Executive and life coaching for
purpose-led founders.
The journey begins within.
I bet you have a beautiful vision for your company.
But why did nobody tell you building a company was freakin’ hard?!
That it would test you, stretch you, and consume you like nothing else.
That being a founder would be both an immense privilege and an emotional roller coaster you can’t get off.
I’m guessing you’re the type of person who’s always overachieved—from school, to your career, to building your business.
And that you also want to make a positive impact on the world — to solve meaningful problems, create something that wasn’t there before and leave a lasting legacy.
But lately, bridging the gap between where you are now and where you want to is feeling like climbing a very tall and treacherous mountain where the peak keeps on moving up everytime you think you’re getting closer.
Maybe…
You’ve always strived for excellence, but lately, the expectations you’ve set for yourself and your company feel impossible to meet.
You usually feel reliable and capable, but these days your responsibilities are leaving you feeling overwhelmed and anxious.
You used to feel in control of your time, but recently, it’s hard to focus with the fires you’re constantly putting out.
You have great people in your life, but very few of them can fully appreciate what you’re going through as a founder — it’s lonely.
You used to love waking up and working on your company, but now opening your laptop comes with inescapable stress.
You used to feel confident in yourself, but lately, self-doubt is creeping in, about your ability to lead your team to success.
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You know that you don’t have to keep living this way.
You know there’s a leader inside of you that’s ready to level up.
You know there’s a way to build more energy, alignment and self-trust.
I totally get it because I’ve been there. I thought I had my life put together.
I was a founder of a successful and growing startup that was doing something meaningful for the world. I believed I was exactly where I needed to be. That is… until I realized I was not okay anymore.
And when I got honest with myself about how I was holding myself back, how I want to show up in life, and committed to the inner work, everything changed.
25% of all founders have worked with a coach.
70% of exited founders have worked with a coach.
Founders who are willing to do the inner work see the outer results, AND feel so much more confident, free and authentic along the way.
Here’s how things can shift for you too:
Energy
You’re feeling energized and fulfilled, having gained clarity on a vision for your company and life that is both aligned with your values and deeply inspiring.
Focus
You’re focused on work that’s both highly impactful and energy-giving, and your business metrics are thriving as a result.
Confidence
You feel confident as a leader, as you fundraise, sell and manage a team, because you’ve overcome the negative stories and quieted the inner critic in your head.
Trust
You trust your own intuition because you’ve reconnected with yourself and your body’s wisdom. And your team trusts you more too because they sense this.
Ease
You feel more ease and presence in your day because you’ve intentionally organized your time in a way that works best for your energy and life.
Magnetism
You feel more magnetic in your relationships as you become happier, kinder to yourself and confident that you are exactly where you’re meant to be.
All of these shifts will have you climbing to new levels of success in your business, and finding a new capacity for joy, energy and meaning in your life.
I get that this may feel like a distant possibility, and that there are many obstacles standing in your way… but I want to remind you that this IS possible for you.
A year ago I was mentally breaking down in my company and today I feel more aligned, in flow and happier than I ever have in my life.
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“Working with Roslyn has helped me find a clear sense of direction again and her support has helped me move forward with confidence and practical tools I can rely on. She’s shown me how to approach each challenge with a fresh perspective, which has made all the difference in my journey.
Instead of feeling overwhelmed, I now feel empowered and motivated to keep pushing forward. I’m grateful for the clarity and growth I’ve gained through our work together, and I feel ready to take on what’s next with a renewed sense of purpose.”
The Within Coaching Container
A 3-month coaching program designed to help you look within to clarify your vision, level up as a leader, and find confidence, ease and fulfillment in building your company.
The Within Coaching container is focused on helping you tap into your intuition to rediscover your aligned vision, break free from the thoughts and behaviors holding you back, and step into the leadership and impact you were always meant to have.
I can imagine you’re a critical thinker, questioning whether this is truly possible for you.
So I want to share a testimonial from one of my clients who was feeling the same way:
My natural disposition is not one of optimism or self-assuredness. And as such I approached coaching with a guarded skepticism. But Roslyn recognized that and let me come at it at my own speed while helping me find a direction for our work together that would be the most meaningful to me. The progress I've made, not only towards my goals but also in my belief in achieving them, has been remarkable. After a fairly stagnant couple of years I feel as creatively productive as I can remember in my adult life. Roslyn's coaching has helped me to identify the obstacles I was constantly running into and to find pragmatic ways past them. Her approach does not feel as though it is pulled from a playbook and applied generically. Rather, each question or prompt feels tailored and intentional to what I am trying to accomplish. As a result I leave each of our sessions feeling the optimism that can often seem elusive.
Hi, I’m Roslyn
I’m a CPA turned startup founder turned executive coach.
When I left a Big 4 accounting firm to co-found a women-run, mission-driven sports media startup—one that would be accelerated by global brands and recognized in Forbes 30 under 30—I thought I had everything I ever wanted: meaningful work, an amazing team, and endless opportunities for growth.
But then, one morning, I woke up and had a breakdown. I was experiencing founder burnout and it left me feeling emotionally exhausted, apathetic about my life, and deeply ashamed.
Ultimately my burnout was a manifestation of the misalignment I was feeling from my authentic self, from my soul. I had adopted a persona of this successful, put-together female founder that I thought I needed to be to be accepted in the world. In doing so, I suppressed other parts of myself—parts that were important and that needed to be seen, honored and expressed in my work and life.
Over the last year, I’ve been on a profound healing journey that’s sent me deep within myself and brought me much closer to who I want to be in this world.
Today I coach purpose-led founders through the Within Coaching Container.
My approach blends my experience as a startup co-founder, CPA and Head of Operations, Finance & Growth, with my coaching training and my own personal healing journey. This gives me an ability to coach my clients as whole people, not just startup leaders. I consider myself an executive and life coach because I recognize how all aspects of ourselves and our lives are interconnected.
What’s included?
Retreat Day
One 3-hour retreat day to set the foundation for our work together
1:1 Coaching
12 1:1 hour-long coaching calls to support you in moving towards your vision
Resources
Worksheets and guides to complement our sessions and advance your progress
Text Support
Email, text and voice note support so you never feel alone between sessions
Community
(coming soon)
Access to the Within community when it launches, so you can connect with other purpose-led founders doing the inner work to complement their outer work
When you click the button below you’ll be sent to my calendar to schedule a complimentary 45-minute consultation.
We’ll use this time to ensure we’re a perfect fit and that this coaching program is right for you.
FAQs
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One of the key areas we’ll focus on together is gaining clarity on your vision, defining your most important goals, and learning how to prioritize and optimize your time accordingly. This work will actually give you back time, so the one hour per week you invest in coaching will not only save you time in the long run, but it will also help you feel less stressed, reactive, and overwhelmed throughout your day.
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Now is a great time to lay the foundation to ensure that your burnout doesn’t get any worse. When we wait too long to listen to our bodies, clarify what we truly want, and make the changes needed to thrive, we risk further deteriorating our mental health and our performance. Doing this work now will set you up to succeed and find more joy in your work today.
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As a CPA turned startup founder turned executive coach, I understand that you want to ensure you’ll see a return on this investment. If you’re committed to this work, investing in yourself will always pay off. In our coaching sessions, we’ll focus on leveling you up to increase your impact in your business while also working to improve your relationship with money. Often, a scarcity mindset is based on old programming and limiting beliefs, that together we’ll work together to release. I also offer a monthly payment plan if that’s more manageable, and we can explore flowing the expense through your company for tax efficiency.
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It will vary depending on what challenges you bring into our sessions and the shifts you’re hoping to make in your life. My approach is rooted in the belief that you already have the wisdom within yourself to drive the change you’re seeking, so you’ll be actively involved in identifying the steps you want to take between sessions. When appropriate, I’ll provide materials and exercises to guide your work and the time you want to spend on them is entirely up to you.
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Absolutely! I love working with people that are ready to make a jump into a more aligned life. Having gone through the transition from corporate to entrepreneurship myself, I understand the journey. Now is the perfect time to get clear on your values, your unique gifts and purpose, and what work truly lights you up—and how to translate that into your work and life. I know it can also feel like a scary and vulnerable time, and I’d be honored to be in your corner, supporting you with your plan, the details, and, most importantly, believing in YOU. Let’s get you stepping into all that you’re capable of.
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Yes! I’ve navigated this myself recently, and I’d be honored to hold space for you and guide you through this time. I know it can bring up a range of intense and often conflicting emotions—grief, fear, relief, uncertainty, and confusion. But I also know that it can be a truly magical time to discover who you want to be in this next phase of life, especially when approached with intention and hope. I’d be thrilled to support you as we navigate this journey together.
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As a coach, my approach is rooted in the belief that you have the wisdom within yourself to make the best choices for your business and life. While I may have experienced similar circumstances, you know yourself better than anyone and have the full context. My role as coach is to use my understanding of you and your context to ask you powerful questions and provide useful tools and frameworks to help you make the decisions that are right for you. If you are looking for an opinion on something you are always invited to ask for my advice and if I think it’s appropriate I’ll share it. I’ll always let you know when I’m shifting from a coach role to an advisor/mentor role and back.
More than anything, what I really want for you is to feel like the most expansive, lit up, and expressed version of yourself in your company and in your life.
You’re doing one of the most challenging things in the world by building a company and you deserve to feel support, fulfillment and joy along the way.
If you’re ready to go from stuck, overwhelmed and doubting yourself to clear, confident and in flow, then I’m ready to support you on that journey. Let’s do this together!