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Stephanie Roulic of Startup Boston: “Take an audience-first approach for your tech stack”

Take an audience-first approach for your tech stack. Think about how every single person is going to interact with your tech. This includes the speakers, sponsors, attendees, and your own internal team. If your tech is confusing, no one will have a pleasant experience. As a part of our series about “5 Things You Need […]

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Take an audience-first approach for your tech stack. Think about how every single person is going to interact with your tech. This includes the speakers, sponsors, attendees, and your own internal team. If your tech is confusing, no one will have a pleasant experience.


As a part of our series about “5 Things You Need To Know To Successfully Run a Live Virtual Event”, I had the pleasure of interviewing Stephanie Roulic.

Stephanie Roulic is the founder of Startup Boston, an organization on a mission to connect, celebrate, and educate the startup ecosystem. Their flagship event is Startup Boston Week, where they bring together 3500 attendees in September for a 5-day conference. The organization also organizes events and other initiatives throughout the year to support the startup community. Prior to creating Startup Boston, Stephanie co-founded nDash, a content community platform, where she ran customer success and community.


Thank you so much for joining us in this interview series! Before we dive in, our readers would love to learn a bit more about you. Can you tell us a bit about your “childhood backstory”?

Of course! I grew up in Billerica, Massachusetts, which is a suburb North of Boston. I didn’t have a lot of friends. I was kind of weird. I don’t think it was a bad weird, though.

I was usually reading books, writing screenplays, outlining my dream summer camp, or practicing monologues for theater auditions. I did find “my people” when I joined the high school swim team. I really liked swimming because you’d cheer on for your own teammates, but at the end of the day, you just wanted to beat your personal record. It was a great lesson in understanding that there’s always room at the top, and you want to surround yourself with people better than you so that you are constantly being challenged.

Looking back, I think my creativity is what led me to create events and having a mindset of cheering on others while holding yourself to a higher standard is what led me to the startup world.

Can you tell us the story of what led you to this particular career path?

Would you believe me if I told you I fell into it? I never set out to be an entrepreneur. My first job out of college was as Employee #1 at a content marketing agency, called nDash Marketing. During my time at the agency, I grew close to the founder, Mike Brown, and he had an idea for a software company. I then helped him pivot the agency to the SaaS platform it’s known as today, nDash, in August 2016 and became one of the three co-founders.

As a new founder, I had a lot of questions about how to grow a company and I had no one to turn to. Enter Startup Boston. I created this organization as a way to grow my network and to create content around a lot of the questions I personally had.

Can you share a story about the funniest mistake you made when you were first starting? Can you tell us what lesson you learned from that?

Where do I even begin?

For the first Startup Boston Week, which happened September 2017, I thought it would be really cool to have a lot of locations — across both Boston and Cambridge — involved in the conference.

I still stand by this being a good idea, but I did not factor in the amount of manpower we’d need to pull off events on both sides of the Charles River. And we had limited manpower for that first conference. (For those not located in Massachusetts, it’s either a 25-minute car ride from Boston to Cambridge — on a good, no traffic day — or a 40-minute subway ride.)

So for the first Startup Boston Week, we did events in both Boston and Cambridge. And I didn’t realize until day-of how not-thought-through this plan was. It must have been pretty funny to watch me lug the conference signage into the subway. Sprint to one location. Just to sprint back over to the original location an hour later. I definitely got my steps in that week!

Is there a particular book, podcast, or film that made a significant impact on you? Can you share a story or explain why it resonated with you so much?

“The Hard Thing About Hard Things.” Hands down. The best book I ever read.

I feel like every time I pick up that book I learn something new. When I first read it, in 2017, I read a completely different story. I was new to the startup scene and read it as, “This is what to not do when you start a company.” Which isn’t entirely what the book was about but it is what I got out of it during that time in my (very new) career.

I’ve been re-reading the book these past few weeks, here at the end of 2020, and I’m reading an entirely different story. Perhaps it’s because of the pandemic and the effects its had on our economy. Or perhaps it’s because I left the company I cofounded, nDash, and am trying to figure out what’s next. But this time around I’m reading a story of how there is ALWAYS a way up. It may not be the one you were looking for. It may not even be the answer you want. But there is always a way out of whatever mistake you’ve made or circumstances you’re placed in to.

It’s a must-read for any founder.

Can you please give us your favorite “Life Lesson Quote?” Can you share how that was relevant to you in your life?

“Success consists of going from failure to failure without loss of enthusiasm” — Winston Churchill

The life of a founder isn’t easy. You need to know you’re going to fail. It’s not a question of “if,” but “when.” And accepting that truth is a very important step for life, and especially in entrepreneurial life.

Startup Boston wouldn’t haven’t gained traction year-over-year if I wasn’t willing to risk some potential public humiliation to see if a different type of marketing strategy worked or an event format or topic was interesting.

And you know what? Sometimes an event did flop. But I’m still here. We’re still kicking along, and people still love the brand. It’s okay. The big thing is to treat people with respect and to own up when you don’t deliver the results you expect. Don’t pretend it didn’t happen, own it.

Ok, thank you for that. Let’s now jump to the primary focus of our interview. For the benefit of our readers, can you tell us a bit about your experience organizing events in general?

Definitely! I’ve been organizing events for 7 years now.

Right after college, I did an internship with The Anthem Group in 2013. During my short 4-months there, I helped organize events such as Boston’s July Fourth Celebration on the Charles River.

Then, in 2015 and 2016 I volunteered with Geek Girl Tech Con and helped organize their one-day conferences in San Diego, Boston, and Cape Cod. I went from managing social media in 2015 to locking in speakers and helping to plan the agenda for the conferences in 2016.

Shortly after, I started Startup Boston in January 2017, our flagship event was Startup Boston Week, which launched in September 2017. This past September 2020 was our fourth year, we organized 70 events in 5 days, which brought together just about 3500 attendees and featured 260 speakers. We also made the decision in May to pivot the conference to a completely virtual event, which was a lot of fun to figure out!

And, additionally, through the 2020 calendar year, Startup Boston began to organize monthly events. These events consisted of our Cofounder Matching event, Founder Happy Hour, a few workshops, and a one-day Marketing on a Budget Bootcamp.

Can you tell us a bit about your experience organizing live virtual events? Can you share any interesting stories about them?

I’m a huge fan of doing live virtual events. I don’t like pre-recorded. I feel like at that point it may as well be a YouTube video.

For Startup Boston, 2020 was the year of live virtual events, as I’m sure it was for many others. Two weeks after Boston went into lockdown, Startup Boston was actually one of the first organizations to host an online networking event for entrepreneurs. It was a huge hit. We had over 200 people sign-up within the first 48 hours.

HOWEVER, we had SO much traffic for the actual event. We broke the tech. I kid you not. It turned out our event was too much to handle. Many, many people did not have a great experience.

What did I end up doing? I owned up to it. I emailed everyone to apologize and explained the situation. Do you know who was upset? No one. In fact, people thanked us for trying.

Lesson learned? Own up to a mistake. No one worth having in your life will get upset if you do that.

In your opinion, what is an example of a company that has done a fantastic job creating live virtual events? What specifically impresses you? What can one do to replicate that?

Any person — or company — that can do a great job involving the audience in their virtual event is amazing in my book. Too often (and I’m definitely guilty of this) virtual events treat the audience as a passive part of the equation, rather than someone who should be interacting with your content.

I’m going to give a huge shout out to Ande Lyons here. For each of her virtual events — whether it’s for Founders Live Boston or her Startup Life Show (which I was lucky enough to be on), she does an incredible job at pulling in audience participation.

What are the common mistakes you have seen people make when they try to run a live virtual event? What can be done to avoid those errors?

You can tell when someone never meets with their speakers prior to an event.

When you’re holding an in-person panel, for example, speakers have those final minutes prior to the event to meet-up and go over any questions they may have before they start. However, for a virtual event, you do not have this opportunity. And it’s REALLY obvious to the attendees when speakers haven’t had a chance to bounce ideas off of one another or meet each other prior to the event. The chemistry isn’t there, the discussion doesn’t’ flow, it just all seems off and can be super painful to watch.

So please make sure that you organize a call with your speakers prior to the virtual event to go over content and tech for day-of.

Which virtual platform have you found to be most effective to be able to bring everyone together virtually?

I’m such a fan of Remo. On this platform, you’re able to both run a panel and provide people with a place to network. However, since I organized Startup Boston Week 2020, there is another company on the rise here in Boston, Sophya, which I would say gives Remo a run for their money.

Are there any essential tools or software that you think an event organizer needs to know about?

For a virtual conference, you’re going to want a tool that helps attendees organize their schedule, notifies speakers about where and when to dial-in for their event, and provides everyone with a great networking experience.

For us, we piecemealed it together between HeySummit, Zoom, Remo, and Slack. However, I’ve heard great things about Hopin and Run the World. I’d strongly recommend checking one of them out since it does provide you with an all-in-one solution (or close to it). The less number of things you have to manage, the better it will be for you and your team.

Ok. Thank you for all that. Here is the main question of our discussion. An in-person event can have a certain electric energy. How do you create an engaging and memorable event when everyone is separated and in their own homes? What are the “Five Things You Need To Know To Successfully Run a Live Virtual Event” and why? (Please share a story or example for each.)

One. Take an audience-first approach for your tech stack. Think about how every single person is going to interact with your tech. This includes the speakers, sponsors, attendees, and your own internal team. If your tech is confusing, no one will have a pleasant experience.

Two. Think of ways to involve your audience. I can’t say this enough. At an in-person event, this happens organically. During a virtual event, you need to think through this and initiate it. Ways to do this could be providing them with a Slack channel to chat in, involving them in the speaker nomination process, or having them vote on which events they’d like to attend. It’s really important to make them feel that they are a part of the event.

Three. Have help documents for everything. When you’re in-person, an attendee, speaker, or sponsor can easily walk up to someone on staff and ask questions. Virtually, it’s a bit more complicated. Prior to the event, you can save yourself a lot of time (and headaches) by writing up help guides for the attendees, speakers, and volunteers. Additionally, you cannot assume that everyone knows how to use your event tech, such as Zoom or Slack. So make sure you cover all of the bases.

Four. Be accessible to your attendees. It’s important that there is a clear way for attendees to reach out to you with questions. For us, we had someone managing our help channel in Slack and our email inbox. You need close to instantaneous support during your event so no one misses out.

Five. Train, Sleep, Repeat. It’s so important for every single person on your team — and involved in the event — to have a training session prior to showtime. During a virtual event, you can’t always be there to control the outcome. For Startup Boston Week, we had training calls for internal staff, day-of volunteers, speakers, sponsors, and everyone in between.

Let’s imagine that someone reading this interview has an idea for a live virtual event that they would like to develop. What are the first few steps that you would recommend that they take?

The first step, of course, is creating the agenda and understanding who your audience is.

However, after that, the next thing you should immediately think about is the attendee experience: how can you provide them with an event they won’t forget?

Nothing else should happen until you figure this out. Your tech, speakers, marketing materials, everything leading up to the event revolves around that decision.

Super. We are nearly done. Here are our final questions. You are a person of great influence. If you could inspire a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger.

A world-wide mentorship program. Too often we’re caught in our own bubble, it’s great to hear how others are doing things on the other side of the globe. If anyone feels like tackling this with me, hit me up on Twitter!

We are very blessed that some of the biggest names in Business, VC funding, Sports, and Entertainment read this column. Is there a person in the world, or in the US, with whom you would love to have a private breakfast or lunch, and why? He or she might just see this if we tag them.

This one is going to come out of left field, but Taylor Swift. She has successfully re-marketed and cross-promoted herself more times than I can count. That girl is everywhere. Some of her songs I like, others I don’t (no offense, Taylor, if you read this). But I admire her. The brunch (yes, brunch) would consist of picking her brain on how she does it successfully — so that she keeps her current audience while picking up new fans. I need to know her secrets.

Thank you for these fantastic insights. We greatly appreciate the time you spent on this.

Thank you so much for having me!

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