JADE:
Hi, I’m Jade, co-founder and CEO of Epoch. You’re joining us for From Invite to Impact, our interview series where we spotlight event leaders and all the innovative things they’re doing.
Kayla, thank you for joining us.
KAYLA:
Thanks so much for having me.
JADE:
Kayla Drake has spent about 13 years in event and field marketing at IBM, Autodesk, Udemy, Apollo, and most recently StackAdapt, where she was the director of field marketing and ABM. She’s built event programs from scratch at companies going through acquisitions and IPOs.
Earlier this year, she left to start The Event Career Coach, where she coaches event and field marketers one-on-one, mostly people who are the only event person at their company and have nobody else to learn from.
So, Kayla, are you ready?
KAYLA:
I’m so ready.
JADE:
To kick us off, let’s do a quick overview of the different types of events you’ve hosted, who you typically target, and the scale and size of the events you’ve worked on.
KAYLA:
When I was first starting my career, I mostly did trade shows and conferences, as I think most event marketers do. I was thinking at scale and going to the bigger shows.
As I progressed, I started to learn more about field marketing and different types of field events, like executive dinners and happy hours. Then, at companies like Autodesk and IBM, I learned about customer roadshows and big user conferences like Autodesk University and CONEXPO.
I got to try a little bit of everything. I’ve had a pretty robust background in events. I’ve covered probably the whole gamut, quite frankly.
JADE:
You mentioned roadshows and trade shows, which are often quite different. We talked earlier about how field marketing is different from event marketing. Could you share your perspective on that?
KAYLA:
They both do events, right? They’re the same in that regard. But I think the key difference is that with event marketing, you’re thinking about lead acquisition, brand awareness, and thought leadership. You’re going more at scale.
A lot of times, marketers are tied to entire geographies, like all of North America. A field marketing team, on the other hand, is going to be more closely matched to a sales team in its region. In my career, that’s often meant supporting enterprise sales. You might see field marketing managers for the West, Central, and East regions.
They’re a little more targeted, and their tactics are more strategic to their region. Because they’re so closely tied to sales, they also tend to be more revenue-focused. Their field events, which tend to be smaller hosted events, need to tie directly to pipeline. That’s more crucial than general brand awareness.
JADE:
In the same vein, events are often used to drive pipeline. How have you seen events play a broader role in go-to-market strategy?
KAYLA:
Events are making a comeback, let me tell you. Especially in the age of AI, I think everyone is so oversaturated that they’re really wanting face-to-face interactions.
Even this: normally, I’d be on Zoom doing a webinar or a podcast, but now I get to do it in person because people are craving it.
When you’re focused on selling your product or service, an event gets your salespeople into the literal field to talk to prospects and key customers. That solidifies the relationship and keeps it long-term versus a quick purchase. You really want to foster those relationships, and events do that. It’s awesome.
JADE:
You’ve seen events evolve over the past 13 years at prominent tech companies that invest heavily in them. What trends have you noticed that really stand out?
KAYLA:
Trade shows are here to stay. Those well-loved conferences and trade shows are a million-dollar industry that’s not going anywhere.
But especially in the age of AI, I’m finding that people are shifting toward intentional face-to-face activations. A really popular trend is wellness activations. I’m seeing a lot of yoga sessions, morning 5Ks, and pickleball tournaments. Because, quite frankly, if you’re a millennial, you have to choose, right? Run club or pickleball. It’s one of the two.
[Laughter]
The other popular ones I notice are executive lounges curated as a wrapper event around major trade shows.
JADE:
I love that.
KAYLA:
They’re putting these intentional rooms together where you’ve got Wi-Fi and a workstation, food and drinks, and sitting areas for quiet time or networking if you want to have meetings.
It’s almost like a little mini conference offsite, but it’s meant to be calm and focused on conversation. It’s a lounge, like a sports lounge or an airport lounge. Just a nice, bougie little something extra. It’s so popular right now.
JADE:
That’s a good observation. Whatever you see on the consumer side eventually leads into the B2B side, like wellness and these lounge-type events or activations.
KAYLA:
Exactly. Pay attention to your buyer. What are they interested in? What would actually attract them to your event and get them interested, instead of just pitch-slapping them? They can enjoy the time they get to have with you. It’s a win-win.
JADE:
I also see people extract a lot of content from these types of activations because they’re fun and timely. Events are a great way to bring people together, but they can also be useful afterward. Could you share some clever ways you’ve seen people use an event for continuous marketing and campaigns?
KAYLA:
One of my favorite mentors told me you should see events as a vehicle for all of marketing to participate in. Use the whole chicken.
When you have an event, you don’t want to just show up, knock it out, and have that be it. You can get something meaningful out of it. You can focus a product launch around the date of the event. You can create blogs and articles from what you learned and the sessions that took place. Or you can film interviews and content on-site to repurpose for social media afterward.
You can get so much out of an event. It shouldn’t just be show up, execute, and be done. Make use of it for all facets of your marketing team, and you’ll be successful.
JADE:
How do people plan for that successfully?
KAYLA:
A good event marketer. That’s how.
[Laughter]
Good field marketing, good event marketing. If you curate your event list as far in advance as you can, based on what you know about your budget, you can give your team a heads-up well ahead of time.
A lot of people don’t realize that events need weeks, if not months, of planning. With third-party sponsored events, I already know the date. We can focus on those tier-one events and create activations around them, whether they’re hosted or sponsored. Then everyone on the marketing team can get a piece of the pie.
JADE:
Speaking of lead time, have you seen certain planning timelines that should be standard for an executive dinner versus a user summit versus an executive retreat?
KAYLA:
It’s going to differ with every company, but the general timelines I usually give are:
For any hosted event, you need at least six to eight weeks to plan. Working backward, you need a couple of weeks to decide on the date, location, and venue and lock everything in. Then you need at least four weeks to promote it.
For any major trade show or conference, you’re going to need three to four months. And for any user summit or user conference, especially your big flagship event, please give your team at least six months.
JADE:
Yeah.
KAYLA:
You need at least six months, especially to confirm a paid keynote. A lot of times you have to lock them in at least four months in advance. The more time you can give your field and event marketing team, the better.
JADE:
Everyone right now wants to have their own user summit, so I think people are getting thrown into it and hearing, “We want it in two months.”
KAYLA:
Oh, yeah. I don’t think anyone realizes how much work it is or that it takes the whole team. Your whole marketing team is involved. All your executives. There are so many layers and so many vendors you have to bring in.
It’s one of my favorite things to put together, but it takes a lot of resources.
JADE:
Definitely. We host our own conference, so I feel that.
Another part of preparing for an event is making sure we invite people in a timely manner and, even more importantly, bring the right people into the room. How have you approached list building or targeting the right audience?
KAYLA:
It definitely depends on the type of event. For a larger-scale event, say a happy hour, it makes sense to leverage your marketing team. Use your marketable database from a CRM like HubSpot or Marketo, where you can pull a list of people who’ve already opted in.
You can send curated emails that get their attention, followed by outreach from your SDR or BDR team to get them registered and excited about attending.
But the more intentional and smaller the event is, the more you want to rely on your sales team. If you’re doing a nice executive dinner, it’s typically the enterprise sales team going after prospects with open opportunities, particularly late-stage opportunities.
You want the invitations coming from them because otherwise you’re adding a random middleman. Marketing can send one initial email so it feels official, but really, it can be a simple text-based email. Send that, do a simple follow-up, and then send a LinkedIn message.
For emails, I like to use tools like Apollo or Outreach. As the event marketer, I might craft the copy and let the sales team send it. You make it seamless: give them a targeted list you can pull from Salesforce, have them send the emails, and then have them send a personal LinkedIn message:
“Hey Jade, I’d love to have you at our event. You’re the perfect person to have there. Here’s the registration link. Hope to see you there.”
I find you have a higher success rate with people registering and wanting to be there because it feels personal. That’s what makes it more exciting.
JADE:
Have you seen any tactics or copy that convert really well? I remember seeing on your LinkedIn that, to make sure people show up, you send a quick note saying, “Hey, I’m flying in,” with a little photo. I thought that was so clever. We totally took that.
KAYLA:
We like to set good registration goals, but it’s about who shows up, right? There’s always going to be an attrition rate.
If you have fun tactics that create FOMO in advance, use them. When I would fly into the city where I was hosting an event, I’d send a selfie from the airport: “I’m coming into Boston, y’all. Hope to see you there.” It gets people excited.
For very small, curated events, another recommendation is to CC everyone who registers.
JADE:
I remember you saying that. Everyone can see everyone.
KAYLA:
Yeah, you can see everybody’s name. But it has to be a small event, under 15 or 20 people, not a 200- or 300-person happy hour. That would be obnoxious.
You might ask a prompt like, “What’s a fun sport or hobby you’ve tried recently?” Get them responding, and they can start networking in advance. Again, you’re creating FOMO before they even go.
You can also share a behind-the-scenes photo of the venue on LinkedIn: “Get excited, you guys. You’re going to see something special.” Little things that get people feeling like, “Oh, I can’t miss this.”
JADE:
It’s so important now because everyone’s getting invited to and going to events. It’s a crazy market, so anything you can do to stand out is really important.
KAYLA:
And you can’t fail with a really good venue. I have a knack for finding the best local buzz venue, somewhere people want to be.
For example, Trillium Brewery in Boston is popular, well-known, and close to the convention center. It feels like a no-brainer. Think locally. That’s the trick. Don’t go for the tourist attraction; go for the local favorites.
JADE:
I love that tactic. Looking at how AI is being used everywhere, how have you seen it transform event marketing? Are there areas where you’re excited to see AI come in more?
KAYLA:
This one’s kind of tough for me because I have a little bit of nervousness around AI in general. It took so long for us to even get event tech.
Ten years ago, we had a bunch of nothing. Maybe a couple of registration platforms. Mostly, we were operating out of Google, as most event marketers do.
Now I’ve seen the influx, and there’s this huge push to implement AI into processes. But there are some things AI can’t replace in events. I can’t use AI to set up the booth. I can’t use AI to get the swag on the table. It’s a very physically demanding job, as you know.
Where I can see it benefiting us is by taking away the admin portions. If I’m receiving emails from vendors, I could create an agent that automatically uploads information into a project management tool or otherwise streamlines the process.
Auto-creating event brief templates, generating email copy for me, anything that makes the job a little easier given how many tedious tasks there are in field marketing. I’m excited to see what that will do.
JADE:
Definitely. I also see people using it for their data and understanding registrations, cleaning all of that up.
KAYLA:
My only fear with AI for event marketers is having the time to learn. It’s a very busy occupation. The biggest feedback I get from field marketers is, “When am I going to learn this? I know I need to. I know I need to be ahead of the curve on innovation, but when am I going to have time?”
My advice is: don’t gatekeep instructions. If you have GPTs or agents, share the prompt. Say, “Here’s what I did.” Teach your peers. Let everyone learn from you. Share the information. Anything that teaches me quickly is the real winner.
JADE:
You coach so many people who are earlier in their event marketing careers. What part of the event workflow would you tell them to focus on making less manual?
KAYLA:
Everything in the beginning. Given how much time and planning it takes to execute an event, take advantage of anything you can offload and automate through AI.
One thing I think is really fun, and I’m learning this in real time too, is using applications like Claude to create ROI tracking tools after the event.
For example, figuring out how to use Claude with a Salesforce integration so you can pull the report from a particular event campaign and see a clear breakdown of the pipeline generated from that event. That’s going to make you more powerful as an event marketer, a true strategist.
JADE:
I was going to ask you that as my next question. Beyond attendee and registration data, what other metrics or data points would you encourage people to look at more closely?
KAYLA:
Look at all of it. It all tells a story, and I think event marketers are the translators of that story.
It’s not just who registered and who attended. What’s your NPS score, your net promoter score? What feedback did you get from the people in the room? What did you learn from the sales team in the debrief or postmortem after the event?
Then look specifically at your open pipeline and closed-won business. In Salesforce, at the campaign level, understand how many opportunities were opened from that event, not just sourced but also influenced.
Did you see a lead or opportunity progress? Did a customer attend and then renew? Did they expand their deal? Was there an expansion opportunity?
All these data points are relevant to the event’s success story. But that’s also true if the event wasn’t successful. It’s good to be transparent with your data because it’s all learning.
JADE:
I remember you telling me a story about a sales team that wanted to sponsor an event again, but based on the data, you thought they should do something else, like a dinner. Could you talk through how you got there and informed the team that you were pivoting?
KAYLA:
This was actually a client story that I coached her through. She was supporting a very small, niche team on the federal side. If anyone knows, it’s usually a small team with a small budget. It’s very lean, and you have to be scrappy, but it often involves some of the biggest deals in the company.
There was one conference that a federal account executive wanted to continue sponsoring year after year. It was a $20,000 investment, but we were finding zero in net-new pipeline. This field marketer’s directive was to source net-new logos.
However, we kept seeing that almost all the major clients he met at the event were renewing. So we took the data and unfolded the story: what if we went to the event but stopped sponsoring it and hosted a wrapper event instead?
That way, he could still meet with those key clients and be on-site as needed, but we wouldn’t be spending $20,000 on a booth that wasn’t generating net-new leads.
It ended up being the right play. They still have a presence, and now they can grow that hosted event series separately from the conference. They can spend a fraction of the cost, maybe $3,000 or $4,000, to host their own curated executive lounge experience and still work toward closing those major deals.
JADE:
A much higher ROI to report back to the company.
KAYLA:
Exactly.
JADE:
I asked another interviewee this as well: what skill sets do you find set really great event marketers apart?
KAYLA:
We stereotype a little bit, and it makes me laugh. I always say, “I know you’re probably type A, I know you probably have ADHD, I know you’re hyper-organized.”
[Laughter]
“You might have crystals on your desk and your house is surrounded by plants.” There’s a very stereotypical personality.
But the biggest thing is that they’re wicked smart, fast thinkers. Event and field marketers can connect the dots, problem-solve, and figure things out like nobody’s business. You’re a full-time field marketer and a part-time fire putter-outer.
You know how to pivot at the last minute, get things done with very little, and be scrappy. That’s what I see commonly, and that’s why event marketing is so awesome.
JADE:
One hundred percent. You have to be creative now because it’s so competitive.
KAYLA:
Oh, yeah. But event marketing is coming back in full swing. I’m seeing more jobs open up, and a lot of people are switching to contract roles and going freelance, like myself. They’re seeing their careers skyrocket because there’s so much opportunity.
We’re going through an interesting change and transition in our industry right now. But watch: 2027 is going to be a big event year.
JADE:
Absolutely. We’re already seeing that. I was talking to someone about how, because events are coming back in full swing, everyone is fighting for the same ICP, especially in the age of AI. It’s getting harder to stand out with your event.
Have you seen any creative activations or events where you thought, “Oh my god, more people need to be doing this”?
KAYLA:
I mentioned it earlier, but the executive lounge experience is one of my favorites. I think 6sense does a really good job with its Club 6 event.
JADE:
Oh, cool. That’s so cute.
KAYLA:
They’ve made it so popular that you know the event series by name. They do it at all the major trade shows and conferences.
If you’re a 6sense customer, or you’re considering expanding your ABM efforts, you’re thinking not just about 6sense but also about Club 6 at that event.
It’s an interesting play on creating a branded series around your events. That’s often my goal when I build event strategies and teams at the companies I join: get a really strong event series going so it’s almost its own mini brand.
Then it sells itself. People get excited about going, the next year it grows by word of mouth, and the next thing you know, everyone wants to be there, so everyone is there.
JADE:
That’s a good point. It’s like on the consumer side: if you’re a Chase customer, you get access to the Chase Reserve Lounge, and then everyone wants to be a customer so they can get access.
KAYLA:
Exactly.
JADE:
That’s incredible. I’m going to look into Club 6.
KAYLA:
It’s very fun. I highly recommend it.
[Laughter]
Shout-out to that team.
JADE:
Honestly. Last question for you: what’s one belief you personally hold about event marketing that others might disagree with?
KAYLA:
I take this very personally: the details do matter.
When an event marketer becomes obsessed with little things like ironing the tablecloth, making sure the lanyards sit just right, or having specific decorations on the table that are color-coded for a reason, it really does set the tone for attendees. It creates a positive impression.
You’re bringing your sales team into the literal field to do what they do best and sell, and you’re putting a face to the company name, brand, and logo.
Those details at your event matter. They totally matter. I get teased and told I’m way too uptight or that I’m type A. I don’t care, because attendees leave saying, “Wow, what an impressive event.”
That’s always going to be true for event marketers. That attention to detail, we live for that. I stand by it.
JADE:
I love that. That’s a great ending point. Kayla, thank you so much for joining us. That wraps up today’s From Invite to Impact interview featuring Kayla Drake. Thank you.
