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How to Pivot to a Virtual Conference: Behind the Scenes of Startup Boston Week 2020

Updated: Nov 14, 2020

As some of you may know - shame on you if you don’t 😉 - we just wrapped up our FOURTH Startup Boston Week. And it was 100% virtual!

Due to the influx of questions and emails regarding how this conference went and what we did to organize it, in this blog you’ll find some information on how the team went about pivoting our 2800 attendee conference (3400 attendees this year!) to a virtual setting.

Hope you find it useful!

Laying the Groundwork

Before we figured out anything else, we went through the current line-up of 70+ events and asked three, very pivotal questions:

  1. In the virtual setting, are we keeping the same events?

  2. What event formats do we need to change for an online conference?

  3. How can we foster connections during SBW, even though it won’t be in-person?

From there, we then made the tough decisions to cut a few events and to roll back a few new formats we were playing around with. But, we were very excited to explore what tools were out there that would prompt virtual networking throughout Startup Boston Week.

Takeaway from this brainstorming process: as an event planner or community organizer, it’s really important to identify what you can deliver upon when pivoting your conference - and what you have to let go with prior to “show time.”

A few things that we changed in our schedule, just to give you an idea:

Item #1.

We would typically have “Track Days,” but instead, given the Zoom fatigue, we split each track into two half-days. This way, if attendees did want to attend all events within a specific track, they’d be at a computer for 5 hours (at most).

Item #2:

For in-person, we didn’t usually plan for a lunch break. In fact, we’d put our most popular events during lunch so attendees could easily “swing by” during a quick office break. However, in a virtual setting, we slotted in the lunch hour and didn’t hold events during that time.

Why? Behind the scenes, we really needed that hour to change out volunteer teams (we had two different shifts) and to provide ourselves with a mini Zoom break as well.

Item #3:

For in-person events, we’d typically block off 1.5 hours for each event. In addition to accommodating the panel or presentation, that 1.5 hours would also include time for attendees to network prior to event kickoff. In a virtual setting, we dialed the time for each event back to one hour.

Why? After hosting many virtual events over the past few months, there’s a definitive dropoff after the first hour of any event. So it seemed natural to prioritize questions and limit each event to 60 minutes max.

Our Tech Stack for SBW2020

When you organize an in-person conference you have to think about t-shirts, signage, catering, swag...but in virtual. It's the tech stack. Here’s what we used.


In past years, we created an Eventbrite page for every single event (that would mean managing upwards of 60+ Eventbrite pages per conference). This year, we decided to spend the money for a ticketing platform. This way attendees would register once, and could then build their schedule from there.

For us, HeySummit was the right choice for us. Not only because it was designed for a virtual conference, but because it was also the best “bang for your buck.”

Cost: We paid $99/month, which would accommodate up to 7000 attendees.


For all panels, workshops, debates, and presentations we used Zoom. Most of you are familiar with Zoom. This is exactly the reason why we chose it.

Rather than have a steep onboarding process for our attendees, we wanted to make this as easy as possible for them. So we used a tech that most are familiar with.

Additionally, we didn’t want to run into any tech snafus, and in our experience, Zoom has been the most dependable.

Cost: For us, we never had more than 3 events running at any given time, so we invited in 3 Zoom Webinar subscriptions that could accommodate up to 500 attendees ($140 each).

Additionally, we paid for cloud recording storage on each of these subscriptions ($40 for each line) and, in order to upgrade, you have to pay for the standard Zoom subscription as well (three pro plans at $14.99 each) .


For our big ticket networking events - our Opening Party, Job Fair, and Cofounder Matching event - we utilized Remo. Why?

For the Opening Party and Job Fair, we could easily label each table so attendees would know exactly which companies and organizations were exhibiting, making their networking efforts a lot easier.

For the Job Fair, we wanted to replicate an “in person” networking event as much as we could, and Remo provided us with the best layout.

Cost: We used the Director plan, which cost $450 and accommodates up to 200 people.


While we were virtual, we still did want to provide attendees with a chance to mingle and form connections. While we can’t replicate exactly what would happen in-person, we did what we could to really help attendees meet one another in our Slack channel.

We had a Slack channel for each track, in which we shared highlighted notes and partner offers, and we also sported a few other channels as well, all of which were created to help attendees form the best connections we could support. This included Job Postings, a Coffee Buddies channel (we scheduled many 15-minute video speed networking sessions there using Icebreaker!), Mentor Matching, and a few others.

Cost: this was $0.


While Slido is a great platform, we did find out on Monday that it was tech overkill to use it during the conference.

Initially, the idea was to point attendees towards Slido during any of our events to ask speaker questions. However, we quickly found out that attendees felt most comfortable asking questions via the Zoom Chat and pivoted our efforts during the week.

Cost: this was $0.

Main Takeaways

I am so incredibly thankful that we did a trial run of a virtual conference in May prior to Startup Boston Week (check out those takeaways here).

To any organizations or people who are thinking about organizing a virtual conference: I STRONGLY recommend putting together a half-day or full-day conference prior to a week-long one. OR if you’re gearing up for a full-day conference to do a LOT of one-off virtual events.

Event if you don’t have a large number of attendees for those events, it’s well-worth the effort. There are so many things you’ll learn along the way, and there’s no blog post (even this one) that can prepare you for all of the surprises that come up.

What Were Our Surprises, You Ask?

Takeaway #1.

When you’re at an in-person conference, you can tell when the speakers have arrived. Likewise, you know when attendees are getting restless prior to going live.

Write up training guides for everything. We did one speakers, another for attendees, and a third for our internal team. And then go into the assumption that most won’t read the guide.

If we were to do this again, I would absolutely make training calls mandatory for speakers and would likely have an open forum for attendees to ask questions prior to the event. I think that would minimize a lot of frustrations and panicked emails.

Takeaway #2.

Tech will always stop working on the day you need it the most. ALWAYS. Without fail. Always.

So in the guide you create for all parties involved in your conference, please outline your Plan B, Plan C, Plan D, Plan E, you get the idea. I can’t begin to explain how many backup plans I outlined prior to the conference. I think most of the team will tell you that my big catchphrase in the weeks leading up to it was “I don’t want any surprises.”

Because I didn’t. I wanted a plan for anything that could potentially happen. And I’m pleased to say that there was (almost) nothing that caught me off guard.

So what did catch me off guard?

Initially we weren’t going to be sharing recordings of the events. But automated emails from HeySummit (I still don’t know where they came from!) told attendees repeatedly that recordings will be made available.

So, spoiler alert: we’re editing the videos and they will be made available. Stay tuned for when they’ll be live by signing up to our mailing list at the bottom of this page.

Still Have Questions?

If you have questions that aren’t addressed in this blog, then I hope you’ll shoot me a note on Twitter (I’m @stephroulic). I’m always looking to write blog content that’s useful to you, so I’m more than happy to incorporate some of your questions into my next post about organizing virtual events!

And you can watch ALL events from SBW2020 right here.


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