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12 March 2019 

Event Heroes: How InsightSquared Is Scaling Their Event Brand

Brandon Rafalson
Event Heroes: How InsightSquared Is Scaling Their Event Brand

Each month we interview an events professional who is breaking the mold. This month we spoke with Maddie Vesey—the events lead at InsightSquared—about scaling a company conference, launching an event roadshow, account-based marketing and Boston.

In 2017, the revenue intelligence software company InsightSquared launched their first ever conference. The goal of Ramp was to create a community where operations professionals could learn, network and grow. Today, InsightSquared is on the cusp of their third annual conference and first ever roadshow.

Maddie Vesey has worked at InsightSquared for just about two years. In that time she’s worked her way from a supporting marketing role to the head of InsightSquared’s event strategy. Quintessential to Maddie’s approach is a data-driven mindset that values experimentation, analysis and iteration.

Topic discussed in this Event Heroes interview include:

  • Growing a career in events
  • Scaling a user conference
  • Launching an event roadshow
  • Measuring and experimentation
  • Sales and marketing alignment
  • Integrating account-based marketing into events

Listen to the highlights or read the full interview below.


Note: This interview has been edited and shortened for clarity.

Brandon: You’ve been at InsightSquared for almost two years exactly. During that time, you’ve gone from a marketing campaigns associate to managing InsightSquared’s third annual Ramp conference and first ever roadshow in addition to some other events. I’m curious. What led you to where you are today in your career?

Maddie: Totally. I actually started at InsightSquared right out of school after attending Northeastern University here in Boston, and I came in as a marketing campaigns associate really to help with things on the execution side. What got me to where I am now is being able to jump in wherever needed.

I’ve been lucky enough to see Ramp from the very beginning. When I started, the team was just getting the first Ramp off the ground. It’s been really exciting to have had a small part the first year, a larger part the next year, and to now be owning the entire program. Especially, given that both the company and conference has continued to grow.

Coming up on my two-year anniversary here at InsightSquared, I’ve seen a lot of events and continue to collect data so that we can continue improving our event strategy.

Brandon: In 2017, Ramp was the conference for sales operations professionals. In 2018, Ramp became the go-to conference for all revenue operations professionals. Now in 2019, Ramp is expanding its offering to marketing professionals, as well. What are some key changes that the Ramp team is making to cater to this new audience segment?

Maddie: In 2017, like you mentioned, we primarily catered to sales operations and tried to build up that community, and what we realized is that while sales ops is a huge piece of the puzzle, there’s actually a greater ecosystem that’s working together for the success of an organization.

We noticed a shift from organizations having only a sales ops function towards building out revenue operations teams. Marketing, sales, and biz ops roles are now coalescing to form the revenue ops function. That’s why we shifted in 2018 to be the revenue ops event of the year—to include business operations, marketing operations, sales operations, and in some cases customer success ops.

We’re really trying to bring together all of the professionals under the revenue operations umbrella.

As we continue to grow, we want to elevate rev ops pros from just being spreadsheet machines to having a seat at the strategy table with their sales and marketing counterparts. That’s why we’re now creating content for Ramp 2019 that applies to ops, marketing, and sales leaders in order to align the entire go-to-market team.

Ramp 2017 - Fenway Park

Ramp 2017 - Session

Ramp 2017 focused specifically on operations professionals.

Brandon: When it comes to event content, do you have specific tracks that are going to be catering for maybe these non-operations team members?

Maddie: The first year of Ramp, everybody was in one room for one day and everybody saw all the same content. That’s when it was really focused on sales ops, and so everybody could really learn from all of those sessions.

Last year, we had a customer-focused day about the product, and then we had a thought leadership day with two different tracks. We started to sprinkle in some more sales and marketing content, but it was still mostly focused on operations.

This year we will see a mix of really high-level thought leadership sessions relevant to all sales, marketing and operations professionals—mixed with some more granular, tactical sessions for each function.

We want to feel like we’re speaking to everybody so they can bring back tangible content to their teams that impact the business right away, but we also want people to look at their careers and how they can grow as individuals.

Brandon: As mentioned above, this is the first year that Ramp is going on the road. This is a very exciting step for Ramp and for InsightSquared as a whole. What makes now the right time for a roadshow? How do you and your team plan to capture the Ramp experience for attendees across the country?

I think when it became super clear to me that this was a necessity in our 2019 event strategy is when we went to a large trade show out in San Francisco and we noticed that our session out off thousands was the only one that had “revenue operations” anywhere in the title or description.

Knowing that our audience and our ops community is at events like that and that they don’t receive content that’s super valuable to them is a real bummer and something that we want to solve with Ramp—but that only happens for two days once a year. There are folks—especially if they’re not local to our office in Boston—who are going to events and potentially not getting the content and community that they’re looking for. That’s what we’re trying to solve.

We’re going to some of the top cities that we have customers and prospects in—Austin, San Francisco, New York City, and Chicago—all before Ramp happens in June. Our focus is really to give these attendees a taste of Ramp. This may look like a thought leadership session, a fireside chat with somebody in the operations space, or maybe a panel with a sales leader, marketing leader, and operations leader to see how they align.

The dream goal is to help establish revenue ops communities throughout the country so that when members have a problem, they have each other to go to.

Brandon: One thing that stands out about the marketing team at InsightSquared is just how just how data-driven you all are. What metrics do you plan to use to evaluate the success of Ramp and the Ramp roadshow?

Maddie: Yeah, for anybody who doesn’t know, InsightSquared is a very data-driven organization. We sell sales and marketing analytics platforms, so I’m part of a data-driven marketing team which has actually become my favorite thing about working here.

Events are tricky. They’re about community-building and thought leadership, and brand comes into play. I think, unfortunately, if you view an event as purely for lead generation, you’re probably going to be left disappointed a lot of the time.

My mission statement for Ramp is to create a revenue operations community that doesn’t exist elsewhere and establish Ramp as a thought leader in that space.

I think one of the best ways we capture that information is by sending a survey after every event, and it’s pretty lengthy for Ramp.

I’ve actually poured through all of those survey responses from 2017 and 2018 and they really do impact how we approach the next year, even our trade show sponsorships and smaller events.

Some of the feedback that I’ve gotten has really shifted the way we look at events. While it might not be quantitative, the qualitative feedback we get is super impactful.

We also look at our customers. Say they came to Ramp on the Road San Francisco, did they end up coming to Ramp? We look at that number. Did they grow their footprint? Did they renew more easily? Did they buy an additional product? Are they helping us with referrals or case studies? Are they logging into the product more? These are all things that we look at to try to see how our events are impacting our customers.

On the prospect side, we look at how they progress through the funnel, especially compared to those folks who don’t attend events.

Brandon: Could you speak a little bit more on how the event team or the marketing team works with other teams within the organization to help pull off something like Ramp or Ramp Roadshow or the other events that you might be attending in other capacities?

Maddie: The team that I rely on most outside of marketing is the ops team. Obviously, they help me with our tech stack. They help put in place processes, SLAs, and things that I might need. They really help me figure out how to be strategic about the way I’m measuring and reporting on events, and investing in future events.

Luckily for me, they’re also our target audience, so by spending a lot of time together already, I can pick their brains and say, “I was thinking about this topic for a session at Ramp. Would that being interesting to you?”

I also work super closely with the sales leadership to make sure that the sales team has an open line of feedback back to me. Without the sales team, we wouldn’t have a full room at any of our events. They’re expected and fortunately excited to reach out to all those folks that they do have personal relationships with over the months or years.

Brandon: Speaking to some other event organizers, something I’ve often heard is, “Yes, my sales team should be helping me promote this event, but it’s really hard to get them to stop focusing on typical sales calls.” Are there any specific reasons you chalk up to the sales team being so enthusiastic?

Maddie: This is definitely a challenge that I have heard from a lot of marketers and not something that I’m totally immune to. It’s something that we’re always trying to improve upon. I think the good thing for us is that the more and more Ramp grows, the more that our internal team can see the value.

One thing that I’ve invested in this year is having a timeline from the very start. This might sound simple, but having ticket goals laid out six months in advance for every month, having all of our call blitz days scheduled all the way up until Ramp, and then getting everybody excited about those days or about those call blocks can can be a huge undertaking.

Brandon: How do events fit into InsightSquared’s greater account-based marketing strategy? How does your team attract, engage and track the journey of target accounts?

Maddie: The biggest way that ABM comes into play with events is through personal relationships. Our account managers know what information is most relevant to each one of their customers and how to make it a valuable proposition for their customers.

As part of our ABM strategy internally, we do have our priority accounts, which we are invested in bringing on as customers, and so I work closely with the sales team to say, “Okay, from our priority accounts, who do we want to see at Ramp? Who do we think it will be really impactful for?” Then from that list, we do something special—maybe it’s inviting them to a VIP evening event at Ramp or sending a personalized, direct mail invitation.

Last year we sent monogrammed luggage tags for the top 200 contacts who we wanted to attend Ramp with a card that said, “Here’s to flying high. See you at Ramp.” It’s definitely about that surprise and delight, being focused on who we’re inviting, and expressing the value that they’ll get out of an event like Ramp.

Ramp 2018 - Speaker

Ramp 2018 - Networking

Ramp 2018 evolved into the go-to conference for all revenue operations professionals.

Brandon: How within the events or marketing team do you cut back on cost and time with these event campaigns that you’re running? Are there any particular hacks or tactics that you use?

Maddie: Right when I started is when Ramp was going to have its inaugural event, and our CMO at the time made a smart decision in my opinion and he said, “We’re going to do Ramp and we’re gonna do Dreamforce and that’s it.”

That was a huge shift, I think, in company culture because we were used to just going, going, going, going, going. Having two events that were far away in the year allowed the marketing team to put a strategy in place, to have strong SLAs in place with our teams, to get everybody rallied behind these two events and commit to making them successful.

While we’re continuing to grow our events, I think we’re keeping that sort of DNA of being careful when we sign on for something and looking at what the investment is and doing some math and saying, “What return do we think we’ll get here and how can we be as strategic as possible?” I think that has allowed our team to do less heavy lifting.

As we continue to build out these plans, it’ll become easier and easier to efficiently grow our event strategy. It’s bringing that data-driven nature of InsightSquared. Finding little things, making them better and pulling that into events where I don’t think it normally lives.

Brandon: Going into 2019 and beyond, any particular trends or strategies that you’re excited to implement?

Maddie: We are moving into the marketing world with our new marketing analytics tool, and so we’re starting to create content and go to events where marketers are, which is a big movement on our end. We’re going to SiriusDecisions Summit for the second year in a row.

Then a shameless plug for you guys, I’m super excited that Bizzabo moved to unlimited events. Being able to log into one platform and see all of my upcoming events and manage it from there is very helpful.

Brandon: Okay, so what’s one piece of advice you’d give to someone who was gearing up to launch their first roadshow?

Maddie: Pick a location that feels comfortable and relevant. We did a trial Ramp on the Road event in November in Boston at a brewery that I go to in my free time. It was where we know we have customers and partners and prospects and where I could have the support of the full team because we’re all based here.

Don’t worry about getting it perfect the first time. Make sure that your team is on board to do this new thing that nobody’s done. You don’t know how it’ll run yet. Just give it your all and then measure it and change from there.

Brandon: Okay, now for the really serious questions. I understand that you have a lot of experience in dance and choreography, so I’m wondering what are some of your greatest influences?

Maddie: My passion besides events is dance and choreography. I sort of focus on tap and musical theater, so I think my biggest influences right now would be a group called The Syncopated Ladies which is like five or six women who all tap dance.

Also, Sutton Foster who is just an amazing dancer, singer, actress, everything. She was just an understudy in Thoroughly Modern Millie and then they asked her to step up and be the standing person, and then she just took off.

Brandon: What’s one of your favorite things about Boston in the summertime?

Maddie: Other than Ramp, because that happens every summer, there are a few things. Going to a Red Sox game at Fenway Park is an unforgettable experience. I live in the North End which is Little Italy. Walking around the harbor over there is always fun. Then, if I ever have people visiting from out of town who’ve never been to Boston, I always make them go on a duck boat tour. I’ve been on five duck boat tours. I could practically lead them by now.

Brandon: All right. Final Question. How do you stay inspired and keep your creative instincts fresh?

Maddie:  I think consuming content from different companies, people and brands is powerful. You can see what other companies are doing, what’s working, what’s not working, what I like and what I think works well for InsightSquared’s brand.

I’m also just fortunate enough to be surrounded by a creative and passionate marketing team and the greater team at InsightSquared. They definitely keep me motivated and inspired. We have awesome brainstorms about anything and everything about Ramp and how we can make it a special and exciting event for our attendees.

That’s all for this Event Heroes spotlight, but you may be interested in checking out these other Event Heroes:

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