Hack Is Back

As the dim glow of my laptop illuminated the quiet hum of the late-night office, I found myself in a familiar, yet still quite novel setting. This wasn't the caffeine-fueled college hackathon of my youth, where the stakes were low, yet couldn't feel higher. No, this was something more structured, more refined, and yet as commonplace as they come. This week was my first in-person hackathon since my college days, and with a twist-—I was not just a participant but also one of the organizers for Compass's GenAI hackathon.

The experience was a blend of nostalgia and new challenges. As an organizer, I was tasked with juggling my responsibilities while also diving deep into the trenches with my team to create. This hackathon was set against the backdrop of a corporate environment, complete with the guardrails and structured chaos that come with it. In this blog post, I'll walk you through my journey from newbie to seasoned organizer, detailing the experience of the past few months leading up to the event and the hackathon itself.

Past Hackathon Experience

My hackathon journey began with PennApps at the University of Pennsylvania in the fall of my freshman year, a time when hackathons were just starting to capture the imagination of campuses across the country. My first foray into this world was at an event held in the modest confines of Towne 100, where about 80 of us gathered not for glory or significant prizes, but for the sheer joy of creating. Our tools were basic, our projects meme-filled, and our professional ambitions limited.

As the years progressed, so did the scale of these events. What started as a small gathering of like-minded techies soon ballooned into a major event on the university calendar. By my senior year, the hackathon had transformed into a grand spectacle, attracting over a thousand participants from around the globe, including places as far-flung as Hong Kong and Switzerland. The stakes had risen dramatically, with six-digit prize money that seemed astronomical to me as a college student. The engineering quad buzzed with energy, ideas flew at the speed of an overclocked Core i7, and the air electrified with the potential of what could be.

One of my most vivid memories from those days was from the fall of 2013. I had pushed past the 36-hour mark, coding through the night to bring my collaborative editor, Codify, to life. I remember collapsing into bed at 4 am just before the submission deadline, only to be jolted awake a few hours later with the news from a friend that my project had made it to the Top 20. The rush to present in front of an audience of a thousand hackers, the pride in my work, and the eventual acceptance that my practical, yet unglamorous, project wouldn't win against more flashy entries—-it was a rollercoaster of emotions that I'll never forget.

These experiences laid the groundwork for my understanding of what makes a hackathon truly special. It's not just about the code or the competition; it's about the community, the shared struggle, and the collective triumph of turning ideas into reality. As I transitioned from a participant to an organizer at Compass, these lessons became the cornerstone of how I approached the monumental task of bringing together a diverse group of professionals to innovate under pressure, fostering an environment where creativity and collaboration were front and center.

Compass Background

Compass stands at the forefront of the real estate technology sector, not merely as a participant but as a pacesetter. Our mission is to simplify and enhance the buying, selling, and renting processes through innovative technology that benefits both clients and real estate agents. This commitment to innovation is embedded in our DNA, driving us to continually push the boundaries of what technology can achieve in the real estate market.

However, the journey through 2022 and 2023 has been fraught with challenges. The real estate market faced a significant downturn, leading to a series of cost optimizations at Compass, including three rounds of layoffs. These were sobering reminders of the volatile nature of the market and the need for agility and caution in our strategic planning. Despite these hurdles, our dedicated engineering team of several hundred remained committed to the vision of transforming the real estate landscape through technology.

Organizing

Motivation

The genesis of the Compass hackathon began in early spring, amidst internal discussions about the potential of generative AI within our platform. When whispers of a possible hackathon began circulating, I seized the opportunity to steer the event towards Gen AI. My dual objectives were clear: to catalyze the creation of forward-thinking projects and to shepherd these innovations swiftly from concept to deployment, cementing real business impact.

Format

The format of the Compass hackathon was deliberately designed to break the mold of traditional tech-only events. We envisioned a collaborative arena where not just engineers, but real estate agents, designers, and support staff could contribute equally. This inclusive approach was aimed at fostering a holistic view of the challenges and opportunities within the real estate sector, ensuring that the solutions devised were comprehensive and impactful.

Preparation Phases

1. Idea Solicitation: We began by casting a wide net across the company to gather insights and challenges directly from the agents and staff at the front lines of the real estate industry. This phase was crucial in ensuring that the hackathon addressed real, pressing needs.

2. Grooming: The collected ideas were then thematically organized and refined into structured project prompts, ready for teams to tackle. This step transformed raw insights into actionable challenges.

3. Participation Solicitation: Next, we reached out to our pool of engineers, designers, and product managers, gauging their interests and expertise to ensure alignment with the project themes.

4. Matching: With a diverse array of projects and participants, we meticulously formed teams, balancing skills and interests to maximize innovation potential and collaborative synergy.

5. Event Launch: Finally, we equipped teams with the necessary tools and guidelines, setting the stage for the hackathon. This included everything from API keys to collaboration protocols, ensuring a smooth kickoff.

Execution

The role of an organizer in such a diverse setup was both exciting and daunting. My days were filled with logistical coordination, from ensuring technological infrastructure was in place to facilitating effective communication among participants from vastly different professional backgrounds. To aid in this, I developed an internal service complete with a user-friendly SDK to empower teams to build impressive projects with minimal technical overhead. Not to mention the detailed hackathon guide that delineated specific roles and responsibilities of each type of participant.

The weeks leading up to the event were a whirlwind of activity—-curating ideas, matching teams, and preparing communications, all while managing the usual logistical challenges associated with any large-scale event, such as catering and venue setup. This meticulous preparation was aimed at not just facilitating a successful hackathon but at ensuring the long-term impact of our hacks beyond the day.

Compass Hackathon Experience

The culmination of months of planning and preparation was a three-day event that brought together the diverse talents of Compass. Here’s a detailed look at how the days unfolded, highlighting both the challenges and triumphs of the hackathon.

Monday: Kickoff and Initial Coding

The event officially began on a crisp Monday morning. I arrived at our New York headquarters at 7:30 AM, ensuring that the breakfast setup was seamless—-a crucial start for a day expected to stretch late into the night. Despite the fatigue from a late-night flight and adjusting to a new timezone, the excitement was palpable as participants from various parts of the country started to arrive.

The morning was spent in a flurry of activity: directing participants, helping teams access the necessary API keys (a reminder of why we send out those instructional emails!), and ensuring everyone was ready to dive into their projects. By lunchtime, I was able to sit down with my team to outline our project, Compass Ignite—-an automated marketing planner designed to not only schedule but also create content. The afternoon buzzed with queries about leveraging the APIs and LLMs I had set up, interspersed with my own coding efforts for our project.

Dinner provided a brief respite, offering a valuable opportunity for face-to-face interaction with executive leadership. The discussions were not just about the day’s progress but also about broader strategic directions and potential impacts of the hackathon outcomes. The day concluded around midnight, with teams leaving the venue buzzing with ideas and partial implementations.

Tuesday: Full-Throttle Development

The second day started early again, with me sneaking in some coding before the influx of morning participant questions. This dual role of organizer and participant was more challenging than I had anticipated, balancing the immediate needs of the event with the goals of our hack.

The day was punctuated by technical support, strategic discussions, and an unexpected interview with Fast Company about how Compass is integrating generative AI into its operations, spotlighting the hackathon as a key initiative. By evening, our team had made significant progress—-functionally integrating the components of our project. We wrapped up the coding by 10 PM and spent the next hour recording our demo video, a crucial element given the decision to avoid live demos to circumvent potential technical glitches.

Wednesday: Presentations and Judging

The final day was as intense as it was rewarding. With many teams, including ours, submitting their projects in the final hour. The morning was a scramble to organize the demo videos into a coherent presentation for the afternoon session. The anticipation and excitement were tempered by a technical hiccup during the demos—-audio issues due to an oversight in speaker setup relative to ambient noise levels. This led to a quick pivot to distributing links to the recorded demos with normalized audio, ensuring all projects were presented in their best light.

Despite the challenges, the event was a pretty resounding success. The executive panel of judges were so impressed by the quality and innovation of the hacks that they decided to triple the prize pool. In a gratifying conclusion to our efforts, Compass Ignite tied for the first-place prize, a testament to the hard work and creativity of our team.

The hackathon not only reignited the spirit of innovation and collaboration but also realized the true potential of cross-disciplinary teamwork in tackling real-world problems. The feedback was overwhelmingly positive, with participants appreciating the opportunity to work with colleagues from different parts of the company and learn about aspects of the business they were previously unfamiliar with. This event was a significant step in reinforcing the culture of innovation at Compass, setting the stage for future collaboration.

Conclusion

Reflecting on the entire experience of the Compass hackathon, I'm faced with a few hearty conclusions. One, while it was no PennApps, I'm glad we achieved more than a coding competition. The challenges of organizing such a diverse and inclusive event were met with an enthusiastic embrace of new ideas and each other, proving that the collective effort of users and builders can lead to great outcomes, even in hackathons.

Two, the feedback from participants definitely highlighted our logistical hiccups, particularly the audio normalization failures during the demo presentations. It's also something I've started noticing in other events and presentations far more often, now that I've been bitten by it myself. When someone's demo video on a corporate call is impossible to hear, I now just have a healthy dose of sympathy for the organizer more than anything.

Three, thankfully, these criticisms were dwarfed by the positive response to the event's format and execution. Participants valued the opportunity to step out of their usual roles and engage with colleagues from different sectors of the company, gaining new insights and perspectives. This cross-pollination of ideas not only enriched the projects but also strengthened the communal bonds within Compass, cemeting a deeper understanding and appreciation of each other's roles and challenges.

While the task of organizing the hackathon was daunting and at times overwhelming, the rewards were unmistakably worth the effort. The event surpassed expectations, catalyzing a wave of enthusiasm around generative AI that I hope will continue to spread through Compass in the months and years to come. Most importantly, executive support for implementing these ideas seemed through the roof, and ensures my professional focus to come will stay right where I want it, locked in on these LLM-powered platform opportunities.

And of course, while I look forward to once again diving into the frenetic, sleepless world of hackathons, I'll definitely make my next role one of just a hacker :)