When to Hire a Virtual Assistant for Your Travel Business with Chelsey Benkner
Feeling like you've hit the ceiling of what you can handle alone? In this episode, Ali Raymer sits down with Chelsey Benkner, owner of Ready Jet Go Travels and founder of Outwork Collective, a VA company built specifically for travel advisors, to talk about when and how to start delegating.Ali shares how she found Chelsey: her assistant of three years quit right before her busiest season, and a podcast episode led her straight to Outwork Collective. From there, they break down the real milestones for hiring a VA, what to delegate first, how VAs are trained and matched for the travel industry, the ROI math behind it, and the fear of losing control that holds so many advisors back. They also cover how AI and a VA work together, and why "good enough" beats waiting for perfect.If you're drowning in your own business but scared to hand anything off, this episode is your blueprint.Outwork Collective: https://outworkcollective.com/Ready Jet Go Travels: https://www.readyjetgotravels.com/0:00 Who this episode is for0:43 How Ali met Chelsey1:45 Chelsey's start: building Outwork Collective by accident4:19 Why other advisors needed this too5:44 The timing that forced Ali to finally get help6:59 Ali's V1, V2, V3 business evolution7:55 Is there a sales threshold for hiring a VA?9:46 The SOP wake-up call11:56 What ROI actually looks like with a VA14:39 Ali's 5 pm moment15:49 What to delegate first: digital itinerary building17:56 Inside Outwork Collective's travel-specific VA training19:23 How VAs are matched to advisors23:35 The emotional side: letting go of control24:26 Why perfect isn't the goal (the 80% rule)28:48 Tactical tip: audit your week29:45 Low-risk tasks to hand off first31:40 Combining a VA with email templates33:51 AI vs. a VA: how they actually work together38:28 Final advice: what to do this weekFAQHow do I know when it's time to hire a VA?There's no universal number. A million in sales is sometimes treated as a benchmark, but that ignores life seasons and available time. A better starting point is around half a million, even at just a few hours a week.What should I delegate to a VA first?Digital itinerary building. It's low-risk since clients don't see it until you hit publish, and it gives a new VA a clear window into your clients, destinations, and preferred hotels.How is the ROI on a VA calculated?Think investment, not expense. If a VA costs around $400/month and one extra sale covers that, they've paid for themselves, and every sale after is pure gain.How are VAs trained for the travel industry?Outwork Collective runs a travel-specific "boot camp" covering consortia, host agencies, suppliers, and commission structure, plus how to spot issues proactively, like a missing airport transfer.How are VAs matched to advisors?Based on personality and working style after a consultation call. Some advisors are direct and task-focused, others prefer a warmer approach, and matching happens before CRM training begins.What's the biggest emotional hurdle to hiring a VA?Letting go of control. The key shift: a task delivered at 80% still takes real work off your plate. Giving feedback, instead of quietly fixing it yourself, gets a VA to 100% over time.Do I still need a VA if I use AI tools?Yes. AI isn't autonomous and can drift over time. The best approach is using AI to build a foundation, then having a VA manage and refine it before it reaches the client.What can I do this week if I'm considering a VA?Start recording yourself doing tasks. Narrate what you're doing on screen. It costs almost no extra time and builds a training library ready for when you hire.
