Expensify Blog

Another update: As of 2009/10/26, this position has been filled and we’re not accepting new applications.  Thanks for reading, and good luck in your search!

Update: Lots of feedback on this latest Craigslist post.  Equal parts fan mail and hate mail, with a few genuine applications — some of which are quite good.  The upshot is skip the XHTML requirement if you prefer.  But if you do decide to submit it, it’ll be viewed very favorably.

Hi. I’m David, the CEO and founder of Expensify. I’m looking for someone to hire, full time preferably but contract if necessary, who is the following (in order):

1) Really cool to work with. This doesn’t mean you’re some crazy party person or ride scooters throughout the office. Just a solid, nice, hard-working, compatible, fun person who jokes a lot and has a good time while doing amazing things. For example, we take the team overseas every year for 4-6 weeks. We leave family and friends behind to go find a remote beach with power and internet (easier said than done!) and work very, very hard all day and night while having a really fun time. (We’ve done Thailand, Mexico, India, and most recently Turkey. Next year is TBD.) Is that interesting to you? We’ve worked for the first year out of coffeeshops, and are currently squatting in a 19th floor penthouse lounge area at one of our teammates’ apartment building because it has a great view and free wifi. We have the money for an office, but honestly, it’s just not important to us. Sure we’ll get an office someday (and probably sooner than later, as the team grows), but in the meantime we find the nomadic lifestyle is actually *more* productive and *more* invigorating than a daily commute. Does this resonate with you, or creep you out?

2) Super talented, in a general way. There’s just too much that needs doing, and it’s way too varied from day to day, for anybody to do just one thing. Sure, everyone has their general areas of focus, but we need someone who is actively inspired by learning new things that take them out of their comfort zone. If the day after hiring you for a design job I said “Ok, we need someone to sneak into this conference and plant this business card in the hand of this person — we’re all busy, it’s up to you,” do you think “wtf, that’s insane” or “hell ya, I’m on it!” Same thing goes for “I need you to write a compelling blog post once a month” or “time to get an office, find one and fix it up to be nice on a budget of $X” or whatever. We find the best generalists can do anything they set their minds to, and generally excel further and faster than a specialist could. Does this describe you, or do you think such a thing is impossible?

3) Specifically talented in design. While generality is important, we actively lack certain skills that we need you to bring to the table. Namely: you’ve got to be a really good designer. If all goes according to plan, you’ll spend most of your time developing a really compelling visual brand for the site, promotion materials, etc. So you’ve got to really love this and be good at it.

How does this sound so far — something you might be interested in? To throw a few more specifics in, we’re looking for someone who:

- Knows Photoshop, HTML/CSS down cold. Obviously.
- Can make nice icons, charts, and other graphics from scratch.
- Is good at finding and using non-crap stock photography.
- Has a clean, crisp design style. We don’t need super duper fancy or glitzy. Just professional and compelling.
- Ideally can hang in PHP and JavaScript. You won’t need to do much with it, but ideally you could work around it without breaking it.
- Maybe has experience with Dwoo, PHP, lighttpd, Ubuntu, or SVN? These are some of the tools you might come in contact with.

Finally, and this is actually an important one:

- Is really, really enthusiastic to work with us.

The reason for the last one is that we just don’t have time to interview or even consider anyone who isn’t just totally, totally amped for this opportunity. If you’re the one, we will move mountains to get you. Every single person we’ve hired has required that we bend over backwards — anyone who’s any good at all comes with strings attached. That’s fine, I’d expect nothing less.

But we need that level of commitment in return. If you’re just thinking “Meh, I might as well apply because I’m unemployed / hate my job and have nothing better to do,” then please, seriously, save us both the time. I only want to hear from you if you are thinking “OMG, this sounds like the best opportunity I could possibly imagine. I didn’t know there were teams like this in the real world, and I certainly didn’t think they were hiring.”

Before getting into the application process, here’s a bit about us. We’re a 5-person team consisting of 4 tech folk and 1 tech-savvy marketing person. We raised $1M earlier this year (in a massively over-subscribed round that involved us turning away some very, very big-name investors) and have most of it still in the bank. We’re on the tail end of really honing our product, and looking for someone to bring a professional polish we just can’t do ourselves.

As for what the company does, honestly, to the right candidate it won’t matter. Just by reading to this point you should already have decided if you’re going to apply. But suffice it to say, we are disrupting an established, multi-billion-dollar industry with a extremely innovative business model that we feel will net real success measured in a rare currency for this valley: dollars. We’re not out to get eyeballs or usercounts, we’re going to make cold hard cash.

Anyway. If you’ve decided you want to apply, here’s where the rubber meets the road. Remember how I said “only apply if you’re super amped?” Now’s the time to prove it. The application process is very strict. If you don’t follow it, I can’t promise a response. But if you do actually follow the rules, I promise I’ll respond to you within 1 week of your application with either specific next steps or a clear rejection. I hate to be hard on this point, but our last job post generated over a hundred responses (despite involving perhaps an hour of essay questions) and I don’t have another 100 hours to review applications.

1) Redesign our homepage (http://expensify.com) and send it to me in beautiful XHTML as a JPG. That’s right, I actually said that.

At this point you might be thinking “no way am I giving you a free design”. If so, ask yourself that: “do you honestly think I’m going to take your design without hiring you?” Think about it: if it’s worth taking, it means you’re good, and that you’ve got the job. And if it’s not good, then there’s no risk of me taking it, right? So what have you got to lose?

Alternatively, you might be thinking “no way am I spending that much energy on this job application.” If so, congratulations! You just determined that you’re not right for this job. After all, a key requirement for the position is that you want it so much you’re willing to work hard to get it — if you’re not willing to work hard for it, you’re by definition not qualified, so cool. This test has already accomplished its job and everybody wins.

Next, you might be thinking “Look, I’m willing to work hard for it, but I don’t have the hours it’ll take.” If so, let me ask you this: how many hours would you be willing to spend going through rounds of in-person interviews (including all the time it takes to get here and back)? I imagine quite a few. Why not take a few of those hours and spend them in the comfort of your <insert comfortable container here> doing the thing that you claim to love, while simultaneously proving that you’re the ideal candidate for the job you claim to want very badly?

2) Explain your design. Why did you do it that way and not another? What are your priorities, and what do most people do wrong that you do right? What does your design help us say about ourselves, and how does this distinguish us from our competition?

3) Tell me about yourself. What about this job post appealed to you, and what turned you off? How would you recommend we do it differently? What have you done with your life so far, what do you want to do with the rest of it, and how will a stint at Expensify help you on your path?

4) Include a link to your portfolio, or links to specific sites or pieces that you created.

And that’s about it. It’s a tall order. But I’m really, really hoping you’ll take it by the horns and do something amazing with it. After all, every single day with Expensify will far, far more challenging than this. Might as well get a taste now.

Thanks. I hope to hear from you soon.

David Barrett
Founder and CEO of Expensify
Follow us at http://twitter.com/expensify
Personal blog: http://quinthar.com
Company blog: http://blog.expensify.com
Recent coverage:
http://www.techcrunch.com/2009/09/28/outright-com-leaves-beta-adds-new-partners-to-streamline-small-business-accounting/
http://gigaom.com/2009/09/14/where-do-your-biz-bucks-go-expensify-outright-team-up-to-find-out/
http://blogs.salesforce.com/the_appexchange_blog/2009/08/app-of-the-week-expensify.html
http://venturebeat.com/2009/08/12/expensify-raises-1m-for-online-expense-reporting/
http://www.techcrunch.com/2009/03/11/expensifys-free-expense-report-system-takes-the-hassle-out-of-reimbursements/

Another update: As of 2009/10/26, we’ve got more than enough applications to make a decision and aren’t accepting any more.  Thanks for your interest, and good luck in your search!

Update!: We’ve re-posted this with a greater focus on data-driven, performance-based marketing. If you didn’t apply before, now’s your chance!
Also: Our preference is to hire full time, but we’re open to hiring a contractor to this role: if you’re interested but would prefer a contract, let us know!

A bit about us:
———————–
We’re a 4-person startup working like mad to disrupt a multi-billion dollar financial industry from the bottom up. The company is named Expensify, and we do “expense reports that don’t suck.” We do that by importing your expenses *and your receipts* straight from your credit card, submitting PDF expense reports by email, and by reimbursing entirely online — now with QuickBooks support. Basically, we’re the expense report system you always wish existed.

That might or might not sound exciting to you, and that’s okay. Most of the *really* exciting things can’t be shared openly. But needless to say, it’s a real problem that affects millions of people — people who spend a lot of money — and there are already billion dollar companies who focus on this problem alone.

We have users, investors, partners, awards, and a crapload of good technology (not the least of which is an iPhone application, with BlackBerry, Palm, and Android on the way). We pay pretty decent salaries, are very generous with equity, and provide solid benefits.

We’re really happy where the product is at overall, but we also realize our limits: we don’t have the DNA to blow out this product in a huge way. So we need more new DNA in the team. Which is why we’re talking to you.

A bit about you:
————————-
The most important thing is that you are awesome. You work incredibly hard on a huge diversity of tasks. You can do pretty much anything you set your mind to, often better than people who have spent their whole lives doing it. You have more ideas than you’ll be able to accomplish in a lifetime. Does this sound familiar? If it doesn’t that’s fine. But it means I’m probably not talking to you.

Next, you’re cool to be with. We work really hard, sometimes from really distant locations. (Every year we go overseas to work from a remote beach: we just got back from Istanbul, but previous years — in a previous startup — we’ve gone to Thailand, Mexico, and India.) You’ve got to be extremely passionate about your work, but also respectful that sometimes things don’t go your way, and that that’s okay: everyone will return the favor, so in the long run, if you’re right more than you’re wrong, you’ll end up getting your way regardless.

(Incidentally, we work 3 days a week together — M/W/F; the rest your on your own. We don’t currently have an office, we’ve been doing the coffeeshop thing for the past year, but we’re considering getting a space downtown SF now that the team is growing)

If all those are taken care of, then ideally you would also be a whiz at performance-based internet marketing. You’ll never, ever be pigeonholed, and you’ll be involved across the board in decisions big and small. But we are specifically looking for someone to pick up and run with the following responsibilities:

- Write a bunch of SEO-optimized copy for the site
- Rebrand the entire site and product with a professional style
- Establish a multi-tier pricing plan
- Do a short, intense SEM burst to gather data
- Calculate the cost to acquire customers for each tier
- Re-optimize everything (site, pricing, keywords, etc)
- Repeat this process endlessly
- When we’re confident with SEM, add lead gen
- When we’re confident with lead gen, try affiliate
- Keep adding new channels

This is a very experienced, performance-based, number-crunching and ROI-focused role to manage a comprehensive marketing campaign for Expensify. You have a history of successfully establishing low-cost methods of acquiring customers using the full range of internet tools: SEO, SEM, lead generation, affiliate marketing, etc. All the resources of Expensify at your disposal, as well as full authority to go out and hire outside specialists as needed, but ultimately this role is about actively executing rather than delegating.

Next steps:
——
We’ve got a process worked out. It involves you answering a bunch of the standard interview questions up front, in your first email to us. This saves everyone time (if you’re willing to spend hours with us interviewing on the phone or in person, why not spend half that time in email?), lets us talk with more candidates than we could feasibly do otherwise, and we find the best candidates actually enjoy the process. If you don’t enjoy it or don’t have time for it, it’s probably a sign that this job isn’t right for you and that’s great! We’ve saved you the time applying, and us the time turning you down! For everyone else, here are the questions without further ado:

1) What’s your story, in a nutshell? What have you been up to with your life, and ultimately, what do you want to do?

2) What about the above job post most appealed to you? Why do you want to work with Expensify?

3) What about the above job post causes you concern? There’s got to be at least one thing about it that rubbed you wrong. What was is it?

4) We’re currently thinking something along these lines; what are your thoughts?
a. Write a bunch of SEO-optimized copy for the site
b. Rebrand the entire site and product with a professional style
c. Establish a multi-tier pricing plan
d. Do a short, intense SEM burst to gather data
e. Calculate the cost to acquire customers for each tier
f. Re-optimize everything (site, pricing, keywords, etc)
g. Repeat d-f endlessly
h. When we’re confident with SEM, add lead gen
i. When we’re confident with lead gen, try affiliate
j. Keep adding new channels

5) Which of the tasks in (4) can you (or would you) do yourself, without any outside help whatsoever, and which would you delegate to contractors?

6) For those tasks that you’d delegate to contractors, do you have specific people or firms in mind, ideally with who you’ve worked in the past? (Don’t exaggerate here: if you come interview I’ll ask for specific names so I can follow up with them, as in effect your success depends on their success.)

7) What kind of budget would you need to succeed in your role (both for the ads themselves as well as for contractors), and how do you measure success?

Do you think this role is scoped correctly to make the best possible use of your skills? Which of these tasks do you think you shouldn’t do; which aren’t listed that you should?

9) If you were hiring for this role, what questions would you ask (that I’m not asking) to separate out the good from the great?

10) And most importantly: how did you file your last expense report, and did it suck?

Please send your answers to dbarrett@expensify.com whenever convenient, along with a resume (if you have it, but don’t fret if you don’t). I guarantee I’ll reply to you if you actually fill out the questions. Thanks, I look forward to hearing from you soon!

-david
Founder, CEO of Expensify
You should follow us at http://twitter.com/expensify