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This CEO Job is a Lot Harder Than I Expected

Posted on 02/25/2015

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Everyone wants this grand vision statement. Now that I’m CEO, they ask, where is the company going?

I’ll get into that in a minute. But first, let’s walk through some other parts.

Windward at the Beginning


Back in the earlier days at Windward.

When I started Windward more than a decade ago, I was the CEO. At first it was just a few of us and the CEO job had no real responsibilities. As the company grew, it needed more attention at the CEO level, and I was not spending the time and effort that role required.

Basically I was out to lunch in that role and the company suffered for it.

We Hired a Focused CEO

The board brought Shirley Clawson in as CEO and she did a great job growing the company. And I learned a lot about being an effective CEO by watching her. What she did, what she focused on, what she required of all of us.

I also during that time expressed my opinion way too often about what I thought she should do as CEO. I think her suggesting me as CEO when she stepped aside is her revenge.

 The Windward CEO Role Today

So I now find myself back as CEO, but now of a much larger company where CEO is clearly a full-time job. I’ve learned a lot and am learning more every day. This is not an easy job.

  • There’s times I want to dive in and just do something myself but have to instead get others to execute.
  • There’s parts of the company where I need to learn a lot about how to best manage it (primarily sales).
  • There’s working with everyone to figure out what we should focus on and how we should structure things.

With some of my team members today. (They wore Hawaiian shirts in honor of my b-day.)

And at the same time we must continue to develop, market, & sell the software. And answer everyone’s questions about what’s going to change. And…

The direction of the company hasn’t changed. Our focus remains OEMs, SIs and Enterprise sales. We’ll continue to do our best to deliver exceptional service. And we’ll continue to improve our existing products and deliver new products.

The change I bring is a stronger focus on these goals, figuring out what we have to change and improve to reach them.

We also will become a bit more of a product-centric company with me in charge because my background is development. I try to keep it even but my “even” is different than it would be for someone with a non-development background.

I think this is a good thing because at the end of the day what makes our customers successful is our delivering a product that gives them a superb solution. That has always been Windward’s strength.

 What’s Coming Up

And with that, what will you see over the next year?

The biggie we’re working on is a template designer that runs in your browser. Similar to the desktop Word & AutoTag, but all in the browser, all written in typescript. We have the basic editor working and it’s awesome. I hope to release it this year.

We’ve also repurposed Javelin to be our RESTful engine. For languages other than C#, VB.NET, & Java, this is the engine. It is being changed to be just the engine, removing the Web pages & scheduler. Why? Because that’s the primary way it is being used and it becomes easier to configure and administer removing the extra parts that are not used.

Finally, we’re focusing on making AutoTag easier to learn & use. It’s already easy, but that ease can always be improved. This will include items like a table wizard, color coded tags, overlay help and more. My personal goal is the average number of questions that come in to our support desk per user is under 1. And once we hit that, we’ll continue to work at it to get it to approach 0.

I’m hopeful that our customers will see a few differences with me in charge. For prospective customers, we will improve the evaluation process so it is faster and easier. And for our employees, that we create a system that helps them be more productive and enjoy their jobs even more.

If you have suggestions, comments, etc., drop me an email. I’d like to hear from you.

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Author: David Thielen

Dave, Windward's founder and CEO, is passionate about building superb software teams from scratch and dramatically improving the productivity of existing software teams. He's really proud that he once created a game so compelling (Enemy Nations) that a now-professional World of Warcraft player lost his job for playing it incessantly on company time. You can read more from Dave on his personal blog, and at Huffington Post.

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