So You Want to Host a User Conference: A Guide for Startups

We asked experts from HubSpot's Inbound, SalesLoft's Rainmaker, and Lessonly's Yellowship for their tips on making a SaaS user conference a success.

Article by
Emily Brungard

Last week, we hosted a group of leaders from across the High Alpha portfolio for a master class on how to plan and host a user conference. Experts from HubSpot, Conga, ExactTarget, SalesLoft, and Lessonly came together to share their thoughts and first-hand experiences planning conferences with our companies.

Their general consensus on user conferences can be described in just a few lines from the event:

I haven’t seen a single market leader SaaS company that doesn’t have a great user conference.
Tim Kopp
In a feature war, which we are in within the software space, the community you build around a brand will sell a deal.
Kyle Lacy
Putting your customers on stage and your CEO and product people on stage isn’t entertaining. If you’re going to do that, don’t host a user conference.
Kim Darling

With many of our portfolio companies planning their first conferences in the next several months, there were a lot of shared questions. If you’re considering hosting a conference of your own, read on to hear from six user conference experts.

Salesforce's Dreamforce conference is one of the largest in the world.
Dreamforce is one of the largest user conferences in the world.
Salesforce’s Dreamforce, which drew more than 170,000 attendees in 2018, is one of the largest user conferences in the world. (Photo credits: GPJ)

Should I Host a User Conference?

Kyle Lacy, CMO, Lessonly: “If you build a company with raving fans, you should have a conference.”

Kim Darling, VP Marketing and Executive Producer, INBOUND, HubSpot: “This is the big difference between hosting a user conference and an industry event. For an industry event, it’s about everyone coming together, it’s about how you learn and grow together, how do you collaborate, how do you make those connections. A user conference has a very different expectation, because your customers are paying you for your service, your software, throughout the year — the expectation then is a free ticket, free breakfast, lunch, and dinner, and a party, travel paid for, all these things.”

Tim Kopp, Managing Partner, Hyde Park Venture Partners; Former CMO, ExactTarget: “Terminus took an event that was already happening and bolted onto it — I think there’s a place for that. Particularly if you’re very early on in building a category and you’re very event thin, these are two hacks to get to a user conference before you actually do one. I like doing city tours in smaller settings — I would never do a user conference before I did city tours. You get the muscle memory built up around how you take care with 50, 100 people. And then I like the bolt-on idea, where you take another event that’s happening and hijack an audience for some momentum. It’s a good place to start when you’re starting out.”

Daniel Incandela, CMO, Conga: “Listen to your attendees. Ask them what speakers they like, what food they like, everything. We wanted to host an industry conference, but we found that our attendees wanted to talk to users, watch demos, and learn. It was very much a user conference, not an industry conference.”

When Should I Host My First User Conference?

Tim: “We knew it was time when we had something important enough to say. There’s a tipping point where you have enough customers, but you have to have developed and shaped a narrative where you get a gut sense where you have to unleash it on the industry.”

Kyle: “For me, the decision was pretty simple. At my first board meeting after joining Lessonly in my first VP of marketing role, Scott Dorsey said we should do a user conference. I said ok, and then I walked out of it thinking ‘oh no, what did I just do?’. But we’re really lucky that Max [Yoder] keeps a very long leash on us, and from an executive level we had a lot of support.”

Lessonly's Yellowship conference
Lessonly’s Yellowship user conference took place in Indianapolis, and User Conference Master Class attendees got to experience their event for themselves.

How Do I Pay for The Conference?

Tim: “You’re fighting gravity if you don’t acknowledge that the whole thing is about lead gen. Give me $500,000 and I will give you $500,000 of closed/won new business that we would not have otherwise generated. It might not be the best marketing tactic in the world, but it gives dollar for dollar return while we’re powerfully activating the brand. Once you build the credibility that you can do that, then it’s about turning up the dial and framing choices. We’d say ‘If we can put in another half million dollars, we could get Richard Branson, we can do XYZ. Then you can activate partners and a partnership ecosystem to drive a lot of the monetization.”

Brian Montminy, VP Finance and Operations, Lessonly: “You have to show value before people will pay [to sponsor your event]. We have someone internally who is in charge of partnerships. He leads that and takes that quota. It’s about having people who are close to your product partner. We have a strategic partnership with Zendesk, and a lot of those partners are with us kind of as an ecosystem around Zendesk.”

Kyle: “We also have sponsorship packages, from Platinum and down. For us, the revenue thing is important, but my team isn’t really that focused on getting people to sponsor. We focus on the experience. We want the room to be filled in the sponsor lounge, but I spend most of my time trying to surprise and delight, not how many people we can fit in the sponsorship room.”

Kim: “HubSpot invests in INBOUND. That’s a big thing — how much money are your companies willing to invest in this?”

Jonathan Dew, Senior Director, Brand Experience, SalesLoft: “In 2015, we had about 250 attendees, and not one of them paid a dime. By 2016, they got a stage, Rainmaker got some sponsors, and had about 475 people attend, and they were starting to generate some revenue from the conference.”

What Event Pitfalls Should I Watch Out For?

Daniel: “Everything is going to go wrong. It’s like seeing how the sausage is made behind the scenes — it’s chaos. One thing I’ve seen trip up a number of people is approval for content. Managing executives to adhere to a deadline or not change their minds three minutes before they go on stage is very difficult. I struggle with that still. Also, if it’s in the budget, hire a contractor that has put on these events who knows everything. You can’t expect to be the number one event logistics person in the company when you’re doing 30 other things. Hiring really good people is worth the investment. If you don’t keep close track of the budget, it’s going to get out of hand really quickly.”

Tim: “If you have a scarcity mindset in running events, it won’t work.”

Kim: “As a person leading an event, you have to be prepared to expand your mind across a broad sweep of things. Like, how are you going to make the budget work? How are you going to get it all done? What’s the latest podcast? Who’s the person in Hollywood you need to get as a speaker? There’s a lot. And it’s fun.”

“Food is very, very expensive. It costs $4.89 for an apple at the Boston Convention and Exhibition Center. It’s $59 a gallon for coffee, which is one of the more reasonable ones — I believe it’s $69 or $79 at Moscone. Food is incredibly expensive and it’s not always the quality that you want to give your attendees, so we’ve brought in food trucks, and it’s been a huge hit. When you look at your investment model, look at food and beverage. We do not offer free coffee to all pass types anymore, and it saved us hundreds of thousands of dollars. If you can find those silver bullets — and you have to weigh it — that’s really, really key.”

Brian: “I think you need to set really clear expectations with partners on the ancillary events they plan as well, saying ‘This is Lessonly’s conference, we’d love you to be here, but these are the things you can and can’t do around the schedule.’”

Jonathan: “Being interactive is super important. We try to be very interactive in how we set up stuff, and how we make people come together. Always be actionable. I want to set it up so that things fall into a 30/60/90 plan. What are [attendees] going to take away and do in the next 60 days, in the next 90 days after an event. I want them to walk out with something, because the number one thing their boss is going to do when they return from the event is ask them ‘Was it worth the money?’ I want them to say, ‘Yes, and I’ll show you how it was worth the money, because we’re going to do these things in the next 30 days.’ Build your content so that people have something to walk out with.”

“Inclusivity is another huge thing at SalesLoft. We sell to salespeople, and we refuse to become ‘brotopia.’ I have goals set on how many people of color I’m going to have on stage, how many women in sales I’m going to put on stage. It can’t just be middle-aged white guy after middle-aged white guy. It’s super important to us.”

How Do I Track my User Conference?

Daniel: “Our attendance numbers are through the roof, which is not normal. I’m used to 50/50 attendance. I don’t know why it’s so high at Conga, but I think people are really passionate about what we’re doing. Our persona is someone in legal ops or sales, people that are very much dealing with process and data, and I don’t know if they’re just more committed to getting help and education than marketers, but it is an exceedingly high number. We also manage room blocks to track attendance, look at registration numbers, and use previous conversion rates to predict the future.” The sales dev team plays a critical role in post-event follow up. CS and salespeople follow up based on their relationship. Nurture campaigns happen in the background.

Brian: “Our goal was to cover a set percentage of the event with revenue. A lot of finance people will just say ‘where’s the ROI, where’s the ROI’, and I’m not just going to sit up here and make stuff up — attribution is really hard, especially when you’re in a B2B business primarily focused on enterprise. No deal is going to come only to your website and then close. We know that Yellowship in and of itself isn’t going to be the one thing that drives revenue — it’s a portfolio of things that we do over a prospect’s time as they’re interacting with Lessonly. But we do know that this is a huge driver of urgency and keeping people engaged.”

Tim: “I’m responsible for driving ROI, so I need a lot of prospects there. I wanted all my top prospects there. We would orchestrate their time to have executive touch points and special touch points. We went as far to say if you don’t drive at least 10 prospects to attend, you don’t get to attend.” Sales and customer success had quotas to meet.

Kyle: “We have a ticket goal, but we don’t think about it in terms of percentage of our customer base. I’m all over the enterprise sales team leading up to the event, telling them that they need to get their prospects and customers here. There are huge upsell opportunities that can happen when Big Customer A meets Big Customer B.”

Kim: “We track things like NPS, media, social media, ROI on sales deals. One thing that I look at is the percentage of the overall spend that the company is putting in.”

Jonathan: “Data doesn’t feel, it doesn’t have feelings. We capture data all the time — you just have to figure out how you want to use it. You probably already have it — you don’t need to run another survey. That’s going to help you devise your content and all of the other pieces that go along with that.”


Thinking about sponsoring a conference? Read our tips for getting the most from your sponsorship.

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