Now hiring…

As some of y’all might know, one of the ways in which I make a living is by running an award consulting service, PointsPros.  I have a small team of people who work with me there, and we take great pride in helping people maximize their miles and points.  I know we’ve helped several of you as well, and I am incredibly grateful for the support and patience you’ve had with our “growing pains”.

We’ve had more business than we can realistically handle for some time now, and I’d like to bring on another person.  I tend to think of you guys as my best source of advice, and as I’ve done with so many other things, am reaching out to you for help.

Last time I listed a job posting I was completely blown away by the hundreds of thoughtful and diverse responses I received.  It was incredibly humbling, and to be honest quite overwhelming, so I’m a little nervous to start that process again.

That being said, I’m hoping I can describe the role I’m hiring for a bit better this time, and hopefully find someone who is a good fit.

I am looking for:

Someone that’s passionate about travel and miles. This hasn’t changed.  I am the luckiest person in the world to be able to do what I love everyday, and am thrilled that I’ve been able to surround myself with similarly passionate people.  We need someone who loves miles and the opportunities they provide, and wants to share that with others.

Someone that writes and communicates well.  Goodness knows I could do a better job of proofreading, so I’m hardly one to talk, but this is an essential skill for this role.  Between us we are sending hundreds of emails a day, and being able to communicate clearly and effectively is critical.

Someone that is reliable and timely.  Obviously we all travel, and I’m not going to ask anyone to commit to a Monday-Friday 9-5, but by the same token this isn’t a Monday-Friday 9-5 ;-).  We have clients all over the world, and the internet insists on staying up all night, so I need someone who can consistently spend at least an hour or two a day responding to requests, but is also able to spend larger chunks of time as needed.  Realistically I need someone who can commit to at least 20-25 hours a week for now, and potentially more in future.

Someone that loves helping people.  At some point, only a portion of what we do has anything to do with travel or searching award space.  Much of our time is spent exploring options with people, or explaining why other options won’t work.  I can’t imagine this would be any fun for someone who didn’t enjoy teaching and explaining and generally helping others.

Someone who is self-motivated, and able to work independently. As the proud owner of an extensive pajama collection I can certainly appreciate the benefits of working from anywhere, though it can be difficult to get up every day and go “to work” when work is “the sofa”.  I am fortunate enough to have a great team, and we have fun when we’re together, but 99% of the time we’re working solo.

As far as job skills go, my team and I are absolutely willing to train as needed, but we’ve learned that the most successful person will be one who:

  • Has a solid understanding of the three major alliances, their carriers, and destinations
  • Is familiar with the tools and tricks for searching award-space in at least one program
  • Is creative, flexible, and solution-oriented

Overall, we’re looking for someone who is excited to sink their teeth into something that has tremendous potential, but is also patient (and stable) enough to be able to put up with the limitations and challenges of what is still very much a “start up”.

If this sounds like your kind of crazy, send us an email to tiffany at pointspros dot com.   We will be accepting applications through Saturday evening, and will be looking to bring someone on in early June.  Please go easy on us, and thank you!

Filed Under: Misc.
  1. @ Robert — You don’t have to be a US citizen, though do have to be authorized to work in the US.

  2. It would be great if you could clone Tiffany! She was so wonderful to work with on my challenging trip next January from Boston to Australia/NZ! Very patient at explaining all of the complex routing rules and answering all of my newbie questions!

  3. I’d be interested.. I am providing help to people for free already. Might as well get a little for it. Feel free to email me. Thanks Ben.

  4. @ Rebecca D — Hah, thanks for the kind words. She’s a gem (not only with award bookings, but much better at the whole hiring process than I am). 🙂

  5. This sounds very interesting. Consulting my family and peers with miles/points/credit cards is something I already really enjoy doing for free.

    I’m familiar with all of the major alliances – but my specialty is with Alaska Airlines and their partners.

    I travel a lot but my hours are great. Please contact me if you are interested. Thank you.

  6. This is the kind of part time job I would enjoy! Unfortunately, don’t think I have enough time to do it due to college 🙁

  7. Hope you find someone as nice and competent as Jordan. He recently helped make arrangements for my brother and I for the Winter Olympics next year in Sochi. Was initially disappointed I wasn’t able to work directly with you as you were out of the country traveling, but as you said, Jordan was “awesome.”

  8. Congrats Lucky. I just started my award booking service and wish I could be as successful as you. Who knows, if I get a really hard challenge, I may refer them to you 😉

  9. I used your service as well (Jimmy was amazing). In retrospect I probably could have done it but was nervous/scared(?) for my first redemption. I’ve been collecting miles for years, so am up to date on most things in the world of the “hobby”. That said I’m certainly interested.

  10. Lucky,

    This is off topic — but I must say, I appreciate the passion you bring to the topic. Your comment about being “able to do what I love everyday” really hit the mark. It shows in your blog, and that’s why I read you.
    I happen to also be a lucky one, doing what I absolutely love to do for a living — there is no line dividing “work” from “home life” because it’s all the same. I appreciate it when I see this is others.
    I wish you luck, and look forward to using the services of your team in the future. I know you will hire only the greatest — as the comments before mine have complimented your existing team.
    Thanks again!

  11. Awesome. Hope you find someone as good as Andrew. I’ve used him a few times now and he is extremely responsive and a great communicator. good luck!

  12. If I may ask. Did you hire someone the last time you were looking? I read your posts on the hire but never saw a post on the filling of the position. (I could have missed it though)

    I was interested last time and I am still interested?

  13. This is a great opportunity for someone like myself who has the time and passion to get into the industry and at the same time work for a group of people who are great at what they do…count me in!

  14. @ Corridor! — It was a very drawn out process due to changing circumstances, but I did hire two people from it. Will be sure we do a better job communicating it this time.

    @ Winston — Not at all, it’s a “remote” position!

  15. I applied last time you posted a job opening and never heard back. Not bothering this time. :-7

    Hope you find someone great.

  16. I applied last time you posted a job opening and never heard back. Not bothering this time. 😉

    Hope you find someone great.

  17. @Lucky You should post a complex routing and invite those who can suggest a solution to apply. Their skills on the search will come to the front. You can deal with the communication part after that :). Surprised to hear the size of your team though. Good luck with the hire.

  18. Ben, should the applicant be working only on this or can you pursue this as an additional career opportunity?

  19. Hi Ben, just to clarify.
    You can be a non usa citizen but you should live in the usa and have a workpermit ? (as I would love to apply but living in europe)

  20. @ PhatMiles — It could go either way. The key is that the applicant is able to put in consistent hours throughout the week, whether it’s two hours a day or ten hours a day. It could be a part time position to begin with and eventually a full time position, but if it’s the right person they can probably start part time or start full time as well.

  21. I see a couple “applicants” have already disqualified themselves by displaying their total lack of understanding the simple direction on how to apply. lol

  22. Ben,

    FYI – A work permit(mostly H1 and L1) doesn’t authorize the work permit holder to make money from someone other than his employer (legally). Now if you pay cash via paypal and keep it under the table, its a different story.

  23. @ Jeff,

    That’s correct. Then again, I don’t know if Ben has a legal entity setup for award consulting (and pay taxes on earnings)

  24. For what it’s worth, I’m told that everyone should have been responded to by now. Thanks so much for the overwhelming interest in the position, it really is humbling!

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