Lead with clarity.
Prepare for what’s next.

Jennifer Olsen
Certified Executive Coach & Exit Planning Advisor

Meet Jennifer

I help business owners and senior leaders unlock powerful opportunities for transformation, growth, and impact. With decades of experience as both an entrepreneur and executive, I’m committed to hands-on coaching that drives real results.

Throughout my career, I’ve had a passion for big work. I founded, grew, and sold Resourceful, a consulting firm focused on strategic HR and organizational and business impact for companies in the Pacific Northwest and beyond. After a successful exit, I went on to direct the Northwest HR consulting practice for the acquiring multibillion-dollar company, OneDigital. I have worked closely with a range of impact-focused organizations, from family-run businesses and global foundations to large life science companies and service-driven nonprofits.

What truly energizes me is connecting deeply with clients to zero in on the most powerful levers to accelerate progress and impact. My coaching approach is thoughtfully personalized, blending my business experience with a dynamic toolkit that evolves to meet each leader exactly where they are. I have an MBA from the University of Washington, a Certified Exit Planning Advisor (CEPA) credential from Exit Planning Institute, and an executive coaching certification from the Hudson Institute—and I am committed to continuous learning and growth.

I'd be delighted to explore how we might work together to help you clarify your vision, lead with confidence, do big work, and prepare for what’s next.

Read more about my background on LinkedIn or check out a few of my favorite client success stories here.

Certified Executive Coach, Hudson Institute of Coaching

Certified Executive Coach, Hudson Institute of Coaching

Associate Certified Coach, International Coach Federation

Professional Certified Coach, International Coach Federation

MBA, Technology Management, University of Washington

MBA, Technology Management, University of Washington

Accredited Practitioner, Integrative Enneagram

Accredited Practitioner, Integrative Enneagram

Diamond Power Index Certified

Diamond Power Index Certified

Leadership Circle Profile Certified

Leadership Circle Profile Certified

Coaching Supervision, Goldvarg Consulting Group

Coaching Supervision, Goldvarg Consulting Group

Certified Exit Planning Advisor, Exit Planning Institute

Certified Exit Planning Advisor, Exit Planning Institute

“I wasn’t even really considering going out on my own. I just knew I wasn’t happy with where I was. I had no clarity about what I was going to do next, or what it might look like. After a short period of time, Jennifer could see things in me that I couldn’t see. It soon became super clear.”-B, Business Owner
“Other coaches I’ve experienced want everyone to have a particular leadership style. Jennifer’s coaching philosophy is more flexible. She believes that finding and being one’s authentic self is the best approach.” -L, Nonprofit Executive Leader
“Jennifer has a way of questioning that allows YOU to see the truth more clearly. She helps you understand things that may be obvious from an outsider’s perspective, but when you are in the thick of things with your blinders on, you don’t see at all.”-N, VP Operations and Engineering
“Jennifer has been a thoughtful, insightful, and highly supportive partner in helping me to improve upon my leadership skills and professional relationships across the organization and with our many global partners.”-J, Deputy Director
“I interviewed three potential coaches. Jennifer was clearly the best choice. She has such high emotional intelligence and empathy.”-M, Operations Leader
“It has been so helpful to have a sounding board to sketch out possible challenges and situations. The process has helped me understand and articulate my goals as a leader.”-R, Senior Public Health Leader
“I wasn’t even really considering going out on my own. I just knew I wasn’t happy with where I was. I had no clarity about what I was going to do next, or what it might look like. After a short period of time, Jennifer could see things in me that I couldn’t see. It soon became super clear.”-B, Business Owner
“Other coaches I’ve experienced want everyone to have a particular leadership style. Jennifer’s coaching philosophy is more flexible. She believes that finding and being one’s authentic self is the best approach.” -L, Nonprofit Executive Leader
“Jennifer has a way of questioning that allows YOU to see the truth more clearly. She helps you understand things that may be obvious from an outsider’s perspective, but when you are in the thick of things with your blinders on, you don’t see at all.”-N, VP Operations and Engineering
“Jennifer has been a thoughtful, insightful, and highly supportive partner in helping me to improve upon my leadership skills and professional relationships across the organization and with our many global partners.”-J, Deputy Director
“I interviewed three potential coaches. Jennifer was clearly the best choice. She has such high emotional intelligence and empathy.”-M, Operations Leader
“It has been so helpful to have a sounding board to sketch out possible challenges and situations. The process has helped me understand and articulate my goals as a leader.”-R, Senior Public Health Leader

Services

COACHING FOR BUSINESS OWNERS

Build high-performing teams
Set and stay accountable to goals
Maximize the value of what you’ve built
Prepare for succession and the next chapter

Learn more here.

COACHING FOR SENIOR LEADERS

Step into new roles with confidence
Build high-performing teams
Manage organizational change

Learn more here.

Work in Progress

I continually invest in my own learning and growth to inspire my clients with fresh insights and ideas. Here’s what I’m working on and learning right now.

BOOK PROJECT

I’m working on a book that will help business owners prepare themselves for the emotional journey of selling their business so they can better articulate what they want and decide what’s right for them. I’ll share stories of my own journey selling a business as well as stories from others who have walked the same path. If you’d like to participate, or you know someone I should talk to, please get in touch!

NEWSLETTER

I've started a new newsletter, What's Next, On Purpose, exploring what it's like to navigate change—in business and in life. Twice a month, I share honest stories from my own transitions and conversations with others who've walked a similar path. 
Subscribe here.

READING

I’m reading several books for fun and for new insights on leadership and systems thinking, including Thinking in Systems by Donella Meadows, Falling Upward by Richard Rohr and the Throne of Glass series by Sarah Maas. The first prompts reflection on relationship systems when two organizations merge, the second prompts musing on next life chapter planning, and the third is just for fun.

MUSIC

I’ve created a trio with two friends and we recently had our first public performance! I’m also continuing to take drum lessons, along with occasional lessons in vocal performance, guitar and viola. Learning, singing, and building community through music bring me immense joy.

TRAINING

I believe the best coaches never stop learning. While I’ve spent years helping business owners navigate transitions, I recently earned a Certified Exit Planning Advisor (CEPA) credential from Exit Planning Institute. I’m already putting new insights to work, helping business owners plan their exits on their terms and create a vision for themselves beyond their business.

Ready to take the next step?

GET IN TOUCH