This stay-at-home mom turned CEO says her career began serendipitously when her husband wanted to buy a livery business and she was ready to take on a new venture. Nearly 30 years later, Silvestro has learned she has a knack for navigating a predominantly male industry, juggling children’s and grandchildren’s schedules and making each client feel like a VIP.
How has Hoyt made a name for itself? Interestingly enough, a friend of mine and I were having lunch one afternoon. We were racking our brains to come up with a way to differentiate the Hoyt experience from other local competing livery companies. We decided a slogan was in order—something that would stick and that people would remember. At that table is where ‘Hoyt’s Here’ came to life.
What has been the biggest challenge you have faced in your career and how did you overcome it? I think the biggest challenge I’ve faced in my career was leveling the playing field between men and women in the business world. Since I was working in predominately male territory, I spent a great deal of time making male executives comfortable talking business and finances with me in addition to working together to finalize deals. It took a lot of preparation for questions that would inevitably be thrown my way and a great deal of confidence in my abilities. Finally, a shift was made from businessmen wanting to speak only to my husband, as they believed he was the brains behind the operation, to realizing that if they wanted something done, they needed to speak to me.
How have you balanced motherhood and career? Since my husband and I believe you should never put all of your eggs in one basket (hence our seven different businesses), work-life balance has always been a challenge and a goal. As owners, we have had to sacrifice many nights, weekends and even holidays, working and covering shifts. With that, however, I was also fortunate enough to make my own hours when it wasn’t a busy time at the office. It gave me the flexibility to attend sporting events, dance recitals and class trips with my children. I have always put them first. I now have two beautiful grandchildren, and to top it off, I am a recent foster mom to two 7-year-old twin boys. It’s like I get a second go-around with having children—soccer games, karate classes and homework. They keep me young.
Statistics show companies with women in leadership roles outperform those without. In your experience, why do you think that is? I truly believe that women bring something to the proverbial table that many men struggle with. We are great multi-taskers and much more organized. We also bring a level of diverse thinking that never once existed in the workplace. Oftentimes women are scrutinized for being too emotional and not entirely driven by the bottom line. It works to our advantage, however, that we put a high premium on building relationships. These connections are important to success and to sales. It sets us apart as leaders.
Hoyt Livery: 21 Cross St., New Canaan, CT, 203-966-5466,
