Featured Founders: Brent Hobson & Jason Goddard from Wytebox

2 min read  |  Nov 14  |  Grayson Tummings

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Welcome to our Featured Founder series, where you’ll meet startup founders from Tampa-St. Petersburg who are building and scaling their ventures to solve some of the world’s greatest challenges. We interviewed Brent Hobson and Jason Goddard from Wytebox, an AI-native project management platform built for the future of software development and project management. 

What were you doing previously and what inspired you to launch your company?

We were serial entrepreneurs and SaaS leaders (Atlassian, Workday, SAP) who kept telling our teams to “just ship the feature” instead of updating Jira. We were creating the very misalignment we hated. We were inspired to build what we always needed: a tool that provides perfect alignment with zero manual effort.

What pain point is your company solving? What gets you excited to go to work every day?

The pain point is that manual project management has an unacceptable opportunity cost. Teams are forced to skip it to build or sell, and misalignment is the result. We’re excited because we’re the first to make alignment an effortless byproduct of work, not a separate, manual task.

Name the biggest challenge you faced in the process of launching the company. How did you overcome it?

Our biggest challenge was nailing the message. Our initial pitch wasn’t landing. We overcame it by pivoting to “project management on autopilot.” That message resonated immediately, leading to 10+ new customers and 80% of our ARR in just the last two weeks.

Where do you see your company headed next?

We’re raising $850k to hire a couple AI/ML and Data engineers and a growth lead. The next 18 months are about scaling our PLG motion and building out our “ground truth” data moat—transforming our tool into the indispensable “Alignment OS” for all work.

Give us a tactical piece of advice that you’d share with another founder just starting out.

Stop selling what your product is and start selling why it matters. If your message isn’t landing, it’s the wrong message. The market will tell you when you’ve nailed it—listen, pivot, and then hit the accelerator.

Why Tampa Bay?

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