Reach Capital Future of Work Advisors: Pamay Bassey, Dermot O'Brien, David Landman, Guillermo Miranda, Maisha Gray-Diggs, Gordon Trujillo


Announcing Our Inaugural Future of Work Advisors

Education is in the DNA of Reach Capital: Former teachers, administrators and edtech founders make up our founding team. Throughout the years we’ve also built an advisory network of K-12 and higher-ed leaders who help keep our ears close to the ground. This collective experience and expertise not only help us make smarter investment decisions, but also enable us to support our founders as they build lasting, impactful businesses.

A few years ago, Reach expanded its investing scope to workforce education, economic empowerment and career mobility. We added amazing companies to our portfolio, including Stepful, which helps to train and healthcare workers; WorkWhile, a worker-first labor marketplace for hourly workers; and Springboard, which upskills employees in on-demand digital skills. Complementing these efforts, we launched a blog series, People Matters, to highlight the voices and insights of top HR and People leaders. We also published ReimagineWork, a data-informed report on emerging workforce trends and the need for a powerful skills engine to power the next labor market revolution.

As we did in K-12 and Higher Ed, we actively sought out experts who could help us understand what the true needs for workers and employers were, separate the signal from the noise in a crowded market, and better support our portfolio of founders. Today, we are excited to announce that first cohort of advisors!

Our advisors represent a range of mid-sized to large, global companies across a diversity of industries: aerospace, finance, IT, health and enterprise tech, to name a few. They are a wealth of knowledge and expertise and we feel lucky to have them part of the expanded Reach family. Here’s why they are excited about the future of work and partnering with Reach.


Gordon TrujilloGordon Trujillo is the Head of Learning and Development at DaVita. He was formerly the Head of People Systems at Visa and the Global Head of Digital Learning at Accenture. 

“By augmenting human capabilities with personalized learning through technology, we aim to make humans super, enhancing their potential and abilities. There has never been more potential to transcend this field and it will require our collective expertise to re-think, re-imagine and then re-mix to solve the next generation opportunities.


Maisha Gray-Diggs

Maisha Gray-Diggs is the VP of Global Talent, Inclusion, and Experience at Eventbrite. Before Eventbrite, she was a senior talent acquisition leader at Twitter and Microsoft. In her People Matters interview, she focused on what employers need to do in today’s market to source and retain talent. 

“Advisory opportunities like this don’t come around every day for someone like me. What excites me about the innovation happening in ed-tech is that we are thinking about how to make technologies relevant for as broad a group of learners as possible. #InclusiveDesign #TechnologyForAll.”


Guillermo MirandaGuillermo Miranda was the Chief Learning Officer at Boeing and, before that, the Chief Learning Officer at IBM. Guillermo was our inaugural People Matters profile feature and spoke about how people leaders need to get more engaged in how their work overlaps with the core business.

“The partnership with Reach Capital provides a fantastic opportunity to witness first hand all the wave of innovation and technology disruption happening across EdTech and the broader people collaboration space.”


Dermot O'BrienDermot O’Brien was most recently the Chief Transformation Officer at ADP and, before that the EVP of Human Resources at TIAA. You can read his People Matters feature on how he helped build the “Win as One” culture at ADP that removed silos and improved morale and performance.

“I’m excited to be part of the journey in upskilling people’s lives in academic and business settings through innovative learning and enabling solutions.”


Pamay BasseyPamay Bassey is Chief Learning and Diversity Officer for the Kraft Heinz Company. Prior to Kraft Heinz, Pamay served as the Global Head of Learning Platform and Professional Development for BlackRock, was president of The Pamay Group, an e-learning design and strategy company, and started her career in Accenture’s Media Technology Group.

“I am excited to influence and shape the future of education by supporting innovative edtech startups that have the potential to revolutionize learning methods and outcomes. I look forward to collaborating with forward-thinking entrepreneurs, industry experts and investors – sharing my experience, gaining exposure to the latest advancements and trends in educational technology, and fostering continuous learning.”


David LandmanDavid Landman spent 20 years at Goldman Sachs and was most recently their Global Head of Talent Development. His People Matters interview focused on how he helped to improve retention through an important but often forgotten skill: listening!

“I want to support the visionary founders, innovators and investors who are redefining what it means to thrive at work”


If you are a company tackling issues related to the future of work and eager to learn from our amazing community of advisors, please reach out to!