Ask-an-Advisor: When and How Do You Go from a Solo Operation to Hiring a Support Staff?

August 31, 2026

This is 2026’s fifth edition of TMR’s Ask an Advisor series, a regular column where a team of travel advisors tackles questions from others in the industry. All questions from this series have been submitted by readers and vetted by the TMR editorial team.

Dear Ask-an-Advisor,

I’m incredibly grateful to have more clients than hours in the day, but I am rapidly hitting a wall trying to handle absolutely everything myself. For advisors who made the transition from a solo operation to hiring your first support staff, how did you know it was finally time, and what was the very first task you handed off?

Sincerely,
One Overwhelmed Advisor

Jennifer Schwartz, Owner, Zig Zag with Jenn

With the support of my host agency, I’m still a solo operation! But I’m definitely teetering on the edge of hiring an assistant. I know I’ve reached the point where I need to start delegating the concierge-style, administrative, data entry, and auditing tasks that don’t require me personally.

The one major thing I have outsourced is social media marketing. As my business grew, I knew I wanted a polished, professional presence, but I also knew that spending hours creating and editing content wasn’t the best use of my time or my skill set. I’ve always loved photography, but pulling everything together into cohesive content was eating up my evenings and weekends. And, quite frankly, I have zero marketing background.

One principle I’ve always tried to stick to is knowing when to call in a professional. As I scrolled through social media (and I know we all do) I could immediately tell the difference between content created by someone with a trained marketing eye and content that simply looked nice. I wanted someone who understood not just aesthetics, but how to turn content into engagement, trust, and ultimately, revenue. I had already learned this lesson early on when I launched my agency. I outsourced my branding and website because I recognized that great design is its own expertise. I had the vision for my business, but I wanted someone with the creative skill to translate it into a brand that felt cohesive, intentional, and authentically me. That investment has shaped my brand voice and presence from the very beginning.

For social media, I set an annual marketing budget, interviewed several smaller agencies whose aesthetic aligned with my brand, and it became pretty obvious who was the right fit. That decision has been invaluable. It has given me back countless hours while ensuring my business shows up consistently and professionally.

Looking ahead, I know my next hire will be an assistant. As much as I enjoy wearing all the hats, I’ve realized that continuing to do everything myself isn’t how my business will scale. At this point, I know I need to spend more of my time doing the things that only I can do and let someone else take ownership of the rest.

As the founder of zigzag Travel, Jenn Schwartz brings a unique and highly professional perspective to the luxury travel market. After more than a decade of experience in the legal field, she transitioned her sharp analytical skills and attention to detail into the hospitality industry, focusing exclusively on high-end, bespoke travel. Jenn specializes in crafting personalized, immersive itineraries tailored to each client’s unique preferences.

Savannah Sharp, Travel Advisor, Trip Guy Travel

Most advisors recognize that a CRM is powerful, yet it often ends up serving as a storage system rather than a relationship tool. It still surprises me how many agents either don’t use one or aren’t utilizing their CRM to its full potential.

While many established agents with large client bases offload CRM management to an administrator, those who haven’t reached that point must ensure every client—including leads—is added to a client card with full names, dates of birth, emails, and phone numbers at a minimum. Having this data ready allows you to focus entirely on the booking entry once a lead converts. You should then document the vendor, commission rate, travel dates, hotel brands, and loyalty rewards. Modern CRMs, like Vacation CRM, simplify this by using AI to automate data entry directly from booking confirmations.

While this may seem like a significant undertaking, distributing the effort between the quoting and booking stages provides a wealth of actionable knowledge. You can then use tools like ChatGPT or Gmail’s AI writer to leverage travel dates and payment deadlines to automate client check-ins. Managing this efficiently ensures you stay present for your clients while keeping all essential information in one accessible place.

Regarding client-facing communication, I like to use ChatGPT to create steady templates for my emails, though I always add a personal touch so clients never feel like just a number. If a client wanted a purely automated experience, they would use an AI bot to book; our value lies in that personal connection. Utilizing features like email scheduling allows you to draft these communications during slow periods, enabling you to “set it and forget it” without losing the high-touch feel.

Savannah Sharp has carved out a distinct niche in the industry, specializing in custom FIT travel throughout Europe and Asia. With nearly a decade of experience, she focuses on designing highly personalized itineraries, destination weddings, and experiential travel for clients across the United States. Her expertise spans luxury accommodations, immersive cultural experiences, and specialty trips such as equestrian and small-group journeys.

Lesley Sawhook, Owner, Exclusive Travel Partners

As a travel professional for 17 years and travel agency owner for 10 years who has not stopped booking travel (I book over 1 million in sales annually and have for the past 14 years) I have not hired anyone to help with day to day tasks.

I am fortunate that my husband who is also the co owner of my agency is able to help me with daily with tasks like entering bookings into the CRM as well as helping run the agency. We do have a leadership team who helps us tremendously on the agency front by supporting our agents and us.

I will say, I’m not sure all of this would be possible if we weren’t empty nesters, if the timing of everything would have been different I would have needed to hand off some tasks.

Lesley Sawhook leads a national team of travel professionals alongside her husband, Tim. With over 17 years of experience in the industry, she prides herself on delivering excellent customer service and utilizing social media to drive business growth. Lesley has personally maintained over a million dollars in annual sales for the past 15 years. She manages both her personal and agency social media accounts, achieving significant reach on TikTok (@LesleyETP), where she has over 250,000 followers.