COACHING AS A CALLING

Coaching isn't just what I do — it's who I am.

I partner with executives, individuals, and teams to do the inner work that creates outer transformation. Through coaching, facilitation, and the wisdom of tools like the Enneagram, we explore what's beneath the surface, address what's not working, and build the capacity to move forward with clarity, balance, and purpose.

OUR ANNUAL REVIEW

HI, I'M JAYSON!

My coaching practice is the culmination of decades spent walking both corporate and personal paths of growth. From Wall Street to nonprofit boardrooms, from solo travel across 37 countries to deep immersion in healing and meditation, I’ve consistently followed a thread of transformation—mine and others’.

MORE ABOUT ME

FUN FACTS ABOUT JAYSON

BEYOND THE BIO

I have worked as an investment banker, a dive master, and a Krav Maga self-defense instructor

I’ve been to over 80 countries across 7 continents, including a 3-year solo-backpacking adventure.

I’ve practiced Vipassana meditation for over 20 years including ten 8-10 day silent retreats.

My partner and I run a free dog sitting service for friends called Camp Jandi (we love cats too).

I have extensive experience with a variety of therapeutic modalities including: cognitive behavioral therapy, Internal Family Systems, somatic therapy, and psychedelic-assisted therapy.

I have eaten fried tarantula and been bit by 2 different poisonous spiders (karmic payback?)

I have over 1000 hours of training in coaching and related-modalities and an insatiable thirst for more.

PARTNER ORGANIZATIONS

I am proud to be a coach in a number of coaching schools and partner organizations, including:

COACHING

AS WITH LIFE, HAS MULTIPLE LAYERS OF MEANING:

WITH INSIGHT

THE CAPACITY TO GAIN AN ACCURATE AND DEEP INTUITIVE UNDERSTANDING OF A PERSON OR THING.

Our work follows a vertical coaching model to support deep, lasting change by expanding self-awareness and inner capacity. It's rooted in my training with New Ventures West, Aletheia, and Enneagram frameworks.

WITHIN SIGHT

CAN BE SEEN FROM A CERTAIN PLACE; CLOSE TO THE 'DESTINATION'

Change starts from day 1. You will be invited and supported in looking at yourself from new perspectives. Each step takes the client further into their own unfolding (note that I do not say ‘each step takes the client closer destination’ because one of the lessons is that the destination is a mirage… it’s the progress on the journey that ends up becoming the goal.)

WITH IN SIGHT

EACH WORD ITSELF ENCAPSULATES A KEY COMPONENT OF THE COACHING WORK.

WITH - This work is co-creative – it is a synergistic, connected dance between client and coach. As coach, I will help point to new ways of being in the world, I will support and encourage you.

IN - The work is always inward first, and only then can it be extended outward through right action. Thus, our coaching work is a non-judgmental, compassionate way of examining ourselves

SIGHT - Our work will involve tapping into the five senses and our sixth sense, intuition, to go beyond the habitual patterns of our mind, build new neural pathways and habits in order to deepen our growth.

WORK WITH JAYSON

A COMMITMENT TO TRANSPARENCY

Like all strong organizations, we believe in measuring our outputs, tracking outcomes for clients, and keeping stakeholders updated on what has been happening. Each year, I create a brief Annual Review to share with clients, partners, prospects, and other interested parties. Click below to explore the most recent Annual Review document.

2024 ANNUAL REVIEW

A GLOBAL PERSPECTIVE

Before founding WITHINSIGHT, I built a career that spanned industries, causes, and continents.

I began in investment banking in NY and then Australia, later scaling Room to Read into a $40M nonprofit, and then managing two global philanthropic portfolios support social innovators worldwide – collectively working with colleagues across over 15 countries and six continents.

My coaching and facilitation spans the globe, working with Founders & CEOs, emerging leaders, and dynamic teams across all industries.

A COMMITMENT TO

CONTINUING EDUCATION

I believe that for coaches to to best serve my clients, we must be continuously expanding our coaching craft and working on our own development.

In addition to the formal training programs listed below, I am an avid reader of coaching and leadership topics, a client of several coaches/therapists/guides, and a life-long investor in my own personal and professional growth.

Georgetown University

BS in Business Administration - 1998

New Ventures West

Certified Integral Coach - 2019

Coaching Circles Facilitator - 2021

International Coaching Federation

ACC Certified Coach - 2020

PCC Certified Coach - 2022

Aletheia Coaching Methodology

Level 1 - 2020

Level 2 - 2020/21

Integrative Enneagram Solutions iEQ9

Accredited Practitioner - 2022

Enneagram for Teams - 2023

CP Enneagram Institute

Certified Enneagram Coach - 2023

Developing Enneagram Skills - 2020

Providing Effective Enneagram Solutions (typing & assessing) - 2022

Enneagram Prison Project

9 Prisons One Key - 2020

Racial Healing Allies

Racial Healing Allies Workshop - 2020

Education for Racial Equity

Fdns. Somatic Abolitionism - 2022/23

Reparative Communal Consultations for White Bodies - 2022-23 (ongoing)

Stozzi Institute

Embodied Leadership Core - 2020/21

Embodied Transformation - 2021

Somatic Body Work - 2021

Somatics, Trauma & Resilience - 2021

Hendricks Institute

Evolutionary Playground - 2023

Body Intelligence - 2023

Coaches Rising

Inside Coaching - 2020

Re-Imagine Leaderships - 2023/24

HAVE MORE QUESTIONS ABOUT JAYSON?

See additional FAQs about Jayson’s work on each of the service pages.