Startup Weekend

Organizing Startup Weekend, the Freshworks way!

Written by on May 14, 2018

On 14 April, 2018, I had the opportunity to organize a ‘Startup Weekend’ event at Freshworks. 

The 54-hour event was designed to give aspiring entrepreneurs a chance to turn their ideas into prototypes with the resources available to them.

Part of my job as the organizer was to ensure that the participating teams were provided with the resources they required to build their prototypes, and also see to it that the teams possessed diverse skill-sets.

Organizing the Startup Weekend

This sounds like an easy task but the organizing team and I were met with a plethora of challenges which would nearly jeopardise the event. We managed to tackle these challenges, and learnt a lot along the way. I’m putting some of these things down so you can learn from our experience and don’t make these mistakes yourself.

Challenge 1 – Surviving the odds

One of the primary objectives for the event was to have the right mix of designers, developers, and sales individuals so that the teams formed could be self sufficient. But this proved to be a tall order.

While there were good communicators who could pitch the idea, trying to find people who can actually build a prototype was harder than expected. Around 65 registrants were needed to break-even with our expenses, but we had just 20 registrants by the final week before the event. To compound that, about 90% of our registrants at the time were from sales, which completely defied the balance that we were looking for.

In attempt to tackle this, I approached a colleague from the Freshsales marketing team and the product head of Freshteam since they have experience in handling such events. They had suggested certain active startup communities on social media that I could target, and also gave me tips on experimenting with our pricing so that it appeals to different communities.

Though we weren’t able to get immediate results, we were able to see these efforts paying off towards the end. A shoot up of enquiries from different channels helped us get registrants with diverse skill-sets from 20 to just over 65 in the final week. Having come a long way from the brink of cancelling the event, it was now time to redirect our efforts towards ensuring a smooth experience for our participants.

Challenge 2 – Overcoming uncertainty

The day of the event had finally arrived.

Somewhere amidst the excitement and nervousness of hosting the event, I found myself in a precarious position.

Since the venue accommodated both small and large organisations, security had always been a primary concern for the authorities.

Prior to hosting an event which predominantly had participants from outside, certain security measures had to be put in place.

I sought help from a colleague from the corporate marketing team for this since he had organized multiple larger events at this venue. Not only was I able to seek out permission from the right people, (which believe me is tougher than it sounds when you’re new to the organisation), I also had a fair idea on what sort of issues I could expect.

For instance, though the space where the event was being conducted had power outlets, it wasn’t enough for all the participants. With the event format resembling a hackathon, this was very important for the participants to work on their ideas using their devices. Extra junction boxes were made available to accommodate this need, even before the problem occurred.

There were many such potential issues that were solved which helped us stay more organized and prepared.

Challenge 3 – Presenting opportunities

Most events like this are expected to have a return on investment.

When you have participants who are investing their time and money to attend an event you are organizing, there must be some value from it for them.

There were three ways in which we ensured this:

  • Event partners who can provide the right opportunities outside the event
  • Experienced mentors and judges to guide them
  • Adequate resources for them to push through till the final day

We recognized startup incubators to be a great way for aspiring entrepreneurs to get the required exposure to work on their ideas. With this in mind, we were keen on getting some of the most recognised incubators, like TiE Chennai, IIT-M, and Paypal on board. The participants had the opportunity to get selected for incubation programs to continue working on their ideas post the three-day event.

The next area of focus was creating a productive environment for learning, and bringing in the right judges and mentors to ensure this happened. I turned to colleagues who were previously founders of startups (Frilp and Chatimity) that were acquired by Freshworks.

Startup Weekend - The audience

The event was planned such that each team had the opportunity to have a one-on-one session with the mentors. I had taken the liberty of asking the participants for their feedback on the event. One of the participants said this:

“These sessions helped us not only evaluate our ideas, but also to look past the surface and analyse the downfall areas that need to be addressed by integrating go-to-market strategies, user onboarding experience, etc.”

This was, in retrospect, one of the biggest value adds for participants from the event.

Lastly, we managed to make sure all the required resources were provided. From stocking up on nourishments to providing a fully equipped stage for the final presentation, everything was taken care of. The facility manager of Freshworks was instrumental in ensuring that everything was in place in the venue. I’ve always heard that sponsors can be very difficult to work with but our sponsors present (Nestle, Redbull, Reynolds, to name a few) were very accommodative and ensured that all the participants were equipped to burn the midnight oil and work.

Out of the 14 teams that stood locked in their positions to present their ideas to the panel, three teams were selected. The winning teams had a membership opportunity with TiE Chennai and many other incubation opportunities at stake. One of the three teams, a food venture, even had their first set of customers at the venue.

Startup Weekend - Glad to have been part of it

The whole thing left me feeling euphoric.

Despite not being directly involved in the Startup Weekend, Freshworks folks stepped in and came to my aid on more than one occasion. As I watched the hard-work from my participants and the organisers pay off and result in a successful event, I realized a large part of it was possible only thanks to the teamwork involved. It is to this teamwork that I credit the event’s success.

Startup Weekend - The whole gang


Arjun Sampath

Business Development Executive at Freshworks