Our Story

Oak Lane was built on a simple truth: sustainable growth requires both strategy and empathy. Born from years of helping under-resourced businesses navigate systems not built for them, we became the firm we wished existed — one that meets leaders where they are and helps them imagine new pathways to success.

Today, we integrate strategy, operations, and communications into one disciplined approach, guided by our signature HOUR Strategy™ Framework, so that clarity always translates into action. We are a Boston-based, minority and LGBTQ+-owned advisory firm, and our deepest commitment is to the founders, organizations, and communities who deserve a clearer lane forward.

Meet The Founder

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Reginauld S. Williams, MPP

Founder + CEO

Reginauld "Reggie" Williams is an entrepreneur and educator with over a decade of experience in business advising, impact investing, and public policy. He specializes in growth marketing and business strategy for C-Suite executives, driving transformative initiatives across various sectors. Reggie has collaborated with leading organizations such as the Give Black®️ Alliance, Aras Corporation, Emerson College, United Way of Massachusetts Bay and Merrimack Valley, and Innovate@BU.

Experience Highlights include:

  • Vice President, Senior Business Consultant at JPMorgan Chase: Providing tailored, executive advisory services to business owners across New England centered on sustainable growth through the Coaching for Impact® program.

  • Director of Small Business at Dorchester Bay EDC: Managed a $4.5M capital assistance fund, supporting 300 small businesses across six Boston neighborhoods through culturally-responsive advising services.

  • Director of Communications at Massachusetts Budget and Policy Center: Led strategic communications and public affairs initiatives, highlighting the impacts of state fiscal policy through over 20 episodes on the Good Trouble! Podcast.

Reggie is pursuing his doctorate at New York University’s Steinhardt School of Culture, Education, and Human Development. He holds a Master’s degree in Public Policy from Tufts University, with a focus on community development and social welfare policy. Actively involved in philanthropy, he served on the boards of organizations such as BAMS Fest and The Dimock Center.

Our Approach: The HOUR Strategy™ Model

At Oak Lane, we use our signature HOUR Strategy™ Framework to guide our clients through transformation:

  • Human-Centered Design

  • Organizational Alignment

  • User Experience Strategy

  • Revenue Operations

This model ensures that strategy and storytelling are never siloed from systems and that growth is always grounded in purpose.

Our Services

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Consulting

Tailored engagements for organizations seeking hands-on strategy, structure, and execution.

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Advising

Flexible support for leaders seeking a strategic thought partner.

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Workshops

Interactive, half or full-day human-centered experiences designed to align teams and accelerate growth.

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Clients & Collaborators

  • City of Boston Office of Economic Opportunity and Inclusion
  • Equality Fund at The Boston Foundation
  • Creative Re/Frame
  • Boston University
  • Give Black Alliance
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  • Delivering on Equity Collective
  • KR Design Studio
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  • The Teacher's Lounge
  • The Social Butterflies