How We Ran a Virtual Summit with 20 of the Biggest Software Brands and How You Can Too
October 14, 2020
Customer Journey

Creating a virtual summit four months into a pandemic might have been a questionable decision. Remember, that was back when things like Zoom Happy Hour and virtual hangouts with friends and family were a thing.

Even with the knowledge of such distractions, we forged forward with the plan and, oh yeah, we decided to do it in a little over three months.

The FlyOver Tech Fest was a success because of the fantastic speakers from organizations like Zendesk, Sprout Social, Sales Assembly, ActiveCampaign, Dwolla,, and 16 others.

There were also over 400 registrants who listened to the over 8 hours of content from 18 different sessions that all focused on doing more with less.

We’ve been asked how we did it. So, we put together this post to provide a lens into our planning and to remind us of the grind when we start planning for the second Fest next year.

The Why

As we started to develop the concept for the Fest, we read a lot about planning virtual summits. Everything we read said to start with the end in mind, to really plan out our goals and answer these three questions:

  • What do you want to teach your attendees?
  • Which tangible skills, lessons, or key takeaways do you want everyone to have at the end of your event?
  • Does this relate back to the greater purpose of our business and help accomplish any meaningful business goals?

The pandemic illustrated the obvious, we were doing more with less daily, and we knew we were not alone. All organizations were forced to shift or lean on technology more to balance remote staff and keep business as usual.

We also wanted to widen our net a little, just to be transparent. We built a pretty great conversational AI solution that solved the lead follow-up problem in the real estate industry, but it is not just a product for Realtors. It is a product that has evolved to solve lead follow up problems in other industries. Plus, we were on target to launch a pretty cool new product, with the planned launch of our AI Email solution. We knew an event like this could help us make new connections and provide ample opportunities, maybe even a few new clients.

So, we started brainstorming and came up with ‘flyover’ first, mostly tongue and cheek, because of the previous connotation tied to that term and our region.

Then, to differentiate from the other virtual summits, we decided on the ‘tech fest’ aspect. Our initial thoughts were to make it the Coachella of virtual summits, but that part of our branding found its way to the cutting room floor after a bit.

Yet, in the vein of differentiating, we didn’t want long drawn out sessions that would put our registrants to sleep, no matter how engaging our speakers were. We decided to keep the sessions short, no more than 20 minutes to keep it moving, and provide a good user experience.

The Plan

Before we started any outreach we created a wish list of speakers who we thought would make sense given our concept. We had some big names on that list, even including the Iowa native Aston Kutcher. After all, he is in the tech space and he loves Iowa just like we do.

But, his name settled a little lower on the list because we didn’t have an immediate connection to him. Instead, we reached out to those speakers who we were connected to. A crazy thing happened, they accepted, or they passed but connected us to other speakers in their networks.

Before we knew it we had the foundation to a pretty great event, which meant we never even reached out to Ashton. It seemed the concept of talking about companies in flyover country doing more with less resonated.

Our Fest had legs, and even an awesome list of initial speakers. 👏

Virtual Summit.

The How

We realized shortly after the first speakers started accepting that we had to put-up or shut-up and really drill down on getting the back end in order because the last thing we wanted to do was get a pie in our face from not following through.

But, as we said before, we’re an AI company with one marketer and a staff laser-focused on supporting our customers and building sweet products.

We needed help.

The Platform

So, rather than trying to spin up our own registration website, we decided to do more with less and engage a solution built to host events. After quite a bit of research, we decided on HeySummit.

HeySummit provided everything we thought we needed going into it. It is a platform that integrates with the usual video sites, Youtube, Vimeo, and Zoom to name a few. It has a landing page builder, plus the capabilities to accept registrations and provide a great user experience. The image below is a shot of their Dashboard:


For us, it was a gold mine, and getting that spun up allowed us to then focus on the other major backend item, video production.

Video Production

The last thing we wanted to do was try to produce the Fest ourselves. We may have been able to get by, but getting by was not our end goal. We wanted to provide the best user experience we could and make this thing look professional.

After a little brainstorming, we reached out to our friends at The Pixel Labs to see if they’d be interested in taking on the challenge. We’d worked with the fellow Iowa company before and we knew they produced fantastic videos. But, we didn’t know if they’d want to produce a live event like this or even if it was in their wheelhouse.

Thankfully, they were interested, and just hearing that lifted a big weight off our shoulders.

Video Production.

The Promotion

We initially thought we could get 1,000 of our closest friends to attend the Fest, that was even after we read that we should set realistic goals. Looking back that number was very aspirational considering we’d never done anything remotely close to this and we didn’t have the largest network.

Our plan started in July the initial outreach efforts to like-minded organizations and publications close to us. We initially went the route of submitting story ideas on regional publications like the Silicon Prairie News, Clay and Milk,, and many others.

We knew we had minimal reach on our own and our speaker networks certainly would help, but we needed earned media to truly get to the masses.

We got picked up by a few publications, you know who you are and we thank you the heck out of you. We had interviews with several larger publications, but they decided to pass on our story. 😢

Then, we turned to social media. Rather than creating new handles for the Flyover Tech Fest, we decided to use on our own Structurely platforms, even though we don’t have a large following on those platforms. But, we knew we had the leverage of an amazing speaker list and the brands they work within our back pockets. So, we thought we could get the word out to the masses with our plan and the help of our speakers.

Looking back, we may have teetered a little too close to the obnoxious line with our @ mentions of the brands and speakers. But, we knew sending out a Tweet – for instance – just to our followers would fall flat without their help.

sending out a Tweet.

We decided to mimic the rollout plan from SaaStr and release only a number of speakers each week rather than just rolling them all out at once. This allowed for a little suspense and a great opportunity for ongoing content. Our weekly rollout plan included a blog post on featuring the weekly speakers and focusing on the tangible lessons learned from each session.

Here is the initial marketing plan.

We remained optimistic during the first few months as registrations trickled in slowly. We read that 60% of registrants would wait until the week before or the day of to register, plus we knew we were guilty of doing that ourselves.

Video Production.

Guiding the Speakers

So, with the belief we would eventually get registrants, we then focused on supporting our speakers.

Our speakers are rock stars in their businesses which keeps them very busy. So, to help guide them along the way we planned several touchpoints.

We initially reached out to them with a warm introduction just to let them know who their contact was and to let them know they’d be getting an email from the HeySummit platform.

We leveraged the initial speaker email template in HeySummit to send them a link to their speaker dashboard in that system. We were able to find their bios and headshots online so most of that initial effort was just to have them review the content so they could make changes if they wished.  

Then, as our backend structure started to mature we would send them emails with links to social content, here is an example of the Google Drive we created for the speakers with social assets.

example of the Google Drive.

Lastly, we sent them a Speaker Guide that walked them through the day-of expectations. As we said before, our speakers are very busy individuals, so even though we laid out all the directions in the Guide we knew it was likely they would not read every word.

So, as a last point of clarity, we sent out an email with the subject line that read – The 1 Link You Need for FlyOver. That email had an initial link to their Tech Room and then, in true marketer form, several other links that we thought they might need.

We also created a Slack group for speakers to join for day-of troubleshooting that turned out to be a great assist. Not all of our speakers joined the group, but for those that did it helped to have a means of communication with them for last-minute questions, etc.

Looking back

We’ve been overwhelmed with the success of the Fest. It was a huge success, even though it is soon for us to see if it has any benefit to our revenue numbers.

Numbers aside, we learned a tremendous amount about putting an event together. But, more importantly, we learned a ton by listening to the amazing speakers; their tangible lessons learned will have a tremendous impact on our business that will transcend revenue.

Most of our technical issues were minor with the exception of chat. Even though chat worked during the two times we tested, it failed us during the live event. Ideally, you would have found the chat option below the video page during each session. We even had a member of our team ready to moderate the chat with the end-goal of creating conversation and a transition to the Do More WIth Less Facebook group.

success of the Fest.

We were pretty bummed chat failed, but the show had to go on.

If we had one suggestion for a lesson we learned along the way, it is to not rely on your speakers to push your messages. Our speakers were tremendous and they did share with their networks and helped us grow the Fest. But, our expectations were a little lofty considering how busy each of the speakers were.

Our word of wisdom to you is to work harder to get contacts with your earned media opportunities way before you start creating your event. If you can leverage those relationships to get stories about your event published it will go a very long way towards hitting your goals.

Good luck with your planning. Reach out to us if you have any questions, we’d be happy to help.

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