How To Take an In-Person Event Online: Q&A with Startup Boston

2020 has become the year of online events — from team meetings and family happy hours to weddings and professional conferences. 

We’ve learned that online events have the potential for record numbers of attendees, global participation, and the opportunity to wow audiences. However, it can be challenging to leave behind the excitement and familiarity of in-person events for the new and evolving virtual landscape.

Stephanie Roulic, founder of Startup Boston, has navigated that transition firsthand. COIVD-19 hit in the midst of her planning the fourth annual Startup Boston Week, a free, week-long event series with 70 sessions that bring together entrepreneurs, company leaders, innovators, and industry experts. After three successful years of drawing hundreds of attendees to learn and connect, she was faced with the task of translating that highly anticipated in-person experience into an informative, enticing online format. As the COVID-19 pandemic continues, it’s a challenge that more and more event organizers will have to grapple with. 

So, we sat down with Stephanie (virtually!) to get the inside scoop on how she and her team pivoted and reimagined their massive yearly event. In the interview below, the Startup Boston founder shares what excites her about the world of online events and tips for getting the most out of an online event experience. 

CIC: Let’s start with some simple background. How did you get started with Startup Boston?

Stephanie Roulic: I founded Startup Boston in 2017. I was a new startup founder myself and had a lot of questions. I went to some events, but they were light and fluffy and didn’t provide the answers I was looking for. So I thought, “I’m going to go create a bunch of events to answer the questions I have and build my network along the way,” and Startup Boston Week was born! Startup Boston Week went really well the first year, and now we are gearing up for year four. As a result of that success, we’ve spun out into the organization Startup Boston that presents events throughout the year in addition to our flagship event, Startup Boston Week

CIC: Planning these large in-person events takes so much time and organization. What was the experience like for you to pivot your 2020 event plans in the face of a crisis?  


SR: The minute COVID hit, Christine Zimmermann, our head of marketing, predicted that this will probably go on for a long time. We were fortunate enough to have her foresight, and we started pivoting the conference the minute the shutdown happened in March. We already had some other in-person events planned throughout the year, so we decided to do all of those virtually. 

It’s been a trial by fire approach. We had our first online event shortly after the shutdown, and it didn’t go so smoothly in terms of our tech setup. But we did another one and started to figure it out! 

We ran a day-long Marketing Bootcamp in May, and that was our real trail run for Startup Boston Week. We had to see: Can we do a mini-conference online? 

We are always super focused on planning events that have actual takeaways. On a virtual platform it is even more important. Because if you aren’t providing people with connections they can’t get normally or you’re not providing people with actual information they can use immediately following the event, then they will just zone out and not listen to you. There’s also less room for content mistakes; it’s frustrating for the presenters, as an event organizer you feel like you’ve failed, and attendees don’t leave with a good experience. So as we go into the virtual world, we have been working on centering those take-away points of an event even more. 

CIC: That’s what we’ve heard so many times and discovered ourselves: A virtual event is like a television broadcast. It needs to be meticulously planned and you need to be really on top of it. 

SR: I hope that that continues after this! It really forces people to think about what they are doing. There are so many cool events happening right now, like Founders Live has a really cool online event experience and Pitch Madness did a great in-person event that’s now online, and it’s just a whole new level. I hope it continues even when we go back to in-person, because everyone’s getting some awesome and creative content right now.

CIC: On the logistical side, do you have a preferred platform? How did you choose that platform?

SR: We definitely did a ton of research on all of the platforms. We’re using Zoom because everyone is on Zoom already, so the learning curve is shallow. There are so many other things that can go wrong during an event, so I wanted to minimize the potential of tech failing us. We’ve used other platforms in the past, and I am okay trying something new for year-round events. But for something like Startup Boston Week, where we’re doing 70 events in five days, I just do not want to stress about the tech not being able to support traffic or the speakers being confused. 

CIC: Are there any new and exciting elements of virtual events that weren’t options for in-person events that you can now tap into?

SR: I would make the argument that it’s easier to connect at virtual events than it is in person. If you’re already social, talking in the chat box is second nature. If you’re shy or more of a homebody, the chat box can be a lower risk way to start making connections with people and build your network. 

As an organizer, if you understand the tech you’re using and if you think ahead, you can facilitate those interactions. During our bootcamp in May, for instance, we had the speaker speaking on one screen and we had no attendees drop off during the entire time, which is in itself impressive. We had, on average, 130 people in each event who then stayed for the entire presentation, and we also had all these people networking in the chat box on the side. I was in the chat telling people to ask questions, ask speakers questions, make some connections, share some info — basically prompting interactions the whole time. 

We’ll be doing the same at Startup Boston Week. Anyone who has attended our past events knows that at the beginning of every session, I make people move around and network for 15 minutes. This year we’re going to do a version of that but online. We’re also going to open up a Slack channel just for attendees. For the week before, during, and the week after, you’ll be able to touch base with people who you want to talk to — speakers, sponsors, and attendees. 

CIC: Do you have any tips for anyone who might be a hesitant networker but is trying to get their foot in the door in a virtual way?

SR: There’s one sentence that I think will work every time, and I’ve given this advice to people and heard that it works: Drop a note along the lines of “Hey, my name is [X] I’m from [organization]. I do [XYZ]. Please connect with me if there’s something I can help you out with. I would love to support you.” No one is going to be upset by that.

I think the worst thing you can do online is ask, ask, ask, ask. When people do it in person, you actively avoid them in the room. But if you lead with a happy, open heart that’s willing to help, it’s going to go over well whether you can help them or not, because you’re approaching with the right mindset. 

An in-person session at Startup Boston 2019 explored the keys to successful networking.

CIC: I love that advice. I feel like that’s very similar to advice that I’ve gotten about in person networking as well: Don’t focus on the sale, focus on what you can do for the other person to help them! And now you can do it in your pajamas…

SR: Pajamas are key, that is the core advice. 

CIC: So for my last question — looking ahead to Startup Boston Week 2020, are there any speakers in particular, sessions, or content areas that you’re really excited about this year?

SR: Yes! We launched two new tracks this year, a student track and a data analyst track, so we now have a total of ten. I’m excited about that because we’re connecting with even more groups of people and really pulling them into the startup scene. 

The second thing we’re really excited to be doing is hosting a founders essentials bootcamp on Wednesday morning, September 23. The bootcamp includes four, 30-minute events and one hour-long event providing very informative, hyper-detailed content to founders on how to successfully grow their business. We’ll be answering a lot of questions about equity, hiring things from a legal standpoint, IP management, and so on. We’re really breaking down the nitty gritty legal and admin details for building a company. 

Key takeaways for planning or attending online events

  1. Practice makes perfect, and plan ahead. 

  2. Hone in even more on what you want your audience to learn and take away from your event.

  3. Virtual networking is possible and effective.

  4. When networking online or in-person, focus on how you can help those around you.

Additional resources for planning online events

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