Meet Jill Strada | Founder & CEO, Stradagy Group LLC

We had the good fortune of connecting with Jill Strada and we’ve shared our conversation below.

Hi Jill, how has your work-life balance changed over time?
For me, balance is about finding harmony rather than strict division, allowing me to engage in both my professional and personal passions in a meaningful and fulfilling way. The music and media industry is a 24/7 business, so by embracing a “lifestyle career” perspective I’ve steered away from the conventional 9-to-5 routine. This flexibility has been invaluable, offering me the freedom to prioritize tasks effectively while also nurturing personal interests and relationships.

When I reflect on balance, it’s not just about how I divide my time. It’s more like finding a middle ground where my work and personal life support each other. It’s about fostering an environment where I can thrive professionally without compromising my most meaningful personal experiences, especially those with my son, husband, family, and friends. For example, last year my family and I spent a few weeks in Italy and Greece, where I had such a wonderful time creating lifelong memories, however I was still on a few zoom calls and conducted a couple strategy meetings while in a café or while sitting on the balcony of our room overlooking beautiful scenery! My “lifestyle career” approach has not only shaped my work/life balance but has also defined my personal perception of success.

Let’s talk shop? Tell us more about your career, what can you share with our community?
My career began in Orlando, FL when I started as an intern at 102 JAMZ. I literally fell in love with radio during that internship. For me, broadcast media combined my love of music, creativity, marketing, and community into one beautiful career opportunity. I was a hustler, working two jobs, in school full-time, and spending the rest of my time working at the radio station or at radio station events. I was promoted several times, embracing each new position with excitement and gratitude.

The turning point came when I received a call about a life-changing opportunity at HOT 97 in New York – an Assistant Program Director & Music Director position. Despite not having roots in New York, I felt a profound connection to that city since childhood and decided to take a leap of faith. It became the place where I honed my talents, gained valuable wisdom, strengthened my skillset, and expanded my industry connections.

One lesson I learned is that whether I was completely fearless, or scared to death but took a leap anyway, believing in myself and taking a risk always turned out to be the best thing I ever did! Over the last 25 years, I’ve expanded, redesigned, and reinvented heritage brands, groomed both creative and executive talent, and developed and grew new radio station stations from the ground up.

My unique strength lies in striking a balance between art and science in the creative business space – a trait that is uncommon in this field. Often, individuals lean heavily towards creativity while sidelining analytics, strategy, and the business aspect, or vice versa. Yet, I thrive in both areas. My passion for creating and innovating matches my love for diving into analytics, strategy, and the business side of things. It’s this fusion that sets me apart and fuels my success in the creative landscape.

Drawing upon my entrepreneurial spirit, a solid foundation in brand marketing, a deep passion for the music industry, and a genuine love for grooming and leading talent, I founded my latest venture, Stradagy Group, an endeavor that truly reflects my journey, values, and reputation. One thing I value most is integrity, specifically the principle of being true to your word. It’s the foundation where trust, respect, and credibility are established and nurtured, forming lasting and valuable connections in all aspects of life. It’s the basis that all relationships, collaborations, and endeavors are built. Without it, connections falter, opportunities fade, and credibility disappears.

The fusion of creativity, strategy, and unwavering integrity will continue to guide my journey, setting me apart and fueling my success in the ever-evolving landscape of the creative industry. I take pride in making a positive impact on the individuals and brands I serve, and I am enthusiastic about the opportunities the future holds!

If you had a friend visiting you, what are some of the local spots you’d want to take them around to?
I would give them a mix of a touristy vibe and local, laid-back energy. So, we would hit up South Beach and stroll Ocean Drive one day, then hang out at Hollywood Beach and bike ride the boardwalk on another day. We would grab a Cafecito in Little Havana and maybe play dominoes with the locals while we’re there. I would take them to Wynwood to check out the walls and street art, we’d go to the Frost Museum, and maybe catch a Heat or Dolphin game. A spa day at the beginning and the end of the trip is a must, so we would go to the spa at the Mandarin Oriental for massages and facials. We’d hit up Las Olas to check out the shops and we would eat at as many amazing restaurants that Broward and Dade County have to offer!

Who else deserves some credit and recognition?
In my journey, there are several individuals and influences that have contributed immensely. I want to dedicate a shoutout to Rich Reis, Alex Cameron, and Kim Guthrie, all veteran broadcast media executives whose leadership has been invaluable to me. Their guidance and insights have shaped my professional growth both while we worked together, and continuously throughout my career.

And I must also extend my utmost gratitude to my family and friends whose unwavering support, love, and encouragement have been the bedrock of my personal and professional endeavors. Their belief in me has fueled my confidence and resilience.

Website: https://www.stradagygroup.com

Instagram: https://www.instagram.com/jillstrada/

Linkedin: www.linkedin.com/in/jillstrada

Facebook: https://www.facebook.com/jillstrada