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How Unleashing Our Engineers Helped Transform Our AI Culture

How Unleashing Our Engineers Helped Transform Our AI Culture

Dan Cunningham, Chief Technology Officer, Chatmeter

At Chatmeter, we monitor, analyze, and respond to millions of online reviews, social posts and surveys, helping our customers boost their businesses and uncover real consumer insights. This type of data was ripe for an AI transformation, especially since we’d been using traditional machine learning models for years. Fully incorporating AI into our product would help enable our customers to have a deeper understanding of their data, save time through automation and uncover real actionable insights that simply were not possible before.

But to get there, we first needed to make AI foundational to our culture, not just our technology.

When OpenAI released ChatGPT, I was both excited by the possibilities that modern large language models represented and concerned with how to move quickly as an organization to embrace such a transformational technology. I knew we wanted to invest heavily in AI and be more than just casual users of this technology. To be successful, we needed our entire team excited about the possibilities, digging deep into the inner workings of large language models, and ultimately to become experts in everything related to AI. This kind of change was not something I would be able to do on my own. We needed champions within our teams, and we needed everyone on board quickly.

I believe good engineers are motivated by curiosity, autonomy, and the opportunity to learn and discover solutions on their own. Forcing abrupt technology ultimatums will usually have the opposite desired effect, demoralizing individuals, creating resistance, and ultimately leading to failed endeavors. Over the years, we’ve discovered that hackathons are fun and effective ways to allow engineers to experiment with new technologies. They allow for creativity, autonomy and provide a healthy competitive aspect that brings out the best in everyone on the team. Hackathons have other benefits as well: engineers are forced to time box, which leads to simpler solutions, using off-the-shelf components that often yield a more shippable product. I’ve seen some of our quietest engineers fully embrace these (healthy) competitions, forming connections and taking risks that wouldn’t happen in their typical day-to-day work. We even give an award for the most ambitious failure and ask those teams to present their failures and lessons learned.

With all this in mind, we held our first of many AI-themed hackathons, “Happy Hol-AI-Days." We had every developer, data scientist and QA engineer on the team participate with dozens of entries. This participation included several projects, like a simple company social post generator, automatic AI review responding and advanced vector embeddings search. Many of these projects eventually became part of our product offering or were foundational to the back-end architecture for our new AI services.

Here's what made our hackathon successful, and what I tell others who are thinking of organizing one at their companies.

  • Don’t rush your hackathons. They need planning. We do four to five a year. The minute we’re done, we’re planning the next one.
  • Create a theme and make it a big event. Use the lead-up time to get people excited and encourage them to form teams and think of a project.
  • Carve out two full days for your event.
  • Set expectations. Not everything submitted is going to be deployed to production.
  • Have a presentation deck that people can fill out right before the demonstrations with their projects, any supporting screenshots or videos and lessons learned.
  • Timebox each presentation to a few minutes. No exceptions. No one wants to sit for six hours of demos.
  • Invite the whole company to attend the hackathon demos and vote on awards. We recognize Most Ambitious Failure, Most Shippable, Most Creative and Best in Show, among others.
  • Keep it fun and make everyone feel welcome.

To further enable our teams with AI, we made sure everyone had individual OpenAI API accounts, started a biweekly AI primer series led by the data science team, and launched an AI Slack channel which we lovingly call “#Team-Data-Nerds.”

Lastly, my message to the team was to party like it’s 1999. I started my career toward the end of the dot-com era, and it was a fantastic time to be in technology. We knew we were on the cusp of something special with the rise of the Internet, Linux, and the open-source community. I believe our engineers are part of another transformative moment in history, and I want them to feel empowered to take advantage of this opportunity and realize they’re right at ground zero of the next revolution.

Dan Cunningham is the Chief Technology Officer of Chatmeter. He has a 20-year track record of building high-caliber software engineering organizations based on a culture of innovation, curiosity, and a love of creating great software and technology.


The views expressed in the commentary above are the personal views of Dan Cunningham in their individual capacity and do not necessarily reflect the views of PSG Equity L.L.C. or its affiliates (collectively, “PSG”) or any of its or their employees, officers or directors, or the portfolio companies that PSG manages. The views expressed above reflect the personal views of Dan Cunningham as of the date of publication of the above commentary and are subject to change without notice. Neither Dan Cunningham nor PSG undertake any responsibility to advise any reader of the above commentary of any changes in the views expressed above.

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