The Challenges of Running a Startup Through the Eyes of the CEO

By: Ishveen Anand, @IshveenAnand

Everyone knows that startup life is challenging. As CEO + Founder of OpenSponsorship, a marketplace that connects brands to professional athletes, teams and events, I am no stranger to challenges. Thus, I figured it would be nice to give the readers of Front Office Sports an insight into some of the real challenges of running a sports tech startup, and how we think about solving them.

If at any point you have ideas, comments or feedback, feel free to drop me a note at my email address below.

So this past month a lot of focus internally has been on the matchmaking process we implement between brand and sponsorship opportunity. What makes one NFL athlete better than the other for a nutrient or headphone brand? What data do we need to collect to support the match? Should the pricing be coming from us, or the athlete? Do we suggest to the brand how much they should spend, or just ask them a budget?

The biggest thing with challenges like this is that there is no right answer. Let’s think about dating sites — some people prefer Tinder i.e. a free-for-all; others like a highly curated but still expansive selection like Happn based on location, and then others want very few options such as a Coffee meets Bagel. All three have their place, and it’s no different in any other matchmaking service whether you think insurance, hotels or recruitment.

At OpenSponsorship we started off by offering a non-curated marketplace where brands and athlete, teams, events could communicate freely. This created a good amount of deals, but also led to some brands informing us that finding the right match was taking too much time. However, if we switch off the open communication and give brands too few options, there is very little difference between us and a traditional agency. So it seems the trick is to have something in the middle — a good number of options with matches suggested by the platform, backed up by data and reason. This solution would allow the brand to think less, trust the technology and become more efficient in its sponsorship process.

By honing on in what we wanted to achieve for the brand and athlete to enter a deal easily and successfully, we needed to decide what data points would be of relevance to us, as well as considering time and cost to implement. Social media geography, interests, pricing all play a part, and so an algorithm combining these criteria and more will lead to success. Having outlined the business goal, the challenge is passed over to our CTO to pull in the various data points, and integrate to the platform. After which point, our front-end developer decides how this will be framed for the user to see. It’s a a team project, and only once everyone buys in that we have the right solution and it’s the right priority thing to address, do we move forward.

We are in the midst of doing this now, so wish us luck, and I will be sure to give a update in the next “Challenge” article.

Ishveen is the CEO and Founder of OpenSponsorship. She can be reached via email at