We’re excited to introduce you to the always interesting and insightful Jennifer Connolly. We hope you’ll enjoy our conversation with Jennifer below.
Alright, Jennifer thanks for taking the time to share your stories and insights with us today. So let’s jump to your mission – what’s the backstory behind how you developed the mission that drives your brand?
My mission is to work smarter, not harder. Growing up I saw my parents work hard to give us a great life. They had jobs that supported a nurturing, present balance at home raising a family. They taught me to work for what I wanted. From an early age if I wanted “more” than what they offered, I worked for it. I had the mindset that no-one could tell me no, if I bought it myself. I worked 2 jobs in high school and through college. Always believing that the only way to make more money was to work “more”. When I was becoming a mom I thought a lot about how to have a better work-life balance. I thought back to my parents always being present. I asked myself how I could provide the life I envisioned for my family while still contributing financially. My husbands work ethics were driven by his childhood as well . He was rooted in a stable government career that provided us with the stability and benefits we needed as a family. For me, this meant I could get creative in how I contributed to our family both financially and in my presence. I constantly thought about how to work smarter, not harder. To be honest, I didn’t want to work over 40/hrs a week just to make enough money to fund the lifestyle I wanted because then, I’d have no time left to relish in it. I wanted to enjoy life. A life that isn’t defined by what I do for work. But we all need money! I found that life with Sidekick. Ironically, my life is in fact defined by what I do for work. I understood my mission differently as it came to fruition. My view on that changed but the mission never did. Working smarter, not harder doesn’t mean I don’t work hard. I work dang hard! But for me, working smarter means making my time worth more. My goal is to work less hours and make more money. So I learned to be efficient and put a large value on my time.

Jennifer, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I began my career in Real Estate in my mid-20’s. After only a few years as an Agent, I noticed a growing need for Transaction Coordinating support among agents. As technology evolved, the demand for organized transaction support increased, and colleagues became interested in my service.
I discovered my niche by combining my industry knowledge as an agent with my meticulous administrative skills to help other agents streamline their processes and grow their businesses. This led me to expand my support beyond my market center, prompting me to establish my own LLC.
Sidekick Services is a Transaction Coordination business dedicated to supporting real estate agents and aspiring Transaction Coordinators. I specialize in managing transactional support for both listings and sales. As a Transaction Coordinator, I oversee the timeline of each deal, ensure deadlines are met, provide expert support in local and state compliance and facilitate day-to-day communication between attorneys, lenders, and agents from contract to closing.
As a consultant, I collaborate with agents to understand their business goals and identify growth opportunities. I offer best practices and leverage my extensive network to address their specific needs. Whether it’s revamping a system, creating growth plans, expanding their team, or establishing new infrastructure, my goal is to help agents overcome obstacles and achieve their objectives.
In addition to my TC support, I offer coaching and training for aspiring Transaction Coordinators. Through virtual one-on-one sessions, I guide individuals in building their TC business from the ground up. My training covers everything from the essentials of transaction management to advanced strategies for scaling their business, providing a comprehensive foundation for success.
I’m incredibly proud of the success Sidekick Services has achieved. Reflecting on the early days, I remember dreaming of finding a way to balance staying home with my kids while earning a meaningful income. Every year since has surpassed my expectations, and I continually set ambitious goals, grateful to see them come to fruition.
What sets me apart is my intuitive understanding of my agents’ needs and my personal approach. I prioritize a stable relationship, candid conversations, and maintain a steady presence. This personalized touch creates a positive and supportive experience for my clients.
Where do you think you get most of your clients from?
The best source of new clients for me has always been referrals. There’s no better testament to the quality of service I provide than having a satisfied agent recommend me to their colleagues. Referrals are powerful because they’re built on trust — someone is vouching for your work based on their personal experience. For me, that’s incredibly rewarding, as it means I’ve made a positive impact and have earned their confidence. It also fosters stronger relationships with new agents, since they come to me already feeling more connected and assured in the value I can bring to their business. My goal is always to create lasting partnerships, and referrals are the foundation of that.

Any stories or insights that might help us understand how you’ve built such a strong reputation?
My reputation within the market has been built on a deep knowledge of compliance and a thorough understanding of the transaction process — often better than the agents themselves. I make it a priority to stay ahead, getting things done efficiently and anticipating the needs of the agents I work with before they even think to ask. By being proactive and detail-oriented, I save them time and stress, allowing them to focus on what they do best: serving their clients. Staying educated on compliance is another cornerstone of my work. The real estate landscape is always changing, so it’s important for me to be well-versed in the latest regulations and best practices. This expertise has earned me the trust of agents and ensures that transactions are not only smooth but also compliant and risk-free.
Contact Info:
- Website: https://www.sidekickservicestc.com/
- Instagram: https://www.instagram.com/jennconnollyrealestate/
- Facebook: https://www.facebook.com/sidekickservicesllc
- Linkedin: https://www.linkedin.com/in/jenniferconnolly1/?original_referer=

Image Credits
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