How To Run A Virtual Kickoff That Actually Works With Drift's Maria Casella, Mark Siciliano, And Jackie Wright

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This is a podcast episode titled, How To Run A Virtual Kickoff That Actually Works With Drift's Maria Casella, Mark Siciliano, And Jackie Wright. The summary for this episode is: <p><span style="color: rgb(0, 0, 0); background-color: transparent;">A pretty common tradition at the beginning of each year at tech companies is the Company Kickoff. This is usually where the entire company comes together to talk about what they’ve achieved, what is up next, and how to get there.</span></p><p><br></p><p><span style="color: rgb(0, 0, 0); background-color: transparent;">These are usually massive in-person events, and obviously, this year that just isn’t happening. In this episode, we dig into how companies can adapt the kickoff format to be a truly virtual event, and have it actually work.</span></p><p><br></p><p><span style="color: rgb(0, 0, 0); background-color: transparent;">The trio with the playbook to pull it off came from our own team at Drift: Mark Siciliano, our VP of Sales Productivity &amp; Strategy, Maria Casella, Drift’s Chief of Staff, and Jackie Wright, the Executive Assistant to our CRO.</span></p><p><br></p><p><span style="color: rgb(0, 0, 0); background-color: transparent;">In our conversation, we talk about what it looks like to run a virtual kickoff during a pandemic, how to manage the competing expectations and content of different C-suite members, and how one of our filming sessions for Kickoff was actually the first time that our CRO and CMO ever met in person!</span></p><p><br></p><p><span style="color: rgb(3, 28, 51);">Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️&nbsp; review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @DriftPodcasts</span></p>

Sean Lane: Hey, everyone. Welcome to Operations, the show where we look under the hood of companies in hyper- growth. My name is Sean Lane. A pretty common tradition at the beginning of each year at tech companies is the company kickoff. This is usually where the entire company or the sales organization comes together to talk about what they've achieved, what's up next and how to get there. But here's the thing, these are usually huge in- person events. At some companies, people fly in from all over the world, just to be together with their colleagues for the kickoff. And obviously, this year, that just isn't happening. So, I was curious if and how companies were going to adapt the kickoff format to be a truly virtual event. Data told me that companies weren't just going to axe the kickoff altogether. First, the collaborative nature of kickoffs and of sales teams in general is not going to go away. Salesforce's state of sales report said that 77% of sales people say that selling collaboratively with other departments is critical to their success. So, then the virtual challenge just becomes engagement, right? According to a Brainshark survey, 61% of reps and leaders wished that their sales kickoffs were more interactive, and that was when they were in- person. So, my ultimate question became, how do you run a virtual company kickoff that actually works? Luckily for all of us, I found the perfect trio to help us answer this question. And that trio is actually the group behind Drift's own virtual kickoff that we held at the beginning of February 2021. In today's episode, you're going to meet Mark Siciliano, our VP of sales productivity and strategy, Maria Casella, Drift chief of staff, and Jackie Wright, the executive assistant to our CRO. In our conversation, we're going to talk about what it looks like to run a virtual kickoff during a pandemic, how to manage the competing expectations and content of different C- suite members, and how the filming of one of our sessions for kickoff was actually the first time that our CRO and CMO ever met in person. But first, let's start with a basic premise. These kickoffs are probably the most expensive meetings your company has. They are massive efforts that take the entire company out of their normal day- to- day. So, I asked Mark, who has 20 plus years of kickoffs under his belt. Why do we even do kickoffs anyways?

Mark Siciliano: Most people think it's all about motivation, inspiration and education, but quite frankly, it's one time out of the year where everyone gets together, and we are able to get on the same page from the jump. So, if it's once a year to start off a calendar year, ideally it's supposed to establish what our main drivers are as a business, and that everyone is transparently aware from the CEO, from the CRO down what's important. And then we can take our marching orders from that to combine that message with everything we do throughout that year. So, we always are looking back to that original kickoff that had our goals for that fiscal. And so, if you do that correctly, it's incredible. If you drop the ball in any one direction, it could have less of an impact.

Sean Lane: Yeah. I'm curious about the inverse reaction, right? So, if things don't go as well and you don't necessarily get the impact that you're looking for. I would imagine there's also like a perception amongst the team that these things aren't a valuable activity.

Mark Siciliano: Well, you may have read it somewhere that typically when somebody does a kickoff, 80% to 90% of what's delivered is forgotten less than 24 hours after it's complete. And so, you can say all the greatest things in the world, and as Jackie and Maria can attest, everyone gets back to their day jobs. So, you forget a one- day message or a one- hour session or a 15- minute moment with your CRO, but if you are all in line and everything that comes after the kickoff is a reinforcement of what was delivered, then you hit a home run. So my job as someone that has done too many kickoffs is not as much the kickoff, but what we do to reinforce it afterwards.

Sean Lane: You heard Mark right. 80% of what is delivered at a kickoff is forgotten in the first 24 hours after that kickoff. That's bonkers. So, what remains isn't just the content of the sessions themselves, but the emotions that you can create during these events, and as Mark said, the crucial reinforcement that comes afterwards. We're going to get back to the content and the reinforcement a little bit later in the episode. But first, let's hear from Maria. As a chief of staff at Drift, Maria is very often behind the scenes facilitating and organizing the biggest company- wide events, kickoffs, quarterly all- hands, you name it, Maria is usually at the center. And in the past year, like so many at other companies, Maria has been dealt a very different hand in terms of what's possible. After running our first company- wide virtual event at the midpoint of last year, Maria was once again at the center of this event and on a bigger global scale.

Maria Casella: I think our kickoffs have continued to evolve, especially as the business has grown. Planning a kickoff for 100 people, 200 people really different than planning a 400- person kickoff with people all around the world now, not just in one or two offices. And like you said, not all together in person now, so how do you keep people interested, how do you keep it relevant to everyone, and how do you make it engaging even from a virtual standpoint? So we did a couple of things differently. It was awesome to have Mark here, because he's obviously done this many times, and sort of we're able to lean into his expertise on how do you craft a theme, and how do you set the stage before the day even starts. And so our teams help, we were able to send everyone kickoff swag boxes in advance that were branded, not just with Drift, but also with the theme of what was happening. You can see the calendar behind Mark's screen. That's sort of our company calendar was sent along with that, which came up in the meeting as well, and set the stage. So, even though it was virtual, we were able to have a physical touchpoint that every employee got. And then I think we also leaned into being digital, and that also presents some real big advantages. We were able to pre- record all of our keynotes. We have an amazing design and video team here, and so they were able to really uplevel those productions. So, whether it was animating slides or getting different angles from speakers, or re- editing keynotes where we wanted a different impact for the end of the keynote. Those are advantages that you don't get when you're going live. And it's really nice when you're trying to uplevel to be able to pre- record some of those keynotes, and make sure that they're really perfect and they're hitting all the right notes, which you can only do when you're inaudible.

Sean Lane: For people who are thinking about doing something similar for their own kickoffs, how do you decide which of those sessions you should prerecord, and really level up the production value versus the ones that might actually be more effective live? Did you guys have a way of thinking about which ones fell into which bucket?

Maria Casella: I think for us, it was pretty natural. The longer keynotes were all prerecorded. I think things that were alive were awards, and things where you want it a little bit of a human element, we ended up post... When we did our debrief, we loved a lot of the prerecorded sessions that the quality was really up, and it was really beautiful. So, I think that's something we're going to continue to lean into and take advantage of.

Sean Lane: I have to stop here to echo and emphasize Maria's praise of our video and creative teams. They took this virtual event, and instead of shying away from the challenges it presented, they embrace them. As a company, we look at Apple and their keynote events as a role model and inspiration for the look we aspire to have for our own events, whether they be external or internal. And our creative teams rose to the challenge with highly produced keynote videos, music transitions, it blew me away. And now moving forward, what they produced will be the bar and the norm that everyone at Drift expects. Maria also mentioned that she, Mark, Jackie and the team had selected a theme early on to help frame the entire kickoff. Picking a singular theme or message for the entire company for the entire year carries lot of weight. So, I was curious how they went about picking one in the first place, and what they came up with.

Mark Siciliano: Themes have evolved, and for folks that do these, there's generally a circuit of themes that reinvent themselves every five years or so. But what has happened over the last four or five years is that companies are recognizing that if kickoffs are going to be impactful, the theme has to be a part of the growth of the business. So, at Drift, we recognize that we're at a crossroads in terms of our opportunity to go from a hyper- growth company that starting a category to a larger enterprise- wide business solution. And so, we felt we put all these pieces in place, and Maria and I came up with this idea of Showtime, meaning not only was it add an opportunity, but we were ready internally, but it also made people think of things outside of the business, meaning sport or theater where you have to come together as a group, and there are opportunities where everyone plays a part, that's the Showtime Lakers as an example. Or if you're thinking theater, Showtime is, there's always a script and a director, but every day there's a different audience, and you have to come prepared to be nimble and adjust and be tailorable in your message. And so, we not only decided to create that as a message for year one, but Maria and I said," You know what? Our leadership has a two and three- year plan, why don't we establish our themes across two or three years, so that it kind of maps to our strategy?"

Sean Lane: Wow. So, you know what the next couple of kickoffs are going to be?

Mark Siciliano: Oh, absolutely. Maria, maybe you can add, but I think that's how we thought about it, right?

Maria Casella: Yeah. I think every year you want a theme that's inspiring and that's exciting and that feels relevant, but I think leaning into not just like what's inspiring this year, but how do you tie that story together for multiple years inaudible that have been here and have the context, but those are all themes that are exciting whether or not you're a new Drift employee or you've been here for five years, because they can go in the context or they can be new themes.

Sean Lane: As an audience member and a participant in the kickoff, the thing I appreciated about the theme was you guys gave us this kind of overarching framework for what Showtime meant in the context of the two days that we had kickoff, but a bunch of people throughout those two days came forward and gave their version of what Showtime meant to them. And so it wasn't this one singular answer, right? And so depending on which part of the team you're in, which function you're in, that was a little bit open to interpretation, which I liked and appreciated. Jackie, you've obviously handled a ton of the logistics and under the hood, and execution of getting this thing from idea to actually running it for two days. I'm curious for you was picking the theme, the first big domino to fall before you were able to go off and running, or what is the actual very beginning of the planning process look like?

Jackie Wright: Yeah, definitely. That's a great question. I think that being a virtual event gives you a little bit more leeway as far as logistics go. Normally for a live event, you would have to plan, like start contracting or looking at different properties about a year out. Looking at this one, theme is definitely one of our key things to look at right away. And I think that even before that, making sure to align the company event with any department specific events, like the sales kickoff event happening is really important. And so bringing in all the key collaborators across the company to start is a great place, and from there, the theme should come out of that group that can then guide all of the rest of the teams from there.

Sean Lane: How far in advance should people start, Jackie? Like what amount of time is the right amount of time? I know there's always going to be a rush at the end, but how far in advance do people need to start planning out the content and the schedule and all that?

Jackie Wright: Yeah. So, it depends on what your role is. If you're the co- planner of the event, I would say if it's a live event, like I said, look a year out to start looking at destinations and get RFPs from different venues, and things like that, for logistics and things like that, for content. And I super appreciate as a planner that we have three years of themes, because that makes my job super easy for the next three years, because we'd have to start there as far out as possible basically. But at about six months out, I like to start the conversation with the core cross- functional collaborators, and just really nail down a date so that we can put something on the team's calendar. So, like when they're looking at vacations and things like that, it's really helpful that the whole team is able to be there, and so the more leeway we can give the team to plan around the event, the better. So, nailing down a date is really important, which obviously is a cross- functional thing. And then from there, about a quarter out is when we really start getting the core collaborators on the content together, and start building out the agenda, and we just kick off weekly committees for the core team members, and bi- weekly for the different content committees from there to make sure that we're really working towards not having to rush last minute.

Mark Siciliano: That doesn't even scratch the surface in the importance of someone in Jackie's role as you run this through, given what support is appreciated over the actual two days or three days. And maybe we'll get into that a bit, but to understand that the behind the scenes view of that is incredible to see in action to be fair. So, although I've done kickoffs that the work that's done obviously in the pre- planning and scheduling, but the content and the like is absolutely amazing.

Sean Lane: Put simply, having a Jackie on your team, makes your kickoff hum. Fun fact, by the way, Jackie who runs these events out of Asana actually helped run the first ever kickoff at Asana. With someone like her, every detail, every line item gets the time and attention it deserves. And most importantly, you don't end up with a bunch of important details falling through the cracks, because people are scrambling to get things done at the last minute. So, whether you're running the show completely on your own, or you have a team of people helping to plan your kickoff at your company, start at your event date and work your way backwards, just like Jackie did. I also thought it was interesting that this team even picked a two- day event in the first place. And Jackie pointed out to us that they split the kickoff up into two different parts. One that was company- wide and had more of the corporate messaging, and the other that was team- specific. So, while this group focused on the sales kickoff after the corporate one, there were parallel kickoffs going on with every other function inside of the company. And that split, that doesn't just happen. So, I asked Mark why that's where we landed?

Mark Siciliano: We recognize that there are a number of lines of business within an organization where their leaders need opportunities for their people to come together, and speak about their unique issues. And then there are other more broad spectrum opportunities for the entire company be there together. And so, in a virtual world that meant having unique breakout sessions that were specific to a post- sale group or a pre- sale group or a sales group like ours. We wanted to make sure that all groups were afforded opportunities to hear from our customers. So, our customer sessions were open to everybody, right? And everyone can come listen to those folks, but for something that may be unique to customer success, it wouldn't be something that would land with a sales audience, so you wouldn't want to force them to sit into that. So, because we were limited to time and effort, we said," Let's combine or let's kick off our kickoff with the corporate message and story from our leadership, and then allow our C- suite to have unique kickoffs based on what they felt was best for their organization." At least that's where I'm coming from. The other two might have their own opinions, but that's how I try to balance it out.

Sean Lane: Maria, I'm curious how you kind of manage the internal dynamics of those different C- suite members, because I would imagine, they all have a unique perspective, they all have certain things that are going on with their team that they want to accomplish over the course of this period of time, and so you have the most direct access to them as you're going through this process. What does that look like? And what did you learn about how to both funnel them together on a single message for the company- wise stuff while still allowing them to have that flexibility at the team level?

Maria Casella: Yeah, I think we think about, kind of going back to the theme, like you want to set the stage with the whole company at the beginning so that when those breakout sessions happen, each individual team has the context of where's the company heading this year, what's happening at the higher level, and how does my work and the work that we're reviewing in those breakout sessions contribute to that bigger piece? and then in a virtual- first world, I also thought a lot about what leaders do we want to make sure are on the stage, if you will, and that the whole company can hear from. We have hired so many people in the last year that have never met anyone else at Drift in person, and we've hired some really amazing leaders that other people have never met or other people have never seen if you're not in that department. And so the all- company session is also a great opportunity to give those leaders some time to share their vision, share what they think is going to happen this year or where they want to take their teams to give the other teams perspective. And you want to keep it at a high level so it's relevant and it's engaging, but I think it's a great opportunity for people to put faces, and see somebody live in action talking about where they're heading this year, not just" No. Oh, yeah, I saw an email six months ago that we hired a new leader in this other area of the business."

Sean Lane: Yeah. That's an interesting angle that having been here for a little while, I wouldn't really think of kickoff as an opportunity to introduce some of those leaders to a huge chunk of the company, whether you're brand new or not. You might not have interactions with a lot of those people, and so when we talk about some of the video content that was produced for kickoff, they were heavily produced, really high quality stuff. And so it's interesting to think about the fact that for a lot of people, that was their first interaction with a lot of those leaders, and their impression of them, their takeaway of them is going to be driven by that experience.

Maria Casella: Yeah. Even for the leaders themselves, right? It was the first time that our CMO and our CRO, Trisha and Todd got to meet each other, because they were filming a session together. And so, they were six feet apart, but they inaudible seeing each other outside of that computer screen for the first time, and that sort of made for a nice human interaction between them. And I think the team liked seeing that, and I think it's fun to see those interactions.

Sean Lane: And Jackie, Maria mentioned some of the social aspects of meeting people, and being able to interact with folks you don't necessarily interact with. And that's a huge thing you might lose by having to do a virtual kickoff as opposed to an in- person one. Was that something that you guys talked about in terms of how do you replicate that type of interaction in the best way possible?

Jackie Wright: Yes, definitely. We talked about how to... I would say more talk about how to create a shared experience, so not replicate that particularly, but more on how to make the team feel united even from afar. So, like as Maria was mentioning, sending the swag boxes out to people. We take for granted so much the benefits of a live event from being able to just grab a beer with somebody after a session, and organically meet folks to just handing out swag when they get there and things like that. And so having moments when people can open their boxes together, all do share things at the same moment is really important and also too leaving space for organic things to happen. So, we had a couple of really cool things that we never could have planned happen on kickoff, because we've made the space for a couple of live attractions that were happening live for the whole team, as well as some activities that were just goofy, and got people laughing and interacting with one another. Drift in general has the Zoom chat goes off in all of our meetings, and so that really landed itself to a shared experience as well with everybody really engaging in the event and still participating. And so if that's not part of your culture, like really making sure people are there, have their cameras turned on the whole time or participating in the Zoom chat, asking polls or whenever you can do live to make sure that it's an interactive event, and that everybody is participating rather than just watching a video the whole day is really important. And one of the things that Mark did to help create that format is he's really a stickler about adding breaks after every 30 minutes, feel like every 30 minutes of content, there should be something that's gets you engaged again. And so he set up the agenda really well to lend itself to that too.

Mark Siciliano: I call it the TED Talk rule. There's a reason why Ted Talks are only 18 minutes long, because that's really the comprehension level when you're watching something over video. And so if you get beyond that, people will get bored or they consider it noise. And so, if you just redirect when you're doing videos, whether it's guess the baby picture, or spin for some swag, or listen to me, do some rap song with a backbeat, it kind of lands with people who believe they're not just interested in shoving content down my throat, they actually want to make this an experience that represents the best of Drift. And I'm the newest Drifter in this foursome, and you can definitely see a uniqueness about Drift. And we tried to make sure that what we delivered mapped to that. I don't know if it necessarily did versus a live session, because I haven't met anyone live at Drift. I think it landed, obviously with the support of all three of you actually. So, I was jacked about it. I thought it ended up pretty good.

Maria Casella: I think the other thing we need to mention is we had two amazing MCs, two different Drifters, one for the all- company session and one for the sales session who just did an amazing job of bridging the different sessions, adding a really human element, connecting the pieces, right? Like here's the first keynote, and we're now going to hand it over to this person and sort of pulling it all together. And those two individuals did such an amazing job, whether it was playing music or doing the live unboxing of the swag, just things that were organic, but then made it feel really human, and to Mark's point added like some just fresh interest between the sessions.

Sean Lane: So, there's a lot of takeaways from the crew here. But overall, what they're really saying is that it is possible to infuse your company's culture into a virtual event. For us at Drift, it's things like how we interact with one another in the live chat on Zoom, or the folks that we pick to be our MCs. For your company, it might be something totally different. These cultural elements combined with Mark's Ted Talk rule of 18- minute chunks made for an engaging digestible couple of days for the people like me who were consumers of the kickoff in the audience, and the content that they were presenting. The team even told me that having elements like the live chat gave them real- time feedback on how the audience was perceiving the sessions in a way that an in- person event might not have. So, they've got their theme, they've got the production value, the schedule, the cultural elements. With all of these things in mind, the operator in me wanted to know how this trio actually pulls the whole thing off? And it turns out that it all comes back to a critical document that Jackie creates called the Run of Show Doc.

Jackie Wright: So, we had one planning sheets that was shared with a lot of folks, anybody that was involved in the content, and most of the leadership team that had the agenda, and a lot of detail with all of the session objectives and things like that. This is something separate that was shared mostly with just the core folks that were involved in the run of show, including the MCs and the core committee. It was a tab for each day that had each session to the minute, anytime anything happened, it had a line item for it. So, from music playing, to Slack reminders, to the session starting, to the introduction of the session and the music that rolled in, and then the content starting, to the transit to the next session, breakouts, everything was in there with the music that should be playing at that moment, the exact minute it should be happening. And so, as we were going on, obviously we weren't to the minute on any of those things, but we had an idea if we were off on how we can get back on track, and everybody was on the same page on where we should be, so we could communicate really clearly on what we should do troubleshooting in the moment. And when we were planning, the couple of days prior as we were doing dry runs, that document was really helpful to make sure that we had all the details in place, and that's how you pull off the seamless event. If you're not running through that event, minute by minute, couple of days prior, there's going to be inaudible in the middle, and because we did that, I think it went a lot smoother day off.

Sean Lane: How many of those dry runs did you all do?

Jackie Wright: A lot. Mark probably did a lot more than me to be fair. We did at least two hours with the MC himself, and then we had a couple of core committee meetings, probably at least three hours of core committee meetings, where we were going through that run of show document ourselves, and then Mark and each of the pillar leads, so that our other productivity team members so it's two of them, they each had their own dry runs with their content or presenters. So Mark, how many dry runs did you end up doing?

Mark Siciliano: It ended up being about a couple of weeks worth of dry runs. So, we broke down our kickoff into three buckets, not including the corporate delivery, which was itself a big event. And so those three, probably six dry runs a piece with separate deliverables by, I call them inaudible, people responsible for the content that so many people outside of this team stepped up to deliver their own Showtime. You know what I mean? In a way it was their opportunity to shine in front of the organization.

Jackie Wright: It's another benefit of recording ahead of time lets you... For it to be fair, Maria, didn't have to do crosstalk, because she prerecoded.

Mark Siciliano: Lucky devil.

Jackie Wright: Yeah

Maria Casella: Well, it goes both ways. I think that you still have to do practice sessions, because the quality when it's prerecorded is expected to be higher. You get the advantage of if you don't hit that line just right, or if something's stuck in the middle of the story, you can re- record it. So, you definitely don't have to practice till perfect, but you definitely have to do a lot of practice making sure the flow was really good, the tone is right. I will also say we had an amazing video team, but making sure the speaker is... Lighting and background, and a lot of it being on Drift brand, that all takes time. The overall takeaway is all of the investment upfront is worth it when the final product is really good, and resonates to what Mark was saying, and people retain... What we talked about at the beginning of this, when you retain that and when it all fits together really well, it's magic. But it takes a lot of upfront work, and a lot of behind the scenes work from a lot of people on the team.

Sean Lane: That level of prep is critical for a couple of reasons. First, for recorded sessions, you have to start that prep even further in advance, because you need the time built in for recording, editing and more editing. And second, with facilitators like Mark and Jackie and Maria, they have to have the trust and the faith that the content they've prepared is going to stay at a really high level when they pass the reigns off to any single presenter. One lackluster session, and you might lose some folks in your audience. Okay. So, we said at the top of the show, how quickly people can forget, and are likely to forget most of what they hear at a kickoff. And Mark told us that reinforcement helps play a really critical role in making sure that some of the key concepts are retained. So, after all that work, what does that reinforcement look like? How do we measure that this massive event was worth it?

Mark Siciliano: That's a loaded question, but I'll keep it simple. We have technology that allows us to see people in action today, right? So, with that technology as opposed to doing role plays or having them take a test, or try to amplify what you've shared in the kickoff, you actually work with your first line managers to address the things you want your sales team, in our example, want them to deliver in front of a customer. We actually get to see that and critique that, and have them understand that these are the big rocks we want to see focused when you're working with customers. And so with us, it was literally a week after the kickoff that I was looking at recordings of our people, sharing the new sales message, talking in storytelling mode, sharing how a business case should be presented. Those were our three big rocks, and we are measuring that consistently. As you know, we do a sales all- hands each month, and each month I will go back... Like our focus for those monthly meetings are going to be," So how are we doing against our sales kickoff mantra?" And you will hear success stories from people, and usually that resonates. That's like," Oh, that successful person is doing something really good. I should replicate that. I'll do well if I follow that practice." So, that's what we're doing, that reinforcement. You don't want to be a bother. It's a fine line between stuffing training down people's throats versus not for nothing, but if you do this, you're going to have a higher propensity to win more business. And that's a validation we have to earn. We can't just say," Follow this methodology, and you're going to win deals." If that was the case, every tech company would be a$ 100 million business. It's not. Less than 10% are$ 100 million businesses. So, what does that mean? That means gaining the trust of your sales team, establishing that what you're presenting to them makes a difference to their bottom line. If you can do that with folks like Jackie and Maria, that's how you win.

Sean Lane: All right, Jackie and Maria, I know both of you decently well, I know the way you think, and I know you're already looking ahead to the next time we do this, what we could be doing better and what we're going to improve. Without giving away too many secrets, right? DC wouldn't want us to give away the store here. What's next, right? We're a digital- first company at this point, this concept of a virtual kickoff is not going to change. Where do we go from here?

Maria Casella: I think we're going to lean into the things that worked well this time or that we liked. We really liked the prerecorded sessions. I think it allowed us to uplevel the quality of the kickoff, which has been our goal every year, but this wasn't the next step function up, so you're going to see us leaning into that some more. I think the cohesive theme, that sort of goes before, during and to Mark's point continues well after, that's something we're going to do again. We already have the theme for next year, depending on what happens in world. Is next year virtual or in- person? I think there're a lot of questions there that'll still be answered as we see how this year develops.

Jackie Wright: I totally agree. We'll be just building on the foundation we've established. With this past event, I project- managed it all in Asana, and this time I created an Asana template, so that we can get ahead of ourselves and plan anything from six months out down to the day of down to post and following up debriefing. We're going to continue to streamline in those kinds of ways. As Maria mentioned, it's up in the air what 2022 will look like as far as virtual versus live events goes. So, we're trying to figure out at this stage, like what's a good mix to having those leadership conversations on what we want to do as far as a digital- first world, but having shared experiences live too. We used to have this thing called Camp Drift in the fall that I've never been able to attend. So, I hope we come back with that and figure out how to align our kickoff events, and still do virtual events as well. And so, it's definitely virtual events aren't going anywhere, so figuring out how we can get better and better at those, I think is really important. Another big focus for us on the sales team is we're transitioning into field operations, and so really figuring out how we can align both the sales and the customer team events. And then also to cross go- to- market, how we align with the marketing team and what's going on with their kickoffs, and really making sure that all the departments and all of Drift is moving forward towards our dynasty together.

Sean Lane: Before we go, at the end of each show, we're going to ask each guest the same lightning round of questions. For this trio, I thought it'd be nice to split up our normal questions amongst the crew. Ready? Here we go. Maria, best book you've read in the last six months?

Maria Casella: The new Netflix culture book or the Amazon book, Working Backwards. It's kind of a tie.

Sean Lane: Okay. Jackie, favorite part about working on sales kickoffs or kickoffs in general?

Jackie Wright: Working with so many people. It's a great cross- functional collaboration moment. And also too, working with the MC, Nick, I'd never worked with him before, such an awesome opportunity to meet a lot of the team, and really get people fired up which is so fun.

Sean Lane: Mark, least favorite part about kickoffs?

Mark Siciliano: The aftermath, the 30 minutes after kickoff is the worst. It is a melancholy moment that you put all of this time into, and you feel for a moment that it's all going to just be forgotten. And that part is when you start second- guessing yourself, regardless of the fanfare you always are going to... And Jackie knows this, you sort of become self- critical, so that 30 minutes after, before your first bourbon, generally is the thought of," Did I do what I needed to do?" You get that sort of FOMO moment, and so.

Jackie Wright: Next time we're going to do a committee happy hour, right? Following... I'll toast a meeting crosstalk.

Mark Siciliano: Yes. I hope so.

Sean Lane: crosstalk maybe to the catalyst for the bourbon.

Jackie Wright: Yeah.

Mark Siciliano: Yes, yes, absolutely. Absolutely.

Sean Lane: All right. Maria, someone who impacted you getting to the job you have today?

Maria Casella: I think our founders. I think I was candidly not remotely looking, I was really happy where I was. I thought I was going to a casual second round, like meet and greet, it was a full second round interview when I met both of our founders, and I never looked back. The vision, what we're building, and then honestly, having these podcasts, being able to research them and listen to the podcast before we ever meeting them, gives you a ton of context, and you learn a lot about people and the culture and what it's like to work here.

Sean Lane: And my experience, at least with listening to them is the realization that when you do meet them in person, that they're exactly the same as they are on the podcast, which is a really weird thing, right? And kind of gives you a sense of the authenticity of the people too, that's a strange dynamic. All right. Last one, I'm going to ask each of you to answer. Jackie, maybe we'll start with you. Normally, my question is one piece of advice for people who want to have your job someday? So, I'll say you can either say that, or one piece of advice for people who want to run a successful kickoff. You guys pick. Jackie, you want to kick us off?

Jackie Wright: Yes. I would say... Well, my primary role as an executive assistant, I would say if you want to be an executive assistant, you need to make sure you're doing it for the right reasons. It can't be to just be around the C- suite, it can't be a stepping stone into another job. It needs to be, because you love to support people that you're a servant leader at your heart, and if you are, then it's a really great role.

Mark Siciliano: I'll take the same question. If somebody wants to be in my position, which officially is vice president of productivity and strategy, it's really trying to know every facet of the business, and to be the collaborator across the organization. I always share that it's amazing what you can accomplish when no one cares who gets the credit. In my line of work, you tend to get the blame if things go wrong, and not too much credit if the revenue numbers hit, because you got a lot of A types who are trying to sell and meet their quota, but understanding of the business and sharing strategies that help them improve and improve their bottom line. If you can do that, you'll be very successful in my role.

Sean Lane: All right. Maria, bring us home?

Maria Casella: Yeah. I think advice for somebody that wants to be in this role, I would say, get curious about companies that are growing fast, and how you can be part of that growth story. And a lot of it will be ambiguous, and a lot of really uncomfortable and just lean and do it, like this role didn't exist when I interviewed, I actually interviewed for a different role, and I got this role between interviewing and starting. We never know goals for this role, there were no goals for this role, there was a slight framework, but just lean into the ambiguity and get curious about what companies are out there that you want to be a part of, and then find a way to be of that story and continue to lead into that growth.

Sean Lane: Thanks so much to Mark Siciliano, Maria Casella, and Jackie Wright for joining us on this week's episode of Operations. If you want to learn more about running virtual events, Drift's marketing team has actually put together a virtual events certification on our website. You can go to insider. drift. com. Again, if you're not a member of Drift Insider, tons of courses, tons of certifications available on there, and they just launched a brand new one about virtual events. If you aren't subscribed to our show yet, make sure you're subscribed wherever you get your podcasts, you can get an episode into your feed every other Friday. Also, if you want to watch some of our episodes, they are now available on YouTube, on Drift's YouTube channel. So, go ahead and check those out as well. And last, but certainly not least, if you're enjoying the show, if you're learning something from it, please, please, please leave us a six- star review on Apple Podcasts. Six- star reviews only. All right, that's going to do it for me. Thanks so much for listening. We'll see you next time.


A pretty common tradition at the beginning of each year at tech companies is the Company Kickoff. This is usually where the entire company comes together to talk about what they’ve achieved, what is up next, and how to get there.

These are usually massive in-person events, and obviously, this year that just isn’t happening. In this episode, we dig into how companies can adapt the kickoff format to be a truly virtual event, and have it actually work.

The trio with the playbook to pull it off came from our own team at Drift: Mark Siciliano, our VP of Sales Productivity & Strategy, Maria Casella, Drift’s Chief of Staff, and Jackie Wright, the Executive Assistant to our CRO.

In our conversation, we talk about what it looks like to run a virtual kickoff during a pandemic, how to manage the competing expectations and content of different C-suite members, and how one of our filming sessions for Kickoff was actually the first time that our CRO and CMO ever met in person!

Like this episode? Be sure to leave a ⭐️⭐️⭐️⭐️⭐️⭐️  review and share the pod with your friends! You can connect with Sean on Twitter @Seany_Biz @DriftPodcasts