Meet Cheryl Dillon
Hi, I’m Cheryl Dillon, the founder of Funderful Experiences.
For more than three decades, across careers in sales, recruiting, consulting, business ownership, and coaching, genuine connection has been the engine behind everything I’ve done. Not as a strategy I learned from a book, but as a way of showing up that made business not just successful but enjoyable.
Today I bring everything I’ve learned – and lived – to three distinct areas of work: helping professionals develop the relationship-building skills that move their business forward, creating connection experiences for local businesses that make their space memorable, and growing Connected Hearts, a community for women in midlife who are ready for real friendships, fresh perspective, and shared joy.
A Career Built on Connection
My professional journey has always centered on one thing: people.
Early in my career, I taught professionals how to use emerging computer technology and developed the training curriculum myself – an experience that shaped how I think about making complex skills accessible and practical. That instinct for turning real-world knowledge into teachable frameworks has stayed with me ever since.
From there I moved into IT sales, where I was awarded Rookie Salesperson of the Year in my first year and Salesperson of the Year in my second. Those early years taught me that results follow relationships, and that the people who thrive are the ones who know how to show up with genuine interest, not just a polished pitch.
I then established an executive recruiting practice as a solopreneur, where networking wasn’t optional, it was everything.
Finding and building relationships with candidates, cultivating rapport with hiring managers, and earning the trust of clients through consistent, sincere follow-through was how the business survived and grew.
I spent more than a decade in human resources and recruiting consulting, working inside organizations across multiple industries, forging meaningful working relationships with executives, hiring managers, and teams at every level.
Then my husband and I co-owned a cooking school for children – our first experience running a physical space and serving a community of families who trusted us with something that mattered most to them.
For the past 18 years, I’ve served as co-founder and Divorce Coach at Equitable Mediation Services – a two-person practice my husband and I grew from the ground up. In addition to guiding clients through one of the hardest experiences of their lives, I developed the business – cultivating referral partnerships, networking, developing online courses, and creating the systems that allowed us to serve more than 1,000 couples across six states.
What I’ve discovered in more than three decades and through every role, industry, and reinvention, is that real connection doesn’t just drive results. It makes the work feel worth doing.
That belief is what led me to found Funderful Experiences. Because whether you’re a professional trying to grow your business, a local venue owner wanting to create something memorable for your customers, or a woman in midlife looking for true friendship – genuine connection is at the center of it all.
Credentials & Training
- Certified Professional Coach (CPC)
- Graduate of the Institute for Professional Excellence in Coaching (iPEC)
- B.A. in Psychology, University of Connecticut
- Event Planning Certificate Program, San Diego State University
Rooted in The Community
I believe meaningful connection starts close to home. Since relocating to North County, I’ve made it a priority to be an active and contributing member of the community I now call home.
I’m a proud member of the Carlsbad Chamber of Commerce, an organization that has deepened my connection to the local business community and the entrepreneurs who make North County thrive. I’m also a member of the Woman’s Club of Carlsbad, a commissioner on the city’s Senior Commission, a volunteer at the Carlsbad Senior Center, and previously volunteered at Rancho Coastal Humane Society, where I adopted my dog-ter, Wrigley.
These aren’t just resume lines, they’re what showing up actually looks like.
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Celebrating the launch of Funderful Experiences with the Carlsbad Chamber of Commerce - surrounded by community, connection, and the kind of support that makes everything feel possible.
A Little About Me
I spent most of my life in New Jersey, where I mastered the art of saying exactly what I’m thinking, followed by five years in Chicago (Go Cubs!). I’d wanted to live in San Diego my whole life, and in 2018, after one too many Chicago winters, I finally convinced Joe, my husband and best friend for more than two decades.
When I’m not working, you can find me singing, tending my garden, shaking up a craft cocktail, or watching a Cubs game (sometimes all at the same time,) usually with Wrigley standing in front of me, toy in mouth, making very clear that whatever I’m doing is less important than her.
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Wrigley, taking a well-deserved break after all that toy mockery.
