6 Learning and Development Leaders in Boston, MA

Last updated: 5 August 2026

Introduction

If you are looking for learning and development leaders in Boston, start with the people shaping how others learn, lead and work. This list covers current practitioners across healthcare, higher education, schools, consulting and organisation development. It includes Boston and its immediate learning ecosystem, including Cambridge and Chestnut Hill.

The list is not ranked. Each person is here because a current public role or practice connects with learning and development and because the work offers something useful to notice. Use it as a starting point for your own reading, conversations and decisions, then check the latest profile before making contact.

Why learning and development leadership matters in Boston

Boston is a dense learning city. Hospitals, universities, schools, technology companies, professional services firms and community organisations all need people who can turn expertise into better practice. That makes the local L&D picture broader than one job title or one type of employer.

The people below show several ways the work can be done. Some lead internal talent systems. Some design learning experiences. Some connect development to health, education or community outcomes. Together, they make the field easier to see and give leaders a more useful set of questions to ask about their own teams.

1. Judith Alexander

Senior Manager of Learning and Development, City Connects, Boston College

Judith Alexander is Senior Manager of Learning and Development at City Connects, part of Boston College's Mary E. Walsh Center for Thriving Children. The Boston College directory places her in a current learning and development role, while her LinkedIn profile connects that work with the centre's education and community focus. She is a useful name for anyone exploring learning leadership beyond a standard corporate training brief in Boston and Chestnut Hill. It is also a reminder that capability building can be measured through stronger relationships and better access to support, not only course completion.

Her work sits where professional learning meets the wider conditions that help students thrive. City Connects works with schools and communities to connect students with supports, and the centre's 2024 progress report identifies Alexander in senior learning and development work. That gives her profile a distinctive scope: learning is part of a wider system involving educators, families, community organisations and the practical needs of children. The lesson for L&D teams is to look at the whole setting around learning, not just the session itself.

2. David DeFilippo

Principal, DeFilippo Leadership Inc.

David DeFilippo is Principal of DeFilippo Leadership Inc. in the Greater Boston area. His professional profile describes an active leadership and talent practice, and Chief Learning Officer records his experience as a former chief people and learning leader. That combination makes him relevant to organisations looking for learning work tied to culture, leadership behaviour and business change. His profile also shows why strong L&D work often needs both internal context and an outside view.

A distinctive part of DeFilippo's profile is the bridge between in-house leadership and independent practice. The same industry profile notes his work as a coach in Harvard Business School executive education and his writing on leadership and talent. For Boston leaders, that offers a practical reference point: learning and development can be a function inside an organisation, a specialist advisory practice, or both. The right shape depends on the problem, the audience and the change leaders need to sustain.

3. Debra Hamilton

Vice President, Talent Management, Boston Children's Hospital

Debra Hamilton is Vice President, Talent Management at Boston Children's Hospital in Boston. Her LinkedIn profile describes work across talent management, leadership development and team effectiveness, while a professional learning agenda identifies her current title and organisation. She belongs in this list because the role connects people development with the complexity of a large clinical system. That context calls for learning that is practical, careful and connected to the work of many different professionals.

Hamilton's scope is a reminder that learning leadership is not limited to courses or classrooms. In a children's hospital, development work has to support specialists, managers, teams and the wider mission at the same time. Her profile is especially relevant for Boston people leaders who are designing development that needs to strengthen both individual capability and how teams work together under pressure. It also highlights the value of connecting talent work to the quality of the service people provide.

4. Dyan Madrey

Organisation Development Consultant, Massachusetts Institute of Technology

Dyan Madrey is an Organisation Development Consultant at MIT in Cambridge. The MIT staff page says she assesses development needs and creates learning opportunities aligned with talent objectives, while her LinkedIn profile places her in the Boston-area learning and development community. Her background includes talent development work in healthcare and financial services. That mix gives her a grounded perspective on how learning needs change across sectors, roles and organisational cultures.

Madrey offers a useful example of the consultant side of internal learning work. Her remit is not simply to schedule training. It involves diagnosing needs, shaping opportunities and connecting them to the goals of a large institution. For leaders in Boston and Cambridge, that is a helpful way to think about organisation development: start with the work and the people system, then decide what learning response is needed. The method is simple, but it protects teams from buying a course before they understand the real need.

5. Leah Waldo

Director, Learning Design, Technology, and Media, Harvard Graduate School of Education

Leah Waldo is Director of Learning Design, Technology, and Media at the Harvard Graduate School of Education in Cambridge. Her Harvard staff profile confirms the current role, and her LinkedIn profile places her in the local learning and education network. The role is a strong fit for people interested in how learning design changes when technology and media are part of the experience. It also reflects the growing need to make learning useful across different formats, devices and levels of access.

Waldo's work points to a broader definition of development. Good learning is not only a matter of content. It also depends on the design of the experience, the tools people use and the way ideas travel through a community. For Boston organisations, her profile is a useful prompt to ask whether a development programme is genuinely designed for how people learn, work and share knowledge now. That question can improve both formal programmes and the everyday learning that happens between people.

6. Michael Fenlon

Executive Director of Advances in Learning, Harvard University, VPAL

Michael Fenlon is Executive Director of Advances in Learning at Harvard University's Vice Provost for Advances in Learning. The Harvard profile describes work focused on tools, technology and platforms that extend educational access, and his LinkedIn profile confirms his current Harvard connection. His earlier people and future-of-work experience adds a clear organisational learning perspective. He is a useful profile for leaders thinking about learning as infrastructure rather than as a series of isolated events.

Fenlon is relevant because his work treats learning as a system that has to reach people at scale. That is a useful lens for Boston employers building leadership and professional development across large or distributed groups. The practical question is not only what content to deliver. It is how to make good learning easier to find, use and carry into everyday work. When access is designed well, learning becomes part of the operating rhythm rather than another task people struggle to fit in.

What these leaders show

The common thread is not a single method. It is the discipline of connecting learning with the work people are actually trying to do. In one setting that may mean helping students and schools thrive. In another it may mean building clinical capability, strengthening leaders or making learning easier to access at scale.

That is why the best starting question is usually not “What training should we run?” It is “What needs to work better, and what would help people do that work well?” The answer may involve a programme, a redesign of the role, a better team conversation or a simpler way to share knowledge.

How to use this list

Start with the setting closest to your own. If you work in healthcare, look at how learning is connected to teams, safety and professional practice. If you work in a university or school system, notice how learning design, community needs and access shape the work. If you lead a business, use the profiles to widen the question beyond courses and content.

Before you contact anyone, read the current source linked in the profile and decide what you are actually trying to solve. A clear brief will help you tell the difference between a learning need, a leadership need and a wider organisational problem. It will also make any first conversation more useful.

Frequently asked questions

How was this list built?

The selection began with Boston and Cambridge searches across healthcare, higher education, schools, employers and independent practices. The final profiles were chosen from current public role evidence, a live professional profile and a clear connection to learning and development. The wider candidate file keeps weaker or unresolved names private rather than presenting them as settled facts.

Does this list rank people?

No. The order is editorial and has no quality meaning. It simply gives the article a readable shape.

Should I contact every person on it?

No. Choose the people whose setting and scope match your need, then check their current public profile before reaching out. A short, specific written brief is usually more helpful than a broad request for “training”.

Conclusion

Learning and development in Boston is a wide field. It includes people working inside hospitals, universities and schools, as well as consultants and designers who help organisations build capability in different ways. The strongest work starts with the real challenge and respects the context around it.

If you are building a development plan, use these profiles as prompts. Ask what your leaders need to do differently, what your teams need to practise and what support will make the change stick after the workshop or programme ends.

Related Reading

For more practical ideas, read Working Genius: Complete Implementation Guide for Teams and Leaders, 100 Essential Training Topics for Managers and 100 Proven Strategies for Leadership Team Development.

If you are planning a keynote, workshop or facilitated leadership session, email jonno@consultclarity.org with the outcome you want the session to create.

About the author

Jonno White is a Brisbane-based leadership consultant, keynote speaker and Certified Working Genius Facilitator, and the author of Step Up or Step Out. He works with schools, corporates and nonprofits around the world. To enquire about a keynote, workshop or facilitated leadership session, email jonno@consultclarity.org.