Code, Create, Compete: Inside Shipwell’s AI Hackathon

By Charles Dickerson, VP of Engineering at Shipwell

There’s a special kind of contagious energy experienced when engineers, product managers (& even the CEO!) are truly excited. That energy fuels faster ideas, sharper collaboration, and a sense that innovation is inevitable. That’s exactly the kind of momentum we saw last week during Shipwell’s AI Hackathon.

Nine cross-functional teams came together for a fast-paced, virtual innovation sprint. Over two focused days, each team tried out different AI code editors - Claude, Windsurf, or Cursor - to build or enhance a product feature using the latest in agentic workflows. We wrapped things up with a two-hour live demo session to share results and award prizes to the top three projects.

And while the competition added some friendly fire, the real win was what it unlocked for our teams - and ultimately, for our customers.

Why Do An AI Hackathon?

AI continues to evolve at a breakneck pace, with agentic workflows now changing how software is developed. With these coding tools reshaping how programmers work across the entire industry, we designed the AI hackathon to give our developers a chance to reset and rethink their processes for turning ideas into code. Whether they’re building autonomous test frameworks, automating common customer workflows, surfacing platform performance improvements, or prototyping top customer feature requests - every project is rooted in providing hands-on experience and real-world value.

"This is more than just a fun event. It's an opportunity for our team to grow. AI is evolving quickly, and it’s becoming essential for developers to understand how to work with autonomous agents. I’m super excited about what our teams are building - not just because it’s technically impressive, but because it’s going to make us better engineers, and that means a better product for our customers."
— Charles Dickerson, VP of Engineering

Big Thinking = Bigger Results

Within two days, our teams tackled ambitious, high-impact projects that show promise for future development & implementation. By embracing AI to automate manual processes, enhance developer productivity, and improve operational efficiency, we spun up tools like:

• Improved and new AI assistants that more easily connect using updated API calls and the latest LLM protocols
• Weather & predictive port congestion alerting that proactively identify shipments at risk by using NOAA data, visualized on a map interface
• Denied party screening & harmonized tariff codes dashboard using integrated AI for duty calculations and NLP interactions for easier trade compliance
• Hollistic, real-time platform performance diagnostics to predict detect bottlenecks, increase uptime/stability and improve QA velocity

With additional experimentation and customer interest, several of these practical, product-focused initiatives will feed directly into our roadmap and inform the future of AI in transportation. 

Taking Home The Win

While there were four teams that either got first, second or third votes from each judge, team Night Owls walked away with a unanimous vote for number one. For their project, they took a hard look under the hood at Shipwell’s AI assistant, Swifty, to see where enhancements could be made.

Through discovery and experimentation, they came up with a way to both improve Swifty’s capabilities using the latest Modern Context Protocol (MCP) architecture, while better integrating it into the Shipwell application. Their demonstration of Swifty performing complex actions like bulk creating shipments from external data and filtering long lists of shipments by user request (and being able to recall from a previous query) blew the judges away.

Runners up were teams Trailblazers and Dream Team, for their work on an autonomous carrier onboarding assistant and the creation of a centralized tool to track and manage deployments within the Shipwell production environment.

AI Hackathons Benefit Customers Most

The more proficient our developers become with AI agents, the faster we can iterate, fix issues, and bring new ideas to life. For our customers, that translates into:

• Faster delivery of new features and enhancements
• Increased platform stability and responsiveness
• Quicker turnaround on bug fixes
• More intelligent, user-focused automation within the product

“I've been personally experimenting with agentic workflows, and it's clear they’re transforming how we work. Watching our teams take this on and build real solutions so quickly is incredibly exciting. This AI Hackathon perfectly reflects who we are at Shipwell - innovative, modern, and always planning for the future. We stay ahead by investing in our people, uncovering the future of AI in transportation by pushing the boundaries of what technology can do for our customers.”
— Greg Price, Co-founder & CEO

A Culture That Builds Forward

Events like this AI Hackathon are part of what makes Shipwell unique. We don’t just adopt new technology - we explore it, test it, challenge it, and find out how it can make us better. And we do that together, across disciplines and teams.

As someone who’s been in engineering for many years, I’ve never been more optimistic about the tools at our disposal or the talent on our team. This hackathon has shown me that when you pair cutting-edge AI with passionate, curious teams, you unlock something truly powerful.

We’re building what’s next. And we’re just getting started.