Inside the SaaStr 2023 Drama: WINN.AI’s CEO Shares Their Perspective

Published September 25, 2023

In a recent turn of events at the illustrious SaaStr Annual 2023, the world's largest SaaS community event, WINN.AI, under the leadership of Eldad Postan-Koren, found itself at the center of controversy. This massive gathering brought together over 12,500 SaaS executives, founders, and venture capitalists for three full days of immersive experiences.

SaaStr's essence was its community-centric approach, bringing together professionals from diverse backgrounds to celebrate innovation and collaboration. However, amidst this vibrant backdrop, the incident involving WINN.AI's ejection from the event raised questions about the fine line between innovative event marketing and maintaining professionalism.

“Our team came out to SaaStr with the goal of celebrating salespeople, who are often the hardest working individuals at conferences and tend to be overlooked. We wanted to put them at the center of our attention, show them our appreciation for their hard work and professionalism,” Eldad said. “We decided to do so in a few ways - first, by handing out gift bags created specifically for them and hyping them up, and later, by offering a short activity to help them recharge in a memorable and playful way.”

Staying true to their hype squad theme, the WINN.AI team caught the attention of security on day one and was asked to tone down their activities. But despite their adherence, they were asked to exit. “Eventually, we were asked to leave, as we were wandering around the booths area and handing out swag not being an official sponsor at the conference or having a booth of our own,” Eldad continued.

For the rest of the conference, their team regrouped, adjusted their plans and activities, and continued taking part in SaaStr without any further incidents, still achieving their goal of engaging and networking with salespeople who were at the event. 

When asked about SaaStr's focus on networking and business interactions, Eldad firmly believes that their team's behavior aligns with the professional atmosphere typically expected at such events. “SaaStr is an event known to put innovation at the forefront of its content and activities - both in terms of the companies and products that are showcased at the conference, and in the way companies do marketing at and around SaaStr,” he said. “It is where human connections and ground-breaking ideas are celebrated, which is exactly what our team set out to do. We took a fresh approach to event marketing and found a unique way to reach our target audience.”

Eldad continued: “We had one main goal for the conference - celebrating salespeople. It’s been a challenging time all around in the SaaS landscape, especially for sales teams. They are under tremendous amounts of pressure, with targets becoming even more aggressive and resources cut down. We wanted to take the time to support and appreciate sellers, and simply show them a good time. This reflects the mission of our company as a whole - WINN.AI is built entirely with the common salesperson in mind, designed to help them reach their goals by taking busywork and non-sales tasks off of their hands. As a product built to support salespeople, this is exactly what we wanted to do at the conference as well. We received great feedback from the people we met at SaaStr - they appreciated the thought and gesture, and the salespeople loved being the focus of attention for once. Beyond the incident, I’d say we definitely succeeded in achieving what we set out to do at SaaStr.”

Despite the behind-the-scenes drama, Eldad and his team expressed the exceptional and rewarding time they had at the event: “Though at times challenging, SaaStr was an amazing experience for us. We had a great time meeting so many people from the community in person, as well as some of our own customers, and connecting over a mutual passion for sales, AI and innovation.”

“WINN.AI’s overall approach is to be outstanding - to push boundaries and conventions, aim for excellence, and always try to generate our own path by doing things differently,” Eldad concluded. “Our strategy with events and conferences will continue to align with that - finding ways to take part in these events and stand out, while respecting the rules and regulations for each conference.”

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