Bringing Silicon Valley to the Midwest

timszotinc —  April 9, 2014 — 18 Comments
This is where I live.

This is where I live.

I work for the best Silicon Valley Start-up, Expensify.  I also live right off the shore of the largest body of fresh water, Lake Superior.  Most importantly though, I’m helping to bring Silicon Valley to the area I love and much-needed jobs along with it. 

In January of 2013, I was approached by another employee of Expensify that lived in the same area as I did.  He wanted to bring jobs to Northern Wisconsin and Upper Michigan.  He had been experimenting with three people for a couple of weeks to see if it was a viable option to staff a midwest workforce alongside our international team we already had in place and still stay cost-effective. These jobs could be seen as basic data entry positions easily trained to anyone with minor computer knowledge, but there is a growing amount of complexity as Expensify moves more into the global market and receives data from around the world to process for our clients.  The best part, the agents could work from home!  He was also looking into the possibility of bringing entry-level developer jobs to the area.  Where did I fit into all that?  He needed someone to help get it all started, maintain, and manage it.

At the time I was running my own computer repair business full-time out of my home and did contracted computer IT for local businesses.  After hearing his initial pitch about Expensify and what his vision was for the area, I was sold.  When you live in a town with a population of under 6,000 people, and don’t want to move out to Silicon Valley, you never really think you would get a chance to work for a San Francisco based tech start-up.  So, I started working for Expensify as an independent contractor, slowing building a data entry workforce, training them on the work in person and then allowing them to work from home after that.

Fast Forward: One Year Later

I’m now a full-time member of the Expensify team and Expensify has brought over 30 jobs to the area and is still expanding!  Exploring more than just data entry jobs too.  How about some Help/Support Email Agents and some more entry-level developer jobs?  We’re looking to utilize an area and its population that most companies never think about.  Even better: we’re still staying cost-effective despite previously relying on a solely international-based workforce as our local employees have shown to be extremely accurate and efficient. This in turn pushes our international team to higher standards increasing performance across the board.

It’s extremely exciting to be a part of a company that is willing to bring Silicon Valley to an area that only hears about it from the news.  But the best part is to see the expression on people’s faces when I tell them that I live in Northern Wisconsin, but I work for a San Francisco based company.  It always leads to awesome conversations.

18 responses to Bringing Silicon Valley to the Midwest


    Welcome to the Silicon Prairie. We (SmugMug) have been doing the same thing for years now. There’s 4 engineers here in MN, plus a QA person, also a handful of BizDev/Support folks in IL and MI.


    Thanks for the welcome! There is a lot of untapped potential that I believe more companies should take advantage of.


    Northwest Indiana here, running our small iOS dev shop, 9magnets, LLC. Huge fan of the Silicon Prairie myself :-).


    Buffalo = same thing … 🙂


    In such posts, it also never hurts to mention the cost of housing in the Midwest. In a neighborhood I lived in Richmond, Indiana, decent starter homes near a greenway and about a mile from downtown are going for about $30,000 currently. Nicer 3 bedroom homes are available for ~$100,000. According a cost of living calculator, you would need to make $140,000 in Mountain View, CA to match $50,000 in Richmond, Indiana.


    That is a great point. Where we are focusing most of our hiring, most homes are going for well under $75,000. Cost of living makes a big impact on the cost effectiveness of what we’re doing.


    timszotinc, I neither endorse nor denounce the website I’m going to link to, but I don’t get the impression you’ve heard of it, and maybe you should have by now, so here it is: Cheers.


    Hey! I’m a Software Engineer living in Wisconsin and your none of your job postings say anything about a town/city in Northern Wisconsin. Do you have a link to where any postings in Wisconsin?


    Shame on me for not proof reading, “Do you have a link to where any postings in Wisconsin?” should be “Do you have a link to any job postings in Wisconsin?”


    This is why the future of an open internet matters. I’m also in Wisconsin, doing software development.


    Interesting. I never thought that this was a problem within US. I mean, I’ve seen a lot of US-only remote jobs.

    Btw, are you (Expensify) considering international (Europe) candidates for engineering roles as well? But since you mentioned “cost-effectiveness” as one of the main reason for hiring internationally, I guess you might be looking in places like India, right?


    I’d love to here more about the opportunities – especially the entry-level developer jobs. I currently have an entry-level dev role at IBM in Lansing. Unfortunately, not long after I was hired they transitioned this Center to focus primarily on testing. The domain knowledge has been great, but I want to code. I’m just starting to look for other work and this made my eyes light up. I’d love to hear more! I’ll be checking out the Expensify site in the mean time!


    Hey there!

    Actually about 20% of our staff are not from the US. (Namely, from France, Italy, Australia, and Venezuela.) We’re always looking for talented engineers and we have no bias towards where you’re from! If you’re looking for a job, we’d love to talk to you!


    Hey Ryan,

    Will do! After I finish some contract job during the next couple of months. I’m mostly a generalist, but have a preference for C++ tasks (i.e. when cpp is the right tool 😉 ).


    Hey Justin!

    We don’t have a specific posting or requirements, we’re just looking for awesome talented people who are great to work with! You would be working mostly remote, however we’re a family style organization so ideally you would be open to driving up to Ashland, WI occasionally for team meetings or when someone from San Francisco flies in.

    That being said, we’re flexible when it comes to great people, so go ahead and apply and we’ll try our best to make it work!

    More info on how to apply here:
    NOTE:If you are applying to work remote, send your email to, not


    Hey Justin!

    We don’t have any thing specific to Wisconsin, we’re just generally looking for awesome talented people who are great to work with!
    The position would be remote, but we’re a family style organization so ideally you would be open to driving or flying up to Ashland, WI every once in a while for quarterly meetings or when someone from San Francisco flies in.

    More info on working at Expensify can be found here: but, send your email to instead of jobs@expensify as they are handled by different people. Thanks!


    What kind of data entry jobs do you have on staff at Expensify? Arn’t all of the reports filled out by the end user of the service or from integrations from the bank/credit card?

Trackbacks and Pingbacks:

  1. The Expensify Family is Growing! Our Mid Year Recap « Expensify Blog - July 31, 2014

    […] we’ll be adding another 4 people to the support team who will be working remotely from the Upper Peninsula in […]

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