Dylan Richard

Technologist, Engineering leader, Car nerd, Quaker, Proud papa

Relevant Experience

Director, Software Engineering

PayPal, Inc (Braintree/Venmo/PayPal). Chicago, IL 2015-Present

Integrated modest team, managed a technical organization of 150 engineers, designers, and managers. Spearheaded diversity conversations to change substantively how we hire, how we manage and how we measure teams to value whole contributions, not just derivative technical skill. Set organizational structure and development processes to maximize cross-functional collaboration and to deepen understanding of the customer’s needs.


modest, Inc. Chicago, IL 2012-2015

Responsible for technical direction, product vision, all code and growth and management of technical staff and built a team of 20 that pioneered the idea of contextual commerce.

Shared responsibility in day-to-day operations and all founder operations (hiring, growth, investor relations, legal and acquisition).

Acquired by PayPal, August 2015.

Director of Engineering

Obama for America Chicago, IL 2011-2012

Responsible for technical direction, all code, and management of technical staff.

Architected the technical infrastructure or President Barack Obama's successful reelection campaign.

VP, Engineering / Lead Architect

skinnyCorp/threadless.com Chicago, IL 2009-2010

Responsible for technical direction of skinnyCorp/threadless.com properties, all code, and management of technical staff.

Architected full RESTful API (unreleased). Initiated performance reviews for all front and backend code. Mentored/Advised technology team. Facilitated weekly code reviews, technical discussion. Led recruitment efforts leading to doubling of technical staff.

Director of Software Development

skinnyCorp/threadless.com Chicago, IL 2008-2009

Responsible for all front and backend code for the Threadless family of sites. Directly manage a team of six developers in maintaining and developing all aspects of the threadless family of sites. Mentor development team in PHP, CSS, HTML, and JS best practices. Develop internal coding standards, lead code reviews, develop deployment and testing strategies for entire suite of sites and applications.

Lead Engineer

skinnyCorp/threadless.com Chicago, IL 2007-2008

Responsible for refactoring front and backend code for the Threadless family of sites. Rearchitected the eCommerce system to a services based system used across multiple consumer facing properties and fully integrated with all existing custom fulfillment and customer service systems. Lead refactoring of frontend for maintainability, performance and cost.

Senior Developer

Crate&Barrel Northbrook, IL 2000-2007

Responsible for developing highly scalable Windows client applications. Responsible for the redesign and rearchitecting of several internal data intensive web applications. Mentor development team in CSS, HTML, and JS best practices. Selected projects include forecasting and ordering tools and Crate&Barrel's point of sale system.


TechStars Chicago (2011-Present) Mentor

Chicago Friends School (2015 - Present) Clerk of Board, Board of Directors, Strategic Planning Committee, Finance Committee, Digital Communications Committee

Lake Forest Friends Meeting (2015-Present) Finance Committee

Technical and general advising (2012-Present) Various startups, government agencies, and nonprofits.

Starter League (2012-2015) Advisor

Fox College (2008-2013) Graphic Design Program Advisory Committee


Growing teams, executive management, scaling technology, scaling teams, Python, PHP, JavaScript, HTML, CSS, SQL, nosql, APIs, business model growth and evaluation, strategy and strategic modeling, problem solving, mentorship, strategic & technical advising, hiring/interviewing training, empathy, active listening, and a nuanced approach to understanding difference in a tech context.


University of California at Berkeley Berkeley, CA 1997-1998


Available upon request.

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