How Virtual Assistants Help One Advisor Manage His Business

Running a start-up, one-person travel agency can be difficult, especially one that’s built on the concept of regularly-departing, owner-escorted cruises. It’s nearly impossible to juggle group organization, travel planning, marketing, and accounting when you’re almost always on the road.

That’s what Seth Wayne, of Sail with Seth, discovered when he launched his business.

The former brand ambassador for Holland America Line started his agency in late summer 2022 after being laid off after the pandemic. The idea for the agency came from a post-pandemic experiment at Holland America, which saw Wayne embark on two escorted Holland America cruises to reassure passengers that it was safe to venture back out to sea.

Both were so successful that when Wayne found himself adrift after his layoff, he realized he could do more with the concept.

Quickly overwhelmed by business

Since February 2023, when his first escorted group cruise set sail, Wayne has hosted 13 cruises, across eight cruise lines, four continents, and three rivers. Looking forward, he has two more sailings booked this year, seven next year, and he already has five on the books through fall of 2026.

“I was definitely burning both ends of the candle,” Wayne told TMR.

It was a lot to keep track of and it wasn’t long before he was having trouble keeping it all together.

“I knew that I could not keep up with the back end of things and also deal with the customers when I was traveling,” he said. “I’m always out on the road, but also running the business and entertaining guests at the same time.”

While at CLIA’s Cruise360 conference in 2023 things came to a head.

“I felt like both sides of my world were crashing in. I was thinking, I really need help. I don’t know what else to do.”

His brother, a small business owner himself, suggested Wayne look into bringing on a virtual assistant from the Philippines.

Looking outside North America for help seemed like the perfect solution.

“There was no way I could afford [someone in the U.S.] and do the whole U.S. taxes as a small business owner with limited resources,” he explained.

His brother suggested OnlineJobs.ph. There is a fee to use it, but you can filter through candidates to find exactly who you’re looking for.

Narrowing the search for a virtual assistant

Among the traits he looked for when he started his search were: travel experience, organization skills, proficient English writing skills (most Filipinos speak excellent English), and the ability to work U.S. hours. He added in other traits once he narrowed down his search and progressed to interviews, of which he did five.

“Someone with a good personality… someone who knows what’s going on around the world, and that also can work with me on a day-by-day basis. Just personality traits…” he said.

There was also a writing test, because this person would be communicating with his clients by email.

He also paid close attention to the requested fee per hour.

“You can hire someone for 55 cents an hour or you can hire someone for $500 an hour. I didn’t want to go bottom of the barrel. I wanted someone with a little bit more experience,” he said, adding that someone who is asking for 55 cents an hour should be a red flag.

In June 2023, he hired Mariah.

“She has been a godsend to me and truly is a friend,” he said.

Within a couple of months, Mariah was handling all his spreadsheets, organizing trips, booking travel, and doing bookkeeping. She even learned how to use the cruise lines’ booking engines so she could do more than air bookings.

Less than a year later, he hired a second VA, Joie, to do his social media.

Though he considers himself tech-savvy, he wanted someone younger who already knew how to do “all the fancy stuff.”

Today, Joie handles his Facebook, Instagram, and YouTube.

Room to breathe and grow as an owner

“I’ve had extreme success” Wayne told TMR, adding that having two assistants he can trust makes a huge difference for him as an agency owner.

“It’s a huge relief knowing that someone is there to get back to my guests and to make postings on social media. It’s given me more time to be more creative in honing my relationships with cruise lines and being able to grow the brand and explore more email marketing,” he said.

Tips for making the most of your own VA relationship

To get the most out of your virtual assistant relationships, Wayne was crystal clear on a few things.

1. Narrow down what you want

Wayne admits that he threw Mariah into the deep end when he first hired her. Desperate for help with so many aspects of his business, he gave it all to her to do right away.

“I basically threw her to the wolves and said, you’re everybody and everything,” he explained.

If he had to do it again, he said he’d start with just one or two tasks – which is what he recommends others starting out with VA’s do.

Begin, he said, by narrowing down the exact help you need. Struggling to keep up with emails? Concentrate on emails first. Then you can layer in more tasks as time goes on.

He also recommends that advisors look for VAs with some type of travel experience. In the Philippines, he said, it’s easy because so many Filipinos have worked for travel-related call centers, so they’re already familiar with geography.

Another benefit to hiring a VA in the Philippines, he said, is there’s an entire community of virtual assistants who work U.S. hours.

“Most assistants [in the Philippines] work overnights. There’s a whole community over there,” he said, adding that Mariah has made it clear she wants to work overnight.

2. Treat them with respect

“As with anyone, if you treat them with respect, they will work harder for you,” Wayne said.

To Wayne, both Mariah and Joie aren’t just VA’s who live on the other side of the world. They’re critical members of his team.

“I don’t want them to just be little robotic machines. I want them to feel that they’re a part of my team… to feel that they are not just a data entry person,” he told TMR.

During a trip to the Philippines to meet up with both Mariah and Joie, Wayne bought Mariah a new MacBook when he noticed her laptop was on its last leg.

“Even for American workers, we’re not appreciated enough… When you create a decent work environment, I feel that you get respected times 10,” he added.

Part of treating VA’s with respect is paying them a decent wage, and even benefits. He gives both Mariah and Joie paid vacation time.

Someone who is working overnights and doing multiple tasks for you deserves more than a dollar an hour, he told TMR.

“Respect their pay,” he said.

3. Build trust

Hand in hand with respect, Wayne said that building trust is critical. Depending on what you’re having your VA do, they might be handling customer credit cards or have access to your social media log-ins.

He said that trust building starts with the interview and initial calls.

One thing Wayne did as part of building trust with Mariah – and he doesn’t necessarily suggest this is the right course of action – was to skip using a tool that OnlineJobs.ph recommends. It’s an app that both the employer and VA install on their computer. It lights up green when the VA is working, allowing the employer to keep track of them.

“I told her [Mariah] right away, I’m not putting anything on your computer. I know if you’re not working. If you don’t answer emails and the spreadsheets are blank, I know you’re not working,” he said.

He did the same thing with Joie, though he admits it was a “gamble.”

“If they’re going to be a part of my company, we have to build that trust. I’m not going to build trust in someone who has a light on their computer… It has worked out well for me. They’re treated more like a person and a friend rather than someone who is just tethered to their computer.”

When asked how long he waited before giving Mariah access to his client’s credit card info and personal details, he said it was “about a couple of months of getting to know her really well.”

4. Meet them in person

Like many employers with virtual employees (and he does see them as employees), he’s arranged off-site meetings to build morale and brainstorm business ideas.

“I went to the Philippines and we did a three-day workshop. I flew them in from their province because they don’t live in Manila. We stayed at a hotel for three days and basically made a map of how things could be done easier, how we could all trim our workloads a bit…” he said.

He even flew Mariah to meet his clients in Tokyo when her Visa was denied and she was unable to join one of his group sailings.

“I flew her to Tokyo to meet my guests… I wanted her to really feel that she was a part of the Sail with Seth family,” he said.

Many of the guests even brought her gifts because they feel they know her from emailing with her throughout the booking process.