WHY ME
There are a lot of executive coaches. There are very few who have actually lived the life you're living.
I've been in your seat
I spent 29 years in investment management — as an analyst, a portfolio manager, and a team leader. I know what it feels like to carry other people's capital, to build and lead a team, to perform under pressure when the stakes are real and the results are public. I'm not learning your world from the outside. I lived it for nearly three decades.
I know the rooms you're walking into — and what the destination looks like.​
I've spent 29 years on the investor side of the table — evaluating management teams, forming views on leadership, deciding where to put capital based on the people running the business. I know exactly what investors are looking for when they sit across from a founder or an executive.
I know what builds conviction and what quietly destroys it. And if you're building toward an IPO or managing a public company — I know what that destination demands of a leader. I know how equity value gets built or eroded by the way a leadership team shows up. That's not something you learn in a coaching program. I serve on boards. I'm a board director. I know what the conversation looks like from the other side of that table — how boards evaluate management, what good governance actually looks like, and how to show up in a boardroom in a way that builds trust and creates real dialogue rather than performance. I bring both rigor and range. I'm a CFA charterholder and a certified leadership and performance coach. That combination is unusual by design. I wanted to bring the same analytical rigor I used to evaluate companies to helping people understand themselves. The work we do together is structured, disciplined, and grounded in real frameworks — not just conversation. I've lived the balancing act too. I know what it's like to carry all of this while also being a mom to teenagers and a wife. The ambition doesn't pause when you walk through the front door. The mental load doesn't either. Figuring out how to show up fully in your career and still be present at home — that tension is real, and it's rarely talked about honestly in professional settings. I'm not going to pretend I've solved it perfectly. But I understand it from the inside. And that matters when we're doing this work together.
THE WORK
WHERE WE FOCUS
The work looks different for everyone. But it almost always comes back to these six things.
01
VISION
Where you’re actually going. Not what you’re supposed to want. What success looks like on your own terms.
02
CLARITY
The quality of your thinking under pressure. What drives your decisions. The blind spots you can't see from inside.
03
PRESENCE
How you show up in the rooms that matter. Communication, hard feedback, and how you're perceived when it counts.
04
IMPACT
Your team's performance is a reflection of your leadership. Culture, retention, and what the organization actually delivers.
05
GROWTH
Transitions. Inflection points. Closing the gap between who you are and who you're capable of becoming.
06
RESILIENCE
Sleep, energy, recovery — not as wellness topics, but as performance variables. Sustainability is a competitive advantage.
WHAT'S POSSIBLE?
The work starts with you. But it doesn't end there.
When you get clearer on what's been in your own way the decisions get better. The ones you've been circling, you make. The conversations you've been avoiding, you have. The move you haven't quite let yourself commit to, you commit to.
For some people that move is internal stepping into a bigger role, taking on more responsibility, finally being seen the way you know you're capable of being seen. For others it's external a different seat, a harder challenge, the next chapter that's been forming in the back of your mind. Either way, the path forward gets clearer. And you stop waiting for someone else to recognize what you're ready for.
For those leading organizations, the impact goes further. Your team starts telling you the truth. Problems surface earlier. The culture shifts — not because you mandated it, but because you changed first. Your organization starts delivering closer to what it's actually capable of.
For public company leaders, it shows up in how investors see your management team and in what your company is worth. For founders, it shows up in the raise, in the rate of growth, in the room when someone decides whether to bet on you.
​
The personal and the organizational aren't separate. They never were. When you perform at your best, the people and the business around you rise with it.
Senior Sales Leader, Big Tech
I have had the privilege of knowing Rayna Hannaway for approximately a decade, and she has been an invaluable resource for career advice and guidance throughout that time. Rayna has a remarkable ability to help you think differently and outside the box, combining excellent listening skills with clear, actionable direction. Most recently, when I needed to transition into a different role, I engaged Rayna for formal career coaching, and the experience was transformative. She guided me through a deep introspection process, asking thoughtful questions that helped me identify what I truly enjoy and what matters most to me both professionally and personally. Rayna helped me discover what really drives and fulfills me, and as a result, I've made meaningful changes in both my professional and personal life. For any professional open to outside guidance, Rayna brings a unique ability to elevate your career to the next level while ensuring you're balancing personal growth and operating at your maximum capacity. I highly recommend consulting with Rayna if you're ready to take yourself to the next level.
Skincare Startup CEO
I came to Rayna at a moment when I needed to think differently about how I was running my business. There were patterns that kept showing up around hiring and around how I was allocating my time and energy. I knew I needed an outside perspective to help me see them clearly and move past them.
Rayna has a way of asking the questions that get underneath the surface quickly. She helped me understand what was actually driving some of the decisions I kept making, and from there we worked on building a stronger foundation. How I think about hiring. How I make strategic decisions. How I structure my time so the most important things actually get done.
She also encouraged me to engage seriously with AI as a real strategic tool for my business. That was not a conversation I was expecting to have, but the way she framed it, not as a technology trend but as a genuine lever for a founder at my stage, completely changed how I am thinking about it.
Rayna brings something rare. The ability to see both the human and the business clearly at the same time. She is direct without being prescriptive. She listens carefully and then asks exactly the right question. For any founder who feels like they keep running into the same walls, she helps you understand why and what to do differently.
Financial Services Startup COO
Rayna has been an incredible executive coach and thought partner over the seven months we’ve worked together. When we first started, I was navigating increased responsibility while managing the pressures of a high-growth, fast-paced startup. She helped me think deeply about how to stay true to myself while building influence and driving meaningful outcomes in a short period of time.
During this time, I was also promoted to COO. Rayna played a meaningful role in helping me step into that transition with openness and confidence. She challenged me to rethink how I approached new opportunities, especially as my scope expanded and I began leaning more into formal leadership. Our work together around radical candor and building buy-in was especially impactful. She helped me see that I could lead in my own way, and that I didn’t have to fit a predefined mold.
Along the way, Rayna encouraged me to go deeper and stay grounded, particularly in high-stakes conversations. She gave me tools to create boundaries, extend grace to myself, and embrace the reality that work and life move in seasons. Even when it felt intense, she helped me reframe those moments as part of growth.
I feel incredibly grateful to have had Rayna in my corner during such a pivotal period. She has helped me become a more thoughtful, confident leader and a better partner both inside and outside of work. I would wholeheartedly recommend working with her.
