Flight 2020: Takeaways from hosting a virtual summit for founders

Posted: 13 October 2020

2020 has been an avalanche of Zoom events. So, as we were planning the fourth annual Flight, our early stage GTM focused event for enterprise founders, we had a debate about whether we should still go ahead or not. Do we really need one more Zoom event? Will it be valuable even when people will not be able to meet each other? Can the learnings still be as valuable virtually? In the end, the decision to go ahead was clear and the reason for that was simple: there is no other event like it in Europe.

The first steps of go-to-market for an enterprise software company are extremely hard. At Flight, we bring together world-class enterprise software founders and executives to share very concrete lessons and learnings on how to navigate finding and closing the first customers, bringing on the first commercial hires, and scaling to product-market fit and beyond – all while avoiding some pitfalls they have experienced themselves. In order to make sure the content hyper-relevant for every attendee, we keep the event invite-only for founders of early stage enterprise software and deep tech companies. By doing so, both the speakers and the attendees get the most out of the event.


“Really, really stellar. Thanks so much for including me. I’m on a lot of these zoom events, exclusive or not, from top tier VCs or not, and this one stands out as one of the most valuable ones by far.”
–Flight 2020 attendee

This year on October 13th we were fortunate enough to host an absolutely stellar lineup of speakers, such as David Sacks, Marten Mickos, Jennifer Bers and Anthony Kennada, and the event was attended by around 150 founders and executives from across Europe.


Selected nuggets from the event

In our opening talk, Aneel Lakhani shared 10 hard truths about the first steps of going to market. Among others:

  • Focus focus focus! 5 use cases + 3 verticals + 2 GTMs is mediocre. 1 use case + 1 persona gives you a 10x story improvement.
  • Your customer’s story is more important than your story – so you need to make their story awesome by focusing on their pain and how you can transform their story.
  • Whoever knows how to sell your product runs your business. You need to learn how to find customers, convince them and their teams, onboard them and make them fall in love with your product. Only then can you recruit someone to take over.


Followed by Melissa Lester’s talk about how important great messaging is to get in front of customers. From getting the “why you, why now” right to a tailored industry snippet and selling your value prop to closing off with a concise call to action. Increased conversion rates, here we come!

“I really enjoyed how practical this was for enterprise sales / b2b – most conferences try to cover that and much more, which dilutes them badly I think. I already managed to make use of Melissa’s messaging tips in my round of cold emails tonight.”
–Flight 2020 attendee

We wanted to balance these highly concrete lessons with some softer, more inspirational talks as well. Nick Mehta, CEO at Gainsight, shared his human-first leadership approach. As Nick put it, the “war-time CEO” mantra is too widespread and the war metaphor gives CEOs an excuse to forget that business is still fundamentally about leading human beings. Leadership is Human and should be centred around that first. This starts with the “why” and the values of your company. At Gainsight, the values they defined at the start have stayed the same to this day.


Any hesitation we had about hosting Flight virtually was thrown out of the window very quickly as the event kicked off. The quality of content, the attendee engagement and the feedback after the event were all fantastic. However, we will keep our virtual events to a minimum and optimise for quality over quantity. We hope the 2021 version can take place in person again.

If you are interested in attending Flight 2021 or any of the smaller events we host throughout the year, please do not hesitate to get in touch!

/Crane Team


Full Flight 2020 agenda (October 13th)