Rayna Lesser Hannaway, CFA

Insight of an Investor. Judgment of a Director. Curiosity of a Coach.

Helping leaders, boards, and investors navigate complexity, align strategy, and create long-term value.

About Rayna & Pure Path Ventures

My Story

For nearly three decades, I have studied companies, leadership teams, and markets. I began my career as a technology analyst just before the dot-com boom, a moment that showed me the difference between bold visions that endure and those that collapse. Over the years, I have analyzed thousands of businesses, managed portfolios, built and led teams, and advised boards, gaining a clear view of what drives lasting performance and where cracks often emerge.

What I have learned is this: durable success is not about a single decision, leader, or idea. It is about how all the pieces- strategy, execution, leadership, culture, and capital fit together. When they align, momentum builds. When they do not, even the strongest vision can falter.

Today, I work with leaders, investors, boards, and organizations to bring clarity in moments of change, disruption, or growth. I help identify what truly matters, ask the questions that uncover blind spots, and guide people and teams toward decisions that create long-term value.

My approach is rooted in three perspectives. The first is the discipline of an investor, sharpened through decades of evaluating companies, capital allocation, and markets. The second is the judgment of a board director, grounded in governance, oversight, and the responsibility of stewarding strategy and risk. The third is the curiosity of a coach, focused on listening deeply, reframing challenges, and helping leaders and investors grow into their full potential.

I believe leadership and performance is not just about results. It is about resilience, clarity, and purpose. My role is to be a trusted partner, helping leaders, investors, and companies thrive in complexity and lead with lasting impact.

My Approach

My work combines coaching and advisory support to meet each client’s unique needs. I see coaching as a space for reflection, discovery, and growth, while advisory brings perspective, experience, and practical guidance. Together, they create a powerful combination: coaching helps uncover new ways of thinking, and advisory translates those insights into clear strategies and actions. This dual approach allows me to support leaders, boards, and investors not just in exploring possibilities, but in building the confidence and discipline to act on them.

Because no two people or organizations are the same, I tailor my approach to the context, challenges, and aspirations at hand. With leaders and boards, this may mean balancing deep listening and powerful questions with structured frameworks and lessons learned from decades of analyzing companies and management teams. With investors, it often means exploring the behavioral side of decision-making — the biases, habits, and blind spots that can either undermine or strengthen long-term performance.

What anchors all of my work is a commitment to helping people align purpose with performance. Whether I am working with a CEO navigating disruption, a board facing strategic choices, or an investor seeking clarity in how they think and act, my goal is the same: to create insight, build resilience, and empower people to lead and decide with lasting impact.

How We Can Work Together

Today, I work with people through coaching, consulting, and board service across both for-profit and nonprofit domains.

Coaching
One-on-one coaching designed to help leaders and investors gain clarity, strengthen resilience, and expand their impact. Together, we uncover blind spots, build on strengths, and create a roadmap for growth that is both personal and professional.

Advisory & Consulting

Strategic guidance rooted in nearly three decades of experience analyzing companies, markets, leadership teams, and organizations. I help both for-profit and nonprofit enterprises sharpen strategy, navigate disruption, and align decisions with long-term value creation.

For Small & Mid-Cap Companies
Institutional investors can be difficult to reach and harder still to win over. Having been one of the largest shareholders in many of the companies I followed, I understand what drives conviction and what raises red flags.

I help leadership teams sharpen their strategy and messaging so that investors see the value clearly. From capital allocation choices to governance practices to how you tell your story, I bring the perspective of a long-term investor who has spent nearly three decades evaluating thousands of companies.

The outcome is stronger investor relationships, a clearer narrative, and a foundation for enduring value.

Board Service
As an experienced investor and director, I bring financial acumen, governance expertise, and a deep understanding of what drives sustainable performance. I contribute actively to board discussions on strategy, risk, capital allocation, and leadership — across both corporate and nonprofit boards.