backgrounds
Engineering Manager/Senior Engineering Manager
AUG 2018 - JUN 2021 · 2.9 years
* Line managed up to 2 teams working on complementary domains * Shaped charters to better focus the teams and prioritize critical efforts, including advocating for and creating a new team * Advocated for and participated in the creation of a new organization of teams to focus on gaps in Twitter’s analytics and learning infrastructure (later became engineering lead for that group) * Championed the prototyping, redesign, and implementation of high scale real-time (>1M EPS) and batch data (TBs) processing pipelines to compute and serve customer-facing video metrics, getting stakeholder and leadership buy in and eventually resulting in lower run the business and maintenance costs for this critical infrastructure * Collaborated with teams across the company to adopt common infrastructure for generic time series aggregation and serving * Advocated for increased funding and drove hiring for increased headcount * Focused the team on driving customer impact via customer interviews, participation in OKR setting, and shaping milestones around customer delivery * Grew careers for individuals on the team, providing opportunities, mentorship, and feedback leading to multiple promotions across various levels of seniority * Drove creating team processes that better solved pain points for the team and stakeholders * Built relationships with stakeholders and cross-functional partners in order to help the team drive more impactful progress
Staff Software Engineer/Technical Lead
JUN 2015 - AUG 2018 · 3.3 years
* Responsible for the consumption of media on Twitter across Web, Android, and iOS, direct technical contributor to Web and Android * Key technical contributor to the end to end architecture of media consumption for live NFL games in 2016, at its peak serving 1M concurrent customers across multiple different clients (Web, Android, iOS, Roku, Amazon Fire TV, AppleTV, etc) * Lead engineer on integrating PeriscopeTV consumption into the Twitter applications, coordinating efforts across multiple teams and clients to hit challenging deadlines on a technically complex re-architecture and integration project * Led the development for key media experiences such as Watch Mode, 360 Video, Audio Playback, More Video Recommendations, and more * Drove a focus on quality and testability as video advertising grew across the platform to become the largest source of income for the company * Collaborated with management and other leads to create and drive OKRs, team process, and team culture * Mentored junior engineers both on and off the team including summer interns
Software Engineer
APR 2013 - JUN 2015 · 2.3 years
* Contributed to the original rollout of native video on the Twitter platform as a fullstack web engineer, as well as learning and filling in as an Android developer to meet initial deadlines until we could hire one full time * Helped build a content management system for advertisers to manage their video assets * Built advertiser configuration tools for the TV Targeting ad product
JAN 2009 - APR 2013 · 4.3 years
Software Engineer
JAN 2011 - APR 2013 · 2.3 years
Software engineer working on Zipcar's full web stack. Technologies and concepts include - Ruby on Rails - Torquebox - RESTful web services - queueing systems - JQuery - SQL (Oracle + PL/SQL) - tcl Major projects worked on - Implementation of modern RESTful API for consumption by web and mobile apps - Refactor of authentication code for sharing across multiple technology stacks - Productization of zipcar.com and related technology assets for launch under new international brand - Localization and internationalization of zipcar.com and related technology assets for launch in Spain - Integration of acquisitions - Fix issues found by third party security audit of zipcar.com and tools
Software Engineering Intern - Web Applications
JAN 2009 - OCT 2009 · 10 months
- Designed and implemented a custom web crawler for verification of valid HTML - Audited site for ADA compliance and fixed issues found - Enhanced custom built CMS
JAN 2010 - DEC 2010 · 1 year
Software Developer Intern - RQM
JAN 2010 - DEC 2010 · 1 year
Technologies and concepts include - Java - Jazz framework - Dojo framework Major projects worked on - Contributed to implementation of major "copy" feature of RQM 2.1.0 - Refactored migration code to better handle designating upgrade paths from older than one versions of RQM - Re-architect lab management code to more tightly couple lab instances with their configurations for easier editing and customization
JUN 2007 - DEC 2009 · 2.6 years
Computer Technician + Application Developer
JUN 2007 - DEC 2009 · 2.6 years
- Designed and build custom timesheet LAMP application - Co-designed and built basic HTML website to be the public face of Resnet - Diagnosed and fixed issues with student computers -- malware -- hardware issue diagnosis -- setup and install software for students
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