Community//

Jessica Wise of HelpSquad: “Plan ahead and give yourself more time than you think you need to prepare”

Plan ahead and give yourself more time than you think you need to prepare. We pulled our event together in 30 days. In hindsight, it made the planning and organization process more stressful than it needed to be. We pulled it off successfully, but at times it felt very rushed. If you’re going to host […]

The Thrive Global Community welcomes voices from many spheres on our open platform. We publish pieces as written by outside contributors with a wide range of opinions, which don’t necessarily reflect our own. Community stories are not commissioned by our editorial team and must meet our guidelines prior to being published.

Plan ahead and give yourself more time than you think you need to prepare. We pulled our event together in 30 days. In hindsight, it made the planning and organization process more stressful than it needed to be. We pulled it off successfully, but at times it felt very rushed. If you’re going to host a successful, professional virtual event, I recommend giving yourself at least 60 days to plan and execute. Depending on the size of the event, you might even want to give your team more time.


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 Jessica Wise.

Jessica Wise is the Creative Marketing Manager for HelpSquad, a 24/7 live chat agent service and an avid customer experience blogger.


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”?

I was born and raised in Northeastern Pennsylvania. Growing up in a rural area, I spent a lot of time outside. This led to me being more into play that involved imagination than play that involved tangible toys or games. From an early age, I loved participating in any activity that required thinking outside the box (i.e. hide-and-seek, tag, etc). I think this part of my personality has definitely carried through to adulthood.

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

I have my B.A. in Professional Writing, but, after graduating from Kutztown University, I quickly realized that I didn’t feel fulfilled or challenged enough by simply writing news articles and editing textbooks (I live in a rural area. So, the job opportunities for writers were limited to these types of roles at the time.). In 2013, I decided to take some graphic and web design classes to beef up my resume. As I delved into learning more about design and advertising, I found myself fascinated with the marketing industry. Luckily, my training in graphic/web coupled with my writing background made me the perfect candidate to take on marketing as a full-time career.

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?

I know this sounds terrible, but I honestly can’t think of one off the top of my head. I’m sure there is one. It’s just not coming to mind.

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 Cheese Monkeys: A Novel In Two Semesters” by Chipp Kidd. In my junior year of college, I took a desktop publishing class and the professor made reading this book a requirement. At the time, I was annoyed and thought about blowing off the assignment. She already had us working laboriously on creating extensive magazine layouts (for which we also had to provide all of the content). So, why the reading assignment?

By the book’s end, I understood her reasoning. The novel is about graphic design students making their way through one of the most difficult design courses of their college career. The most enthralling part of the book turns out to be the assignments the students are given and the resulting projects and critiques. The student who meets the project guidelines, yet also produces the most “out-of-the-box” idea almost always gets the grade and the praise. This is a lesson that stuck with me. No matter what you’re doing, never stop being creative and always be original.

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

“Sometimes when you’re in a dark place you think you’ve been buried but you’ve actually been planted.” This is a quote by author and Australian Evangelist, Christine Caine, that I absolutely love. Everyone has a story and goes through difficult times…that’s part of life. This quote has helped me through more than once.

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?

My experience with organizing events has been extremely diverse and different with each professional role I’ve held. I view this as a positive because now I am ready for anything! It’s also helped me easily adapt to hosting online events.

In my first post-college role, I organized job fairs (everything from writing the job descriptions and creating flyers to helping employers set up their booths). In the following years, I worked for an industrial tool company and planned all of their trade shows (this included booking hotels, airfare, registering attendees, ordering giveaways and designing the booth layouts and graphics).

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

The first virtual event I ever organized was in September of 2019. That year we had really begun to place a strong focus on the importance of customer experience. Through our marketing efforts, we had formed some really great relationships with CX experts and authors like Shep Hyken, Jeff Toister, and Chip Bell (to name a few). We thought it would be a great idea to put together a virtual conference that could serve as a platform for them to share their insights with small businesses around the world. Hence, #SmallBizCX19 was born.

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?

Apple sticks out in my mind the most because of their “Apple Event” live streams. It’s estimated that over a billion people worldwide are iPhone users (not to mention the users of other Apple products), yet Apple finds a way to host engaging, virtual product launches that appeal to every user. To replicate this kind of universal appeal, any event planner would have to thoroughly and deeply understand their audience. What are their needs? What are their frustrations? What do they respond positively to? What connects them as a whole?

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?

The number one mistake people make is not rehearsing, and I don’t mean just once. Several run-throughs should be conducted in order to ensure everything runs smoothly. My Dad always taught me that “proper planning prevents poor performance.” The more practice and planning you put into your event, the less margin there will be for error (i.e. missed transitions, flubbed lines, dead air, etc.)

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

Honestly, Zoom has always been my go-to. Whether I’m planning a virtual office holiday party (which I did this year) or hosting a webinar conference, Zoom is versatile and easy-to-use.

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

The number one thing I would say here is…no matter what tools you use, make sure you understand your software integrations. For example, we live streamed our CX Zoom conference via YouTube. It took us several tests and tries before we figured out how to connect both platforms properly for seamless streaming.

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?

For smaller events or meetings, make sure everyone attending has a chance to participate and say something. Nothing can make someone feel less engaged than standing on the sidelines unnoticed. For larger events, provide a way for the audience to ask questions. For example, YouTube live streams offer an adjacent window where viewers can chat and ask the host questions.

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.)

1. Plan ahead and give yourself more time than you think you need to prepare. We pulled our event together in 30 days. In hindsight, it made the planning and organization process more stressful than it needed to be. We pulled it off successfully, but at times it felt very rushed. If you’re going to host a successful, professional virtual event, I recommend giving yourself at least 60 days to plan and execute. Depending on the size of the event, you might even want to give your team more time.

2. Create digital promotional materials and a landing page before you invite your guest speakers. Prior to the event being even a thought in our minds, we were lucky enough to have built strong relationships with some of the top customer experience influencers in the industry. When we decided to have the event, we started reaching out to our contacts immediately to see if they would be willing to participate. This was definitely putting the cart before the horse. Many CX influencers were excited about the event and immediately agreed to attend, but they also asked for any marketing collateral we had to promote the event. We had created any yet, and I felt that made us look a bit unprepared. So, I recommend creating a landing page where attendees can sign-up, and I also recommend having shareable social media posts available before you contact your guest speakers. The earlier they can get the word out to their followers the better.

3. Make sure you have an appropriate branded backdrop for when you or your team is on-screen during the event. We were so busy scheduling speakers, doing social media promotions, updating the webpage and deciding on how we would stream the event, that we didn’t think about our backdrop until it was too late to have something made or ordered. Luckily, we had some nice branded banner posters from a previous event that worked out just fine.

4. Think about and plan for transitions! You will need to have proper transitioning between speakers. Whether you do it with ads or music or a branded screen that lists the time for the next speaker, make sure you have something in place so you don’t have dead air or a blank screen.

5. Do several practice runs with the technology you intend to use. Run-through the event itinerary with your team as if it’s actually happening. We used Zoom to meet with each guest speaker and a live YouTube feed to broadcast the event to viewers in real-time. As first-time virtual event planners, the technology aspect of setting up the event took us a few tries to nail down. We were glad that we had done run-throughs several times in the days leading up to the event.

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?

Brainstorm first!! Write down a general description that details the purpose of your event and choose a tentative date and time. Then, create a list of possible speakers, performers or participants along with content ideas (speech topics, learning exercises, workshops, performances, etc). Create an outlined itinerary that provides a timelined breakdown of your event

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.

I try to do at least one kind of thing (big or small) for someone else each day. It can be for someone I know or for someone I don’t know. When you’re in the Dunkin Donuts drive-thru, pay for the car behind you. Pay for a Veteran’s meal when you see them eating out at a restaurant. Help an elderly person with their groceries. If everyone did just one kind thing for someone else each day, just imagine how much brighter the world would be.

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.

Stevie Nicks. I’m a huge fan and have always wanted to meet her. She’s a great writer and being a writer myself, I would love to pick her brain about her creative process.

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

Share your comments below. Please read our commenting guidelines before posting. If you have a concern about a comment, report it here.

You might also like...

Community//

Jessica Vogol of Movable Ink: “Focus on the event’s purpose”

by Tyler Gallagher
Community//

Jennifer Best of ‘All American Entertainment’: “Make Room for Interaction”

by Tyler Gallagher
Community//

Krista Mashore: “Have a team behind you”

by Tyler Gallagher
We use cookies on our site to give you the best experience possible. By continuing to browse the site, you agree to this use. For more information on how we use cookies, see our Privacy Policy.