This article was adapted from Stephanie's appearance on the Sales Enablement Innovation Podcast. Listen to the full episode here.

The shocking announcement that made everything 10x harder...

For those of us in SaaS or B2B sales, we got pretty comfortable with virtual kickoffs from 2020 onwards. Sure, they had their challenges – keeping people engaged in Zoom rooms, orchestrating breakouts, making sure Bob from accounting wasn't on mute for the entire Q&A session. But we figured it out.

Then came the curveball: "Hey Steph, we're going back to in-person."

Suddenly, it wasn't just about sharing screens and managing Zoom fatigue. We're talking:

  • International travel coordination
  • Physical swag that actually needs to arrive on time
  • Branded banners in hotel lobbies
  • Content that needs to work in a physical room (spoiler: that 12-point font isn't going to cut it)
  • Multiple days of programming instead of just a few hours

The complexity multiplies exponentially (and coffee becomes your best friend.)

Logistics for in-person sales kickoffs

Before we even think about content, let's talk about actually getting everyone in the building on time and on budget. Here are my top three lessons learned:

1 - Project management perfection

This isn't a two-week planning cycle, folks. When we're talking big SKOs, you need to start four to eight months in advance. Your project management skills need to be absolutely on point.

We're talking weekly, biweekly, and monthly updates for different audience groups. You need to engage cross-functionally and with external vendors in ways that virtual events never required. If you thought managing a virtual kickoff was like herding cats, in-person events are like herding cats while juggling flaming torches.

2 - Budget management becomes real

Virtual kickoffs? Maybe you spent money on some digital swag or upgraded your Zoom account. In-person events? For some of you, this might be your first time managing a seven-figure event budget.

That's not a typo. Seven figures.

Every decision has financial implications. Venue selection, catering, transportation, activities, swag, AV equipment... it all adds up faster than you can say "sales quota."

3 - International logistics will test your sanity

Here's something I hadn't fully appreciated until I was in the thick of it. When you have 400 people coming from 20 different countries, you're dealing with:

  • Flight bookings and coordination
  • Visa applications (yes, visas – I didn't think of it either at first)
  • Time zone adjustments
  • Different arrival and departure days
  • Dietary restrictions from around the globe
  • Cultural considerations for activities and content

Getting your head around the logistics of physically moving that volume of people into one space is critical. Start early. Then start earlier than that.

Content strategy for multi-day events

Now let's talk about the meat of the matter: content. When you're dealing with two, three, or even four days of programming, the game changes completely.

The leadership pre-game strategy

Here's something that might seem counterintuitive: bring your leadership team in a day early.

I know what you're thinking. "That's unnecessary complexity, Steph. Why would I do that to myself?"

Hear me out. Running through all the key content with leaders the day before accomplishes three critical things:

First, it's an incredible dry run. You'll discover things you never would have caught otherwise. That font that looked fine on your laptop? Way too small from the back of the room. That pillar in the venue that wasn't in the floor plan? Now you need to reconfigure your entire seating arrangement.

Second, you get buy-in at a whole different level. When leaders are physically in the room, they'll interject with questions your sellers will ask. "Oh, this is going to raise concerns for my Australia team." "Have you thought about how this impacts our enterprise accounts?" Getting ahead of these questions is gold.

Third, your sales leaders leave that session confident and prepared. They know what their teams are about to hear and they have the answers ready. Nothing undermines a kickoff faster than a manager saying "I don't know, I just heard this too," when their team starts asking questions.

Audience segmentation matters more than ever

If you're running a revenue kickoff, you might have:

  • Frontline sellers
  • Customer success teams (or account management, or client success – whatever you call them)
  • Solutions architects or engineers
  • Sales leadership

Each audience needs different things from your content. Let's say you're rolling out new AI functionality (because who isn't these days?). What your sales team needs to know is fundamentally different from what your solutions engineers need to know, which is different again from what customer success needs.

In a virtual world, you might have gotten away with one-size-fits-all sessions. In person? You have the opportunity (and the responsibility) to create targeted tracks that actually serve each audience.

The speaker selection reality check

Here's a truth bomb: your best Zoom presenters might not be your best in-person speakers.

Virtual presenting lets us lean on speaker notes, stay in one spot, and hide behind slides. But audience death by slideshow in your SKO isn't an option. In-person presenting requires what I call the "razzle dazzle factor": high energy, charisma, and the ability to work a room.

Great in-person speakers:

  • Move around the stage
  • Make eye contact with different parts of the room
  • Think on their feet without speaker notes
  • Engage the audience in real dialogue
  • Emit confidence that gets people excited

Choose your speakers based on who can command a room, not just who knows the content best. Those who are able to use humor or storytelling to elevate their SKO presentations are strong bets. Sometimes that means coaching your subject matter experts or pairing them with natural presenters.

Managing the three rings of stakeholder circus

One of the biggest challenges of in-person SKOs is stakeholder management. I break it down into three groups, each requiring different communication strategies:

Ring 1: Your core project team

These are your ride-or-die folks – directors from product marketing, key sales leaders, your events team. They're in the trenches with you, owning tasks and deliverables.

For this group, you need a proper project management tool. I've been using Asana and love it. Everyone can see what's connected to what, who's doing what, and when things are due. You should be meeting at least weekly, but the real magic happens in the ongoing collaboration within the tool.

Ring 2: Key stakeholders

Think VP-level folks who need to know you're on track but don't need to know how the sausage is made. They care about three things: timeline, budget, and major decisions.

Biweekly updates work well here, maybe shifting to weekly as you get closer. Keep it simple – a spreadsheet or slide deck with high-level status updates. "Marketing materials are 50% complete, on track for completion next week." That's the level of detail they need.

Ring 3: Executive oversight

Do not – I repeat, do not – put executives in your project management tool. They don't want it, they don't need it, and it will only create confusion.

What executives care about:

  • Are we on time?
  • Are we on budget?
  • Are there any issues that need their attention?

Monthly updates initially, moving to biweekly as you get closer. One slide or a bullet-point email. That's it.

And here's the key: be proactive with these updates. Don't wait for them to ask. Tell them upfront what they'll get and when, then deliver consistently. Nothing should ever surprise your executive team. If there's an issue, it should have been flagged and escalated through your other stakeholder rings first.

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Pro tip: leverage executive assistants.
They're often underutilized goldmines of insight. They'll tell you what topics matter most to their exec, how they prefer to receive information, and when you might need to loop them in earlier than planned.

Survival tips for your first in-person SKO

If you're staring down your first in-person kickoff, let me share some hard-won wisdom:

Define your swim lanes early

When someone says "You own sales kickoff," it's tempting to try to control everything. Don't. You'll burn out faster than a cheap candle.

Identify your key collaborators early and carve out clear swim lanes. Know what only you can do and focus on that. Maybe you've got someone who's incredible at vendor management and logistics. Let them own it, even if the Virgo in you wants to control every detail.

I once partnered with someone who was absolutely incredible at logistics and vendor management. While every fiber of my being wanted to know when people were arriving, what they were eating, and when the activity sheets would be delivered, I had to let go. She'd give me the information I needed – "Steph, I need final agenda timing to coordinate catering" – and I trusted her to handle the rest.

Focus on what only you can do

This bears repeating because it's so important. In the chaos of planning a successful SKO, it's easy to get pulled into everything. Resist that urge.

Your unique value might be:

  • Content strategy and speaker coaching
  • Stakeholder alignment and communication
  • Overall experience design
  • Cross-functional collaboration

Whatever it is, protect that focus. Everything else can and should be delegated to your trusted partners.

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More tips from the trenches on planning SKOs

The verdict: Is it worth it?

After all this talk of logistics nightmares, budget management, and stakeholder juggling, you might be wondering... is in-person really worth it?

Let me be clear: absolutely, unequivocally yes.

Those last six weeks before my first in-person kickoff with hundreds of people from almost two dozen countries? I wasn't sleeping. I was living on protein bars and coffee. But the payoff was incredible.

There's something magical about people who've only known each other through screens finally meeting in person. The relationship building, the hallway conversations, the impromptu problem-solving over lunch – none of that happens to the same degree virtually.

I saw people literally solving customer problems during coffee breaks. "Hey Steve, I'm about to respond to this email. Do you know about this feature?" That kind of real-time collaboration is priceless.

But here's what really sold me: the feedback. One piece of feedback I received still gives me chills: "I've been here for X years. This is hands down the best event I've ever been to. I feel more connected, more knowledgeable, more confident to go have conversations with my customers than I've felt in all my years here."

That's the power of in-person. Yes, you can build culture and knowledge virtually, but it takes so much longer. A well-executed in-person SKO can accomplish in three days what might take months of virtual touchpoints.

Your turn to take the plunge

Planning an in-person sales kickoff is one of the most challenging things you'll do in enablement. It's also one of the most rewarding. The late nights, the stress, the juggling of a million moving pieces... it all pays off when you see your revenue team come together, energized and aligned.

If you're in the thick of planning right now, remember:

  • Start early (then start earlier still)
  • Build a strong team and trust them
  • Communicate proactively with stakeholders
  • Focus on what only you can do
  • Choose speakers who can work a room
  • Plan for the unexpected (because it will happen)

And hey, if you want to talk about the nitty-gritty details, or how to customize sneakers in company colors so you can wear running shoes throughout your entire kickoff, connect with me on LinkedIn. We enablement folks need to stick together, especially when we're planning events that could rival small weddings in complexity.

The transition back to in-person events isn't easy, but the impact on your team, your culture, and your business results makes it all worthwhile. Trust the process, lean on your network, and remember – coffee really is life during SKO season.