How to Hire a VA Who Already Knows the Travel Industry
One of the most common things that comes up in my one-on-one strategy calls is assistants. Specifically: I need help, but I don't have time to train anyone, and I have no idea where to find someone who actually understands this industry.
That's exactly the problem Chelsey Benkner from Outwork Collective is solving. Chelsey joined me on 7 Figure Cruise Business to walk through how her company works. By the end of the conversation I was reconsidering my own staffing situation.
Listen to the full episode here
The Gap She's Filling
Most VA agencies can find you a competent person. What they can't do is hand you someone who already knows that one wrong letter in a passenger name is a real problem, or who understands how a CRM functions in a travel business, or who has any context for what your day-to-day actually looks like.
Chelsea started Outwork Collective after going through the process herself. She sourced her own VA, trained her over three years, and watched her business go from $150K to over a million in sales. Now she and her VA train other VAs in the travel industry before matching them with advisors.
How the Process Works
It starts with a consultation call. Chelsea wants to understand your business, your pain points, and your personality before making a match. They've turned people away when the fit wasn't right, and they actively refer out to other services when someone needs something different.
Once you decide to move forward, there's a six-month commitment and a $500 sign-on fee. That fee covers two weeks of dedicated training where your matched VA learns your specific CRM and SOPs before their first day. Chelsea recommends starting with five to ten hours per week and one task at a time, rather than dumping everything at once.
The minimum is five hours a week at $397/month. Full-time, 40 hours a week, runs $1,797/month. Advisors are typically matched and up and running within 2-3 weeks of the consultation call.
Why Cruise-Focused Advisors Have an Advantage
Chelsey made a point I hadn't considered: advisors who are niched down into cruises are actually easier to staff efficiently. A cruise-focused VA quickly becomes an expert in a specific set of cruise lines rather than needing to learn every type of travel product. A VA can handle all of the research, quote pull, itinerary comparison legwork using consumer-facing websites even without supplier portal access, freeing you up for the sales conversations only you can have.
Where to Start Delegating
My recommendation for where to start is your post-booking tasks. I did a whole episode on the first ten minutes after processing a deposit, and this is exactly the kind of work that's perfect for a VA: important, repetitive, and completely trainable.
Here's what I hand off immediately after every booking:
Check the confirmation and note if it's in a group
Report the sale to my host agency
Verify commission is entered correctly in the CRM
Confirm the task list was added
Verify payment was applied to the booking
Add the client to the right segment in the CRM
Claim any cruise line rewards or add to price tracking
None of those tasks require my expertise. All of them take up time I could be spending on the next sale.
Two Things That Determine Whether it Works
Chelsey was generous with advice here, and this part is worth saving.
First: SOPs. If you can't explain a task clearly enough for a stranger to follow it step by step, you're not ready to hand it off. Her recommendation (and mine) is to use a screen recorder like Loom or Komodo while you're doing the task and just narrate out loud. You're doing it anyway. Record it, name it, drop it in a folder. You'll have a video library faster than you expect, and if you ever need to onboard someone new, you're already set up.
Second: Communication. If something comes back not quite right, send it back with specific feedback instead of fixing it yourself. The one time it's faster to fix it yourself becomes a pattern that prevents your VA from ever learning your standard. Chelsey put it well: if you send back "this looks great" when it actually doesn't, the VA has no way to improve because they don't know there's a problem.
How to Connect with Outwork Collective
Chelsey offers consultation calls even for advisors who aren't ready to hire yet. If you're six months out and want to start getting your business ready, she's happy to talk through it.
You can find all of Chelsey's links and contact information in the episode show notes, or find Outwork Collective on Facebook and Instagram.
Free Discovery Call Script: travelbizboss.com/script
Chelsey's Freebies:
50+ Tasks to Delegate Now: http://outwork.myflodesk.com/50-things-7fcb
SOP Generator: https://outworkcollective.com/sop-generator/
Episode Timestamps
1:12 How Chelsey found her own VA and started Outwork Collective
3:55 Thinking about hiring as an investment, not an expense
5:28 ROI math: what one extra commission per week covers
6:38 Chelsey's story: $150K to $1M
10:01 Committing to minimum hours and why it matters
11:43 Screen recording your processes
12:07 How Outwork Collective's process works
15:55 Pricing breakdown
20:44 Tasks that make the most sense for cruise-focused advisors
24:25 Korrine's post-booking task list
30:01 Chelsey's free resource: 50+ things to delegate
32:05 The two things that determine whether it works
39:42 How to reach Chelsey and Outwork Collective
