Ask An Entrepreneur: Shannon Clemonds of Shannon Gail

For our inaugural Ask An Entrepreneur, I spoke to my good friend Shannon Gail Clemonds owner/operator of Shannon Gail. Shannon Gail is a Chicago-based event planning firm producing 90+ weddings and events per year locally and across the United States. The team is comprised of a unique blend of business and event professionals with backgrounds in finance, marketing, design, venue management, hospitality, and catering and prides itself on being the go-to expert in all areas of event production. In its 10 years of business, the company has continued to set the bar for event management standards and has built an impressive resume of corporate and social clientele. 

Shannon obtained a degree in Finance from the University of Illinois and, after a short stint at a downtown brokerage firm, decided to join the quickly-expanding Chicago event industry and become her own boss. Shannon has infused her life, financial background, and personal interests into the SG brand, now comprised of both wedding planning and corporate event production divisions, as well as an editorial-style lifestyle brand where weddings meet fashion, beauty, travel, cooking, and more. Her unique business model and approach to expansion has allowed the team to provide unrivaled client experiences and to evolve into the respected brand it is today.

With a continued passion for entrepreneurship, the inner workings of small businesses, and the desire to give back, Shannon is frequently seen speaking to students at local universities and inspiring future business moguls. She was the 2016 Marketing Chair for the Chicago Chapter of national nonprofit Wish Upon a Wedding. 

The following is my conversation with Shannon:

Len: I know you have been asked this many many times but here it goes again… You were a finance major and had a “regular” job before moving into event planning.  What precipitated that move? What were your thoughts at the time? Did you ever think that SG would grow to the size it is now?

Shannon: I always knew that I wanted to be an entrepreneur. I come from a family of business owners and went to school for Finance, so it was always a matter of what type of company I would start, not who I would go to work for. I originally thought it would be some sort of financial advisory, but when I noticed that couples were often spending $100,000+ for their weddings in Chicago without any formal financial advice, I quickly realized there was a niche for me in the market.

At the time SG was born, I was 19 years old with nothing but a cell phone bill and a $500/month shared apartment in Wrigleyville. I had very little to lose and luckily had the wherewithal to recognize my situation as the ideal environment for risk-taking. I went in full force, despite many critics, and made significantly less money my first year than my friends who went directly into the corporate world. I (often haphazardly) proceeded and truly never could have imagined the magnitude of the brand I would create.

What makes Shannon Gail different than other companies your competitive space?

SG is built from a business perspective, and our events are planned by first setting a logistical foundation of qualitative goals, whether it be a wedding or corporate event. This allows our clients to really have full trust in the execution of the event from all angles. The unique backgrounds of the associates that make up our company give us a vast repertoire of experience and knowledge, as shown by our portfolio of everything from fully transformed wedding spaces to sales-driven retail events launching across the country. The wedding industry is made up of many sole-proprietorships and small businesses, most of which are in the creative field (florists, musicians, etc.) and many often struggle without having the tools to successfully run a business. This is another area where we've really leveraged our makeup. We began with a healthy business model and hired on the creative side.

When you started, it was just you as the sole proprietor. How did you decide it was time to hire your first contractor? Was that an intimidating step? What did you look for in that first hire?

I operated solely for a couple years before I took the step of adding a contractor to my team. For me, learning the processes of adding a team member (such as payroll, legal obligations, etc.) were a bit intimidating, but the addition itself was a natural progression. My personal methodology as an entrepreneur is to very closely attempt to push growth at the same rate as our demand. I only expand my team to meet demand, but never before. If I'm turning clients away, it's time to add, but I never add to my financial obligations unless they will increase the bottom line of the company.

At the time, I was looking for something very different in a team member than I do now. The company was not generating the revenue anywhere near what it can do now, so I was looking for a really honest, organized individual who could take on part-time work to help fill demand with SG. Now, the company is able to support and promise full-time salaries, so we can be much more selective in our hiring. 

How do you go about hiring now? What makes a good event planner and how important is it that a prospect fits into the SG culture and believe in the SG mission?

Honestly, our hiring is probably the most rigorous thing that we do at this point. We get hundreds of resumes each year, but I prefer that a potential contractor is introduced by some kind of personal connection first. To me, this means they are already familiar with the quality and reputation of SG either by being previously in the industry or knowing someone who is. Often times they may be introduced by a fellow vendor or even a current member of our team.

Exactly what I am looking for in terms of a background very much depends on the position I am hiring for. Typically, our planners begin as assistants and put in a couple of years of assisting work before they enter our training program with the goal of becoming a lead planner. I do not look for a specific degree or background as much as I look for the absolute utmost in professionalism, which to me is the foundation of the SG culture. From the very first email to the greeting an individual gives me on the phone, I look for someone who is perfectly polished and mindful that they are interviewing for a career in hospitality. The rest, we can teach in training.

What would you say the SG Mission is?

"Shannon Gail” is synonymous with hospitality, detail, efficiency, and the absolute highest level of service and client experience. We strive to be the leader in our industry, providing unrivaled expertise in all areas of our field and a perfectly seamless and enjoyable process for our clients and vendors. Our relationships are the highest priority. From vendors and industry professionals to clients and guests, every person we come across is met with professionalism, the offer of assistance, and a smile. We strive to make the lives and jobs of all professionals and clients we work with easier by remaining one step ahead throughout the entire planning process and always looking for ways to increase efficiency and decrease their workloads. A perfectly happy client and vendor team is a successful event.  

Do you have a leadership/management philosophy? What is it?

I almost feel like members of my team could answer this question more pointedly than I will, however, I would say that I am someone who puts in the time to hire individuals who I am fully confident in, rather than focusing my time on micro-managing individuals who I do not fully trust to represent my brand. I focus on offering great training and an environment of constant information sharing and allowing my team members to collaborate and thrive. Once the training process is over, our team members assume great responsibility and I truly feel this is what has allowed them to become such strong leaders on their own. Internally, I also manage the company without debt, and this is something I was adamant about. We have very little revolving obligation when it comes to monthly expenses and absolutely no debt on the books.

Moving to strategy, when you started, you focused exclusively on weddings.  Now, you and your team manage many different types of events—from restaurant openings to corporate functions for clients as large as Crate&Barrel. Was it a conscious decision to move into that space or did it just happen when a client came to you with the opportunity?

Our initial introduction into corporate functions was extremely natural and due to our marketing and network on the wedding side. We produced the day of execution of a restaurant and private event venue opening for a colleague. Soon after, we acquired our first large corporate account through social media and began producing wedding registry retail events at locations across the country before becoming deeper involved with multiple departments within the brand itself. Now, the corporate expansion is certainly intentional as we continue to find and develop our niche. As we've grown, our market share has increased, meaning our direct competition has also changed. Because of this, we've recently had to reevaluate our strengths and determine our new differentiator within the last year or so, and it's been paramount to our next stages.

At one point, you expanded to New York. What were difficulties you experienced with that expansion? What advice would you have for other entrepreneurs looking to make similar decisions?

New York was my first, but certainly not last growing pain. I was incredibly young, as was our brand (within the first 3 years or so). I loved to travel and my personal life influenced me to get out of Chicago for a bit. I hired a contractor in New York and even produced an event our first summer in the market. Ultimately, Chicago was growing so rapidly that I had to return back to fuel its' needs and I realized that I absolutely had to have my boots on the ground at such a critical point in my company's development. I learned to remove my personal emotions and agenda from my goals with Shannon Gail, and my most valuable advice as an entrepreneur, which is only to grow organically when you can no longer meet demand. The market will tell you when and if you're ready to expand successfully. 

How important for you to keep up with trends in the event management space? Not only design trends but possible disruptive technologies or trends?

This is incredibly important in our line of work, particularly due to the demographics of our clientele. Not only do we need to keep on top of current fashion and design trends, but we also need to ensure that our various operating interfaces are current, easy, and offering the latest technology in communication, payment processing, etc. The majority of our clientele is currently between the ages of 25-32 so the ease of our processes is a huge part of our evolving foundation. 

Is there anything else you would like to say about starting and growing a small business?

I see our company's growth through the years as a series of incremental decisions; some unsuccessful, but the sum of which have proven to be advantageous to our overall success. I've really worked to keep the focus and commitment of my brand centered around the very same principles on which I started, and been careful to grow organically only when I could no longer meet our increasing demand. I've continued to build the SG team with individuals of varying backgrounds and incredible talents, and worked to maintain the personality and trend of a brand like Shannon Gail, while also keeping myself focused on the internal processes and development behind a healthy organization.  I think the careful blend of the two has propelled us to where we are today.

Thank you for speaking with me today, Shannon. I look forward to watching Shannon Gail continue to grow and evolve!

Find out more about Shannon and Shannon Gail at!

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