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Helping entrepreneurs expedite growth and clarify, simplify, and achieve their vision


Jessica is an expert who helps growth-focused entrepreneurs succeed by implementing EOS to build high-performance leadership teams – and get “Real … Simple … Results”.  EOS is a proven, foundational and holistic operating system that gets everyone in your company executing towards a shared vision.

As a Certified EOS Implementer™, Jessica has found the best framework to share her 22 years of entrepreneurial lessons by becoming a trusted advisor to her client’s leadership teams, helping Entrepreneurs and their Leadership Teams fast-track their growth and simplify, clarify and achieve their vision. As well as help them avoid the blind spots in the entrepreneurial community and live the life of their dreams.

Jessica works with best-in-class-companies (many are YPO’ers) to help them achieve their VISION, gain TRACTION and become HEALTHY cohesive teams. She brings a wealth of real-world entrepreneurial experiences to every client and every client session. She focuses on her select number of EOS clients to help them expedite the transformation and scaling of their companies from good to great. Jessica travels all over the Western US for her clients.

At the age of 25, Jessica founded a best-in-class agency specializing in event/experiential marketing staffing and execution throughout the US, Canada and internationally. The company had an average annual growth rate of 43% over their 18 years, led their niche industry nationally, won the INC 5000 four times, employed 60 internal staff, and nearly 10,000 annual part-time W2 gig-economy employees throughout North America. Jessica dedicated 18 years to serving her clients, which consisted of leading global agencies as well as Fortune 1000 clients to include: Coca-Cola (VEB),, State Farm, Nintendo, Samsung, Singularity University, others.

Jessica is also Regional Developer in Southern California for a hot and emerging Franchise Concept, CLOVR Life Spa, from the same team that created Massage Envy, Great Lash, and The Joint Chiropractic. With CLOVR Life Spa, Jessica and her business partners bring on strong franchisees as well as passive investors to open 55 stores in Southern California over the next 5 years, help them be successful and get major traction.

Jessica is always pursuing a life around her entrepreneurial spirit and building new ventures that reflect her talent, experience, and ability to positively affect the quality of life. Her adventurous nature is contagious with an insatiable appetite for human connection and growth. She loves human experiences, marketing, entrepreneurialism, innovation, problem-solving, and building things to make people’s lives easier.

Jessica is an active member of YPO, a former member of EO, a 2007 graduate of the MIT/EO Entrepreneurial Master’s Program (EMP), and a member of the MIT/Gathering of Titans Program for EMP Graduates. Her main states for working with EOS clients are currently AZ, CA, CO, OR, and NV.

Three Things that make me unique:

22 years of entrepreneurial leadership in running, scaling, and pioneering in highly complex, niche industries nationwide, with nearly 10k field employees.



Driving value to your organization through my obsession to connect people. Creating impactful & inspiring connections that include: new clients, investors, sponsors, fractional/interim executives, suppliers, advisors, etc.


My experience and energy as a facilitator, listener, creative thinker, opportunist, and coach, coupled with holding your team accountable and guaranteeing you results!

What my clients are saying:

"Jessica Stackpoole’s implementation of EOS to our leadership team has been completely transformative.  Her experience and direct approach have made implementation easy and seamless despite the challenges of adopting a completely new system to manage our business. While we are less than halfway through our EOS journey, our business is already seeing positive results and I have no doubt we will be exponentially more efficient and productive as we fully implement the system." 

John David, CSEE
USA BMX, Chief Operating Officer

"My business has grown exponentially since I started it 15 years ago and early on I joined both EO and YPO to help me be more strategic and make better decisions. I came to the realization that I could use a better system to be more efficient with my company meetings and my company goals. I turned to EOS and more importantly Jessica Stackpoole.  EOS is a system that anyone can buy and use BUT having Jessica roll out the concept was a game changer for my company and its leadership. Her background as a seasoned entrepreneur and YPO member brought leadership quality facilitation to my company leadership. I simply cannot recommend her highly enough."

Ken McElroy
YPO Member, MC Companies

“Jessica brings a real world experience to companies that want to professionally implement the EOS Model™ into their organization. We saw immediate results within 30 days of implementing EOS. EOS has been helpful in focusing us on what’s most important to get done, streamlining communication, and issue-solving more quickly and effectively in our high-growth company. We look forward to our L10 meetings weekly, have really gelled as a Leadership Team, and we are getting more Traction.”

Michael Van Guilder
YPO Member, Triumph Capital Group

“Having transitioned from a multinational corporation with thousands of employees to a small startup business, I found myself struggling with the lack of structure and focus. EOS® along with Jessica’s expert implementation and enthusiasm for our success, has provided the structure, laser like focus, and momentum that we share with all current and future employees that will move our business forward at an accelerated pace.”

Chris Poole, Cellar Manager

"Before working with Jessica and implementing the EOS® program, our leadership team struggled how to prioritize the countless demands of running our business. Staying razor focused on our most critical issues has made us more effective and energized our team. We can see results in only two months. I can’t wait to see where we will be a year from now. Jessica is not only a proven business executive who understands how to run a business but she is also an outstanding trainer. She cares about our success and is a valued partner on our way to greater success."

Laura Wright
OnePoint Franchise Accounting
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