Leonardo Santiago is the vice president of communications for Orlando City Soccer Club, one of Major League Soccer’s newest and most buzz-worthy teams. The Lions just completed their inaugural season and narrowly missed the playoffs, an incredible feat for an expansion team. Before that, Lenny was the senior director of public relations for Daytona International Speedway where he had worked for more than 10 years.
Tell us what your responsibilities are for Orlando City Soccer?
Lenny is responsible for — from a strategic standpoint —messaging, positioning and other general communications tasks. Orlando City Soccer Club encompasses the Major League Soccer team as well as the Orlando Pride, the new national women’s soccer team launching in April 2016, and Orlando City B, the club’s return to United Soccer League play later this year.
The club is not without star power with international soccer superstar Kaká and Alex Morgan, arguably the nation’s most popular women’s soccer player.
How did you get started in PR?
Lenny attended Rutgers University where he studied communications. It wasn’t his first choice as he was initially interested in engineering. But he discovered his appreciation for the art of communication including the interpersonal and mass disciplines, as well as journalism and writing. This led him to pursue a career in public relations.
He attained his bachelor’s degree in the late 90s when the stock market was abuzz and just before the Internet bubble popped. Many of his friends went into day trading. Lenny was intrigued but didn’t want to be a broker. Instead, he ventured into investor relations which is essentially financial communications.
His first job was in Manhattan working at a small investor relations boutique agency where he credits the development of his writing skills particularly in becoming more articulate, concise and clear. He also learned the importance of networking, building relationships and formulating a pitch — essential aspects to any job in PR.
From there, it was on to a small pharmaceuticals company where he was the lone communications staffer. He was there for a year handling investor relations when the company was acquired. Lenny wasn’t keen on moving from Maryland to Tennessee, so he looked elsewhere. That was when the opportunity presented itself to join International Speedway Corporation, the parent company of Daytona International Speedway and other motorsport facilities. This would serve as his “foot in the door” of the sports industry.
Lenny continued to perform investor relations until he began trying new roles within the company which included marketing, corporate communications and sports public relations. His ascent led him to heading up communications for Daytona International Speedway.
From Daytona, Lenny moved to Orlando to be in charge of communications for Orlando City Soccer Club, which was a natural transition considering his longtime love of the sport. He describes it as a convergence of his recreational and professional passions.
What advice do you have for someone interested in performing public relations in the sports industry specifically?
Relationships are key, first and foremost. Sometimes getting that foot in the door is the hardest part. If there is a specialized skill that can help you “crack the rotation,” if you will, use it in creating an opportunity for yourself to transition into the public relations department.
For Lenny, it was investor relations that got him to the dance of working for International Speedway Corporation. He knew corporate communications was something he wanted to do and made it happen. For instance, he asked for more responsibility and to be placed on various projects including the construction of a speedway in Seattle. For two years, Lenny was traveling back and forth across the country and serving as the spokesman for the project.
“You have to take advantage of the doors that tend to open for you once you’re inside the organization, once you’re inside the industry, and then from there movement is a little easier for you to advance into the role that you’re ultimately trying to attain.”
What are the hard and soft skills necessary for transitioning in public relations?
Being a strong relationship builder and networker, number one. That can mean knowing how to nurture relationships and keep folks up to speed on their professional lives. Lenny recounts how he’s been able to help former interns and colleagues secure jobs simply because they’ve stayed in contact.
Of course, being a great writer is paramount. Whether it’s a press release, pitch or everyday email, the value of writing concisely and clearly is of the utmost importance.
“Nothing turns off the reader more than a typo or poor grammar or just the inability to express oneself clearly, concisely and in few sentences.”
Flexibility is also important. In sports and in general, things can change very quickly. You must be able to identify and change priorities when the situation dictates.
Finally, collaboration. You’re not an island; it’s a team game, forgive the pun.
What does a day in the life look for you in sports PR?
Lenny likes to start his day bright and early.
“You have a plan and five things you want to tackle on any given day, and if you get to two of them, that’s pretty good. If you get to three, you’re a rockstar because so many things pop up. It’s such a dynamic industry.”
These situations are beyond your control and force you to react one way or the other.
Having an early start also affords time to get a reading for the day.
“Just be aware of what’s going on in the news. Be aware of what’s happening in the world because that’s where you’ll likely learn what’s going to affect your day.”
Lenny likes to connect with his team at the get-go. By knowing what’s on everyone’s agenda, he can plan his and his team’s activities accordingly.
You don’t have only your local market to deal with, but also a national and international one. Describe the process of performing PR on a global scale.
For Orlando City Soccer Club, international PR is a significant area of focus. While the local market is very important, there’s also tremendous potential with national and international superstars on the team like the aforementioned Kaká. Those markets that are prime for growing the team’s profile include the United Kingdom, Portugal, Spain, Italy and Latin America. Lenny goes on to say that Orlando City is likely the most popular MLS franchise in all of Brazil.
There is even a person on Lenny’s staff dedicated to international outreach. This individual has great connections with global contacts and is on the phone daily making pitches.
How can being bilingual help set yourself apart in the job market for someone seeking their first PR job?
Lenny is fluent in Spanish and this fact has helped him tremendously considering soccer is an international sport. Additionally, there is a large Hispanic fan base and population in Central Florida and so outreach to this segment is critical. Many players are also fluent and that is key to increasing support for the club. Conversely, for the communications staff to also be able to speak to the players is of great importance for messaging, etc.
You’ve touched on the necessary skills to have before jumping into PR, but what are some common mistakes you’ve seen people make when applying for a communications job?
Before answering this question, Lenny wants to add another key skill for any prospective PR professional: the ability to tell a story. Being able to find the creative story angles and unique items fans will be interested in learning about –such as a player or the inner workings of the team, in the case of Orlando City Soccer Club — is an important attribute to have.
Sometimes this can be developed and for some it’s an innate trait. By the nature of the job, former journalists already have this ability. This gives them a leg up as storytelling will always be a valuable resource.
As for the pitfalls to avoid, not doing the necessary research is a big no-no. You must understand the company and industry, and have a sense for the state of each at that present time. Be prepared to speak intelligently in a job interview.
It’s also vital to have a grasp on current events. No matter the industry you set out to perform PR in, it’s all affected by the outside world. Don’t demonstrate a lack of awareness during an interview because a great public relations professional reads the news.
Don’t forget attention to detail. A typo on a resume demonstrates carelessness at a time when you’re representing yourself to the maximum potential. If you don’t take the effort to showcase the best of yourself, why would an employer take the risk you will for the organization?
Paying attention to the details does not go unnoticed by hiring managers and indicates a real passion for the position.
When applying for a job in the sports industry, It can be easy to get caught up in leading with your affinity for the team/sport. How do you balance that?
Lenny begins by saying everyone in the front office is a fan of the team whether that happened before or after their hire date.
“There’s something to be said about having that passion for the organization and ultimately its success and how much that drives you.”
Knowing that, there is a line and when it starts to obscure professional behavior — that is, you’re there to work as a professional and not be “the super fan” — it spells trouble.
What do you attribute to your personal success in your PR career?
Execution. Lenny likes to get things done from planning to completion.
At Orlando City Soccer Club, things move at a frantic pace to Lenny’s delight.
“I worked in motorsports and that’s a sport that lives at 200 miles per hour. But I now work in soccer and it’s faster-paced.”
This is due to having one to three matches per week and potentially preparing a player announcement or a sponsorship deal. Take, for instance, when the club announced Orlando City B; the Orlando Pride; and the signings of Alex Morgan, Sarah Hagan and Kaylyn Kyle in a span of 10 days. Those are three significant press conferences in three different locations with high profile principals.
Lenny credits his communications staff for handling large projects successfully when it might take weeks for comparable organizations to achieve the same feat.
What perks have you enjoyed working in the PR industry?
Working with outstanding people has been the biggest benefit. From mentors to colleagues it’s been the people that have made the experience the most special.
To name names, Lesa France Kennedy comes to mind. She’s the chief executive officer of International Speedway Corporation and a member of the board of directors for NASCAR. She’s also the granddaughter of NASCAR’s founder and has been recognized as the most powerful woman in sports by Forbes. Lenny worked with her for 10 years and learned a lot.
He also mentions Joie Chitwood III, president of Daytona International Speedway. He’s very supportive of public relations efforts which made the job all the more fun.
Other folks include Chris Brienza, formerly of the National Basketball Association and MLS, and is now working for an agency in New York; Phil Rawlins, founder and president of Orlando City Soccer Club; and Flávio Augusto da Silva, majority owner of Orlando City Soccer Club.
Lenny recalls a presentation Phil gave at Daytona International Speedway at a time he was interviewing for his current position, ironically enough, at which he said, “If you’re not standing at the edge, you’re taking too much space.” That is to say keep asking more of yourself and make the most of life. That has always stuck with Lenny.
And he credits Flávio for being one of the most recognized entrepreneurs in Brazil and realizing his dream to own a soccer team.
How do you suggest finding a mentor?
First, Lenny recommends identifying where you want to work and what you want to do within public relations. Then look for someone who is successful in that area. More than anything, don’t be afraid to reach out.
Students and fellow professionals contact Lenny with various requests — such as this podcast interview — and he does his best to accommodate them. He even explains how friendships have come out of informational interviews he’s conducted in the past.
Lenny explains how Brianne Burrowes connected with him via Twitter. They struck up a friendship and she’s one of those people who have stayed in contact. When a position became available at Phoenix International Raceway, he thought of her and she was eventually hired. That opportunity presented itself because she wasn’t afraid to strike up a conversation and cultivate a relationship.
Is there a book you recommend?
- The Associated Press Stylebook
- Good to Great: Why Some Companies Make the Leap…and Others Don’t by James C. Collins
- Woe is I: The Grammarphobe’s Guide to Better English in Plain English by Patricia T. O’Conner
- What to Do When its Your Turn (and its Always Your Turn) by Seth Godin
“If you enjoy seeing your creative thoughts, your story, your messages… influence opinion, influence behavior and become a bigger story in the media, public relations is the opportunity for you.”
It’s an industry that allows you to work in any business: technology, media, sports, etc.
“It allows you to get involved in such a way where you are impacting how that business is viewed, how it’s received by customers and ultimately how it succeeds. PR is a very very important, influential part of any business, and if you want to have an impact, PR is a great way to do it.”
Can you sum up your best advice to an aspiring public relations professional?
“Always practice your writing, be a creative storyteller, pay attention to detail and don’t be afraid to reach out to people who you feel could be a good mentor.”