Just a scratch behind the ears would be nice

Really if you could just give us a pat on the head ...

Parking continues to be the hot investment in Chicago — you know, that business of the future. SpotHero raised a $50 million round and plans to add about 50 engineers by the end of the year. Love to see all that money turn into jobs at a rate of 1-million-to-one. 

We do feel compelled to mention that this was SpotHero’s Series D round of funding, which, well, we're only human. 

The hot and fresh insurance industry earned the next-largest round of funding, with startup Kin collecting $47 million. The company plans to add nearly 75 jobs over the next year, doubling it's staff. It's also now writing its own policies to homeowners, instead of relying on an outside carrier to issue the insurance under its shiny tech veneer.

Also in insurance, healthcare plan marketplace GoHealth was bought by a private equity firm for $1.5 billion. We’re always wary of private equity takeovers, since inherently their goal is to squeeze out the most profit. This deal is no different, especially because Centerbridge Partners, the firm behind the acquisition, lists P.F. Chang and Big Wolf Resorts as its victories. Those are … not the same, and while the very rich tend to assume their expertise will stretch to every venture, we are skeptical. 

Deere hasn’t been doing great for awhile, but it trotted out the phrase “organizational efficiency” on its latest earnings call. That elegant euphemism for layoffs and cost-cutting is a response to Trump’s “trade war,” which is hurting farmers right along with the tough weather *cough* climate change *cough*.

Fortunately some companies are expanding here. VSCO, which makes a photo-editing app, is opening up a Chicago office out of the new Hoxton hotel and coworking space, planning to hire 20 people by the end of the year. 

The Old Main Post Office, too, continues to attract companies looking to expand. Uber has officially confirmed it’ll be taking over 450,000 square feet in the renovated building, making Chicago its second-largest office behind San Francisco. It also makes Uber the Old Main Post Office’s biggest tenant, at more than double the size of Walgreens. The Federal Home Loan Bank of Chicago will also be moving in, leasing 130,000 square feet

Badass news you might have missed
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Job with badass potential
Director of Marketing at Kin Insurance
Work: Support the sales team, reporting to the COO. Generate as many qualified customer leads as you can, using paid search, direct mail and any other methods you find valuable. 
Downsides: The hiring manager’s bio says he’s a “Chicago native from Sleepy Hollow (true story!).” Nah. Sleepy Hollow is out past Elgin my dude. If you’re not incredibly petty, however, we can understand how this would not be an official downside to the job. Still, there is this line in the job description that gives us pause: “While a bit of creativity is required for this role, we rely on data.” Um. It’s 2019, we all do. Make sure to check the place for artificially inflated egos.
Perks: Well, you know they have the money now. And that switch to becoming an insurance carrier is a critical one. A lot of insurance “disrupters” are really just repackaging someone else's products in a more millennial-friendly format. Writing policy gives Kin more control, and the power and longevity that comes with it. Now’s the time to get in. 

A few other jobs we’re curious about …
Program Manager at Civic Exchange
Help the local journalism we rely on (Chalkbeat! Block Club!) stay funded in this part-time events and fundraising role. It’s a small sum of money, but it’s work you can be proud of, and it does work out to around $35 per hour. And there’s the opportunity to raise enough money that you’re able to turn it into a full-time role. (h/t to the excellent Jane Squad newsletter.)

Director of Global Diversity, Equity and Inclusion at the Wikimedia Foundation
We have a lot of feelings about whose stories get told and how, so even though this job is remote or based in San Francisco, we’re including it. Wikipedia is our public memory. Making it more inclusive invites people in and changes the narratives we tell ourselves.

Inspiration of the week

This otter trying to teach a person how to pet it. To be honest, it’s been a rough week, and we’re not finding a lot of human sources of positivity to point to (besides Lizzo, always Lizzo). So we’re going to spend the weekend making like this otter and asking for what we need. We hope you’ll do the same.

Forward this email to anyone who needs to put it out there. They can sign up here and get bi-monthly reminders to ask for what they need.

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