Windward Career Opportunities

You can work at lots of companies, but you’ll like it better at Windward.

Windward’s first product was the game Enemy Nations. We now create the most innovative and advanced reporting & document generation software on the planet. We are also the sponsor of The Windward Code Wars and the producers of Cubicle War.

Job Openings

We are looking for motivated and passionate candidates who thrive in a fast-moving environment and appreciate the challenges facing a rapidly changing global economy. Windward is not for everyone. But if we are a good fit for you, then you’ll love it here (most days!) We offer:

  • Flexible PTO
  • Medical and dental insurance with company contribution
  • Life and long-term disability insurance
  • 401K plan with company matching
  • Profit sharing
  • Paid Holidays
  • Casual work environment
  • Challenging responsibilities with career growth potential
  • Weekly catered lunches and free snacks
  • Sales quota celebrations (early outs on Fridays!)
  • Dog friendly office - woof!
Current Openings

Working Here

First Day Welcome

Apart from standard,boring office stuff, you are provided with a means of self-defense (nerf gun), a cheerful balloon and a very personal greeting from one of the office dogs.

The People

Everyone at Windward is brilliantly talented, whether it’s mastering JavaScript, helping a customer with a killer problem or making some mean chili. We’re a passionate group – no exceptions.

The Culture

Windward's positive, up-beat, and highly productive environment is geared to the best and the brightest. At Windward, we take our team bonding time seriously and get really creative about activities that bring all of us together. Escape rooms, photo scavenger hunts, mystery murder games, tasting beer brought to us all the way from Vienna by our CEO (for those of age!) and a model bridge competition are just a few examples.

The Company

Love bow ties and a suit jacket? Wear them if you want, but you’ll probably be the only one. Windward offers a casual work environment with energetic, ambitious colleagues. Let’s just say our dress policy is "no bicycle shorts."

Have a question about joining the Windward team? Contact our People Operations at  


We like to think we have a sense of humor here at Windward. Check out our beloved Cubicle War Saga series. We like to see the fun in reporting software! Or see where we have hosted our hackathon, Windward Code Wars.

What Our Employees Have to Say

"I am assigned tasks and expected to figure out the best way to accomplish them. How I do it is up to me— as long as I provide the results. There isn’t someone babysitting me and making my decisions. While I can ask for advice, I’m expected to make the final decisions."
– En-jay H

"The main thing that has kept me here is the continuous education and the challenging work. I’ve been learning new technologies and developing new skills since day one."
– Tomas R

"I like working here because what we do is visible. At Windward we’d rather leave the CYA moves to your gaming avatar."
– Jeff N

"Why I decided to work at Windward.  1. They’re a software company, 2. Ideas are demanded, 3. No hurt feelings over challenging questions, 4. Intelligent talking canines to bounce ideas off of."
– Matt A

"Everyone can look at what we need to get done big picture. Everyone has an immense amount of initiative. Everyone is focused on getting the job done. And equally important, everyone is very professional. I don’t mean professional by dresses nice, etc. but that everyone clearly respects their co-workers and steps up to help others as needed. It’s a very supportive environment."
– David Thielen (CEO)

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