Management Team

Heather Hiles, Founder and CEO (Heather’s Portfolio)

Heather has committed her life to closing the education and employment achievement gaps for youth and adults. Her leadership experience spans more than 20 years, during which she founded and led several private and public sector organizations. Her roster of leadership roles includes: Commissioner, San Francisco Unified School District; Executive Director of Silicon Valley Social Venture Fund (SV2); CEO of Hiles Group (a philanthropy consultancy firm); Co-Founder of EARN (Individual Development Accounts program); CEO of SFWorks (NGO to place women from welfare into careers); and COO of Break the Cycle (K-3rd grade tutorial program). Heather received her B.A. from UC Berkeley and her MBA from Yale University.

Derek Gordon, Chief Marketing & Sales Officer (Derek’s Portfolio)

Derek is a marketing, communications and sales strategy expert with more than 20 years of demonstrable success under his belt. Prior to joining Pathbrite, he was a marketing and sales strategy consultant working with brands such as Daylife, Eventbrite, Visage Mobile, Brocade, Rackspace and Cisco. Before his work as a consultant, Derek served as VP of Marketing for Yield Software, which was acquired by Autonomy / HP; VP of Marketing and Interim CEO of Engage, which was acquired by Spark Networks; VP of Marketing at Technorati, where he developed the company’s first marketing and sales organization; Senior Director of Marketing Communications at Thomson Learning (now Thomson Reuters); and Director of Communications at DigitalThink, the pioneering e-learning company that had a successful IPO and was eventually acquired by Convergys. He studied Mass Communications at California State University, Hayward.

Christopher Gray, Chief Product Officer (Chris’s Portfolio)

Christopher is the Chief Product Officer at Pathbrite, where he is responsible for organizing product strategy and overseeing the product management and design functions. Prior to joining Pathbrite, Christopher launched the computer services business for Symantec, worked as Director of Training for PeopleSoft, and created the online learning platform for Veritas. In addition to Pathbrite, he can be found teaching Bikram yoga, studying romance languages and attempting to play funk music. Christopher holds a master’s degree in Human Resource Development.

Mark Ledford, Vice President, Engineering (Mark’s Portfolio)

Mark has been a technical leader and senior front-end architect building robust web based applications professionally for nearly a decade. Prior to joining Pathbrite Mark lead the engineering of KickApps’s flagship App Studio product from its inception to the company’s acquisition by KIT Digital. Mark’s passion for rich media applications has led to projects with Skype, Adobe, Food Network, the US Courts, as well as many smaller startups in the New York City and San Francisco areas. As Pathbrite’s VP of Engineering and Senior Frontend Architect Mark wrangles product vision into reality. Mark holds a B.A. in New Media Design from the Rochester Institute of Technology.

Regan Caruthers, Vice President, Sales (Regan’s Portfolio)

Regan Caruthers, Vice President of Sales, comes to Pathbrite with over 20 years of sales and sales leadership experience in the education technology field. Regan most recently served as Director of Content Business Development at ed-tech company, Kno, Inc. Prior to that Caruthers served as Director of Business Development at CourseSmart. She also gained valuable experience working as the Director of System-wide Digital Content Strategy for the Office of the Chancellor, California Community Colleges and as Director of Communications and Business Development for the Office of the Chancellor, California State University System. Prior to working for California’s institutional leadership she served as Director of Business Development in the eLearning division for McGraw Hill Higher Education.

Robert Collins, Director, Marketing & Communications (Robert’s Portfolio)

Robert brings 10+ years of experience performing various marketing functions in the technology, media and education sectors. Prior to joining Pathbrite, Robert led a multi-media & technology non-profit education program and served as an adjunct professor at San Francisco State University. Before his stints in education he served as General Manager of Ruby Avenue Media, which was a diversified entertainment company with interests in music and film distribution, live event management and publishing. Robert began his career in International Sales Operations and Product Marketing with Sagent Technology, which went public in 1999. He has a B.A. in political science and economics from Morehouse College.

Ivan Akimov, Senior Platform Architect (Ivan’s Portfolio)

Ivan is a backend lead focused on designing and developing platform architecture, scaling efficiently, and keeping the systems stable and fast. Ivan is a full-stack developer with an emphasis on building lean and mean APIs. Prior to Pathbrite, Ivan has built APIs for startups in San Francisco and Munich, Germany. In addition to backend work, Ivan is always interested in learning and developing new technologies, and has written several open-source projects. Outside of Internet related projects, you can find him biking over the Golden Gate bridge, riding his motorcycle, running and climbing San Francisco hills, and traveling.