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Sales Enablement Soirée: Virtual Vs. In-Person: The Winning Sales Kickoff, Fall 2020

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Cassandra Tenorio: Welcome to our panel on Virtual Versus In-Person the Winning Sales Kickoff. This is such an important topic for so many practitioners today, especially since a lot of them have really had to pivot their sales kickoff strategy to go virtual. And so I’m very excited to hear from our panelists. I love for each of you to just introduce yourself, say your name, your company, and  a little bit about yourself. Kendall, let’s start with you. 

Kendall Michaud: Hi everyone, I’m Kendall Michaud, and I’m currently with HighSpot where I lead our revenue enablement team there internally. Our team helps oversee our foundational programs and strategic initiatives at HighSpot. So those teams we help enable our account development sales and our services teams.

Megan Allen: Awesome. I’ll go next. My name is Megan Allen. I work at ZScaler, which is a cloud security company, as a global sales and buyer enablement manager. Our sales strategy and enablement team focuses on enabling our entire global sales organization from an onboarding standpoint, as well as just continued enablement throughout their careers at Zscaler.

John Hsieh: Thanks, Cassandra. I’m excited to be here with Megan and Kendall. I’m the founder and president of Scale GTM. Prior to Scale, I was the VP of enablement at DocuSign from 2012 to 2019. And this was an incredible journey where we grew from a twenty-five million dollar a year revenue company to over a billion. I found it scaled to help other companies accelerate their sales growth while avoiding the pitfalls. And our secret sauce is really, we start with the buyer today. We work with clients to really understand their buyers and then translate that understanding into improving their messaging, their sales training, and their sales process.

Cassandra Tenorio: Awesome. So I’m excited to talk about this topic today. We only have 30 minutes, so we’re going to jump right into these questions. And I really wanted to start the conversation with talking about why organizations invest in a sales kickoff. So what’s the purpose of a sales kickoff and how has the modern SKO evolved over the years? So, John, I’d love to start with you.

John Hsieh:  Great. I’d love to kick it off, so I’m sure this is going to resonate with everyone that’s watching in that I’ve had the pleasure and the pain of planning over a dozen of these over the years to really make it meaningful. When I think about the purpose, there’s a simple framework that I follow and I call it the three E’s and the E’s are energize, engage, and educate. So energize is the recognition piece, right? It’s the only job where you lose more than you win and you still celebrate those winners. It’s the president’s club announcements. It’s your awards, dinner, or even shout outs during keynotes of specific BDRs or reps that did great throughout the year.

The engaged part is really about us recognizing that the best employees are those that are invested in the business. And often in sales, we talk about commissions, but it’s really important too, that the sales team like everyone else has bought into the vision of the company, the impact that they’re driving with their customers. And even internally, career path, how they can grow in their careers within the organization? This has a real impact on retention and hiring, and it’s something that you can emphasize at SKO.

 And then the third part is the third E is educate, right? So this is your product, your process, your best practices and your sales skill sessions. So these three E’s fulfilling all three of them is a really tough order. So you’re forced to make trade-offs at any particular SKO And yet you’re spending upwards of two, three, $4,000 per attendee, and pretty soon your SKO, budget balloons into the millions or multi-millions. So naturally when you put all these factors together, you want to see more impact out of this investment. And we start to see a transition from SKO as an event to a program. This is really where I see companies moving. So as an example, even at DocuSign pre-pandemic days when I was there, we started transitioning from a pure two day event to a three phased model where we talk about preparing the reps before arriving, doing a set of activities while they’re there and immediately following up post. And we thought about driving it as our strategic Q1 program.

Cassandra Tenorio: We’ve seen this year especially so many organizations having to pivot to a virtual sales kickoff, and this comes with its benefits and it comes with its drawbacks. And so what are some of the biggest challenges that practitioners face when planning a virtual SKO? Kendall, let’s start with you.

Kendall Michaud: Yeah. So, thinking about some of the challenges, everything’s stripped away, right? You know, you don’t have the venue, you don’t have the food, you don’t have the natural social interactions. And I think actually a funny story, we did a training with our account development team on how to show up to SKO. This is because they’re earlier in their career and actually many of them have never even attended a kickoff before. And so we showed them a video of pre COVID SKO with the stage and the lights and everything. And then we showed them post COVID SKO and even myself watching the video I had to go, okay, well, there’s a big challenge ahead of us and that’s driving engagement. I think with challenge comes a lot of opportunities, but I think a lot of people are thinking about how to drive engagement virtually. 

Megan Allen: Yeah. Well, echoing a little bit about what Kendall said, I think the first thing that you think of when it comes to challenges with virtual events is engagement. Like how is everyone stuck at home? They have kids, there’s background noise. Their spouses are also working from home, there are animals that need attention, life is going on. So how do you conform to that while still educating them and keeping them energized throughout the event. So we solved for this with high production quality, really invested in making sure that the general sessions and content throughout was really just the highest quality to keep people engaged.

I think our second biggest challenge was agenda. So when you are a hundred percent making it absolutely clear where they need to be and what they need to be doing at all times is difficult. Well, when you’re in person, you can jump up on stage and say, this is where you need to be next. We’re doing a breakout or we’re doing a break for the next 15 minutes, and then you’re going to come back into the general session. But when people are virtual, it’s hard to keep track of them and put them into Zoom rooms and general sessions when they need to be there. So I think agendas were a bit of a struggle for us, upfront.

And then lastly, I think working with so many different time zones, when you’re a global organization, you have people from all over the world that you don’t want to keep up at midnight. To keep them all in the same general session. So virtually we were running basically three different SKO’s for our EMEA team, our APEC team and our Americas team throughout the entire week. So I think time zones were a big challenge for us up front to get everyone to repeat sessions. But luckily, like you said with virtual, you can prerecord a lot of stuff. So that helped us in a lot of ways.

Cassandra Tenorio: Definitely those are some of the big challenges. Now let’s talk about some of the benefits of delivering a virtual SKO. So Kendall, let’s kick it off with you again.  

Kendall Michaud: I thinkMegan, it was interesting you touching on, you know, running three schools at once. I think that’s definitely a challenge, but it’s also an opportunity to provide personalization. I think like, the logistics of it sound daunting, but really at this point anything’s on the table. And I think that’s one of the biggest benefits is that you can kind of say everything that we’ve done. Let’s not think about it on day one, day two. The initiatives we want to land, it’s really just about, John, like your point, what’s the program, what’s the time going to look like for people? And, so that would really, I would say is the biggest benefit is that everything’s on the table. You’re saving money from flying people out. You’re able to personalize and provide an experience for your global team that you haven’t been able to do in the past.

Cassandra Tenorio: I know John, that you’ve planned probably about 12 of these, you said. Are there any kind of benefits to delivering a virtual SKO versus an in-person one? 

John Hsieh: Well, I think Megan and Kendall, like hit the nail on the head and that this is a really interesting time to reinvent it, right? Like how do you think about things differently? And so I think the pros far outweigh the cons, right? So many of the clients I’ve loved that I’ve been speaking to have looked at this as an opportunity to re reinvent a broken legacy event based model into a program based model that runs throughout the course of Q1. And some people are uncomfortable maybe thinking about it for over the course of three months. And so maybe they think about it as a one month series of things as well. So let me just give you like a solid concrete example here. Right? It talked about the three E’s earlier. So if you look at the third year educated in the legacy SKO world, you may have a breakout where you teach a sales skill and you’ve designed some activity around the table, right?

Where people work on this for 15, 20 minutes. And if it’s on day one of SKO, attendees are looking at their watches and waiting for the evening’s festivities to start. And if it’s on day two of SKO, they’re still recovering from the first day. So in the virtual environment, you aren’t under the same pressure to deliver everything under this artificial time constraint, right? So you can have a session to educate the sales team, say that’s on a Monday on a new sales scale, give them an opportunity throughout that week, Tuesday through Friday to actually apply that skill. Now do you want to build team culture in a virtual environment? You can put people in preassembled teams. Gamify it so they can submit something the following week as well. Right? 

So now in this new world, you have a real program and with a real program, you can track progress. You can measure impact on performance and actually tie back your program to business metrics. Not to mention these things can be reused for future programs like new hire onboarding. So it’s a real opportunity for all the enablement and sales leaders watching this. So strands form SKO to drive this sort of exponential impact.

Cassandra Tenorio: Megan, what are some of the benefits that you’ve seen in executing a virtual SKO this year? 

Megan Allen: Yeah, I think, without repeating too many things, really virtual learning, you don’t have a max capacity or room to conform to an in-person event. I think there’s an opportunity for great networking. I think sometimes when you’re in-person you’re afraid to go up and talk to somebody or come off of, you know, raise your hand and ask a question during the session. So, I think when you’re virtual, it’s a lot easier to type a question in a chat box. Or come off of mute and say something. We incorporated a really great philanthropy event virtually and had some really great social hours where people were doing the philanthropy event together in their homes with their children, with their families, submitting pictures for our like follow-up video at the end of SKO. So I think it opted for a lot of really great networking opportunities for people to talk to people that maybe they normally wouldn’t speak to at an in-person event. 

A couple of other things, or just main state sessions were able to be pre recorded. So allowing us to produce a really highly engaging session, basically sort of making it like a TV show, with animations on screen and visual reference representation in ways that we wouldn’t be able to do if it was live. So this kept everyone really engaged and excited to see what the following sessions would be like virtual boosts that everyone could attend, not having to worry about international travelers, having jet lag and people being able to be in the comfort of their own home home. So stress levels were low and the energy was high because they were really excited to see everybody and interact with people because we’ve been stuck in our homes, not really talking to many people.

Lastly, being able to invite partners and customers changed general sessions was a big SCOtakeaway. John talked a lot about recycling content after which we definitely did as well, but we were able to invite some customers and prospects and partners to our general sessions. So that was a really great way to engage people, into our entire scope and sort of a day in the life of Zscaler. So those are some big benefits that we saw. 

Cassandra Tenorio: Absolutely. I want to kind of pivot and really talk about the role of technology in a virtual school. I think it plays an incredible role, and executing something like this. And so, what are the considerations that you have when really selecting the tools to support and host your virtual sales kickoff? John, I’d love to hear from you.

John Hsieh: So I’ll touch on that in just one second. But, I want to echo something Megan said, which is just even participating on this panel and having interaction virtually with other people is incredibly therapeutic. And so I think being able to create that, I think this probably speaks to the energized piece that the first E which is you can’t underestimate simply getting people together, no matter how imperfect or how difficult it can be. Keeping it simple and having a forum like this, in your school environment is going to be key. Now on the technology part,  this is probably, and I think I talked a little bit about this earlier. This is probably one of the main things that Kendall, Megan, Cassandra, you and other people watching gets their blood pressure boiling. It’s if you think about it, you’ve got to have a virtual SKO hub of some type, right? So you have to place your digital agenda somewhere, then calendaring becomes more of an issue because now if you spread it out over the course of multiple days or weeks, that’s important, then you have to have virtual environments.

So a mainstage environment, a virtual breakout room type environment, a virtual networking session environment. Megan talked a lot about this in terms of production. So you have your live and pre recorded sessions, and if you want to do high production value, you may even look at studio access and might do some sort of speaker training as well, or send technology to your speakers, cameras, mics, et cetera. Finally we can’t forget about the third E right? The educate piece, you have enablement and engagement tools. So, you’ve got great vendors in this space like Kendall’s company HighSpot, there’s another company SalesHood, and they’ve actually extended their platform to provide a purpose-built solution just for virtual SKO.

So people are really thinking about how to enable using tools in a virtual SKO environment. So given all this complexity, this is why we at Scale we’ve actually partnered with Bash creative. They’re an incredible event management company to offer a virtual SKO blueprint and what the blueprint does is combines Bastow virtual event management with buyer centric sales training to help you successfully plan and execute a purposeful SKO around those three E’s: energize, engage and educate. But I guess the key takeaway here is you really have to think about your first virtual environment end to end plan carefully and reach out to others that have done this before, because you don’t have to go it alone. 

Cassandra Tenorio: Absolutely. Technology can also be very limiting when it comes to a scale. You lose a lot of that in-person interaction. So what are you doing to work around that challenge and all the other shortcomings that can come with technology? Megan, did you bump into any of those or anything like that? 

Megan Allen: Yeah, so I think upfront when we first started having some pre-planning meetings, when we had decided that it was going to be virtual there was no way it was going to be in person. It was a little, it was very intimidating. you can think about how technology can work for you or against you. So we evaluated several companies to help us build a truly immersive experience for our SKO. We went with an Olympic theme and built the platform to look like an Olympic village. Honestly, when you entered the platform, it truly felt like you were entering a virtual game. So, we had the keynote arena where we hosted all of our general sessions, kept the Olympic theme going with having a keynote speaker, Apolo Ohno, which is really cool. 

The expo center housed our virtual booths. During virtual booth breakout times, we had people live sitting in those booths and people could just pop in and out of those Zoom sessions to interact with people and learn about what that booth was about. But in the village, is where we had users navigate for our live training breakouts and our entertainment and social events. Then our e-learning center for users to complete the modules, ahead of time, as well as throughout the week. So using gamification really helped keep people engaged throughout the week and stay on task. And then we also assigned people a personalized agendas to follow. So that really helped bright group sizes up, keep people on task, and really overcome that technology obstacle. Because like I said, it’s a little bit like herding cats when you’re virtual and making sure people are where they need to be when they need to be there. So this helped ensure that they were in the right place at the right time. Breakout sized groups were small and manageable. So I would really just say having a solid technology to work with is so important when you’re talking about a virtual scale. 

John Hsieh: Megan, I saw, I think you guys did an incredible job. I saw on LinkedIn, a one or a minute and a half video of a highlight reel around this Olympic theme and immediately, like two things came to mind. One is, wow, that’s really well thought out and incredibly high production value. Incredible. That must’ve been so engaging. But the second thing that I think was so smart was the fact that you guys posted that on LinkedIn, right? Which I think is brilliant. Number one, I think it’s great for the community to see that. And then number two, I think it’s a great recruitment tool as well. Right? So I think with the virtual world, I think there’s a real opportunity to take your SKO events and think about assets that you can potentially share across social media to really drive engagement for folks who are outside of your company.

Megan Allen: A hundred percent. We definitely use that video for recruitment purposes. It was a look how cool this experience was for our learners. Look what we did with the virtual engagement. Oh, and by the way, we’re hiring. So you should come work here. So I totally agree that it was a great opportunity for recruitment. 

John Hsieh: Kudos. Congratulations to you for that. 

Megan Allen: Thank you.

Cassandra Tenorio: How can practitioners really structure the content to help foster retention among sales reps? And so, John let’s kick it off with you. 

JH: Sure. I feel like Kendall should be the expert on this coming from HighSpot, right. All about content. But I think for, I’ll keep my answers short, I think, I hate to sound like a broken record, but if you simply take what you did in the physical world, which already had its limitations and you move it directly into the virtual world, it’s a recipe for disaster. And I would say remove the shackles of a two day event model and think about your content, your sessions, your gamification, the way you celebrate, the way you promote your events, even to recruit future employees and plan those out as a program over the course of Q1. So I don’t think there’s a real secret sauce, like exactly how you change your content, but if you sequence it and time it correctly, you don’t flood people with Zoom fatigue or session after session, and you allow them space to view it, react to it, apply it, and then come back and ask questions. This is where you’re going to get the most benefit and impact.

Kendall Michaud:  I would echo that. I might jump in and just add one thing here. One of our customers said that has resonated with me over the last month and has been justify every minute of live time. And so I think that’s really what the focus is about. The content retention is investing in the pre and the post. It’s a little piece, John, of like, you have your program. Well, the program consists of that content that you’re having accessible after the event. That’s the thing that the rep is going to actually take in the moment of action and go use in their conversation. So whether it’s a new play you might be rolling out at your event if the contents there and they’re trusting that system where the content is, they have it when they’re ready to go actually have that conversation post SKO. 

JH: I love it. That’s a huge takeaway. That’s like a light bulb moment where you just sat there, kind of justify every minute of live time. That’s so great.

Kendall Michaud:  I cannot take credit for it, but I just want to pass it along. That it has really resonated with me and helped as I continue to ask myself that question as I’m planning, 

JH: You should fully take credit for it. 

Megan Allen: Yeah, definitely take credit for that.

Cassandra Tenorio: Is there anything you’ve done Megan to really structure content to foster a tension among reps for your SKO?

Megan Allen: Yeah, I would say the key is in the details. If you take the time to consider all of the details of the end-to-end user experience, you’ll have success with this and with your content. So for keynotes or general session presentations, we spend a ton of time producing. Like John said, if you look at that clip producing high quality creative pre recorded sessions with animations and visuals on screen, we had media clips woven throughout and music here and there to inject some energy and emotion. They really turned out like a TV show in some ways. And the feedback was really incredible from our organization on how engaging those were for training.

If you have modules consider the timing, short and to the point is always best and the same goes for production. So take the time with the video edits to make the sessions great. And then for breakouts, consider interactivity. Are reps having opportunities to engage with each other and the content, or are they just listening to a presenter, share their screen for an hour on a Zoom. And what about an unstructured time for exploration? We actually added a whole space for virtual booths, like I said earlier with scheduled, choose your own adventure exploration time. So this really put it in the rep’s hands or the employees’ hands to jump around and sort of decide where they want it to be and spend their time just like they would if they were at an in-person event. So that experience was highly rated as well. 

JH: That’s really cool. I don’t know how many people watching have kids, but like the big debate in education these days is like asynchronous versus synchronous learning. And this really applies to our world as well. It goes back to while you were saying justify every minute of live time and sort of the flip side of that is really, you have all this offline or not live or offline time, if you will, where people can learn on demand. And so, you get great scale. 

Megan talked about some of the time zone issues when you’re running a global sales kickoff. And so I think. I’m thinking about synchronous versus asynchronous sessions and content is a good way. And thinking about how you balance between those two and leveraging both modalities correctly will help you really draw in the audience and again drive the impact that you’re seeing.

Cassandra Tenorio: I think that the last thing that I really want to touch on for this panel is really understanding the success of your SKO and where you see sales kickoffs growing in the future. So we’ll start with that first part, how do you measure the ROI of a virtual kickoff and what metrics are you really looking at to determine success? John I’ll put this one to you. 

JH: We used to do these like statistical analysis on the ROI of $500 carer of coffee. And the reality is it’s really hard to measure, right? The old world, the legacy model. It’s actually really hard to measure the ROI of hotel rooms, flight spends, et cetera, et cetera. So if you’re still running a model where you’re just translating your old model into the new and roughly doing the same thing, you probably can measure things like attendance, you can do a post event survey as well. So do people enjoy, do they get value out of it? And I think those are perfectly fine things, right?

Those are good, like foundational items. But I, again, I think there’s a really interesting new opportunity here. There’s a new model where you can start. If you think about school as any other program, you run in enablement. You can now start to track program metrics. If you have, for example, sales skills training on pipeline generation, or perhaps you focus on a new pitch, that’s come out along with discovery skills, you can start tracking things like pipeline generation. You can start tracking things like conversion of those early stages in your sales cycle, et cetera. Right. So I think that, in the new world, your ability to track business metrics that matter to the business, you come much more significant. 

Cassandra Tenorio: So, any way that you did this for your recent SKO, Megan?

Megan Allen: Yeah. So I’m hitting on what John said with virtual, you can easily keep track of who attended what, who showed up. Those were part of our metrics of just who showed up to the events, and marking, keeping track of who participated, did they log in exactly and those kinds of things. I love sharing this just because it’s a fun thing we incorporated in we actually had a participation leaderboard to help gamify the week. Because what sales rep doesn’t love a little competition. So we kept track of who attended the virtual booths and activities in our virtual experience, we were able to hide metals that people like had to find them while they were clicking around.

And the more metals they clicked on helped improve their leaderboards score as well. So. I had people pinging me on this side being like, how do I get more points? I want to be on the leaderboard. So I think that trying to gamify it really helped with those metrics and making sure people were staying engaged so that ROI was high. Then I’ll just lastly say, you know, the content that we focused on was intentionally given. Some of our lead indicators or metrics, which makes it easy to track ROI. So for example, from the data we knew we needed to focus energy at SKO on key aspects of the sales process that sped up the deal. So now we have an easy measurement of the result of that with average time to close and sales stage conversation rates after. 

Cassandra Tenorio: Absolutely. How have you seen SKO span beyond just sales? What are any of those other functions that you typically see involved? Kendall, I’d love to hear from you on this one.

Kendall Michaud:  John, you touched on it, the three E’s that for me I think about kickoff being inspiring, motivating, and bringing people together. And that’s just historically the goal of SKO. I think at some level, everyone can benefit from that right now. And we’ve all run into the challenges with communicating in a new message virtually. So for us at HighSpot, we’ve always had some aspect of all company involved in the event. And I think typically if you’re going to pick and choose, it’s anyone who’s interacting with the customer, they have some level of personalization that you’re able to provide. Like Megan, I loved how you did the personalized agenda. That’s something we’re thinking about doing for our teams who talked to different sets of customers and their processes are different. So, you know, everyone can benefit and I think it’s about inspiring confidence. And if that team leaves with new confidence, new energy, or a sense of pride or your company, it’s going to show up in that next conversation with the customer.

John Hsieh: That resonates with me because when I led enablement at DocuSign and both and extra factions, we had both the sales team as well as the customer success team there and because it was a live event, there was a cost associated with every head you invite. And so then we started having to make trade offs around who from product do we invite, who from HR do we invite? Because recruiting wants to be there right as well. So, you start to have these very difficult trade-off discussions. And at DocuSign, we actually converted like just even the term sales kickoff became kind of a misnomer. So, we changed the name to global kickoff, right? So to be more inclusive and again, I think in this new world where there isn’t like a per head cost, per se, as much as there was in the past, you do have a real opportunity to be very inclusive.

But I also think we, as planners of these events, have an obligation. If we’re going to invite them to the larger band, your swath of different folks across the organization, we want to make sure we’re providing value to each of those particular audiences that comes. So I go back to what Kendall said, right? Like make every minute, just by every minute of live time. So I do think like this adds complexity, but it’s good complexity because now you can have additional paths as well for these various teams.

Kendall Michaud: I would argue our product team is like the most engaged group. It’s so fun to see. And I think it helps them have a better understanding of the customers they’re building for. And, so it is about that personalization and what value you’re providing to the attendees.

Cassandra Tenorio: We love to end all of our panels with one quick takeaway for our audience. So I’d love to get from each of you. If our audience could leave with one thing, what would that be? So Kendall let’s actually kick it off with you. 

Kendall Michaud: I think if you’re going to leave with one thing, it’s to throw out the phrase, “this is how we’ve always done it.” Everything is on the table. Take that phrase out of your vocabulary and don’t be afraid to try something new. There are more positives to virtual than there are negatives and have fun. 

Cassandra Tenorio: I love that. John?

John Hsieh: I’ll make sure I look into the camera. I’ve been looking all over the place on my screen. I think many of you are leading the change for your company, and I know it’s scary, but this really is the time for you to show your organization. There’s a new and better way to energize and engage and educate the field. 

Megan Allen:  I would say, don’t look at virtual as a limitation. Leverage it to your advantage here. So get creative and pay attention to every detail. I would also like to say that you may think planning a virtual event takes less effort in time. If anything, I feel like it takes more, especially if you take the time to deliver everything at the highest quality that you can. So get yourself an amazing event agency to support you and an amazing project manager. Ours was Rachel. I have to give her a shout out because without her, our SKO would have not come to fruition. She started planning as far in advance as possible. And yeah, don’t think of virtual as a limitation. 

Cassandra Tenorio: And now we are going to open it up to Q and A. So if you have any questions for our panelists today, type those into the questions section, and we are going to get some of those answered for you.



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