Using Hackathons to Inspire and Accelerate Product Roadmaps

Trevor Nelson
Aug 9, 2019 · 8 min read

The Policygenius engineering team espouses a generative culture, where all engineers are empowered to prioritize and solve problems that drive the technical organization forward. (For a more in-depth description of what generative culture is and how engineering teams can benefit from it, see this article by Dave Kaplan, our Head of Engineering.)

One of the primary ways that we practice a generative culture at Policygenius is with self-organizing Charter Guilds and Tech Initiatives- another important part of building this culture is with periodic internal hackathons.

In this article, we’ll discuss why we think hackathons are valuable tools for driving culture and business impact, how we plan for and run effective hackathons here at Policygenius, and review some of the great projects that have come out of our first two hackathons.

The UAT team points at various things for some unknown reason during the hackathon.

Why hackathons are worth it

Builds a culture of empowerment
While there are many ways of organizing and running hackathons, we strive to make them as bottom-up as possible, with project ideas collectively sourced, democratically selected and teams self-organized.

This feeds a generative culture, where everyone has ownership of the problems we’re solving and feels empowered to affect the direction of the tech/product organization. Our generative culture supercharges the agile product process by allowing more voices to participate in product and tech decision-making.

Recharges product teams
One overlooked benefit of hackathons is that they break up a team’s business-as-usual and we’re able to solve problems outside of our normal team’s priorities. Not only do hackathons provide a change of scenery that has been proven to fight burnout, they also provide dedicated time to be highly creative. There have been all sorts of studies about how creativity refreshes the brain.

True story — I was actually able to use this phenomenon in high school to significantly boost my SAT score. After getting an SAT slightly under automatic acceptance for the college I wanted to go to, I learned that the next time I took the test, there would be a beta writing portion of the SATs that my target college was going to ignore. Instead of studying, I just retook the test in a few months, but doodled during the essay portion and answered my own essay prompt. Giving my brain a break and giving it some time to be creative helped me get over 100 points higher the second time around on my SATs. While it’s a silly anecdote, it’s a real-world example of how creativity can mentally recharge and boost performance.

Screenshot from my *actual* SAT essay

Provides a different perspective
Hackathons force engineers and product folks to solve new problems that require them to approach solutions from a different angle. This can trigger new ideas in their day-to-day project work, and allow them to approach problems from different perspectives.

Utilizing hackathons to spike on new tech can spark new ideas with respect to how engineers design new features or tackle tech debt, and broadens product managers’ and designers’ concept of what’s feasible. The competitive nature of hackathons and their short timeframe also can force participants to work quickly and prioritize savagely. This refines their ability to distill new products and features to a lean MVP on their day-to-day teams, as needed.

How Policygenius plans and runs hackathons

Signs of an effective hackathon: 1) conference rooms that look lived in, 2) lots of whiteboard scribbles.

4 weeks out

  • Create a hackathon planning team of volunteers from product, engineering and design to lead the hackathon prep work.
  • Send out an availability survey to everyone in the product organization. We sent out a Doodle with a bunch of options for the dates of the hackathon. One of the best ways to have a bad hackathon is to do it when half of the office is on vacation or has some big impending project deadlines! We schedule our hackathons sometime in the first few weeks of each tertile (our 4-month planning cycle), so we can start the tertile refreshed.

3 weeks out

  • Send out a Trello board to facilitate project brainstorming. First, we focus on brainstorming problems that we’ve been itching to solve: for example, that our agents spend a lot of time rescheduling medical exams for life insurance applicants. They could be customer, operations, or technical problems that we face at Policygenius, or even just-for-fun projects that broaden the imagination of our product roadmaps. We brainstorm solutions in a separate, later step to allow everyone to think of solutions to problems with fresh, unbiased eyes.

2 weeks out

  • After gathering a bunch of problems that have business impact to Policygenius, we open up the brainstorming board for solution brainstorming. Using the list of problems as inspiration, we add descriptions of new products, features or technical exploration work that could help us solve something meaningful. For example, the above problem with exam rescheduling could inspire a number of solutions, such as a mobile app that reminds users of their medical exams, a calendar feature that allows users to list multiple schedule options, or a way for medical exam providers to directly contact users through Policygenius.

1 week out

  • After there’s been sufficient time to brainstorm hackathon project ideas, we put everyone in a room for project pitches. Recommenders of each product idea have a few minutes to describe the goal of the project, what impact it would have, and why it’ll be technically exciting to work on.
  • After the project pitches, hackathon’ers will spend the next week finalizing their teams. Since the teams are self-organizing, the only “voting” or project selection that happens is if you’re able to convince enough people to join your team to actually complete the project as it is initially scoped.
  • The hackathon planning team finalizes breakfast, lunch and dinner plans during the hackathon, as well as the judging panel and prizes. The judging panel is generally a mix of leads from other departments and an engineering manager, to give the panel collective context on technology, operations and marketing.
  • Once teams are finalized, they do some light discovery work and refine project scope throughout the week so they can hit the ground running.

Day 1

  • All hackathon participants meet first thing in the morning for the Hackathon Kickoff. We review the judging criteria, timeline and finalized project teams.
  • Teams relocate to sit in hackathon team pods, plan out development milestones, and start hackin’!
  • Breakfast, lunch and dinner are provided to maximize the amount of time teams have to work on their hackathon projects. But also because free food is great.

Day 2

  • Teams use the morning to wrap up any last tweaks to their projects.
  • As development starts wrapping up, teams shift towards planning for their demo and presentation. Presentations should focus on business impact, technical “wow” factor, and if there’s a use case for it in production in the future.
  • Hackathon winners are announced after the judges deliberate and the hackathon is officially a wrap!
Something appears to be going poorly.

Hackathon Project Highlights

Flutter app for application process updates and medical exam scheduling

Insurance Chatbot
One of the projects from our inaugural hackathon, this was a chatbot proof-of-concept that utilized Google DialogFlow to answer insurance a user’s insurance questions, generate life insurance quotes, and tell a handful of jokes via both online chat and over the phone. Through this project, we were able to de-risk potential future chatbot functionality and get a better sense of feature complexity.

Example chatbot response using Google DialogFlow

Disability Insurance Quoter
Shameless plug, but the project I worked on last hackathon was an industry-first comparative quoter for disability insurance premiums. We built this quoter on a new tech stack, as a way to evaluate using them in our other quoters to resolve some limitations and tech debt. With this hackathon project, we were able to garner more internal interest in this and are working on a path to production.

Proof-of-concept agent-facing UI for comparative quoting using a new Disability Insurance quoting service

Feature UAT Environments
Focused on utilizing our kubernetes implementation for isolated QA environments for each open PR. This would allow us to move product acceptance to happen before code changes are merged in, keeping master clean and in a deployable state at all times, paving the way for continuous deployment. This team actually continued the work they did from our first hackathon in the next one, which demonstrates the value of keeping hackathon projects self-organizing.

Personalized UAT environment for each feature to keep master branch clean

Wrapping Up

We’re growing!


The easy way to compare and buy insurance.

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