CWC Team
Caitlin Winkley is the fierce visionary behind CWC.
She’s smart as a whip, comes with a wild life story that’ll make your jaw drop and leads with a strong, yet warm and deeply authentic approach.
Caitlin’s one-of-a-kind style can best be described as ‘professional with personality.’
In other words, she’s created a culture that’s serious about what we do, bringing a high level of proficiency and professionalism to every engagement, while also embracing and encouraging genuine self-expression.
At CWC we make growing fun and effective.
Caitlin Winkley
Founder, CEO, Certified Executive Leadership Coach
Caitlin Winkley Coaching, LLC was founded in 2013. Caitlin is truly a coaching pioneer as the multi-billion dollar personal coaching industry we know today was largely commercially unheard of during her beginning. CWC was born out of Caitlin’s own personal transformation and started as a life coaching company. Caitlin swiftly built a successful business and in 2018 was inspired to open her own coaching school. She founded the highly regarded Next Level Life Coach Training which certifies professional life coaches. In time, her focus began to shift to supporting businesses. Through her guidance and programs, Caitlin has helped countless leaders get promotions and excel in new roles, companies explode profits with fresh ideas and individuals have life-altering personal transformations. Caitlin currently performs keynote speaking, executive coaching with top talent and facilitates workshops and trainings for medium to large sized companies. Learn more about Caitlin by reading her full story.


Kaylee Murray
Senior Operations Manager, Certified Life Coach, CYT
Kaylee’s passion and talent for leadership can be felt in all she does. She’s helped streamline and operate multiple programs within the hospitality, wellness and coaching and development industry. Running teams of 20+, she’s highly proficient at seeing the big vision and knowing exactly what steps are needed to implement to make the vision a reality. She’s helped companies with strategy, operations, innovation, thought partnership, efficiencies, systems, regulations, managing inventory, staff and scheduling. Kaylee has also effectively planned and facilitated retreats, workshops, trainings and speaking events. She is unique with a dual skill set of being able to organize and execute. Kaylee is highly effective at leading and teaching groups as well as facilitating profound transformations via one-on-one coaching. Kaylee refers to herself as a serial hobbyist as in her free time you can find her engaging in either jump roping, hiking, playing hockey, traveling the world or hitting the ski slopes.

Carly Pfeiffer
Wellness Specialist, Certified Life Coach, LMT, CYT
Over the last 11 years Carly has been helping people learn to relax their nervous systems and operate from a sense of wellbeing through yoga, massage and coaching. Carly is passionate about helping people reach their maximum performance in life and work. Neuroscience shows us that more of our brain function can be accessed when we show up in life and work from a place of parasympathetic nervous system dominance (aka less stress). Thus, Carly has proven results with teaching corporations how to lower stress via mindfulness exercises, nervous system regulation, goal setting, self prioritization, reparenting practices, strengthening boundaries and self discovery work. She is skilled at leading groups via facilitating workshops, trainings and speaking. She also provides powerful breakthroughs in her one-on-one coaching practice. Personally, Carly loves recharging in nature, getting lost in bookstores, challenging herself to try new things, and soaking up live music!

Donna Osorio
Director of HR, SHRM-CP, PHR, Certified Life Coach
As a Director of Human Resources with more than 20 years of experience, Donna has a “generalist HR experience,” but mostly helps companies in different aspects of HR from, creating company policies, employee relations, heading various initiatives and partnering with the leadership team. She likes to support the team by being the best resource for employee benefits and policies. Donna has worked in different industries including, interior design, manufacturing, non-profit organizations, attorney services, insurance and, most recently E-commerce. Donna has a growth mindset and takes pride in maintaining her SHRM-CP and PHR certifications. This means she’s always learning and knows the best practices and trends in HR. Besides her HR certifications, Donna is also a certified coach. Her coaching skills come in handy when she counsels employees and coaches or advises managers on complex dynamics. In her free time, Donna loves to travel, read books and go to concerts.