February 19, 2019

Meet Jennifer Connolly of Sidekick Services in Greater Boston

Local Stories

Today we’d like to introduce you to Jennifer Connolly.

Jennifer, can you briefly walk us through your story – how you started and how you got to where you are today.
I was working in a Fortune 500 company right out of college and dove into Real Estate knowing a 9-5 desk job was not for me. I worked as an Agent for a few years and quickly saw a need for a Transaction Coordinator within my team and amongst other agents. The demand grew as technology shifted and colleagues of mine began reaching out in need of assistance. I found my niche! I was using my industry knowledge as an Agent and neurotic administrative skills to help other agents grow their business. Eventually, I began supporting agents outside of my Keller Williams Newton market center. It was time to add an LLC stamp to this baby! Now, I support agents all over the Greater Boston Area from top producers in the nation’s largest firms to local small shop brokerages. I have a supportive TC team and now provide consulting and additional Real Estate support to my agent clients.

Has it been a smooth road?

Oh my NO! I quit my full time job to dive deeper into the Real Estate world. As much as my husband supported me, he wasn’t overly thrilled with that decision. Probably because I didn’t give him a heads up. Oops! At the time, we had an infant and another on the way! So, figuring out how to prove myself was hard to say the least.

I had always worked hard, carrying 2 jobs through college until I was married and having my first child. I started thinking, how can I have the best of both worlds? How can I work hard enough to earn all the things I want in life but also have the freedom to relish in them? I want to enjoy life, I want to see my husband not only in passing, I wanted to stay home with my kids while they were babies, I want to travel. Why do you have to work “hard” to be successful? Can’t you just work smarter? I had to be in front of the curve, figuring out what people needed before they needed it. I still have to! This industry is ever evolving, I have to stay current and knowledgeable. Time management is my ever returning demon. I’ve spent a lot of time with my face in my phone instead of on my family and my excuse was, ” I’m growing a business.” I had to learn how to work smarter not harder. It was difficult to ween myself off and learn better time management as success came.

My husband turned his frown upside down once he realized I had not lost my mind but I was actually onto something. He’s my biggest supporter, soundboard, IT tech, CFO, manager, the list goes on. I’d be lost without him!

So, as you know, we’re impressed with Sidekick Services – tell our readers more, for example what you’re most proud of as a company and what sets you apart from others.
Sidekick Services is a Transaction Coordinating/Consulting business for Agents in the Real Estate industry. I specialize in providing transactional support to Agents for their listings and sales. As a TC I manage the timeline of a deal, keep deadlines on track, handle electronic documentation and manage the day to day communication between attorneys, lenders, agents, etc from contract to close. As a consultant, I meet with my agents to learn about their business goals and growth opportunities. I share best practices and my networking rolodex based on their needs. The goal is to learn what is hindering their growth whether it’s a large or small speed bump and help them achieve past that. It’s often project based, revamping a system, growing their team or creating a new infrastructure.

I’m most proud of my success within the company. Some days I’m stunned that this is my reality. In the early days I dreamt of a way to stay home with my kids and make enough money to justify it. Every year since, my jaw drops in awe. So, the next year I set goals that seem even more outrageous but lucky enough I’m reaching them!

I think what sets me apart is having a keen eye for what my agents need and being personally available to them. We meet for coffee, we speak candidly, we’re local. It’s just a good vibe.

Let’s touch on your thoughts about our city – what do you like the most and least?
The innovation! I find myself surrounded by so many interesting, successful, innovative people who are stepping outside of a traditional role and finding ways to make their life work for them. They are not sacrificing things like home ownership, families, traveling, social lives, healthcare, etc… but they are finding creative ways to succeed.
I once heard that most people earn the median salary range of the top 5 people they spend the most time with. Think about it, who are your top 5? Meaning, you are who you hang out with. (OMG, my mom was right!)
In a city like Boston, there is no shortage of inspiring people.

Dislikes, traffic PERIOD.

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