Valerie Weingrad – CSO Chief Sailing Officer

How one woman made the switch from corporate America superstar exec to CSO Chief Sailing Officer of her own company

By Cynthia Good

When you’re in the Greek islands and Valerie Weingrad is your captain, the other skippers set down their Mythos beer and stand up to watch as you pull up to the dock.

She’s used to turning heads-on the Aegean Sea and in corporate America, where she built a reputation for turning “kiss-of-death” accounts into gold.

Working for telecom giants Sprint and Marconi, Weingrad brought in as much as $40 million a year, handling two territories in the Bellsouth and Bell Atlantic states, while most of her colleagues took on one. With a salary in the six figures plus commissions, she learned early that, “Sales is building a relationship and building rapport,” says Weingrad.

In fact, she hatched the idea to create a business of her own during a company vacation doled out for hitting sales goals. As a national account manager for Sprint, Weingrad won the esteemed Presidents Award and a trip to the Virgin Islands. “I swam to this little beach and took off my mask,” says Weingrad. She saw a sailboat gliding through the clear blue water. That’s when she realized, “This is where I want to be.” Then and there, she devised a 5-year plan to leave the corporate world and create the life she wanted. “I didn’t want to be that person who says when they’re old, ‘I wish I had done that.'”

Her beloved grandmother was such a person. As a girl, Valerie and Rose Weingrad would pour over maps together and determine places they wanted to go. “She always wanted to travel to the Mediterranean,” remembers Weingrad. “But she got sick and never got her wish.”

Weingrad was born in Alabama to parents who worked in sales and encouraged her independence. “My dad always said, ‘No matter what you do, your financial independence is most important,” remembers Weingrad. An avid boater, he nurtured her love of the water, though he wasn’t thrilled when she announced her decision to quit her 20-year career to sail fulltime. “He said, ‘But you’re great at your job. You’ve accomplished all this.'”

But Weingrad sailed forward anyway. On her return from the Virgin Islands, she enrolled in additional sailing courses and eventually got her captains license. The final impetus came when the telecom industry took a hit after Sept. 11th, and Weingrad was laid off. The head of HR at Marconi helped her transport the box filled with her many plaques and sales awards because, “it was too heavy to carry,” says Weingrad.

She financed Custom Sailing, Ltd. with existing business credit. “A few times I ran up zero-interest credit cards for cash that I needed. But I really didn’t put capital into it.”

That was seven years ago. Two-thirds of new employer establishments survive at least two years, according to the Small Business Administration. But only 31 percent last seven or more.

She sails five to seven months out of the year-summers in Greece, winters and springs through the Caribbean. Advisors have encouraged her to just run the business, focus on sales and growth and keep an office. “But thats not where I want to be. I love sailing and being out here. I dont want to lose the personal touch,” she says as we pull into the sweet island of Poros-the one you see on postcards. Weingrad is at the helm. “You can’t beat the view from the office.”

So she stays on the yacht, handling charters personally and booking trips while at sea via cell and computer. Still, business has grown as much as 500 percent a year; though it dropped 25 percent in ’08 and even more this year due to the recession. But even now, “Its still paying the bills.”

Skills she used in the corporate world, where she sold “the same box as everyone else,” serve her well today. But, says Weingrad, “If you can establish commonality and trust, then you’re selling them a solution.” Today, she’s selling a once-in-a-lifetime experience and sharing what she treasures most. “If there’s something I believe in, it’s easy to sell. I’m just talking about something I believe in and love.”

As we approach Hydra, one of her favorite islands, it’s clear this is what she loves. The harbormaster sees her coming and waves enthusiastically. Weingrad beams. He tells me, “She’s the best captain in the Saronic Gulf,” and one of the few women. She pulls on tattered gloves (the fingers cut out), grips the oversized steering wheel and begins backing into a narrow spot wedged between two ships in this crowded harbor. Wearing a sun-faded, red hat that reads OCEAN NAVIGATOR, she tells her first mate where to drop anchor. The old Greek men watching from the closest taverna stop their conversation and lean in for a better look.

The mustache-sporting captain on the next boat puts his hands on his hips and yells at Captain Weingrad, “Pull to the left. More, more, more! You need a little more.” Once he realizes she has the 49-foot Bavaria monohull under perfect control he says, as if surprised, “You have a very tough captain.”

Weingrad handles this much better than me. I want to jump out of my seat and tell him that she’s logged more than 40,000 nautical miles, has transported hundreds of passengers, knows every island and is the only non-Greek (and the only woman) ever asked to join the Greek Skippers Union. While this same scenario – first condescending, then paternalistic, then impressed –plays out at nearly every port, Weingrad remains unfazed. “Being a woman, I’d have 10 guys shouting at me,” she says with a grin. “‘Do this, do that.’ I’m like, ‘Thank you.’ And then I do it my way.”

The guys are eager to help. The pushy captain now jumps down to assist. But soon, it’s Weingrad who subtly tells him what to do. She throws him the line, telling him how much of it to pull and which cleat to wrap it around – and you can tell he’s tying his best knot.

Once at dock, Weingrad tells us about the island’s history. No motor vehicles are allowed on Hydra. Donkeys traverse the steep cobblestone steps carrying supplies and tourists. There are tons of stray cats. There’s a small miniature island just off the beach, and she tells us about the weddings that take place there, the cave and rocks where the kids can jump into the sea and the bakery in the alley just to the right of The Pirate Bar. She reveals the best local taverns for dinner – just up the winding footpath, one called Veranda which overlooks the harbor, and another called Sunset, to the right of the marina just up the hill. She knows all the sweet spots: the island butcher, the baker, the best fish market and Sue Parker, who owns and operates Sue’s Boutique where my husband purchases a beautiful, white shirt.

In the morning, we powerboat to Ermioni along the Peloponnese in still waters occasionally flanked by dolphins. Weingrad brings out a tray of fresh baked from town, flaky spanakopita, a crusty pastry filled with local cheese, and another covered with sesame seeds and chocolate inside.

For lunch, she and first mate, Dieter Mezger, prepare spaghetti and meat sauce, colorful salads of ripe local tomatoes, cucumber and dill along with feta cheese, homemade tzatziki, fresh bread and – ah, yes – a bottle of the local wine.

In addition to the food, Weingrad enjoys the people she gets to know well by spending a week or two with them in the close quarters of the yacht.

Many of her guests are repeat customers from the U.S. and Europe; from a group of Ohio schoolteachers, to a family of eight from Spain, to a group of meat eaters and vegans. She’s sailed with Ernest Hemingway’s nephew and the mayor of Marietta, Ga., where Weingrad keeps a house.

Her first customer, Robert Corbett, a top Hewlett Packard exec, has spent two weeks with her at sea – twice. “I enjoyed both experiences immensely,” he says, describing Weingrad as, “a really good person, very articulate, great values, capable as a business person but also a great sailor. She knows her away around the Greek Islands and is successful in a male dominated business.” He adds, “I always enjoy seeing Greek Harbor Masters being confused when they see that the yacht’s skipper is an American woman!”

Rough Seas

If rough seas make great captains, Weingrad is proof. Privately, she shares that it isn’t always easy. “Others think I’m on vacation all the time. I work harder now.” The job is physically demanding (think hoisting sails all day, sponging the deck, scraping off barnacles and cleaning toilets). “I enjoy the cooking and sailing. I don’t like the cleaning part.” And sometimes it’s dangerous. At one point, a man on another boat bullies her when she unplugs his cord from her electrical outlet. She is visibly shaken. Weingrad, now age 50, has been cursed at by fishermen, and has encountered bad weather and precariously crowded harbors. “Sometimes my heart is pounding when the spot is really tight. And then once we’re safely moored, I can breathe again and everything is OK. That’s rewarding.” She takes seriously her responsibility for the half-million-dollar yacht and her passengers. “Most Americans have one vacation a year. It’s a big obligation to make sure they have a great time.”

There are the financial pressures too. As we pull back into the marina in Athens, Weingrad points out her competitor, The Moorings, which “keeps about 100 boats here, but only has about a dozen in use.” Her season is shorter than in years past. “If nothing comes through, we’ll explore new places to take our customers,” she says. She and Mezger plan to head south to visit the Turkish coast with its hundreds of bays from Bodrum through the Gokova gulf, down to Marmaris and beyond. “That’ll be great too.”

Her business model is fairly recession-proof, as most of her out-of-pocket costs are covered by clients up front. She has access to at least 10 yachts and crews at a time and hires them after she has contracts for charters. She learned fast, after having passengers cancel at the last minute, that she needed to require payment in advance. Restaurateurs and guests frequently treat her and her first mate to dinner. Plus, dining and living on the boat keeps expenses down. And for additional income, she brokers larger, more expensive yachts on the side on commission.

“When it’s not fun any more, I’ll do something else,” says Weingrad.

Still, she questions her decision to leave a big, mainstream career – the designer suits and first class travel. “Sometimes I think, ‘Am I crazy?’ These are my prime earning years,” says Weingrad. She admits to missing “nice linens and having something to put away for when I’m old and gray.” But she’s clear about her own definition of success. “It used to be about money and accumulating things. But now, it’s about lifestyle – the ability to go to the places I want – on my terms.”

Weingrad has learned firsthand that while there are no guarantees at sea, there aren’t any in the corporate world either. Jobs and careers come and go, but a calling does not. “Women today are taught to climb the ivory tower. Then what? You have nothing,” she says.

For many, success is measured in promotions, paychecks and P&Ls. For Weingrad, it lives in finding a seahorse on the anchor line and having the freedom to travel with the wind in search of ancient ruins, dolphins and a huge, magical setting moon.

Now it’s cocktail hour and a spectacular sun sets behind Dhokos, which the locals call Whale Island. It reflects a swath of neon red across the Saronic Sea. We are mesmerized.

This is the day’s reward for taking action in the face of challenges and fear. “When people come and enjoy it, they tell their friends and come back. That makes you feel good,” she muses. “A lot of customers have become friends. We get together for dinners and chat on the phone.”

She’s been tempted by job offers, but “relieved” when the pay wasn’t high enough to lure her away from all this. “I don’t think I could go back to an office environment and report to someone. You don’t know how many days you have left.”

As my family and I head out to explore the island and then to dinner, Weingrad and Megzer pack up their fins, masks and spear gun and head to the water. During a recent free dive, Weingrad caught her first octopus. Not afraid to learn new things and go after what she wants, she plans to grow her business and expand travel itineraries. “I’d like to add the South Pacific and Italy and spend more time in the Grenadines.”

Each day, she takes the memory of her grandmother Rose with her and the lesson she learned – to follow your heart. She pulls out a little box and proudly shows me Rose’s small, pear-shaped diamond earrings. “I carry them everywhere,” says Weingrad. So maybe Rose has gotten her wish and made it to the Mediterranean after all.

This year, with prices down, Weingrad plans to buy a boat of her own. She has her eye on a few monohulls between 45 and 60 feet. And she has the perfect name all picked out – “As You Wish.”