Season 2 Teaser
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What is Boston’s Brand Problem? How did the pandemic shine a light on issues of equity and access? What opportunities for growth and positive change have come out of this past year’s challenges? And how are we, as a tech community, coming together to be leaders in our commonwealth and beyond? 

In our first season, we heard conversations between leaders in Boston’s tech community, as they maneuvered through the complex realities of the COVID pandemic. But one conversation, between Anthony Williams of Akamai and Susan Hunt Stevens of WeSpire, left us questioning the very notion of Boston’s place as an incubator of talent and social change. Is Boston truly America’s most racist city? According to a 2017 survey by the Boston Globe, 54% of Black people around the country believed Boston to be unwelcoming to people of color. In what ways is this true, and how are we, as a community, working to fight both the realities and the reputation? 

This season, On the Tech Trail, we take Boston’s Brand Problem out of the shadows and directly tackle the burning questions left from season 1. So, join us as we hear candid stories of challenge and transformation from some of Boston’s most influential voices.  

  • Phyllis Barajas - Founder, CEO of Conexion 
  • Sheena Collier - Founder, CEO of Boston While Black 
  • Anthony Williams - EVP, CHRO at Akamai 
  • Pratt Wiley - President, CEO at The Partnership 
  • Debbie Theobald - CEO of Vecna Technologies 
  • Firdaus Bhatena - Chief Digital Officer at CVS Digital 
  • David Meredith - CEO, Board Director of Everbridge 
  • Tim Rowe - Founder, CEO of Cambridge Innovation Center 
  • Carol Vallone - Board Chair of McLean Hospital 
  • Mark Butler - President of Cigna New England 
  • Katherine Newman - System Chancellor for Academic Programs, SVP for Economic Development at UMASS 
  • Secretary Jim Peyser - Massachusetts Secretary of Education 
  • Liz Reynolds - Principal Research Scientist, Executive Director of MIT Industrial Performance Center 
  • Stephanie Browne - VP of Talent and DEI at Blue Cross Blue Shield 
  • Lee Pelton - CEO, President of The Boston Foundation 
  • Kathleen Mitford - Chief Strategy Officer at PTC 
  • Christina Luconi - Chief People Officer at Rapid7 
  • Art Pappas - CEO, Co-Founder of Bullhorn 
  • Mike Volpe - CEO of 
  • Chris Comparato - CEO of Toast, Inc 
  • Pam Reeve - Vice Chair at The Commonwealth Institute 
  • Aimee Sprung - Director of Digital Transformation at Microsoft Airband 
  • Josh Ness - Sr Manager of Verizon 5G Labs 

Season 2 of On the Tech Trail is brought to you by a joint effort between MassTLC and Matter Communications. Special thanks to everyone who contributed: 

  • Tom Hopcroft - Host  
  • Kristen Keane - Booking  
  • Mackenzie LeBert - Booking  
  • David Riemer - Producer, Writer, Editor  
  • Gabe Gerzon - Producer, Writer  
  • Beth York - Producer, Writer  
  • Shaw Flick - Writer  
  • Mandy Lawson - Editor  
  • Tanner Bjorlie - Graphic Design  
  • Tim Bradley - Executive Producer, Writer 

Music (“All Systems Go”) was written by Michael Thomas Geiger and Jessie Marie Villa, and performed by Mikey Geiger. To read more of the Globe’s groundbreaking series from 2017, head to 

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