On the Tech Trail: Walks with Strategic Leaders

Professionals of color have a very different experience of building a career in Boston, relative to their white peers and colleagues. Throughout the season, we’ve heard stories of these experiences and the work leaders in our community are doing to repair, among other things, our broken talent pipeline. In our final episode of season 2, our guests investigate issues of equity and diversity as they impact career development opportunities here in Boston (and beyond). Are candidates of color discouraged from coming to a city like Boston to pursue professional opportunities? What work is being done to fix this problem? And how are professionals of color able to find meaningful connection with the city? These questions, and more. Highlights from this episode: Stephanie Browne (Chief Diversity and Inclusion Officer at Blue Cross Blue Shield of Massachusetts) recounts the challenges she faced while establishing herself professionally here in Boston Chair of the Commonwealth Institute, Pam Reeve, explains how the pandemic exposed pervasive issues of inequity Art Papas, CEO and Co-founder of Bullhorn, highlights the impact of social media on conversations around corporate social responsibility Chris Comparato, CEO of Toast, discusses new ways for leaders to communicate about complex issues  Microsoft Airband Initiative’s Director of Digital Transformation, Aimee Sprung, talks about the impact and importance of keeping a diverse set of voices in the mix Pratt Wiley, CEO of The Partnership, illustrates why connecting people of color to cultural resources is integral to growing a vibrant and diverse professional community Thank you for following us on our journey this season as we investigated Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we worked to take Boston’s Brand Problem out of the shadows, and onto the Tech Trail. But the conversation doesn’t end here – keep it going on social and let us know what burning questions you have about equity, access, and the city of Boston. 

Boston is a global healthcare innovation hub, but inequality of access to care is a persistent challenge. As we emerge from the pandemic, what are our leaders doing to address these issues and move toward a healthier business and care ecosystem?  In this episode, we’ll hear stories from the front lines about disparity in access, the impact of COVID on the systems that support global health, and the technology that’s moving us forward.  Highlights from this episode: CVS Health’s Chief Digital Officer, Firdaus Bhathena, introduces the current inflection point for the healthcare industry Mark Butler, President of Cigna New England, discusses the tremendous acceleration to healthcare innovation coming out of the pandemic Debbie Theobald (Co-founder of Vecna Technologies) tells us what kinds of disruptive technologies to expect, and the challenges that come along with innovating in a monolithic space like healthcare Joshua Ness (Sr Manager at Verizon 5G Labs) describes the connective and equalizing power of emerging technologies CIC Heath Founder, Tim Rowe, moves the discussion toward mental and behavioral health and introduces how technology is shaping this space Carol Vallone, McLean Hospital’s Board Chair, digs deeper into mental health access issues exposed by the pandemic So, follow us on our journey this season as we investigate Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we take Boston’s Brand Problem out of the shadows — and onto the Tech Trail. 

Technology has the power to exclude. Sure, it can (and often does) connect marginalized communities to resources, but many people lack the access necessary to sustain meaningful growth, both professionally and financially. In that way, what technology provides for some communities, it limits in others. This episode, our guests talk us through a topic that many of us take for granted: access to the internet and the impact of connectivity (or lack of) to our economy and society. We’ll hear about web access as a basic human right, the technology impact of the pandemic on communities of color, and finally how Boston is emerging from this crisis with a plan to improve access, connectivity, and quality of life for everyone. Highlights from this episode: Christina Luconi (Chief People Officer at Rapid7) introduces the idea of “Tech Privilege” alongside other issues of privilege highlighted by the pandemic Pam Reeve (Chair of The Commonwealth Institute, former CEO of Lightbridge, Inc.) digs into internet access as a basic human right Director of Digital Transformation at Microsoft’s Airband Initiative, Aimee Sprung, discusses how the pandemic put a spotlight on connectivity gaps Katherine Newman, the System Chancellor for Academic Programs and SVP for Economic Development at UMass, parses out the nuances of access and opportunity Joshua Ness (Sr Manager at Verizon 5G Labs) tells us how 5G will help bridge existing digital divides Cambridge Innovation Center’s founder and CEO, Tim Rowe, explains how spaces can shape inclusive and diverse communities while providing access to the internet and technology So, follow us on our journey this season as we investigate Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we take Boston’s Brand Problem out of the shadows — and onto the Tech Trail.

Education is at the core of equity issues, and the pandemic shone a spotlight on existing gaps and potential solutions.  This episode, our guests investigate inequities in educational opportunity, the challenges for public education during the pandemic and beyond, and the emerging technology that’s helping close persistent gaps. Join us as we explore what the future of education will look like and what responsibility our leaders have in terms of enabling the kind of social mobility that comes with greater access to learning.  Highlights from this episode: Katherine Newman (System Chancellor for Academic Programs and SVP for Economic Development at UMass) explains the impact of educational opportunity on social mobility Lee Pelton (President of Emerson College and the next CEO of The Boston Foundation) introduces the connection between intergenerational wealth and educational opportunity Massachusetts Secretary of Education, James Peyser, discusses how opportunity gaps manifest themselves in public education Joshua Ness (Sr Manager at Verizon 5G Labs) tells us how 5G will open doors for students and new learning opportunities PTC’s Chief Strategy Officer Kathleen Mitford describes how learning and access to technology present opportunities for social advancement Art Papas, CEO and Co-founder of Bullhorn, proposes some practical alternatives to the traditional four-year degree Liz Reynolds (Executive Director of MIT’s Industrial Performance Center and now Senior Member of the National Economic Council) continues the discussion of skills training as it relates to economic recovery  So, follow us on our journey this season as we investigate Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we take Boston’s Brand Problem out of the shadows — and onto the Tech Trail.

The pandemic has drastically changed how and where we work. For some industries, this meant a total shutdown. For others, it was a new frontier of uncertain work-life balance and hiring challenges. Either way, leaders are looking at a work landscape that has permanently changed in many significant ways. In this episode, we’re addressing something near and dear to the business community: company culture. We know the pandemic catalyzed some seismic shifts, but have we fully realized those impacts yet? And how do we move forward, out of this time of uncertainty, to create inclusive virtual and in-person spaces? Crisis can act as the flame that forges a better future — but what are we, as leaders, doing to ensure that happens? And is this kind of future-forging crisis necessary? Is it inevitable? We answer these questions and more as we investigate the equity issues surrounding workplace culture. Highlights from this episode: Everbridge CEO David Meredith explains the pandemic’s impact through the lens of critical event management Mike Volpe (CEO of Lola.com) points out the unique challenges faced by the business travel industry Chris Comparato (CEO of Toast) digs into the hardships and opportunities the restaurant industry has been grappling with this year CEO of The Partnership Pratt Wiley addresses equity issues surrounding the changing workplace  Christina Luconi (Chief People Officer at Rapid7) discusses how the events of 2020 acted as a lightning rod for long-overdue shifts in corporate accountability Kathleen Mitford (Chief Strategy Officer at PTC) talks talent strategy and the new, more inclusive face of business coming out of the pandemic So, follow us on our journey this season as we investigate Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we take Boston’s Brand Problem out of the shadows — and onto the Tech Trail. 

Boston’s Brand Problem is more than an unfortunate reputation. It’s a sad, historical fact, rooted in the lived experiences of countless people of color who have come to Boston (or avoided it entirely) over time.  This episode of On the Tech Trail, we look at Boston’s earned reputation as unwelcoming to people of color through the lens of those lived experiences. Does the city deserve its racist moniker, and can Boston be an incubator for leadership and innovation if it’s true? What steps are leaders taking to stay accountable and to reimagine Boston’s role as a tech hub? These are serious questions that can only be answered by those who’ve lived it and who actively work to fix the problem. So on this episode, we listen — and we let those personal stories of the Boston Brand Problem speak for themselves, uninterrupted. Highlights from this episode: Sheena Collier (Founder and CEO of The Collier Connection and Boston While Black) recounts how she ended up in Boston after desperately wanting to move anywhere else, what kept her here, and how she uses her access to uplift others in the community Phyllis Barajas (Founder and CEO of Conexión) tells her story of building a career in a city best known for excluding people like her, and how that pushed her to fix the systemic problems that she lived through Pratt Wiley (CEO of The Partnership) shares his story of traveling the country, seeing disparities and inequities everywhere, and ending up back in his home city, where he’s dedicated his life’s work to closing these gaps and providing better opportunities to people of color in Boston So, follow us on our journey this season as we investigate Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we take Boston’s Brand Problem out of the shadows — and onto the Tech Trail. 

We recommend you start with this episode. In this preface to the second season, MassTLC CEO Tom Hopcroft tells the story of how we arrived at this season’s overarching themes, and our guests define some key terms that inform the entire season. 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? Is this just a brand problem, tied up in the city’s unwelcoming reputation, or is it true that Boston is systemically unwelcoming to people of color? And, acknowledging it as a problem, how are we, as a community, working to fight both the realities and the reputation? In season 2, On the Tech Trail, we spoke to 22 leaders in our community to directly address issues of equity, access the so-called Boston Brand Problem. Here are some episode highlights: Anthony Williams (EVP, CHRO at Akamai Technologies) presents The Boston Brand Problem Lee Pelton (President of Emerson College and the next CEO of The Boston Foundation) defines Equity and how it differs from Equality Pratt Wiley (CEO of The Partnership) introduces how the pandemic disproportionately impacted communities of color Stephanie Browne (VP of Talent Acquisition, Chief Diversity, Equity & Inclusion Officer at Blue Cross Blue Shield of Massachusetts) ties the Boston Brand Problem in with local “clique-ish” culture Collected soundbites from some of our season’s guests, to introduce and tease the rest of the episodes, including: Chris Comparato (Founder and CEO of Toast) Kathleen Mitford (Chief Strategy Officer at PTC) Christina Luconi (Chief People Officer at Rapid7) Tim Rowe (Founder and CEO of the Cambridge Innovation Center) Phyllis Barajas (Executive Director of Conexion) Mike Volpe (CEO of Lola.com) Sheena Collier (Founder and CEO of Boston While Black) And, finally, Akamai’s Anthony Williams returns to explain how Boston’s unwelcoming reputation felt like a challenge that he could face and help resolve So, follow us on our journey this season as we investigate Boston’s challenges as a microcosm for bigger issues of equity and access. Through topics like access to technology, healthcare innovations, the future of education, and forward-thinking DE&I strategies, we take Boston’s Brand Problem out of the shadows, and onto the Tech Trail. 

Season 2 of "On the Tech Trail" will ambitiously weave 22 interviews across 7 episodes about equity in Boston, each with their own sub-theme (Healthcare, Education, Access, etc.). With a more narrative approach, S2 features many voices in each episode and supplemental voiceover and sound design to elevate the listening experience. Guests include Stephanie Brown (Blue Cross Blue Shield), Lee Pelton (The Boston Foundation), Pratt Wiley (The Partnership, Inc.), Phyllis Barajas (Conexión), Firdaus Bhatena (CVS), Sheena Collier (Boston While Black), and more.

A Conversation between David Delmar Sentíes (Founder, Resilient Coders) and Pariss Chandler (Founder, Black Tech Pipeline)

A conversation between Sam King (CEO, Veracode) and Dave Krupinski (Care.com).SHOW NOTESA time period of much change. (3:23)Restore a sense of agency (5:10)Another year of change (7:43)A greater degree of awareness, and a stronger response (11:41)Closing the gap between performance and potential (14:50)Being a woman leader in tech (17:41)

A conversation between Bill Wagner (CEO, LogMeIn) and Donna Levin (Co-Founder, Care.com)SHOW NOTESThe Accidental CEO (1:22)An Organizational Framework to run Business (3:56)Continuity and Employee Wellbeing. (5:06)Being Plugged into your Team (7:10)83% of our employees say that they don't want to go back to the way it was. (11:13)How we enable our children, how we enable our workforce. (13:02)We can deal with challenges and we can deal with fire drills. (15:40)

A conversation between Tracey Zhen (President of Zipcar) and Yogesh Gupta (President & CEO of Progress Software) that discusses Tracey's path to leadership as a women in the tech industry, as well as navigating a disrupted industry during COVID times.SHOW NOTESThe importance of a financial background (3:00)Coaching and elevating women (5:27)Innovating fast (6:54)Contributing to more sustainable cities. (10:10)Managing through change (15:34)

A conversation between Aron Ain (CEO of Kronos and Ultimate Software) and Gail Goodman (CPO and cofounder of Pepperlane & former CEO of Constant Contact) that covers Aron's insights into the recent Kronos and Ultimate merger and advice on building and maintaining a strong work culture during the "new normal."SHOW NOTESCreating a merger like no other (0:59)COVID strikes during merger (4:35)Combining two company cultures (5:15)Dealing with employee burnout (8:08)Supporting our teams however we can (15:49)The importance of leadership (17:02)

A conversation with Anthony Williams (EVP & CHRO, Akamai Technologies) and Susan Hunt Stevens (Founder & CEO, WeSpire).SHOW NOTESBoston has a level of intimacy (2:15)Enriched by difference and diversity. (3:35)Leading corporate social responsibility and social issues. (6:50)Engaging people in these questions of equality and social justice (9:33)Being comfortable being uncomfortable. (12:28)Recommending Boston (14:12)Making sure that we're fostering an inclusive culture (16:05)

A conversation with Stefania Mallett (CEO & Co-Founder, ezCater) and Corey Thomas (Chairman & CEO, Rapid7).SHOW NOTESImpacting our new business (3:03)How we treat our partners and customers (4:32)Getting Board Support on Decisions (7:29)Controlling your Reactions (9:30)The single biggest change (11:55)How to Keep your People Motivated (13:58)

A conversation with Mohamad Ali, CEO of IDG and Sophie Vandebroek, Visiting Scholar at MIT. On the Tech Trail takes you inside the minds of remarkable tech leaders in Boston and beyond. You'll get to know them, better understand their journeys, and to gain insights from their strategic decision-making to help you along your own journey. Brought to you by MassTLC & Matter.SHOW NOTESHow I think about my place in society (2:55)All about Community (5:05)Pivoting Business in light of COVID (8:28) Keeping a Global Workforce Motivated (10:22)How Tech is Impacted (12:55)Digital and Virtual are here to stay (15:40)The importance of civic leadership (18:22)

A conversation with Mike Zani, CEO of The Predictive Index & Kirk Arnold, Executive in Residence at General Catalyst. On the Tech Trail takes you inside the minds of remarkable tech leaders in Boston and beyond. You'll get to know them, better understand their journeys, and to gain insights from their strategic decision-making to help you along your own journey. Brought to you by MassTLC & Matter.SHOW NOTESGetting started at The Predictive Index (3:20)How to Scale the Company (5:58)How Coronavirus Impacted Us (8:05)Helping our Alumni land softly (11:30)Helping is the new selling and retention is the new growth (15:39)Showing What You’re Made of (16:40)